药学学报

No.	t_R/min	Compound	Formula	m/z	Adduct	Error/×10^-6	MS/MS
1	1.00	Gallic acid	C₇H₆O₅	169.014 0	[M-H]^-	-1.5	125.024 6, 107.014 0
2	2.42	Caffeic acid	C₉H₈O₄	179.034 8	[M-H]^-	-1.2	135.045 0, 117.032 4, 107.049 9
3	2.43	Danshensu	C₉H₁₀O₅	197.045 2	[M-H]^-	-2.0	179.034 7, 135.046 1, 123.046 0, 109.029 5
4	2.56	Coumarate	C₉H₈O₃	165.054 6	[M+H]⁺	-0.2	119.085 6, 91.054 1
5	3.84	Vanillic acid	C₈H₈O₄	169.049 6	[M+H]⁺	0.3	125.060 1, 111.007 1, 95.066 8
6	5.06	Ferulic acid	C₁₀H₁₀O₄	195.065 2	[M+H]⁺	-0.6	177.055 0, 149.059 2, 134.036 5
7	5.07	6-Methoxycoumarin	C₁₀H₈O₃	177.054 7	[M+H]⁺	0.4	149.060 0, 145.028 7, 134.036 0, 117.033 8
8	5.09	Isoferulic acid	C₁₀H₁₀O₄	193.050 1	[M-H]^-	-2.9	178.027 1, 134.037 4
9	5.39	3, 4-Dicaffeoylquinic acid	C₂₅H₂₄O₁₂	515.119 1	[M-H]^-	-0.8	353.087 1, 191.055 7, 179.034 1
10	5.51	Salvianolic acid D	C₂₀H₁₈O₁₀	417.081 6	[M-H]^-	-2.8	197.045 3, 135.044 9
11	6.16	7-Hydroxycoumarin	C₉H₆O₃	163.039 0	[M+H]⁺	0.2	135.044 7, 117.034 0
12	6.16	Rosmarinic acid	C₁₈H₁₆O₈	359.076 5	[M-H]^-	-1.9	179.035 3, 161.026 3
13	6.17	Isomer of umbelliferide	C₉H₆O₃	161.023 9	[M-H]^-	-3.0	133.028 7, 117.039 1
14	6.28	Azelaic acid	C₉H₁₆O₄	187.097 2	[M-H]^-	-2.0	125.096 7, 123.081 4
15	6.51	Isomer of senkyunolide I	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 8, 179.106 3, 165.090 5
16	6.54	Senkyunolide I	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 8, 189.090 5, 179.078 9
17	6.78	Salvianolic acid B	C₃₆H₃₀O₁₆	717.143 0	[M-H]^-	-4.3	519.093 3, 339.049 5, 321.040 2, 295.061 8
18	6.98	Senkyunolide F	C₁₂H₁₄O₃	207.101 7	[M+H]⁺	0.4	189.091 3, 179.106 0, 123.044 3
19	6.99	Senkyunolide H	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 5, 189.091 1, 179.106 9, 165.089 5, 161.095 7, 117.069 4
20	7.09	New osthol lactone	C₁₂H₁₈O₂	195.137 9	[M+H]⁺	-0.5	177.127 3, 159.117 1, 117.070 0
21	7.42	Salvianolic acid A	C₂₆H₂₂O₁₀	493.113 0	[M-H]^-	-2.0	313.071 8, 295.062 9, 203.034 9, 185.024 7, 159.045 2, 109.030 3
22	9.04	Myrrhanolide B	C₁₅H₁₈O₄	261.112 6	[M-H]^-	-2.5	201.092 1, 187.076 4, 175.112 7
23	9.29	Coniferyl ferulate	C₂₀H₂₀O₆	355.117 0	[M-H]^-	-4.8	311.128 1, 296.104 6
24	9.44	Atractylenolide Ⅲ	C₁₅H₂₀O₃	249.148 5	[M+H]⁺	0.0	135.080 6, 107.084 8
25	9.50	Myrrhterpenoid H	C₁₆H₂₀O₄	277.143 6	[M+H]⁺	0.4	245.120 1, 121.066 8
26	9.63	Commipholinone	C₁₄H₁₆O₃	233.117 5	[M+H]⁺	1.1	119.085 4, 105.069 9
27	9.76	Commiterpene D	C₁₈H₂₂O₅	319.154 3	[M+H]⁺	1.0	227.107 9, 156.093 4
28	9.89	9, 10-Secoisohydro-xyaconido lactone	C₁₅H₁₈O₃	247.132 9	[M+H]⁺	0.2	159.081 8, 91.055 0
29	10.02	Isopimpinellin	C₁₃H₁₀O₅	247.059 4	[M+H]⁺	-3.1	189.091 0, 161.095 7, 133.064 9
30	10.59	MCS134	C₁₆H₂₂O₃	285.147 5	[M+Na]⁺	4.9	187.038 6, 171.116 7, 159.116 4, 145.101 3
31	10.89	Przewaquinone A	C₁₉H₁₈O₄	311.127 8	[M+H]⁺	0.0	283.132 4, 237.056 3
32	10.91	Nortanshinone	C₁₇H₁₂O₄	281.080 3	[M+H]⁺	-1.8	253.086 2, 225.092 4
33	11.06	Tanshinone Ⅱ_B	C₁₉H₁₈O₄	311.127 8	[M+H]⁺	0.0	293.117 1, 283.132 9, 275.106 7, 250.106 9, 247.111 0
34	11.06	1S-Hydroxy-anhydride of 16R cryptotanshinone	C₁₉H₂₀O₅	327.122 5	[M-H]^-	-4.0	283.133 4, 239.143 7
35	11.38	Senkyunolide A	C₁₂H₁₆O₂	193.122 2	[M+H]⁺	-0.5	147.117 8, 137.061 0, 119.084 9, 105.070 0, 93.070 7
36	11.47	Tanshialdehyde	C₁₉H₁₆O₄	309.112 2	[M+H]⁺	0.2	265.123 2, 250.098 6, 235.076 3
37	11.49	Canangaterpene Ⅵ	C₁₄H₂₂O₂	223.169 0	[M+H]⁺	-1.0	119.085 7, 91.054 6
38	11.91	N-Butylphthalide	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.1	173.097 3, 145.100 8
39	12.05	FSA	C₁₈H₂₄O₅	321.169 5	[M+H]⁺	-0.4	185.096 7, 168.095 3, 159.083 4, 145.076 3, 131.086 0
40	12.06	Commiterpene B	C₁₈H₂₂O₄	303.159 4	[M+H]⁺	1.0	211.112 5, 181.065 7
41	12.09	Dihydrotanshinone I	C₁₈H₁₄O₃	279.101 4	[M+H]⁺	-0.5	261.094 1, 233.099 0, 205.103 5
42	12.17	Z-Ligustilide	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.1	173.096 3, 163.111 6, 145.100 8, 117.070 0, 105.069 8, 91.054 5
43	12.27	(1E)-8, 12-Epoxy-germacra-1, 7, 10, 11-tetraen-6-one	C₁₅H₁₈O₂	231.138 1	[M+H]⁺	0.7	145.065 1, 105.070 0, 91.054 4
44	12.37	2-Methoxy-furanogermacra-1(10), 4-diene	C₁₆H₂₀O₃	261.148 3	[M+H]⁺	-0.5	175.112 3, 161.135 2, 91.053 9
45	12.39	Danshenxinkun B	C₁₈H₁₆O₃	281.117 1	[M+H]⁺	-0.6	253.158 7, 235.113 9
46	12.46	Epicurzerenone	C₁₅H₂₀O₂	233.153 4	[M+H]⁺	-0.9	145.102 5, 131.087 3, 95.086 0
47	12.92	9-Methymyrrhone	C₁₆H₁₈O₃	259.132 8	[M+H]⁺	-0.3	211.074 5, 189.092 1, 174.101 8, 161.060 2
48	12.96	Myrrhone	C₁₅H₁₆O₂	229.122 2	[M+H]⁺	-0.5	159.086 6, 145.066 9
49	13.03	Tanshinone I	C₁₈H₁₂O₃	277.085 7	[M+H]⁺	-1.0	262.063 2, 249.096 1, 221.096 3
50	13.08	Cryptotanshinone	C₁₉H₂₀O₃	297.148 3	[M+H]⁺	-0.6	282.126 4, 279.140 0, 268.111 1, 251.144 4, 237.097 3, 227.071 4
51	13.17	Rel-3R-methoxy-4S-furanogermacra-1E, 10(15)-dien-6-one	C₁₆H₂₀O₃	261.148 4	[M+H]⁺	-0.4	175.076 7, 161.060 4, 145.085 2, 131.086 1
52	13.18	Myrrhterpenoid J	C₁₆H₂₀O₃	261.148 4	[M+H]⁺	-0.6	229.125 3, 201.110 2, 196.088 8
53	13.36	Incensole oxide	C₂₀H₃₄O₃	323.257 8	[M+H]⁺	-0.7	163.147 1, 149.133 0, 121.102 3
54	13.46	Methylenetanshinquinone	C₁₈H₁₄O₃	279.101 4	[M+H]⁺	-0.5	261.096 7, 233.099 6, 205.103 1
55	13.66	Levistolide A	C₂₄H₂₈O₄	381.205 7	[M+H]⁺	-0.7	191.110 8, 173.096 4, 149.059 5, 145.100 8, 135.043 8, 117.070 0
56	13.75	Angelicide	C₂₄H₂₈O₄	381.205 7	[M+H]⁺	-0.7	335.200 6, 191.112 2
57	13.81	Olibanumol I	C₂₉H₄₆O₂	427.356 5	[M+H]⁺	-1.2	163.147 7, 149.131 9
58	13.82	Senkyunolide P	C₂₄H₂₈O₄	381.205 8	[M+H]⁺	-0.6	335.201 5, 279.136 7, 191.113 4
59	13.85	Dehydromiltirone	C₁₉H₂₀O₂	281.153 3	[M+H]⁺	-1.1	266.130 4, 253.158 5
60	13.90	Alismol	C₁₅H₂₄O	221.189 9	[M+H]⁺	-0.6	147.116 7, 107.085 4, 103.054 0
61	14.04	Tanshinone Ⅱ_A	C₁₉H₁₈O₃	295.132 7	[M+H]⁺	-0.6	280.110 4, 277.125 9, 266.094 9, 262.100 8, 249.127 6
62	14.19	(-)-α-Cubebene	C₁₅H₂₄	205.194 8	[M+H]⁺	-1.2	105.070 8, 91.057 8
63	14.22	Dihydro-cryptotanshinone	C₁₉H₂₂O₃	299.163 9	[M+H]⁺	-1.0	281.153 8, 253.158 9
64	14.30	Miltirone	C₁₉H₂₂O₂	283.169 1	[M+H]⁺	-0.7	268.145 3, 265.159 0
65	14.46	Lupan-20(29)-ene-3α, 30-diol	C₃₀H₅₀O₂	443.387 6	[M+H]⁺	-1.8	297.247 6, 217.195 1
66	14.68	11-Oxo-24-norursa-3, 9(11), 12-triene	C₂₉H₄₄O	409.346 2	[M+H]⁺	-0.6	219.174 8, 175.148 2
67	14.69	Tsugaric acid A	C₃₂H₅₀O₄	499.377 3	[M+H]⁺	-1.8	439.358 2, 369.273 4, 329.276 2, 255.212 5
68	14.76	11-Carbonyl-β-boswellic acid	C₃₀H₄₆O₄	469.330 6	[M-H]^-	-3.7	407.331 2, 391.300 0
69	14.79	Lupeolic acid	C₃₀H₄₆O₄	455.351 7	[M+H]⁺	-0.7	437.341 9, 271.241 6
70	15.01	Boscartol C	C₂₀H₃₂O₂	305.247 2	[M+H]⁺	-0.9	175.147 0, 159.116 5, 145.101 2
71	15.23	Incensole	C₂₀H₃₄O₂	307.263 0	[M+H]⁺	-0.6	123.118 1, 109.102 8, 95.088 4
72	15.36	Boscartin X	C₂₂H₃₆O₄	365.268 2	[M+H]⁺	-1.2	305.248 5, 175.147 1, 151.111 6, 121.101 2
73	15.79	β-Hydroxyman-subin-13(17)-ene-11-ketone	C₂₂H₃₄O₂	331.262 9	[M+H]⁺	-0.8	189.163 6, 121.101 0
74	16.36	α-Boswellic acid	C₃₀H₄₈O₃	455.350 8	[M-H]^-	-5.0	437.351 8, 409.350 9, 361.063 9
75	16.45	3-Acetyl-11-keto-β-boswellic acid	C₃₂H₄₈O₅	513.357 3	[M+H]⁺	-0.3	497.812 6, 495.347 9, 470.005 9, 453.339 3, 437.328 0
76	16.51	Verticiol	C₂₀H₃₄O	291.267 9	[M+H]⁺	-1.2	107.085 3, 93.069 9, 81.070 5
77	16.53	3α-Acetyl-9, 11-deoxy-β-boswellic acid	C₃₂H₄₈O₄	497.362 2	[M+H]⁺	-0.7	437.342 1, 391.335 8
78	16.67	β-Boswellic acid	C₃₀H₄₈O₃	455.350 8	[M-H]^-	-5.0	409.310 5, 367.391 6, 283.712 5
79	16.91	Cycloartenol	C₃₀H₅₀O	427.392 8	[M+H]⁺	-1.5	189.163 6, 173.131 8
80	17.44	Commiphorane G2	C₂₂H₃₄O	315.268 0	[M+H]⁺	-0.8	145.100 5, 105.069 9
81	17.70	Epilupeol	C₃₀H₄₈O	425.377 0	[M+H]⁺	-1.9	187.147 5, 135.116 7
82	17.72	Lupenone	C₃₀H₄₈O	425.376 7	[M+H]⁺	-2.3	203.179 2, 189.163 1, 147.116 6, 105.069 5, 81.070 0
83	17.85	Incensole acetate	C₂₂H₃₆O₃	349.273 4	[M+H]⁺	-0.9	203.179 9, 163.148 2

No.

t_R/min

Compound

Formula

m/z

Adduct

Error/×10^-6

MS/MS

1.00

Gallic acid

C₇H₆O₅

169.014 0

[M-H]^-

-1.5

125.024 6, 107.014 0

2.42

Caffeic acid

C₉H₈O₄

179.034 8

[M-H]^-

-1.2

135.045 0, 117.032 4, 107.049 9

2.43

Danshensu

C₉H₁₀O₅

197.045 2

[M-H]^-

-2.0

179.034 7, 135.046 1, 123.046 0, 109.029 5

2.56

Coumarate

C₉H₈O₃

165.054 6

[M+H]⁺

-0.2

119.085 6, 91.054 1

3.84

Vanillic acid

C₈H₈O₄

169.049 6

[M+H]⁺

0.3

125.060 1, 111.007 1, 95.066 8

5.06

Ferulic acid

C₁₀H₁₀O₄

195.065 2

[M+H]⁺

-0.6

177.055 0, 149.059 2, 134.036 5

5.07

6-Methoxycoumarin

C₁₀H₈O₃

177.054 7

[M+H]⁺

0.4

149.060 0, 145.028 7, 134.036 0, 117.033 8

5.09

Isoferulic acid

C₁₀H₁₀O₄

193.050 1

[M-H]^-

-2.9

178.027 1, 134.037 4

5.39

3, 4-Dicaffeoylquinic acid

C₂₅H₂₄O₁₂

515.119 1

[M-H]^-

-0.8

353.087 1, 191.055 7, 179.034 1

5.51

Salvianolic acid D

C₂₀H₁₈O₁₀

417.081 6

[M-H]^-

-2.8

197.045 3, 135.044 9

6.16

7-Hydroxycoumarin

C₉H₆O₃

163.039 0

[M+H]⁺

0.2

135.044 7, 117.034 0

6.16

Rosmarinic acid

C₁₈H₁₆O₈

359.076 5

[M-H]^-

-1.9

179.035 3, 161.026 3

6.17

Isomer of umbelliferide

C₉H₆O₃

161.023 9

[M-H]^-

-3.0

133.028 7, 117.039 1

6.28

Azelaic acid

C₉H₁₆O₄

187.097 2

[M-H]^-

-2.0

125.096 7, 123.081 4

6.51

Isomer of senkyunolide I

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 8, 179.106 3, 165.090 5

6.54

Senkyunolide I

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 8, 189.090 5, 179.078 9

6.78

Salvianolic acid B

C₃₆H₃₀O₁₆

717.143 0

[M-H]^-

-4.3

519.093 3, 339.049 5, 321.040 2, 295.061 8

6.98

Senkyunolide F

C₁₂H₁₄O₃

207.101 7

[M+H]⁺

0.4

189.091 3, 179.106 0, 123.044 3

6.99

Senkyunolide H

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 5, 189.091 1, 179.106 9, 165.089 5, 161.095 7, 117.069 4

7.09

New osthol lactone

C₁₂H₁₈O₂

195.137 9

[M+H]⁺

-0.5

177.127 3, 159.117 1, 117.070 0

7.42

Salvianolic acid A

C₂₆H₂₂O₁₀

493.113 0

[M-H]^-

-2.0

313.071 8, 295.062 9, 203.034 9, 185.024 7, 159.045 2, 109.030 3

9.04

Myrrhanolide B

C₁₅H₁₈O₄

261.112 6

[M-H]^-

-2.5

201.092 1, 187.076 4, 175.112 7

9.29

Coniferyl ferulate

C₂₀H₂₀O₆

355.117 0

[M-H]^-

-4.8

311.128 1, 296.104 6

9.44

Atractylenolide Ⅲ

C₁₅H₂₀O₃

249.148 5

[M+H]⁺

0.0

135.080 6, 107.084 8

9.50

Myrrhterpenoid H

C₁₆H₂₀O₄

277.143 6

[M+H]⁺

0.4

245.120 1, 121.066 8

9.63

Commipholinone

C₁₄H₁₆O₃

233.117 5

[M+H]⁺

1.1

119.085 4, 105.069 9

9.76

Commiterpene D

C₁₈H₂₂O₅

319.154 3

[M+H]⁺

1.0

227.107 9, 156.093 4

9.89

9, 10-Secoisohydro-xyaconido lactone

C₁₅H₁₈O₃

247.132 9

[M+H]⁺

0.2

159.081 8, 91.055 0

10.02

Isopimpinellin

C₁₃H₁₀O₅

247.059 4

[M+H]⁺

-3.1

189.091 0, 161.095 7, 133.064 9

10.59

MCS134

C₁₆H₂₂O₃

285.147 5

[M+Na]⁺

4.9

187.038 6, 171.116 7, 159.116 4, 145.101 3

10.89

Przewaquinone A

C₁₉H₁₈O₄

311.127 8

[M+H]⁺

0.0

283.132 4, 237.056 3

10.91

Nortanshinone

C₁₇H₁₂O₄

281.080 3

[M+H]⁺

-1.8

253.086 2, 225.092 4

11.06

Tanshinone Ⅱ_B

C₁₉H₁₈O₄

311.127 8

[M+H]⁺

0.0

293.117 1, 283.132 9, 275.106 7, 250.106 9, 247.111 0

11.06

1S-Hydroxy-anhydride of 16R cryptotanshinone

C₁₉H₂₀O₅

327.122 5

[M-H]^-

-4.0

283.133 4, 239.143 7

11.38

Senkyunolide A

C₁₂H₁₆O₂

193.122 2

[M+H]⁺

-0.5

147.117 8, 137.061 0, 119.084 9, 105.070 0, 93.070 7

11.47

Tanshialdehyde

C₁₉H₁₆O₄

309.112 2

[M+H]⁺

0.2

265.123 2, 250.098 6, 235.076 3

11.49

Canangaterpene Ⅵ

C₁₄H₂₂O₂

223.169 0

[M+H]⁺

-1.0

119.085 7, 91.054 6

11.91

N-Butylphthalide

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.1

173.097 3, 145.100 8

12.05

FSA

C₁₈H₂₄O₅

321.169 5

[M+H]⁺

-0.4

185.096 7, 168.095 3, 159.083 4, 145.076 3, 131.086 0

12.06

Commiterpene B

C₁₈H₂₂O₄

303.159 4

[M+H]⁺

1.0

211.112 5, 181.065 7

12.09

Dihydrotanshinone I

C₁₈H₁₄O₃

279.101 4

[M+H]⁺

-0.5

261.094 1, 233.099 0, 205.103 5

12.17

Z-Ligustilide

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.1

173.096 3, 163.111 6, 145.100 8, 117.070 0, 105.069 8, 91.054 5

12.27

(1E)-8, 12-Epoxy-germacra-1, 7, 10, 11-tetraen-6-one

C₁₅H₁₈O₂

231.138 1

[M+H]⁺

0.7

145.065 1, 105.070 0, 91.054 4

12.37

2-Methoxy-furanogermacra-1(10), 4-diene

C₁₆H₂₀O₃

261.148 3

[M+H]⁺

-0.5

175.112 3, 161.135 2, 91.053 9

12.39

Danshenxinkun B

C₁₈H₁₆O₃

281.117 1

[M+H]⁺

-0.6

253.158 7, 235.113 9

12.46

Epicurzerenone

C₁₅H₂₀O₂

233.153 4

[M+H]⁺

-0.9

145.102 5, 131.087 3, 95.086 0

12.92

9-Methymyrrhone

C₁₆H₁₈O₃

259.132 8

[M+H]⁺

-0.3

211.074 5, 189.092 1, 174.101 8, 161.060 2

12.96

Myrrhone

C₁₅H₁₆O₂

229.122 2

[M+H]⁺

-0.5

159.086 6, 145.066 9

13.03

Tanshinone I

C₁₈H₁₂O₃

277.085 7

[M+H]⁺

-1.0

262.063 2, 249.096 1, 221.096 3

13.08

Cryptotanshinone

C₁₉H₂₀O₃

297.148 3

[M+H]⁺

-0.6

282.126 4, 279.140 0, 268.111 1, 251.144 4, 237.097 3, 227.071 4

13.17

Rel-3R-methoxy-4S-furanogermacra-1E, 10(15)-dien-6-one

C₁₆H₂₀O₃

261.148 4

[M+H]⁺

-0.4

175.076 7, 161.060 4, 145.085 2, 131.086 1

13.18

Myrrhterpenoid J

C₁₆H₂₀O₃

261.148 4

[M+H]⁺

-0.6

229.125 3, 201.110 2, 196.088 8

13.36

Incensole oxide

C₂₀H₃₄O₃

323.257 8

[M+H]⁺

-0.7

163.147 1, 149.133 0, 121.102 3

13.46

Methylenetanshinquinone

C₁₈H₁₄O₃

279.101 4

[M+H]⁺

-0.5

261.096 7, 233.099 6, 205.103 1

13.66

Levistolide A

C₂₄H₂₈O₄

381.205 7

[M+H]⁺

-0.7

191.110 8, 173.096 4, 149.059 5, 145.100 8, 135.043 8, 117.070 0

13.75

Angelicide

C₂₄H₂₈O₄

381.205 7

[M+H]⁺

-0.7

335.200 6, 191.112 2

13.81

Olibanumol I

C₂₉H₄₆O₂

427.356 5

[M+H]⁺

-1.2

163.147 7, 149.131 9

13.82

Senkyunolide P

C₂₄H₂₈O₄

381.205 8

[M+H]⁺

-0.6

335.201 5, 279.136 7, 191.113 4

13.85

Dehydromiltirone

C₁₉H₂₀O₂

281.153 3

[M+H]⁺

-1.1

266.130 4, 253.158 5

13.90

Alismol

C₁₅H₂₄O

221.189 9

[M+H]⁺

-0.6

147.116 7, 107.085 4, 103.054 0

14.04

Tanshinone Ⅱ_A

C₁₉H₁₈O₃

295.132 7

[M+H]⁺

-0.6

280.110 4, 277.125 9, 266.094 9, 262.100 8, 249.127 6

14.19

(-)-α-Cubebene

C₁₅H₂₄

205.194 8

[M+H]⁺

-1.2

105.070 8, 91.057 8

14.22

Dihydro-cryptotanshinone

C₁₉H₂₂O₃

299.163 9

[M+H]⁺

-1.0

281.153 8, 253.158 9

14.30

Miltirone

C₁₉H₂₂O₂

283.169 1

[M+H]⁺

-0.7

268.145 3, 265.159 0

14.46

Lupan-20(29)-ene-3α, 30-diol

C₃₀H₅₀O₂

443.387 6

[M+H]⁺

-1.8

297.247 6, 217.195 1

14.68

11-Oxo-24-norursa-3, 9(11), 12-triene

C₂₉H₄₄O

409.346 2

[M+H]⁺

-0.6

219.174 8, 175.148 2

14.69

Tsugaric acid A

C₃₂H₅₀O₄

499.377 3

[M+H]⁺

-1.8

439.358 2, 369.273 4, 329.276 2, 255.212 5

14.76

11-Carbonyl-β-boswellic acid

C₃₀H₄₆O₄

469.330 6

[M-H]^-

-3.7

407.331 2, 391.300 0

14.79

Lupeolic acid

C₃₀H₄₆O₄

455.351 7

[M+H]⁺

-0.7

437.341 9, 271.241 6

15.01

Boscartol C

C₂₀H₃₂O₂

305.247 2

[M+H]⁺

-0.9

175.147 0, 159.116 5, 145.101 2

15.23

Incensole

C₂₀H₃₄O₂

307.263 0

[M+H]⁺

-0.6

123.118 1, 109.102 8, 95.088 4

15.36

Boscartin X

C₂₂H₃₆O₄

365.268 2

[M+H]⁺

-1.2

305.248 5, 175.147 1, 151.111 6, 121.101 2

15.79

β-Hydroxyman-subin-13(17)-ene-11-ketone

C₂₂H₃₄O₂

331.262 9

[M+H]⁺

-0.8

189.163 6, 121.101 0

16.36

α-Boswellic acid

C₃₀H₄₈O₃

455.350 8

[M-H]^-

-5.0

437.351 8, 409.350 9, 361.063 9

16.45

3-Acetyl-11-keto-β-boswellic acid

C₃₂H₄₈O₅

513.357 3

[M+H]⁺

-0.3

497.812 6, 495.347 9, 470.005 9, 453.339 3, 437.328 0

16.51

Verticiol

C₂₀H₃₄O

291.267 9

[M+H]⁺

-1.2

107.085 3, 93.069 9, 81.070 5

16.53

3α-Acetyl-9, 11-deoxy-β-boswellic acid

C₃₂H₄₈O₄

497.362 2

[M+H]⁺

-0.7

437.342 1, 391.335 8

16.67

β-Boswellic acid

C₃₀H₄₈O₃

455.350 8

[M-H]^-

-5.0

409.310 5, 367.391 6, 283.712 5

16.91

Cycloartenol

C₃₀H₅₀O

427.392 8

[M+H]⁺

-1.5

189.163 6, 173.131 8

17.44

Commiphorane G2

C₂₂H₃₄O

315.268 0

[M+H]⁺

-0.8

145.100 5, 105.069 9

17.70

Epilupeol

C₃₀H₄₈O

425.377 0

[M+H]⁺

-1.9

187.147 5, 135.116 7

17.72

Lupenone

C₃₀H₄₈O

425.376 7

[M+H]⁺

-2.3

203.179 2, 189.163 1, 147.116 6, 105.069 5, 81.070 0

17.85

Incensole acetate

C₂₂H₃₆O₃

349.273 4

[M+H]⁺

-0.9

203.179 9, 163.148 2

No.	t_R/min	Compound	Formula	m/z	Adduct	Error/×10^-6	MS/MS
1	1.00	Gallic acid	C₇H₆O₅	169.014 0	[M-H]^-	-1.5	125.024 6, 107.014 0
2	2.42	Caffeic acid	C₉H₈O₄	179.034 8	[M-H]^-	-1.2	135.045 0, 117.032 4, 107.049 9
3	2.43	Danshensu	C₉H₁₀O₅	197.045 2	[M-H]^-	-2.0	179.034 7, 135.046 1, 123.046 0, 109.029 5
4	2.56	Coumarate	C₉H₈O₃	165.054 6	[M+H]⁺	-0.2	119.085 6, 91.054 1
5	3.84	Vanillic acid	C₈H₈O₄	169.049 6	[M+H]⁺	0.3	125.060 1, 111.007 1, 95.066 8
6	5.06	Ferulic acid	C₁₀H₁₀O₄	195.065 2	[M+H]⁺	-0.6	177.055 0, 149.059 2, 134.036 5
7	5.07	6-Methoxycoumarin	C₁₀H₈O₃	177.054 7	[M+H]⁺	0.4	149.060 0, 145.028 7, 134.036 0, 117.033 8
8	5.09	Isoferulic acid	C₁₀H₁₀O₄	193.050 1	[M-H]^-	-2.9	178.027 1, 134.037 4
9	5.39	3, 4-Dicaffeoylquinic acid	C₂₅H₂₄O₁₂	515.119 1	[M-H]^-	-0.8	353.087 1, 191.055 7, 179.034 1
10	5.51	Salvianolic acid D	C₂₀H₁₈O₁₀	417.081 6	[M-H]^-	-2.8	197.045 3, 135.044 9
11	6.16	7-Hydroxycoumarin	C₉H₆O₃	163.039 0	[M+H]⁺	0.2	135.044 7, 117.034 0
12	6.16	Rosmarinic acid	C₁₈H₁₆O₈	359.076 5	[M-H]^-	-1.9	179.035 3, 161.026 3
13	6.17	Isomer of umbelliferide	C₉H₆O₃	161.023 9	[M-H]^-	-3.0	133.028 7, 117.039 1
14	6.28	Azelaic acid	C₉H₁₆O₄	187.097 2	[M-H]^-	-2.0	125.096 7, 123.081 4
15	6.51	Isomer of senkyunolide I	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 8, 179.106 3, 165.090 5
16	6.54	Senkyunolide I	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 8, 189.090 5, 179.078 9
17	6.78	Salvianolic acid B	C₃₆H₃₀O₁₆	717.143 0	[M-H]^-	-4.3	519.093 3, 339.049 5, 321.040 2, 295.061 8
18	6.98	Senkyunolide F	C₁₂H₁₄O₃	207.101 7	[M+H]⁺	0.4	189.091 3, 179.106 0, 123.044 3
19	6.99	Senkyunolide H	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 5, 189.091 1, 179.106 9, 165.089 5, 161.095 7, 117.069 4
20	7.09	New osthol lactone	C₁₂H₁₈O₂	195.137 9	[M+H]⁺	-0.5	177.127 3, 159.117 1, 117.070 0
21	7.42	Salvianolic acid A	C₂₆H₂₂O₁₀	493.113 0	[M-H]^-	-2.0	313.071 8, 295.062 9, 203.034 9, 185.024 7, 159.045 2, 109.030 3
22	9.04	Myrrhanolide B	C₁₅H₁₈O₄	261.112 6	[M-H]^-	-2.5	201.092 1, 187.076 4, 175.112 7
23	9.29	Coniferyl ferulate	C₂₀H₂₀O₆	355.117 0	[M-H]^-	-4.8	311.128 1, 296.104 6
24	9.44	Atractylenolide Ⅲ	C₁₅H₂₀O₃	249.148 5	[M+H]⁺	0.0	135.080 6, 107.084 8
25	9.50	Myrrhterpenoid H	C₁₆H₂₀O₄	277.143 6	[M+H]⁺	0.4	245.120 1, 121.066 8
26	9.63	Commipholinone	C₁₄H₁₆O₃	233.117 5	[M+H]⁺	1.1	119.085 4, 105.069 9
27	9.76	Commiterpene D	C₁₈H₂₂O₅	319.154 3	[M+H]⁺	1.0	227.107 9, 156.093 4
28	9.89	9, 10-Secoisohydro-xyaconido lactone	C₁₅H₁₈O₃	247.132 9	[M+H]⁺	0.2	159.081 8, 91.055 0
29	10.02	Isopimpinellin	C₁₃H₁₀O₅	247.059 4	[M+H]⁺	-3.1	189.091 0, 161.095 7, 133.064 9
30	10.59	MCS134	C₁₆H₂₂O₃	285.147 5	[M+Na]⁺	4.9	187.038 6, 171.116 7, 159.116 4, 145.101 3
31	10.89	Przewaquinone A	C₁₉H₁₈O₄	311.127 8	[M+H]⁺	0.0	283.132 4, 237.056 3
32	10.91	Nortanshinone	C₁₇H₁₂O₄	281.080 3	[M+H]⁺	-1.8	253.086 2, 225.092 4
33	11.06	Tanshinone Ⅱ_B	C₁₉H₁₈O₄	311.127 8	[M+H]⁺	0.0	293.117 1, 283.132 9, 275.106 7, 250.106 9, 247.111 0
34	11.06	1S-Hydroxy-anhydride of 16R cryptotanshinone	C₁₉H₂₀O₅	327.122 5	[M-H]^-	-4.0	283.133 4, 239.143 7
35	11.38	Senkyunolide A	C₁₂H₁₆O₂	193.122 2	[M+H]⁺	-0.5	147.117 8, 137.061 0, 119.084 9, 105.070 0, 93.070 7
36	11.47	Tanshialdehyde	C₁₉H₁₆O₄	309.112 2	[M+H]⁺	0.2	265.123 2, 250.098 6, 235.076 3
37	11.49	Canangaterpene Ⅵ	C₁₄H₂₂O₂	223.169 0	[M+H]⁺	-1.0	119.085 7, 91.054 6
38	11.91	N-Butylphthalide	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.1	173.097 3, 145.100 8
39	12.05	FSA	C₁₈H₂₄O₅	321.169 5	[M+H]⁺	-0.4	185.096 7, 168.095 3, 159.083 4, 145.076 3, 131.086 0
40	12.06	Commiterpene B	C₁₈H₂₂O₄	303.159 4	[M+H]⁺	1.0	211.112 5, 181.065 7
41	12.09	Dihydrotanshinone I	C₁₈H₁₄O₃	279.101 4	[M+H]⁺	-0.5	261.094 1, 233.099 0, 205.103 5
42	12.17	Z-Ligustilide	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.1	173.096 3, 163.111 6, 145.100 8, 117.070 0, 105.069 8, 91.054 5
43	12.27	(1E)-8, 12-Epoxy-germacra-1, 7, 10, 11-tetraen-6-one	C₁₅H₁₈O₂	231.138 1	[M+H]⁺	0.7	145.065 1, 105.070 0, 91.054 4
44	12.37	2-Methoxy-furanogermacra-1(10), 4-diene	C₁₆H₂₀O₃	261.148 3	[M+H]⁺	-0.5	175.112 3, 161.135 2, 91.053 9
45	12.39	Danshenxinkun B	C₁₈H₁₆O₃	281.117 1	[M+H]⁺	-0.6	253.158 7, 235.113 9
46	12.46	Epicurzerenone	C₁₅H₂₀O₂	233.153 4	[M+H]⁺	-0.9	145.102 5, 131.087 3, 95.086 0
47	12.92	9-Methymyrrhone	C₁₆H₁₈O₃	259.132 8	[M+H]⁺	-0.3	211.074 5, 189.092 1, 174.101 8, 161.060 2
48	12.96	Myrrhone	C₁₅H₁₆O₂	229.122 2	[M+H]⁺	-0.5	159.086 6, 145.066 9
49	13.03	Tanshinone I	C₁₈H₁₂O₃	277.085 7	[M+H]⁺	-1.0	262.063 2, 249.096 1, 221.096 3
50	13.08	Cryptotanshinone	C₁₉H₂₀O₃	297.148 3	[M+H]⁺	-0.6	282.126 4, 279.140 0, 268.111 1, 251.144 4, 237.097 3, 227.071 4
51	13.17	Rel-3R-methoxy-4S-furanogermacra-1E, 10(15)-dien-6-one	C₁₆H₂₀O₃	261.148 4	[M+H]⁺	-0.4	175.076 7, 161.060 4, 145.085 2, 131.086 1
52	13.18	Myrrhterpenoid J	C₁₆H₂₀O₃	261.148 4	[M+H]⁺	-0.6	229.125 3, 201.110 2, 196.088 8
53	13.36	Incensole oxide	C₂₀H₃₄O₃	323.257 8	[M+H]⁺	-0.7	163.147 1, 149.133 0, 121.102 3
54	13.46	Methylenetanshinquinone	C₁₈H₁₄O₃	279.101 4	[M+H]⁺	-0.5	261.096 7, 233.099 6, 205.103 1
55	13.66	Levistolide A	C₂₄H₂₈O₄	381.205 7	[M+H]⁺	-0.7	191.110 8, 173.096 4, 149.059 5, 145.100 8, 135.043 8, 117.070 0
56	13.75	Angelicide	C₂₄H₂₈O₄	381.205 7	[M+H]⁺	-0.7	335.200 6, 191.112 2
57	13.81	Olibanumol I	C₂₉H₄₆O₂	427.356 5	[M+H]⁺	-1.2	163.147 7, 149.131 9
58	13.82	Senkyunolide P	C₂₄H₂₈O₄	381.205 8	[M+H]⁺	-0.6	335.201 5, 279.136 7, 191.113 4
59	13.85	Dehydromiltirone	C₁₉H₂₀O₂	281.153 3	[M+H]⁺	-1.1	266.130 4, 253.158 5
60	13.90	Alismol	C₁₅H₂₄O	221.189 9	[M+H]⁺	-0.6	147.116 7, 107.085 4, 103.054 0
61	14.04	Tanshinone Ⅱ_A	C₁₉H₁₈O₃	295.132 7	[M+H]⁺	-0.6	280.110 4, 277.125 9, 266.094 9, 262.100 8, 249.127 6
62	14.19	(-)-α-Cubebene	C₁₅H₂₄	205.194 8	[M+H]⁺	-1.2	105.070 8, 91.057 8
63	14.22	Dihydro-cryptotanshinone	C₁₉H₂₂O₃	299.163 9	[M+H]⁺	-1.0	281.153 8, 253.158 9
64	14.30	Miltirone	C₁₉H₂₂O₂	283.169 1	[M+H]⁺	-0.7	268.145 3, 265.159 0
65	14.46	Lupan-20(29)-ene-3α, 30-diol	C₃₀H₅₀O₂	443.387 6	[M+H]⁺	-1.8	297.247 6, 217.195 1
66	14.68	11-Oxo-24-norursa-3, 9(11), 12-triene	C₂₉H₄₄O	409.346 2	[M+H]⁺	-0.6	219.174 8, 175.148 2
67	14.69	Tsugaric acid A	C₃₂H₅₀O₄	499.377 3	[M+H]⁺	-1.8	439.358 2, 369.273 4, 329.276 2, 255.212 5
68	14.76	11-Carbonyl-β-boswellic acid	C₃₀H₄₆O₄	469.330 6	[M-H]^-	-3.7	407.331 2, 391.300 0
69	14.79	Lupeolic acid	C₃₀H₄₆O₄	455.351 7	[M+H]⁺	-0.7	437.341 9, 271.241 6
70	15.01	Boscartol C	C₂₀H₃₂O₂	305.247 2	[M+H]⁺	-0.9	175.147 0, 159.116 5, 145.101 2
71	15.23	Incensole	C₂₀H₃₄O₂	307.263 0	[M+H]⁺	-0.6	123.118 1, 109.102 8, 95.088 4
72	15.36	Boscartin X	C₂₂H₃₆O₄	365.268 2	[M+H]⁺	-1.2	305.248 5, 175.147 1, 151.111 6, 121.101 2
73	15.79	β-Hydroxyman-subin-13(17)-ene-11-ketone	C₂₂H₃₄O₂	331.262 9	[M+H]⁺	-0.8	189.163 6, 121.101 0
74	16.36	α-Boswellic acid	C₃₀H₄₈O₃	455.350 8	[M-H]^-	-5.0	437.351 8, 409.350 9, 361.063 9
75	16.45	3-Acetyl-11-keto-β-boswellic acid	C₃₂H₄₈O₅	513.357 3	[M+H]⁺	-0.3	497.812 6, 495.347 9, 470.005 9, 453.339 3, 437.328 0
76	16.51	Verticiol	C₂₀H₃₄O	291.267 9	[M+H]⁺	-1.2	107.085 3, 93.069 9, 81.070 5
77	16.53	3α-Acetyl-9, 11-deoxy-β-boswellic acid	C₃₂H₄₈O₄	497.362 2	[M+H]⁺	-0.7	437.342 1, 391.335 8
78	16.67	β-Boswellic acid	C₃₀H₄₈O₃	455.350 8	[M-H]^-	-5.0	409.310 5, 367.391 6, 283.712 5
79	16.91	Cycloartenol	C₃₀H₅₀O	427.392 8	[M+H]⁺	-1.5	189.163 6, 173.131 8
80	17.44	Commiphorane G2	C₂₂H₃₄O	315.268 0	[M+H]⁺	-0.8	145.100 5, 105.069 9
81	17.70	Epilupeol	C₃₀H₄₈O	425.377 0	[M+H]⁺	-1.9	187.147 5, 135.116 7
82	17.72	Lupenone	C₃₀H₄₈O	425.376 7	[M+H]⁺	-2.3	203.179 2, 189.163 1, 147.116 6, 105.069 5, 81.070 0
83	17.85	Incensole acetate	C₂₂H₃₆O₃	349.273 4	[M+H]⁺	-0.9	203.179 9, 163.148 2

No.

t_R/min

Compound

Formula

m/z

Adduct

Error/×10^-6

MS/MS

1.00

Gallic acid

C₇H₆O₅

169.014 0

[M-H]^-

-1.5

125.024 6, 107.014 0

2.42

Caffeic acid

C₉H₈O₄

179.034 8

[M-H]^-

-1.2

135.045 0, 117.032 4, 107.049 9

2.43

Danshensu

C₉H₁₀O₅

197.045 2

[M-H]^-

-2.0

179.034 7, 135.046 1, 123.046 0, 109.029 5

2.56

Coumarate

C₉H₈O₃

165.054 6

[M+H]⁺

-0.2

119.085 6, 91.054 1

3.84

Vanillic acid

C₈H₈O₄

169.049 6

[M+H]⁺

0.3

125.060 1, 111.007 1, 95.066 8

5.06

Ferulic acid

C₁₀H₁₀O₄

195.065 2

[M+H]⁺

-0.6

177.055 0, 149.059 2, 134.036 5

5.07

6-Methoxycoumarin

C₁₀H₈O₃

177.054 7

[M+H]⁺

0.4

149.060 0, 145.028 7, 134.036 0, 117.033 8

5.09

Isoferulic acid

C₁₀H₁₀O₄

193.050 1

[M-H]^-

-2.9

178.027 1, 134.037 4

5.39

3, 4-Dicaffeoylquinic acid

C₂₅H₂₄O₁₂

515.119 1

[M-H]^-

-0.8

353.087 1, 191.055 7, 179.034 1

5.51

Salvianolic acid D

C₂₀H₁₈O₁₀

417.081 6

[M-H]^-

-2.8

197.045 3, 135.044 9

6.16

7-Hydroxycoumarin

C₉H₆O₃

163.039 0

[M+H]⁺

0.2

135.044 7, 117.034 0

6.16

Rosmarinic acid

C₁₈H₁₆O₈

359.076 5

[M-H]^-

-1.9

179.035 3, 161.026 3

6.17

Isomer of umbelliferide

C₉H₆O₃

161.023 9

[M-H]^-

-3.0

133.028 7, 117.039 1

6.28

Azelaic acid

C₉H₁₆O₄

187.097 2

[M-H]^-

-2.0

125.096 7, 123.081 4

6.51

Isomer of senkyunolide I

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 8, 179.106 3, 165.090 5

6.54

Senkyunolide I

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 8, 189.090 5, 179.078 9

6.78

Salvianolic acid B

C₃₆H₃₀O₁₆

717.143 0

[M-H]^-

-4.3

519.093 3, 339.049 5, 321.040 2, 295.061 8

6.98

Senkyunolide F

C₁₂H₁₄O₃

207.101 7

[M+H]⁺

0.4

189.091 3, 179.106 0, 123.044 3

6.99

Senkyunolide H

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 5, 189.091 1, 179.106 9, 165.089 5, 161.095 7, 117.069 4

7.09

New osthol lactone

C₁₂H₁₈O₂

195.137 9

[M+H]⁺

-0.5

177.127 3, 159.117 1, 117.070 0

7.42

Salvianolic acid A

C₂₆H₂₂O₁₀

493.113 0

[M-H]^-

-2.0

313.071 8, 295.062 9, 203.034 9, 185.024 7, 159.045 2, 109.030 3

9.04

Myrrhanolide B

C₁₅H₁₈O₄

261.112 6

[M-H]^-

-2.5

201.092 1, 187.076 4, 175.112 7

9.29

Coniferyl ferulate

C₂₀H₂₀O₆

355.117 0

[M-H]^-

-4.8

311.128 1, 296.104 6

9.44

Atractylenolide Ⅲ

C₁₅H₂₀O₃

249.148 5

[M+H]⁺

0.0

135.080 6, 107.084 8

9.50

Myrrhterpenoid H

C₁₆H₂₀O₄

277.143 6

[M+H]⁺

0.4

245.120 1, 121.066 8

9.63

Commipholinone

C₁₄H₁₆O₃

233.117 5

[M+H]⁺

1.1

119.085 4, 105.069 9

9.76

Commiterpene D

C₁₈H₂₂O₅

319.154 3

[M+H]⁺

1.0

227.107 9, 156.093 4

9.89

9, 10-Secoisohydro-xyaconido lactone

C₁₅H₁₈O₃

247.132 9

[M+H]⁺

0.2

159.081 8, 91.055 0

10.02

Isopimpinellin

C₁₃H₁₀O₅

247.059 4

[M+H]⁺

-3.1

189.091 0, 161.095 7, 133.064 9

10.59

MCS134

C₁₆H₂₂O₃

285.147 5

[M+Na]⁺

4.9

187.038 6, 171.116 7, 159.116 4, 145.101 3

10.89

Przewaquinone A

C₁₉H₁₈O₄

311.127 8

[M+H]⁺

0.0

283.132 4, 237.056 3

10.91

Nortanshinone

C₁₇H₁₂O₄

281.080 3

[M+H]⁺

-1.8

253.086 2, 225.092 4

11.06

Tanshinone Ⅱ_B

C₁₉H₁₈O₄

311.127 8

[M+H]⁺

0.0

293.117 1, 283.132 9, 275.106 7, 250.106 9, 247.111 0

11.06

1S-Hydroxy-anhydride of 16R cryptotanshinone

C₁₉H₂₀O₅

327.122 5

[M-H]^-

-4.0

283.133 4, 239.143 7

11.38

Senkyunolide A

C₁₂H₁₆O₂

193.122 2

[M+H]⁺

-0.5

147.117 8, 137.061 0, 119.084 9, 105.070 0, 93.070 7

11.47

Tanshialdehyde

C₁₉H₁₆O₄

309.112 2

[M+H]⁺

0.2

265.123 2, 250.098 6, 235.076 3

11.49

Canangaterpene Ⅵ

C₁₄H₂₂O₂

223.169 0

[M+H]⁺

-1.0

119.085 7, 91.054 6

11.91

N-Butylphthalide

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.1

173.097 3, 145.100 8

12.05

FSA

C₁₈H₂₄O₅

321.169 5

[M+H]⁺

-0.4

185.096 7, 168.095 3, 159.083 4, 145.076 3, 131.086 0

12.06

Commiterpene B

C₁₈H₂₂O₄

303.159 4

[M+H]⁺

1.0

211.112 5, 181.065 7

12.09

Dihydrotanshinone I

C₁₈H₁₄O₃

279.101 4

[M+H]⁺

-0.5

261.094 1, 233.099 0, 205.103 5

12.17

Z-Ligustilide

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.1

173.096 3, 163.111 6, 145.100 8, 117.070 0, 105.069 8, 91.054 5

12.27

(1E)-8, 12-Epoxy-germacra-1, 7, 10, 11-tetraen-6-one

C₁₅H₁₈O₂

231.138 1

[M+H]⁺

0.7

145.065 1, 105.070 0, 91.054 4

12.37

2-Methoxy-furanogermacra-1(10), 4-diene

C₁₆H₂₀O₃

261.148 3

[M+H]⁺

-0.5

175.112 3, 161.135 2, 91.053 9

12.39

Danshenxinkun B

C₁₈H₁₆O₃

281.117 1

[M+H]⁺

-0.6

253.158 7, 235.113 9

12.46

Epicurzerenone

C₁₅H₂₀O₂

233.153 4

[M+H]⁺

-0.9

145.102 5, 131.087 3, 95.086 0

12.92

9-Methymyrrhone

C₁₆H₁₈O₃

259.132 8

[M+H]⁺

-0.3

211.074 5, 189.092 1, 174.101 8, 161.060 2

12.96

Myrrhone

C₁₅H₁₆O₂

229.122 2

[M+H]⁺

-0.5

159.086 6, 145.066 9

13.03

Tanshinone I

C₁₈H₁₂O₃

277.085 7

[M+H]⁺

-1.0

262.063 2, 249.096 1, 221.096 3

13.08

Cryptotanshinone

C₁₉H₂₀O₃

297.148 3

[M+H]⁺

-0.6

282.126 4, 279.140 0, 268.111 1, 251.144 4, 237.097 3, 227.071 4

13.17

Rel-3R-methoxy-4S-furanogermacra-1E, 10(15)-dien-6-one

C₁₆H₂₀O₃

261.148 4

[M+H]⁺

-0.4

175.076 7, 161.060 4, 145.085 2, 131.086 1

13.18

Myrrhterpenoid J

C₁₆H₂₀O₃

261.148 4

[M+H]⁺

-0.6

229.125 3, 201.110 2, 196.088 8

13.36

Incensole oxide

C₂₀H₃₄O₃

323.257 8

[M+H]⁺

-0.7

163.147 1, 149.133 0, 121.102 3

13.46

Methylenetanshinquinone

C₁₈H₁₄O₃

279.101 4

[M+H]⁺

-0.5

261.096 7, 233.099 6, 205.103 1

13.66

Levistolide A

C₂₄H₂₈O₄

381.205 7

[M+H]⁺

-0.7

191.110 8, 173.096 4, 149.059 5, 145.100 8, 135.043 8, 117.070 0

13.75

Angelicide

C₂₄H₂₈O₄

381.205 7

[M+H]⁺

-0.7

335.200 6, 191.112 2

13.81

Olibanumol I

C₂₉H₄₆O₂

427.356 5

[M+H]⁺

-1.2

163.147 7, 149.131 9

13.82

Senkyunolide P

C₂₄H₂₈O₄

381.205 8

[M+H]⁺

-0.6

335.201 5, 279.136 7, 191.113 4

13.85

Dehydromiltirone

C₁₉H₂₀O₂

281.153 3

[M+H]⁺

-1.1

266.130 4, 253.158 5

13.90

Alismol

C₁₅H₂₄O

221.189 9

[M+H]⁺

-0.6

147.116 7, 107.085 4, 103.054 0

14.04

Tanshinone Ⅱ_A

C₁₉H₁₈O₃

295.132 7

[M+H]⁺

-0.6

280.110 4, 277.125 9, 266.094 9, 262.100 8, 249.127 6

14.19

(-)-α-Cubebene

C₁₅H₂₄

205.194 8

[M+H]⁺

-1.2

105.070 8, 91.057 8

14.22

Dihydro-cryptotanshinone

C₁₉H₂₂O₃

299.163 9

[M+H]⁺

-1.0

281.153 8, 253.158 9

14.30

Miltirone

C₁₉H₂₂O₂

283.169 1

[M+H]⁺

-0.7

268.145 3, 265.159 0

14.46

Lupan-20(29)-ene-3α, 30-diol

C₃₀H₅₀O₂

443.387 6

[M+H]⁺

-1.8

297.247 6, 217.195 1

14.68

11-Oxo-24-norursa-3, 9(11), 12-triene

C₂₉H₄₄O

409.346 2

[M+H]⁺

-0.6

219.174 8, 175.148 2

14.69

Tsugaric acid A

C₃₂H₅₀O₄

499.377 3

[M+H]⁺

-1.8

439.358 2, 369.273 4, 329.276 2, 255.212 5

14.76

11-Carbonyl-β-boswellic acid

C₃₀H₄₆O₄

469.330 6

[M-H]^-

-3.7

407.331 2, 391.300 0

14.79

Lupeolic acid

C₃₀H₄₆O₄

455.351 7

[M+H]⁺

-0.7

437.341 9, 271.241 6

15.01

Boscartol C

C₂₀H₃₂O₂

305.247 2

[M+H]⁺

-0.9

175.147 0, 159.116 5, 145.101 2

15.23

Incensole

C₂₀H₃₄O₂

307.263 0

[M+H]⁺

-0.6

123.118 1, 109.102 8, 95.088 4

15.36

Boscartin X

C₂₂H₃₆O₄

365.268 2

[M+H]⁺

-1.2

305.248 5, 175.147 1, 151.111 6, 121.101 2

15.79

β-Hydroxyman-subin-13(17)-ene-11-ketone

C₂₂H₃₄O₂

331.262 9

[M+H]⁺

-0.8

189.163 6, 121.101 0

16.36

α-Boswellic acid

C₃₀H₄₈O₃

455.350 8

[M-H]^-

-5.0

437.351 8, 409.350 9, 361.063 9

16.45

3-Acetyl-11-keto-β-boswellic acid

C₃₂H₄₈O₅

513.357 3

[M+H]⁺

-0.3

497.812 6, 495.347 9, 470.005 9, 453.339 3, 437.328 0

16.51

Verticiol

C₂₀H₃₄O

291.267 9

[M+H]⁺

-1.2

107.085 3, 93.069 9, 81.070 5

16.53

3α-Acetyl-9, 11-deoxy-β-boswellic acid

C₃₂H₄₈O₄

497.362 2

[M+H]⁺

-0.7

437.342 1, 391.335 8

16.67

β-Boswellic acid

C₃₀H₄₈O₃

455.350 8

[M-H]^-

-5.0

409.310 5, 367.391 6, 283.712 5

16.91

Cycloartenol

C₃₀H₅₀O

427.392 8

[M+H]⁺

-1.5

189.163 6, 173.131 8

17.44

Commiphorane G2

C₂₂H₃₄O

315.268 0

[M+H]⁺

-0.8

145.100 5, 105.069 9

17.70

Epilupeol

C₃₀H₄₈O

425.377 0

[M+H]⁺

-1.9

187.147 5, 135.116 7

17.72

Lupenone

C₃₀H₄₈O

425.376 7

[M+H]⁺

-2.3

203.179 2, 189.163 1, 147.116 6, 105.069 5, 81.070 0

17.85

Incensole acetate

C₂₂H₃₆O₃

349.273 4

[M+H]⁺

-0.9

203.179 9, 163.148 2

No.	t_R /min	Formula	m/z	Adduct	Error/×10^-6	MS/MS	Compound	Phase	SL	BL
1	1.89	C₉H₈O₃	165.054 7	[M+H]⁺	0.3	119.050 9, 91.054 9	Coumarate	-	+	+
2	2.41	C₉H₁₀O₅	197.044 9	[M-H]^-	-3.4	179.034 4, 135.045 6, 123.045 3, 109.030 2	Danshensu	-	+	-
3	3.49	C₁₀H₁₀O₄	193.049 8	[M-H]^-	-4.4	178.025 6, 134.037 9	Isoferulic acid	-	+	+
4	6.34	C₁₀H₁₀O₄	195.065 1	[M+H]⁺	-0.6	177.163 5, 149.050 9, 134.033 9	Ferulic acid	-	+	+
5	6.96	C₁₂H₁₄O₃	207.101 5	[M+H]⁺	-0.4	189.090 9, 179.106 8, 123.044 8	Senkyunolide F	-	+	+
6	8.15	C₁₅H₁₈O₃	247.132 8	[M+H]⁺	-0.5	159.080 7, 91.054 2	9,10-Secoiso-hydroxyaconido lactone	-	-	+
7	8.90	C₁₅H₁₈O₄	261.113 3	[M-H]^-	0.1	201.092 8, 187.079 4	Myrrhanolide B	-	+	+
8	9.60	C₁₆H₂₀O₃	261.148 5	[M+H]⁺	0.0	175.112 1, 161.095 6, 91.054 3	2-Methoxy-furanogermacra-1(10),4-diene	-	+	-
9	9.87	C₁₅H₂₀O₃	249.148 5	[M+H]⁺	0.1	135.648 5, 107.084 1	Atractylenolide Ⅲ	-	+	-
10	10.14	C₁₄H₁₆O₃	233.117 4	[M+H]⁺	0.6	119.085 1, 105.069 3	Commipholinone	-	-	+
11	10.77	C₁₅H₁₆O₂	229.122 1	[M+H]⁺	-0.8	159.080 5, 145.101 1	Myrrhone	-	-	+
12	11.00	C₁₉H₁₈O₄	311.127 5	[M+H]⁺	-1.1	293.116 0, 283.131 1, 275.099 7, 250.095 3, 247.119 6	Tanshinone Ⅱ_B	-	+	+
13	11.39	C₁₉H₁₆O₄	309.112 0	[M+H]⁺	-0.4	265.122 3, 250.098 9, 235.111 6	Tanshialdehyde	-	+	-
14	11.44	C₁₈H₁₄O₃	279.101 7	[M+H]⁺	0.3	261.092 1, 233.095 9, 205.100 4	Dihydrotanshinone I	-	+	+
15	11.68	C₁₉H₂₀O₃	297.148 5	[M+H]⁺	-0.2	251.142 6, 237.091 1, 227.105 4	Cryptotanshinone	-	+	+
16	11.87	C₁₂H₁₄O₂	191.106 7	[M+H]⁺	0.0	173.098 6, 163.112 1, 145.062 5, 117.069 1, 105.067 9, 91.054 1	Z-Ligustilide	-	-	+
17	12.43	C₁₆H₂₂O₃	263.163 6	[M+H]⁺	-2.0	187.074 9, 171.117 6, 159.077 6, 145.100 6	MCS134	-	-	+
18	14.19	C₃₀H₄₆O₃	455.351 5	[M+H]⁺	-1.0	437.341 3, 271.204 3	Lupeolic acid	-	+	-
19	14.61	C₃₀H₄₆O₄	469.331 7	[M-H]^-	-1.4	407.222 2, 391.952 6	11-Carbonyl-β-boswellicacid	-	-	+
20	15.85	C₁₅H₂₄O	221.189 9	[M+H]⁺	-0.5	147.117 7, 107.085 8, 103.055 2	Alismol	-	-	+
21	16.32	C₃₂H₄₈O₅	513.357 2	[M+H]⁺	-0.5	495.354 1, 453.340 2	3α-Acetyl-9,11-deoxy-β-boswellic acid	-	+	+
22	16.40	C₃₀H₄₈O	425.376 2	[M+H]⁺	-3.7	203.178 6, 189.164 1, 147.116 3, 105.069 3, 81.069 3	Lupenone	-	+	-
23	17.60	C₁₄H₂₂O₂	223.169 0	[M+H]⁺	-1.3	119.086 0, 91.053 7	Canangaterpene Ⅵ	-	-	+
M1	2.29	C₁₈H₁₄O₃	279.101 0	[M+H]⁺	-1.9	279.100 2, 205.087 4	Reduction of tanshinone I	I	-	+
M2	2.38	C₉H₁₀O₈S	277.001 9	[M-H]^-	-1.6	197.045 8, 179.035 0, 135.045 2	Sulfate danshensu	Ⅱ	+	+
M3	2.92	C₉H₁₀O₄	181.050 3	[M-H]^-	-1.9	163.040 2, 135.045 3, 119.050 5, 107.050 3	Dehydroxyl danshensu	I	-	+
M4	3.32	C₁₂H₁₆O₂	193.122 4	[M+H]⁺	0.3	165.127 3, 123.079 7	Dedihydroxylation of senkyunolide I/H	I	+	+
M5	3.35	C₁₀H₁₂O₅	211.060 9	[M-H]^-	-1.3	193.050 7, 178.027 2, 149.024 4, 134.037 5	Methyl danshensu	Ⅱ	+	+
M6	3.90	C₁₅H₂₂O	219.174 0	[M+H]⁺	-1.5	145.101 2, 105.069 5	Dehydrogenation of alismol	I	+	+
M7	4.99	C₁₂H₁₄O₂	191.106 7	[M+H]⁺	0.0	173.095 1, 145.100 7, 135.080 6	Dehydrogenation of senkyunolide A	I	+	+
M8	5.10	C₁₂H₁₄O₃	207.101 7	[M+H]⁺	0.7	189.092 0, 165.055 3, 161.094 7, 133.101 2	Ketone formation of senkyunolide A	I	+	+
M9	5.17	C₁₅H₂₂O₄	267.159 0	[M+H]⁺	-0.3	249.147 9, 231.137 6, 203.142 5, 185.132 1, 119.085 6, 105.069 9	Internal hydrolysis of atractylenolide Ⅲ	I	+	+
M10	5.53	C₁₅H₂₀O₄	265.143 6	[M+H]⁺	0.4	247.133 8, 229.123 6, 105.069 9	Oxidation of atractylenolide Ⅲ	I	+	+
M11	5.89	C₁₅H₁₈O₄	263.128 2	[M+H]⁺	1.5	245.117 1, 203.118 5, 175.111 1	Ketone formation of atractylenolide Ⅲ	I	+	+
M12	6.95	C₁₂H₁₄O₃	207.101 4	[M+H]⁺	-0.6	189.091 8, 179.108 4, 161.096 9, 133.101 2, 121.100 6, 107.085 4	Hydroxyl Z-ligustilide	I	+	+
M13	7.06	C₁₂H₁₈O₂	195.137 4	[M+H]⁺	-2.7	177.127 5, 153.051 1, 149.132 5, 139.110 4	Hydrogenation of senkyunolide A	I	+	-
M14	7.10	C₁₁H₁₂O₄	209.080 9	[M+H]⁺	0.4	165.067 5, 121.065 4, 109.063 5	Methyl ferulic acid	Ⅱ	+	-
M15	7.65	C₁₂H₁₆O₂	193.122 1	[M+H]⁺	-0.8	165.125 7, 147.114 2, 119.085 1, 107.086 2, 93.068 9	Hydrogenation of Z-ligustilide	I	+	+
M16	8.90	C₁₅H₁₈O₄	263.128 1	[M+H]⁺	1.0	245.123 3, 217.127 0	Demethylation and methylene to ketone of MCS134	I	+	+
M17	8.98	C₁₂H₁₆O₃	209.117 0	[M+H]⁺	-1.3	153.089 4, 121.062 6, 107.085 4	Dehydroxyl senkyunolide I/H	I	+	-
M18	9.08	C₁₁H₁₂O₃	193.085 9	[M+H]⁺	0.0	175.073 8, 151.109 4, 147.076 7	Demethylation and methylene to ketone of senkyunolide A	I	+	+
M19	9.16	C₁₆H₂₂O₃	263.164 2	[M+H]⁺	0.0	189.096 0, 161.062 1	Methyl atractylenolide Ⅲ	Ⅱ	-	+
M20	9.32	C₁₆H₂₀O₅	293.138 6	[M+H]⁺	0.7	275.127 8, 247.132 0, 187.111 5	Demethylation to carboxylic acid of MCS134	I	+	+
M21	9.54	C₁₉H₂₀O₄	313.143 6	[M+H]⁺	0.6	271.093 3, 269.152 4, 267.138 1, 254.094 1, 253.085 6, 249.109 4	Hydroxyl cryptotanshinone	I	+	-
M22	9.82	C₁₉H₁₆O₄	309.112 4	[M+H]⁺	0.8	265.121 9, 223.075 4	Hydroxylation and oxidation of tanshinone Ⅱ_A	I	+	-
M23	9.99	C₁₂H₁₂O₂	189.090 9	[M+H]⁺	-0.5	171.080 5, 161.092 0, 143.085 9, 115.053 4	Dehydrogenation of Z-ligustilide	I	+	+
M24	10.10	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.4	173.093 2, 163.086 2, 107.087 3	Dehydrogenation of senkyunolide F	I	+	+
M25	10.11	C₁₈H₁₂O₃	293.080 9	[M+H]⁺	0.1	293.079 6, 249.091 4	Hydroxyl tanshinone I	I	+	+
M26	10.43	C₁₅H₂₀O₂	233.153 3	[M+H]⁺	-1.5	119.085 9, 91.053 7	Dehydrogenation of atractylenolide Ⅲ	I	-	+
M27	10.47	C₁₅H₂₄O₂	237.184 4	[M+H]⁺	-2.1	163.112 2, 123.116 5, 119.086 2	Oxidation of alismol	I	-	+
M28	10.79	C₁₅H₂₂O₃	251.164 0	[M+H]⁺	-0.8	233.152 3, 205.157 6, 187.149 8, 159.119 6, 133.101 4, 105.069 7	Hydrogenation of atractylenolide Ⅲ	I	+	+
M29	10.99	C₁₉H₁₈O₄	311.127 2	[M+H]⁺	-1.8	293.115 2, 267.138 8, 265.086 5, 247.115 5	Hydroxylation and dehydrogenation of cryptotanshinone	I	+	-
M30	11.29	C₃₀H₄₆O₄	471.346 8	[M+H]⁺	-0.2	453.334 6, 409.356 9	Deacetylation of 3-acetyl-11-keto-β-boswellic acid	I	+	+
M31	11.39	C₁₉H₁₆O₄	309.112 4	[M+H]⁺	0.9	291.101 0, 281.117 0	Dehydrogenation of tanshinone Ⅱ_B	I	+	+
M32	11.66	C₁₉H₂₀O₃	297.148 4	[M+H]⁺	-0.3	251.144 0, 237.090 8	Hydrogenation of tanshinone Ⅱ_A	I	+	+
M33	12.64	C₁₂H₁₆O₃	209.117 0	[M+H]⁺	-1.0	191.106 8, 173.132 8, 165.067 8	Oxidation of senkyunolide A	I	-	+
M34	12.68	C₁₃H₁₆O₃	221.117 1	[M+H]⁺	-0.8	193.124 7, 137.059 6	Methyl senkyunolide F	Ⅱ	+	+
M35	12.83	C₃₀H₄₈O₄	471.345 9	[M-H]^-	-4.4	471.346 5, 393.314 7	Hydrogenation of 11-carbonyl-β-boswellic acid	I	-	+
M36	14.01	C₃₀H₄₆O₅	485.325 4	[M-H]^-	-3.8	485.326 9, 423.326 8	Hydroxyl 11-carbonyl-β-boswellic acid	I	+	+
M37	14.57	C₃₂H₄₈O₆	529.350 8	[M+H]⁺	-2.9	511.342 2, 469.333 7, 423.326 3	Hydroxyl 3-acetyl-11-keto-β-boswellic acid	I	-	+
M38	16.38	C₃₂H₄₈O₄	497.361 5	[M+H]⁺	-2.1	479.364 3, 437.340 8	Dehydroxyl 3-acetyl-11-keto-β-boswellic acid	I	-	+

No.

t_R
/min

Formula

m/z

Adduct

Error/×10^-6

MS/MS

Compound

Phase

1.89

C₉H₈O₃

165.054 7

[M+H]⁺

0.3

119.050 9, 91.054 9

Coumarate

2.41

C₉H₁₀O₅

197.044 9

[M-H]^-

-3.4

179.034 4, 135.045 6, 123.045 3, 109.030 2

Danshensu

3.49

C₁₀H₁₀O₄

193.049 8

[M-H]^-

-4.4

178.025 6, 134.037 9

Isoferulic acid

6.34

C₁₀H₁₀O₄

195.065 1

[M+H]⁺

-0.6

177.163 5, 149.050 9, 134.033 9

Ferulic acid

6.96

C₁₂H₁₄O₃

207.101 5

[M+H]⁺

-0.4

189.090 9, 179.106 8, 123.044 8

Senkyunolide F

8.15

C₁₅H₁₈O₃

247.132 8

[M+H]⁺

-0.5

159.080 7, 91.054 2

9,10-Secoiso-hydroxyaconido lactone

8.90

C₁₅H₁₈O₄

261.113 3

[M-H]^-

0.1

201.092 8, 187.079 4

Myrrhanolide B

9.60

C₁₆H₂₀O₃

261.148 5

[M+H]⁺

0.0

175.112 1, 161.095 6, 91.054 3

2-Methoxy-furanogermacra-1(10),4-diene

9.87

C₁₅H₂₀O₃

249.148 5

[M+H]⁺

0.1

135.648 5, 107.084 1

Atractylenolide Ⅲ

10.14

C₁₄H₁₆O₃

233.117 4

[M+H]⁺

0.6

119.085 1, 105.069 3

Commipholinone

10.77

C₁₅H₁₆O₂

229.122 1

[M+H]⁺

-0.8

159.080 5, 145.101 1

Myrrhone

11.00

C₁₉H₁₈O₄

311.127 5

[M+H]⁺

-1.1

293.116 0, 283.131 1, 275.099 7, 250.095 3, 247.119 6

Tanshinone Ⅱ_B

11.39

C₁₉H₁₆O₄

309.112 0

[M+H]⁺

-0.4

265.122 3, 250.098 9, 235.111 6

Tanshialdehyde

11.44

C₁₈H₁₄O₃

279.101 7

[M+H]⁺

0.3

261.092 1, 233.095 9, 205.100 4

Dihydrotanshinone I

11.68

C₁₉H₂₀O₃

297.148 5

[M+H]⁺

-0.2

251.142 6, 237.091 1, 227.105 4

Cryptotanshinone

11.87

C₁₂H₁₄O₂

191.106 7

[M+H]⁺

0.0

173.098 6, 163.112 1, 145.062 5, 117.069 1, 105.067 9, 91.054 1

Z-Ligustilide

12.43

C₁₆H₂₂O₃

263.163 6

[M+H]⁺

-2.0

187.074 9, 171.117 6, 159.077 6, 145.100 6

MCS134

14.19

C₃₀H₄₆O₃

455.351 5

[M+H]⁺

-1.0

437.341 3, 271.204 3

Lupeolic acid

14.61

C₃₀H₄₆O₄

469.331 7

[M-H]^-

-1.4

407.222 2, 391.952 6

11-Carbonyl-β-boswellicacid

15.85

C₁₅H₂₄O

221.189 9

[M+H]⁺

-0.5

147.117 7, 107.085 8, 103.055 2

Alismol

16.32

C₃₂H₄₈O₅

513.357 2

[M+H]⁺

-0.5

495.354 1, 453.340 2

3α-Acetyl-9,11-deoxy-β-boswellic
acid

16.40

C₃₀H₄₈O

425.376 2

[M+H]⁺

-3.7

203.178 6, 189.164 1, 147.116 3, 105.069 3, 81.069 3

Lupenone

17.60

C₁₄H₂₂O₂

223.169 0

[M+H]⁺

-1.3

119.086 0, 91.053 7

Canangaterpene Ⅵ

2.29

C₁₈H₁₄O₃

279.101 0

[M+H]⁺

-1.9

279.100 2, 205.087 4

Reduction of tanshinone I

2.38

C₉H₁₀O₈S

277.001 9

[M-H]^-

-1.6

197.045 8, 179.035 0, 135.045 2

Sulfate danshensu

Ⅱ

2.92

C₉H₁₀O₄

181.050 3

[M-H]^-

-1.9

163.040 2, 135.045 3, 119.050 5, 107.050 3

Dehydroxyl danshensu

3.32

C₁₂H₁₆O₂

193.122 4

[M+H]⁺

0.3

165.127 3, 123.079 7

Dedihydroxylation of senkyunolide I/H

3.35

C₁₀H₁₂O₅

211.060 9

[M-H]^-

-1.3

193.050 7, 178.027 2, 149.024 4, 134.037 5

Methyl danshensu

Ⅱ

3.90

C₁₅H₂₂O

219.174 0

[M+H]⁺

-1.5

145.101 2, 105.069 5

Dehydrogenation of alismol

4.99

C₁₂H₁₄O₂

191.106 7

[M+H]⁺

0.0

173.095 1, 145.100 7, 135.080 6

Dehydrogenation of senkyunolide A

5.10

C₁₂H₁₄O₃

207.101 7

[M+H]⁺

0.7

189.092 0, 165.055 3, 161.094 7, 133.101 2

Ketone formation of senkyunolide A

5.17

C₁₅H₂₂O₄

267.159 0

[M+H]⁺

-0.3

249.147 9, 231.137 6, 203.142 5, 185.132 1, 119.085 6, 105.069 9

Internal hydrolysis of atractylenolide Ⅲ

M10

5.53

C₁₅H₂₀O₄

265.143 6

[M+H]⁺

0.4

247.133 8, 229.123 6, 105.069 9

Oxidation of atractylenolide Ⅲ

M11

5.89

C₁₅H₁₈O₄

263.128 2

[M+H]⁺

1.5

245.117 1, 203.118 5, 175.111 1

Ketone formation of atractylenolide Ⅲ

M12

6.95

C₁₂H₁₄O₃

207.101 4

[M+H]⁺

-0.6

189.091 8, 179.108 4, 161.096 9, 133.101 2, 121.100 6, 107.085 4

Hydroxyl Z-ligustilide

M13

7.06

C₁₂H₁₈O₂

195.137 4

[M+H]⁺

-2.7

177.127 5, 153.051 1, 149.132 5, 139.110 4

Hydrogenation of senkyunolide A

M14

7.10

C₁₁H₁₂O₄

209.080 9

[M+H]⁺

0.4

165.067 5, 121.065 4, 109.063 5

Methyl ferulic acid

Ⅱ

M15

7.65

C₁₂H₁₆O₂

193.122 1

[M+H]⁺

-0.8

165.125 7, 147.114 2, 119.085 1, 107.086 2, 93.068 9

Hydrogenation of Z-ligustilide

M16

8.90

C₁₅H₁₈O₄

263.128 1

[M+H]⁺

1.0

245.123 3, 217.127 0

Demethylation and methylene to ketone of MCS134

M17

8.98

C₁₂H₁₆O₃

209.117 0

[M+H]⁺

-1.3

153.089 4, 121.062 6, 107.085 4

Dehydroxyl senkyunolide I/H

M18

9.08

C₁₁H₁₂O₃

193.085 9

[M+H]⁺

0.0

175.073 8, 151.109 4, 147.076 7

Demethylation and methylene to ketone of senkyunolide A

M19

9.16

C₁₆H₂₂O₃

263.164 2

[M+H]⁺

0.0

189.096 0, 161.062 1

Methyl atractylenolide Ⅲ

Ⅱ

M20

9.32

C₁₆H₂₀O₅

293.138 6

[M+H]⁺

0.7

275.127 8, 247.132 0, 187.111 5

Demethylation to carboxylic acid of MCS134

M21

9.54

C₁₉H₂₀O₄

313.143 6

[M+H]⁺

0.6

271.093 3, 269.152 4, 267.138 1, 254.094 1, 253.085 6, 249.109 4

Hydroxyl cryptotanshinone

M22

9.82

C₁₉H₁₆O₄

309.112 4

[M+H]⁺

0.8

265.121 9, 223.075 4

Hydroxylation and oxidation of tanshinone Ⅱ_A

M23

9.99

C₁₂H₁₂O₂

189.090 9

[M+H]⁺

-0.5

171.080 5, 161.092 0, 143.085 9, 115.053 4

Dehydrogenation of Z-ligustilide

M24

10.10

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.4

173.093 2, 163.086 2, 107.087 3

Dehydrogenation of senkyunolide F

M25

10.11

C₁₈H₁₂O₃

293.080 9

[M+H]⁺

0.1

293.079 6, 249.091 4

Hydroxyl tanshinone I

M26

10.43

C₁₅H₂₀O₂

233.153 3

[M+H]⁺

-1.5

119.085 9, 91.053 7

Dehydrogenation of atractylenolide Ⅲ

M27

10.47

C₁₅H₂₄O₂

237.184 4

[M+H]⁺

-2.1

163.112 2, 123.116 5, 119.086 2

Oxidation of alismol

M28

10.79

C₁₅H₂₂O₃

251.164 0

[M+H]⁺

-0.8

233.152 3, 205.157 6, 187.149 8, 159.119 6, 133.101 4, 105.069 7

Hydrogenation of atractylenolide Ⅲ

M29

10.99

C₁₉H₁₈O₄

311.127 2

[M+H]⁺

-1.8

293.115 2, 267.138 8, 265.086 5, 247.115 5

Hydroxylation and dehydrogenation of cryptotanshinone

M30

11.29

C₃₀H₄₆O₄

471.346 8

[M+H]⁺

-0.2

453.334 6, 409.356 9

Deacetylation of 3-acetyl-11-keto-β-boswellic acid

M31

11.39

C₁₉H₁₆O₄

309.112 4

[M+H]⁺

0.9

291.101 0, 281.117 0

Dehydrogenation of tanshinone Ⅱ_B

M32

11.66

C₁₉H₂₀O₃

297.148 4

[M+H]⁺

-0.3

251.144 0, 237.090 8

Hydrogenation of tanshinone Ⅱ_A

M33

12.64

C₁₂H₁₆O₃

209.117 0

[M+H]⁺

-1.0

191.106 8, 173.132 8, 165.067 8

Oxidation of senkyunolide A

M34

12.68

C₁₃H₁₆O₃

221.117 1

[M+H]⁺

-0.8

193.124 7, 137.059 6

Methyl senkyunolide F

Ⅱ

M35

12.83

C₃₀H₄₈O₄

471.345 9

[M-H]^-

-4.4

471.346 5, 393.314 7

Hydrogenation of 11-carbonyl-β-boswellic acid

M36

14.01

C₃₀H₄₆O₅

485.325 4

[M-H]^-

-3.8

485.326 9, 423.326 8

Hydroxyl 11-carbonyl-β-boswellic acid

M37

14.57

C₃₂H₄₈O₆

529.350 8

[M+H]⁺

-2.9

511.342 2, 469.333 7, 423.326 3

Hydroxyl 3-acetyl-11-keto-β-boswellic acid

M38

16.38

C₃₂H₄₈O₄

497.361 5

[M+H]⁺

-2.1

479.364 3, 437.340 8

Dehydroxyl 3-acetyl-11-keto-β-boswellic acid

No.	t_R /min	Formula	m/z	Adduct	Error/×10^-6	MS/MS	Compound	Phase	SL	BL
1	1.89	C₉H₈O₃	165.054 7	[M+H]⁺	0.3	119.050 9, 91.054 9	Coumarate	-	+	+
2	2.41	C₉H₁₀O₅	197.044 9	[M-H]^-	-3.4	179.034 4, 135.045 6, 123.045 3, 109.030 2	Danshensu	-	+	-
3	3.49	C₁₀H₁₀O₄	193.049 8	[M-H]^-	-4.4	178.025 6, 134.037 9	Isoferulic acid	-	+	+
4	6.34	C₁₀H₁₀O₄	195.065 1	[M+H]⁺	-0.6	177.163 5, 149.050 9, 134.033 9	Ferulic acid	-	+	+
5	6.96	C₁₂H₁₄O₃	207.101 5	[M+H]⁺	-0.4	189.090 9, 179.106 8, 123.044 8	Senkyunolide F	-	+	+
6	8.15	C₁₅H₁₈O₃	247.132 8	[M+H]⁺	-0.5	159.080 7, 91.054 2	9,10-Secoiso-hydroxyaconido lactone	-	-	+
7	8.90	C₁₅H₁₈O₄	261.113 3	[M-H]^-	0.1	201.092 8, 187.079 4	Myrrhanolide B	-	+	+
8	9.60	C₁₆H₂₀O₃	261.148 5	[M+H]⁺	0.0	175.112 1, 161.095 6, 91.054 3	2-Methoxy-furanogermacra-1(10),4-diene	-	+	-
9	9.87	C₁₅H₂₀O₃	249.148 5	[M+H]⁺	0.1	135.648 5, 107.084 1	Atractylenolide Ⅲ	-	+	-
10	10.14	C₁₄H₁₆O₃	233.117 4	[M+H]⁺	0.6	119.085 1, 105.069 3	Commipholinone	-	-	+
11	10.77	C₁₅H₁₆O₂	229.122 1	[M+H]⁺	-0.8	159.080 5, 145.101 1	Myrrhone	-	-	+
12	11.00	C₁₉H₁₈O₄	311.127 5	[M+H]⁺	-1.1	293.116 0, 283.131 1, 275.099 7, 250.095 3, 247.119 6	Tanshinone Ⅱ_B	-	+	+
13	11.39	C₁₉H₁₆O₄	309.112 0	[M+H]⁺	-0.4	265.122 3, 250.098 9, 235.111 6	Tanshialdehyde	-	+	-
14	11.44	C₁₈H₁₄O₃	279.101 7	[M+H]⁺	0.3	261.092 1, 233.095 9, 205.100 4	Dihydrotanshinone I	-	+	+
15	11.68	C₁₉H₂₀O₃	297.148 5	[M+H]⁺	-0.2	251.142 6, 237.091 1, 227.105 4	Cryptotanshinone	-	+	+
16	11.87	C₁₂H₁₄O₂	191.106 7	[M+H]⁺	0.0	173.098 6, 163.112 1, 145.062 5, 117.069 1, 105.067 9, 91.054 1	Z-Ligustilide	-	-	+
17	12.43	C₁₆H₂₂O₃	263.163 6	[M+H]⁺	-2.0	187.074 9, 171.117 6, 159.077 6, 145.100 6	MCS134	-	-	+
18	14.19	C₃₀H₄₆O₃	455.351 5	[M+H]⁺	-1.0	437.341 3, 271.204 3	Lupeolic acid	-	+	-
19	14.61	C₃₀H₄₆O₄	469.331 7	[M-H]^-	-1.4	407.222 2, 391.952 6	11-Carbonyl-β-boswellicacid	-	-	+
20	15.85	C₁₅H₂₄O	221.189 9	[M+H]⁺	-0.5	147.117 7, 107.085 8, 103.055 2	Alismol	-	-	+
21	16.32	C₃₂H₄₈O₅	513.357 2	[M+H]⁺	-0.5	495.354 1, 453.340 2	3α-Acetyl-9,11-deoxy-β-boswellic acid	-	+	+
22	16.40	C₃₀H₄₈O	425.376 2	[M+H]⁺	-3.7	203.178 6, 189.164 1, 147.116 3, 105.069 3, 81.069 3	Lupenone	-	+	-
23	17.60	C₁₄H₂₂O₂	223.169 0	[M+H]⁺	-1.3	119.086 0, 91.053 7	Canangaterpene Ⅵ	-	-	+
M1	2.29	C₁₈H₁₄O₃	279.101 0	[M+H]⁺	-1.9	279.100 2, 205.087 4	Reduction of tanshinone I	I	-	+
M2	2.38	C₉H₁₀O₈S	277.001 9	[M-H]^-	-1.6	197.045 8, 179.035 0, 135.045 2	Sulfate danshensu	Ⅱ	+	+
M3	2.92	C₉H₁₀O₄	181.050 3	[M-H]^-	-1.9	163.040 2, 135.045 3, 119.050 5, 107.050 3	Dehydroxyl danshensu	I	-	+
M4	3.32	C₁₂H₁₆O₂	193.122 4	[M+H]⁺	0.3	165.127 3, 123.079 7	Dedihydroxylation of senkyunolide I/H	I	+	+
M5	3.35	C₁₀H₁₂O₅	211.060 9	[M-H]^-	-1.3	193.050 7, 178.027 2, 149.024 4, 134.037 5	Methyl danshensu	Ⅱ	+	+
M6	3.90	C₁₅H₂₂O	219.174 0	[M+H]⁺	-1.5	145.101 2, 105.069 5	Dehydrogenation of alismol	I	+	+
M7	4.99	C₁₂H₁₄O₂	191.106 7	[M+H]⁺	0.0	173.095 1, 145.100 7, 135.080 6	Dehydrogenation of senkyunolide A	I	+	+
M8	5.10	C₁₂H₁₄O₃	207.101 7	[M+H]⁺	0.7	189.092 0, 165.055 3, 161.094 7, 133.101 2	Ketone formation of senkyunolide A	I	+	+
M9	5.17	C₁₅H₂₂O₄	267.159 0	[M+H]⁺	-0.3	249.147 9, 231.137 6, 203.142 5, 185.132 1, 119.085 6, 105.069 9	Internal hydrolysis of atractylenolide Ⅲ	I	+	+
M10	5.53	C₁₅H₂₀O₄	265.143 6	[M+H]⁺	0.4	247.133 8, 229.123 6, 105.069 9	Oxidation of atractylenolide Ⅲ	I	+	+
M11	5.89	C₁₅H₁₈O₄	263.128 2	[M+H]⁺	1.5	245.117 1, 203.118 5, 175.111 1	Ketone formation of atractylenolide Ⅲ	I	+	+
M12	6.95	C₁₂H₁₄O₃	207.101 4	[M+H]⁺	-0.6	189.091 8, 179.108 4, 161.096 9, 133.101 2, 121.100 6, 107.085 4	Hydroxyl Z-ligustilide	I	+	+
M13	7.06	C₁₂H₁₈O₂	195.137 4	[M+H]⁺	-2.7	177.127 5, 153.051 1, 149.132 5, 139.110 4	Hydrogenation of senkyunolide A	I	+	-
M14	7.10	C₁₁H₁₂O₄	209.080 9	[M+H]⁺	0.4	165.067 5, 121.065 4, 109.063 5	Methyl ferulic acid	Ⅱ	+	-
M15	7.65	C₁₂H₁₆O₂	193.122 1	[M+H]⁺	-0.8	165.125 7, 147.114 2, 119.085 1, 107.086 2, 93.068 9	Hydrogenation of Z-ligustilide	I	+	+
M16	8.90	C₁₅H₁₈O₄	263.128 1	[M+H]⁺	1.0	245.123 3, 217.127 0	Demethylation and methylene to ketone of MCS134	I	+	+
M17	8.98	C₁₂H₁₆O₃	209.117 0	[M+H]⁺	-1.3	153.089 4, 121.062 6, 107.085 4	Dehydroxyl senkyunolide I/H	I	+	-
M18	9.08	C₁₁H₁₂O₃	193.085 9	[M+H]⁺	0.0	175.073 8, 151.109 4, 147.076 7	Demethylation and methylene to ketone of senkyunolide A	I	+	+
M19	9.16	C₁₆H₂₂O₃	263.164 2	[M+H]⁺	0.0	189.096 0, 161.062 1	Methyl atractylenolide Ⅲ	Ⅱ	-	+
M20	9.32	C₁₆H₂₀O₅	293.138 6	[M+H]⁺	0.7	275.127 8, 247.132 0, 187.111 5	Demethylation to carboxylic acid of MCS134	I	+	+
M21	9.54	C₁₉H₂₀O₄	313.143 6	[M+H]⁺	0.6	271.093 3, 269.152 4, 267.138 1, 254.094 1, 253.085 6, 249.109 4	Hydroxyl cryptotanshinone	I	+	-
M22	9.82	C₁₉H₁₆O₄	309.112 4	[M+H]⁺	0.8	265.121 9, 223.075 4	Hydroxylation and oxidation of tanshinone Ⅱ_A	I	+	-
M23	9.99	C₁₂H₁₂O₂	189.090 9	[M+H]⁺	-0.5	171.080 5, 161.092 0, 143.085 9, 115.053 4	Dehydrogenation of Z-ligustilide	I	+	+
M24	10.10	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.4	173.093 2, 163.086 2, 107.087 3	Dehydrogenation of senkyunolide F	I	+	+
M25	10.11	C₁₈H₁₂O₃	293.080 9	[M+H]⁺	0.1	293.079 6, 249.091 4	Hydroxyl tanshinone I	I	+	+
M26	10.43	C₁₅H₂₀O₂	233.153 3	[M+H]⁺	-1.5	119.085 9, 91.053 7	Dehydrogenation of atractylenolide Ⅲ	I	-	+
M27	10.47	C₁₅H₂₄O₂	237.184 4	[M+H]⁺	-2.1	163.112 2, 123.116 5, 119.086 2	Oxidation of alismol	I	-	+
M28	10.79	C₁₅H₂₂O₃	251.164 0	[M+H]⁺	-0.8	233.152 3, 205.157 6, 187.149 8, 159.119 6, 133.101 4, 105.069 7	Hydrogenation of atractylenolide Ⅲ	I	+	+
M29	10.99	C₁₉H₁₈O₄	311.127 2	[M+H]⁺	-1.8	293.115 2, 267.138 8, 265.086 5, 247.115 5	Hydroxylation and dehydrogenation of cryptotanshinone	I	+	-
M30	11.29	C₃₀H₄₆O₄	471.346 8	[M+H]⁺	-0.2	453.334 6, 409.356 9	Deacetylation of 3-acetyl-11-keto-β-boswellic acid	I	+	+
M31	11.39	C₁₉H₁₆O₄	309.112 4	[M+H]⁺	0.9	291.101 0, 281.117 0	Dehydrogenation of tanshinone Ⅱ_B	I	+	+
M32	11.66	C₁₉H₂₀O₃	297.148 4	[M+H]⁺	-0.3	251.144 0, 237.090 8	Hydrogenation of tanshinone Ⅱ_A	I	+	+
M33	12.64	C₁₂H₁₆O₃	209.117 0	[M+H]⁺	-1.0	191.106 8, 173.132 8, 165.067 8	Oxidation of senkyunolide A	I	-	+
M34	12.68	C₁₃H₁₆O₃	221.117 1	[M+H]⁺	-0.8	193.124 7, 137.059 6	Methyl senkyunolide F	Ⅱ	+	+
M35	12.83	C₃₀H₄₈O₄	471.345 9	[M-H]^-	-4.4	471.346 5, 393.314 7	Hydrogenation of 11-carbonyl-β-boswellic acid	I	-	+
M36	14.01	C₃₀H₄₆O₅	485.325 4	[M-H]^-	-3.8	485.326 9, 423.326 8	Hydroxyl 11-carbonyl-β-boswellic acid	I	+	+
M37	14.57	C₃₂H₄₈O₆	529.350 8	[M+H]⁺	-2.9	511.342 2, 469.333 7, 423.326 3	Hydroxyl 3-acetyl-11-keto-β-boswellic acid	I	-	+
M38	16.38	C₃₂H₄₈O₄	497.361 5	[M+H]⁺	-2.1	479.364 3, 437.340 8	Dehydroxyl 3-acetyl-11-keto-β-boswellic acid	I	-	+

No.

t_R
/min

Formula

m/z

Adduct

Error/×10^-6

MS/MS

Compound

Phase

1.89

C₉H₈O₃

165.054 7

[M+H]⁺

0.3

119.050 9, 91.054 9

Coumarate

2.41

C₉H₁₀O₅

197.044 9

[M-H]^-

-3.4

179.034 4, 135.045 6, 123.045 3, 109.030 2

Danshensu

3.49

C₁₀H₁₀O₄

193.049 8

[M-H]^-

-4.4

178.025 6, 134.037 9

Isoferulic acid

6.34

C₁₀H₁₀O₄

195.065 1

[M+H]⁺

-0.6

177.163 5, 149.050 9, 134.033 9

Ferulic acid

6.96

C₁₂H₁₄O₃

207.101 5

[M+H]⁺

-0.4

189.090 9, 179.106 8, 123.044 8

Senkyunolide F

8.15

C₁₅H₁₈O₃

247.132 8

[M+H]⁺

-0.5

159.080 7, 91.054 2

9,10-Secoiso-hydroxyaconido lactone

8.90

C₁₅H₁₈O₄

261.113 3

[M-H]^-

0.1

201.092 8, 187.079 4

Myrrhanolide B

9.60

C₁₆H₂₀O₃

261.148 5

[M+H]⁺

0.0

175.112 1, 161.095 6, 91.054 3

2-Methoxy-furanogermacra-1(10),4-diene

9.87

C₁₅H₂₀O₃

249.148 5

[M+H]⁺

0.1

135.648 5, 107.084 1

Atractylenolide Ⅲ

10.14

C₁₄H₁₆O₃

233.117 4

[M+H]⁺

0.6

119.085 1, 105.069 3

Commipholinone

10.77

C₁₅H₁₆O₂

229.122 1

[M+H]⁺

-0.8

159.080 5, 145.101 1

Myrrhone

11.00

C₁₉H₁₈O₄

311.127 5

[M+H]⁺

-1.1

293.116 0, 283.131 1, 275.099 7, 250.095 3, 247.119 6

Tanshinone Ⅱ_B

11.39

C₁₉H₁₆O₄

309.112 0

[M+H]⁺

-0.4

265.122 3, 250.098 9, 235.111 6

Tanshialdehyde

11.44

C₁₈H₁₄O₃

279.101 7

[M+H]⁺

0.3

261.092 1, 233.095 9, 205.100 4

Dihydrotanshinone I

11.68

C₁₉H₂₀O₃

297.148 5

[M+H]⁺

-0.2

251.142 6, 237.091 1, 227.105 4

Cryptotanshinone

11.87

C₁₂H₁₄O₂

191.106 7

[M+H]⁺

0.0

173.098 6, 163.112 1, 145.062 5, 117.069 1, 105.067 9, 91.054 1

Z-Ligustilide

12.43

C₁₆H₂₂O₃

263.163 6

[M+H]⁺

-2.0

187.074 9, 171.117 6, 159.077 6, 145.100 6

MCS134

14.19

C₃₀H₄₆O₃

455.351 5

[M+H]⁺

-1.0

437.341 3, 271.204 3

Lupeolic acid

14.61

C₃₀H₄₆O₄

469.331 7

[M-H]^-

-1.4

407.222 2, 391.952 6

11-Carbonyl-β-boswellicacid

15.85

C₁₅H₂₄O

221.189 9

[M+H]⁺

-0.5

147.117 7, 107.085 8, 103.055 2

Alismol

16.32

C₃₂H₄₈O₅

513.357 2

[M+H]⁺

-0.5

495.354 1, 453.340 2

3α-Acetyl-9,11-deoxy-β-boswellic
acid

16.40

C₃₀H₄₈O

425.376 2

[M+H]⁺

-3.7

203.178 6, 189.164 1, 147.116 3, 105.069 3, 81.069 3

Lupenone

17.60

C₁₄H₂₂O₂

223.169 0

[M+H]⁺

-1.3

119.086 0, 91.053 7

Canangaterpene Ⅵ

2.29

C₁₈H₁₄O₃

279.101 0

[M+H]⁺

-1.9

279.100 2, 205.087 4

Reduction of tanshinone I

2.38

C₉H₁₀O₈S

277.001 9

[M-H]^-

-1.6

197.045 8, 179.035 0, 135.045 2

Sulfate danshensu

Ⅱ

2.92

C₉H₁₀O₄

181.050 3

[M-H]^-

-1.9

163.040 2, 135.045 3, 119.050 5, 107.050 3

Dehydroxyl danshensu

3.32

C₁₂H₁₆O₂

193.122 4

[M+H]⁺

0.3

165.127 3, 123.079 7

Dedihydroxylation of senkyunolide I/H

3.35

C₁₀H₁₂O₅

211.060 9

[M-H]^-

-1.3

193.050 7, 178.027 2, 149.024 4, 134.037 5

Methyl danshensu

Ⅱ

3.90

C₁₅H₂₂O

219.174 0

[M+H]⁺

-1.5

145.101 2, 105.069 5

Dehydrogenation of alismol

4.99

C₁₂H₁₄O₂

191.106 7

[M+H]⁺

0.0

173.095 1, 145.100 7, 135.080 6

Dehydrogenation of senkyunolide A

5.10

C₁₂H₁₄O₃

207.101 7

[M+H]⁺

0.7

189.092 0, 165.055 3, 161.094 7, 133.101 2

Ketone formation of senkyunolide A

5.17

C₁₅H₂₂O₄

267.159 0

[M+H]⁺

-0.3

249.147 9, 231.137 6, 203.142 5, 185.132 1, 119.085 6, 105.069 9

Internal hydrolysis of atractylenolide Ⅲ

M10

5.53

C₁₅H₂₀O₄

265.143 6

[M+H]⁺

0.4

247.133 8, 229.123 6, 105.069 9

Oxidation of atractylenolide Ⅲ

M11

5.89

C₁₅H₁₈O₄

263.128 2

[M+H]⁺

1.5

245.117 1, 203.118 5, 175.111 1

Ketone formation of atractylenolide Ⅲ

M12

6.95

C₁₂H₁₄O₃

207.101 4

[M+H]⁺

-0.6

189.091 8, 179.108 4, 161.096 9, 133.101 2, 121.100 6, 107.085 4

Hydroxyl Z-ligustilide

M13

7.06

C₁₂H₁₈O₂

195.137 4

[M+H]⁺

-2.7

177.127 5, 153.051 1, 149.132 5, 139.110 4

Hydrogenation of senkyunolide A

M14

7.10

C₁₁H₁₂O₄

209.080 9

[M+H]⁺

0.4

165.067 5, 121.065 4, 109.063 5

Methyl ferulic acid

Ⅱ

M15

7.65

C₁₂H₁₆O₂

193.122 1

[M+H]⁺

-0.8

165.125 7, 147.114 2, 119.085 1, 107.086 2, 93.068 9

Hydrogenation of Z-ligustilide

M16

8.90

C₁₅H₁₈O₄

263.128 1

[M+H]⁺

1.0

245.123 3, 217.127 0

Demethylation and methylene to ketone of MCS134

M17

8.98

C₁₂H₁₆O₃

209.117 0

[M+H]⁺

-1.3

153.089 4, 121.062 6, 107.085 4

Dehydroxyl senkyunolide I/H

M18

9.08

C₁₁H₁₂O₃

193.085 9

[M+H]⁺

0.0

175.073 8, 151.109 4, 147.076 7

Demethylation and methylene to ketone of senkyunolide A

M19

9.16

C₁₆H₂₂O₃

263.164 2

[M+H]⁺

0.0

189.096 0, 161.062 1

Methyl atractylenolide Ⅲ

Ⅱ

M20

9.32

C₁₆H₂₀O₅

293.138 6

[M+H]⁺

0.7

275.127 8, 247.132 0, 187.111 5

Demethylation to carboxylic acid of MCS134

M21

9.54

C₁₉H₂₀O₄

313.143 6

[M+H]⁺

0.6

271.093 3, 269.152 4, 267.138 1, 254.094 1, 253.085 6, 249.109 4

Hydroxyl cryptotanshinone

M22

9.82

C₁₉H₁₆O₄

309.112 4

[M+H]⁺

0.8

265.121 9, 223.075 4

Hydroxylation and oxidation of tanshinone Ⅱ_A

M23

9.99

C₁₂H₁₂O₂

189.090 9

[M+H]⁺

-0.5

171.080 5, 161.092 0, 143.085 9, 115.053 4

Dehydrogenation of Z-ligustilide

M24

10.10

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.4

173.093 2, 163.086 2, 107.087 3

Dehydrogenation of senkyunolide F

M25

10.11

C₁₈H₁₂O₃

293.080 9

[M+H]⁺

0.1

293.079 6, 249.091 4

Hydroxyl tanshinone I

M26

10.43

C₁₅H₂₀O₂

233.153 3

[M+H]⁺

-1.5

119.085 9, 91.053 7

Dehydrogenation of atractylenolide Ⅲ

M27

10.47

C₁₅H₂₄O₂

237.184 4

[M+H]⁺

-2.1

163.112 2, 123.116 5, 119.086 2

Oxidation of alismol

M28

10.79

C₁₅H₂₂O₃

251.164 0

[M+H]⁺

-0.8

233.152 3, 205.157 6, 187.149 8, 159.119 6, 133.101 4, 105.069 7

Hydrogenation of atractylenolide Ⅲ

M29

10.99

C₁₉H₁₈O₄

311.127 2

[M+H]⁺

-1.8

293.115 2, 267.138 8, 265.086 5, 247.115 5

Hydroxylation and dehydrogenation of cryptotanshinone

M30

11.29

C₃₀H₄₆O₄

471.346 8

[M+H]⁺

-0.2

453.334 6, 409.356 9

Deacetylation of 3-acetyl-11-keto-β-boswellic acid

M31

11.39

C₁₉H₁₆O₄

309.112 4

[M+H]⁺

0.9

291.101 0, 281.117 0

Dehydrogenation of tanshinone Ⅱ_B

M32

11.66

C₁₉H₂₀O₃

297.148 4

[M+H]⁺

-0.3

251.144 0, 237.090 8

Hydrogenation of tanshinone Ⅱ_A

M33

12.64

C₁₂H₁₆O₃

209.117 0

[M+H]⁺

-1.0

191.106 8, 173.132 8, 165.067 8

Oxidation of senkyunolide A

M34

12.68

C₁₃H₁₆O₃

221.117 1

[M+H]⁺

-0.8

193.124 7, 137.059 6

Methyl senkyunolide F

Ⅱ

M35

12.83

C₃₀H₄₈O₄

471.345 9

[M-H]^-

-4.4

471.346 5, 393.314 7

Hydrogenation of 11-carbonyl-β-boswellic acid

M36

14.01

C₃₀H₄₆O₅

485.325 4

[M-H]^-

-3.8

485.326 9, 423.326 8

Hydroxyl 11-carbonyl-β-boswellic acid

M37

14.57

C₃₂H₄₈O₆

529.350 8

[M+H]⁺

-2.9

511.342 2, 469.333 7, 423.326 3

Hydroxyl 3-acetyl-11-keto-β-boswellic acid

M38

16.38

C₃₂H₄₈O₄

497.361 5

[M+H]⁺

-2.1

479.364 3, 437.340 8

Dehydroxyl 3-acetyl-11-keto-β-boswellic acid

基于UPLC-Q-TOF-MS/MS及网络药理学探讨活络效灵丹治疗糖尿病周围神经病变的物质基础研究

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张喆 , 李玉琴 , 施亚宁 , 宿树兰 ^* , 范若颖 , 尚尔鑫 , 朱悦 , 段金廒 ^*

药学学报 | 研究论文 2025,60(4): 1124-1136

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药学学报 | 研究论文 2025, 60(4): 1124-1136

基于UPLC-Q-TOF-MS/MS及网络药理学探讨活络效灵丹治疗糖尿病周围神经病变的物质基础研究

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张喆, 李玉琴, 施亚宁, 宿树兰^*, 范若颖, 尚尔鑫, 朱悦, 段金廒^*

作者信息

南京中医药大学, 江苏省方剂高技术研究重点实验室, 中药资源产业化与方剂创新药物国家地方联合工程研究中心, 江苏省中药资源产业化过程协同创新中心, 江苏南京 210023

通讯作者:

宿树兰, Tel: 13809043258, E-mail: sushulan1974@163.com

段金廒, Tel: 86-25-85811291, E-mail: dja@njucm.edu.cn

Exploring the material basis of Huoluoxiaolingdan in the treatment of diabetic peripheral neuropathy based on UPLC-Q-TOF-MS/MS and network pharmacology

Zhe ZHANG, Yu-qin LI, Ya-ning SHI, Shu-lan SU^*, Ruo-ying FAN, Er-xin SHANG, Yue ZHU, Jin-ao DUAN^*

Affiliations

Jiangsu Key Laboratory for High Technology Research of Traditional Chinese Medicine Formulae, National-Local Joint Engineering Research Center of Resources Industrialization of Chinese Meteria Medica and Prescription-Oriented Innovative Drugs, Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Nanjing University of Chinese Medicine, Nanjing 210023, China

出版时间: 2025-04-12 doi: 10.16438/j.0513-4870.2024-1123

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摘要

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本实验通过超高效液相色谱-四极杆-飞行时间串联质谱(UPLC-Q-TOF-MS/MS)、网络药理学探讨活络效灵丹治疗糖尿病周围神经病变(diabetic peripheral neuropathy, DPN) 的物质基础。利用UPLC-Q-TOF-MS/MS技术结合PeakView^TM 1.2软件、Molecule Profiler^TM软件分析活络效灵丹的体外成分及正常大鼠与高脂饲料喂养联合小剂量链脲佐菌素注射所致DPN大鼠的入血成分, 通过Swiss Target Prediction、GeneCards等数据库筛选成分对应靶点及疾病靶点, 利用Venny 2.1平台获得交集靶点, 导入STRING平台及Cytoscape 3.10.1软件构建蛋白互作网络及“成分-靶点”网络图分析其核心成分与核心靶点, 对核心靶点进行GO和KEGG富集分析。实验获得南京中医药大学实验动物伦理委员会批准(批准号: 202310A023)。结果共鉴定出活络效灵丹提取物83个化学成分, 包括丹参酮Ⅱ_A等52个萜类、Z-藁本内酯等11个苯酞类、阿魏酸等15个有机酸类及4个香豆素类、1个酚类成分。在正常大鼠血浆中鉴定出15个原型成分与29个代谢产物, 在DPN大鼠血浆中鉴定出17个原型成分与32个代谢产物。网络药理学结果显示, 3-乙酰基-11-酮基-β-乳香酸、11-酮基-β-乳香酸等5个核心成分可能通过TNF、IL6等27个核心靶点, 调节AGE-RAGE、PI3K/Akt等信号通路发挥治疗DPN的作用。本研究通过UPLC-Q-TOF-MS/MS技术分析了活络效灵丹的体内外化学成分及主要化合物的裂解规律, 结合网络药理学分析其治疗DPN的核心成分, 为阐明活络效灵丹治疗DPN的功效物质基础及作用机制研究提供科学依据。

关键词

活络效灵丹 / UPLC-Q-TOF-MS/MS / 网络药理学 / 糖尿病周围神经病变 / 化学成分 / 入血成分

Abstract

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This study investigated the material basis of Huoluoxiaolingdan in treating diabetic peripheral neuropathy (DPN) through ultra performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) and network pharmacology. UPLC-Q-TOF-MS/MS combined with PeakView^TM 1.2 software and Molecule Profiler^TM software were used to analyze the the chemical components of Huoluoxiaolingdan and blood-absorbed ingredients in normal rats and rats with DPN induced by high fat diet combined with low dose streptozotocin injection. Swiss Target Prediction database, GeneCards and other databases were used to search the corresponding targets of active ingredients and disease targets. The intersection targets were obtained using Venny 2.1 platform, which were then imported into the STRING platform and Cytoscape 3.10.1 software to construct the protein-protein interaction network and the "component-target" network relationship diagram, and the core components and core targets were analyzed. GO and KEGG pathway enrichment analysis of key targets were performed. All experiments were approved by the experimental Animal Ethics Committee from Nanjing University of Chinese Medicine (No. 202310A023). A total of 83 chemical components were identified, including 52 terpenoids such as tanshinone Ⅱ_A, 11 phthalides such as Z-ligustilide, 15 organic acids such as ferulic acid, 4 coumarins and 1 phenol. Additionally, 15 prototype components and 29 metabolites were identified in normal rats' plasma, and 17 prototype components and 32 metabolites were identified in DPN rats' plasma. Network pharmacology results show that 5 core components such as 3-acetyl-11-keto-β-boswellic acid and 11-keto-β-boswellic acid may act through 27 core targets such as TNF and IL6 to regulate AGE-RAGE and PI3K/Akt and other signaling pathways so as to play a therapeutic role in treatment of DPN. The study efficiently analyzed the constituents in vitro and blood-absorbed ingredients of Huoluoxiaolingdan and the cracking regularity of the main compounds, and the core components of its treatment of DPN were analyzed in combination with network pharmacology, which can provide reference for further research of the pharmacodynamic substantial basis and mechanism of Huoluoxiaolingdan in the treatment of DPN.

Key words

Huoluoxiaolingdan / UPLC-Q-TOF-MS/MS / network pharmacology / diabetic peripheral neuropathy / chemical component / blood-absorbed ingredient

引用本文

张喆, 李玉琴, 施亚宁, 宿树兰, 范若颖, 尚尔鑫, 朱悦, 段金廒. 基于UPLC-Q-TOF-MS/MS及网络药理学探讨活络效灵丹治疗糖尿病周围神经病变的物质基础研究. 药学学报, 2025 , 60 (4) : 1124 -1136 . DOI: 10.16438/j.0513-4870.2024-1123

Zhe ZHANG, Yu-qin LI, Ya-ning SHI, Shu-lan SU, Ruo-ying FAN, Er-xin SHANG, Yue ZHU, Jin-ao DUAN. Exploring the material basis of Huoluoxiaolingdan in the treatment of diabetic peripheral neuropathy based on UPLC-Q-TOF-MS/MS and network pharmacology[J]. Acta Pharmaceutica Sinica, 2025 , 60 (4) : 1124 -1136 . DOI: 10.16438/j.0513-4870.2024-1123

正文

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糖尿病周围神经病变(diabetic peripheral neuropathy, DPN) 属于糖尿病常见的难治性并发症, 临床表现主要为针刺样、撕裂样疼痛、感觉异常, 最典型的表现为“手套-袜子感”, 其发病率高, 起病缓慢, 患者不易察觉, 病情复杂且病程较长, 若不及时干预, 将引发足部溃疡、坏疽, 严重者需截肢, 甚至失去生命^[1]。DPN发病机制与微循环障碍、神经营养因子失调、晚期糖基化产物(AGEs) 过度积累、氧化应激及炎症等因素均有密切关系, 且目前临床还没有治疗DPN的特效药物, 一般是通过控制血糖、使用营养神经药物等来缓解, 疗效有限, 还可能出现不良反应^{[2, 3]}。

中医认为DPN属“痹症”, 病因为气血凝滞, 经络气血运行受阻, 造成壅滞凝涩^[4]。活络效灵丹一方来源于名医张锡纯的《医学衷中参西录》, 由当归、丹参、乳香及没药各15 g组成, 合用有养血活血、舒经活络、行气止痛、消积除癥的功效^[5]; 现代药理研究表明活络效灵丹具有抗炎、消肿、镇痛及改善微循环的作用^[6], 临床上应用于治疗DPN, 能明显提升患者的神经传导速度^[7]。目前对活络效灵丹的研究多停留在临床观察水平, 缺乏对全方化学成分的研究, 且方中四药皆“善入血分、通经络”, 但未见其入血成分的相关报道, 缺乏对正常状态及病理状态下动物体内成分的探究, 功效物质基础尚不明确。

因此, 本实验建立UPLC-Q-TOF-MS/MS法, 分别鉴定活络效灵丹的化学成分及正常大鼠与DPN大鼠灌胃给药后体内的原型成分及代谢产物, 结合网络药理学分析活络效灵丹入血成分治疗DPN的活性成分、核心靶点与通路, 为后续探究活络效灵丹治疗DPN的功效物质基础及作用机制奠定基础。

材料与方法

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仪器高分辨液质联用仪配有ExionLC和液相色谱和Zeno TOF 7600质谱仪(美国AB Sciex公司); Unique-R40多功能超纯水系统(厦门锐思捷水纯化技术有限公司); Labconco CentriVap真空离心浓缩仪(北京照生行仪器设备有限公司); BT125D型电子天平(赛多利斯科学仪器有限公司); GL-16G型离心机(上海安亭科学仪器厂); 微型涡旋混合仪(上海沪西分析仪器厂有限公司); 三诺安稳+血糖仪(批号: 2J01B240303, 三诺生物传感股份有限公司); Von-Frey纤维细丝机械刺激针(美国Danmic Aesthesio公司)。

药物及试剂 当归(批号: 231011)、丹参(批号: 230918)、乳香(批号: 230821)、没药(批号: 230920) 均购自苏州市天灵中药饮片有限公司, 经南京中医药大学段金廒教授鉴定均为正品合格药材; 对照品阿魏酸(批号: 110773-201012)、隐丹参酮(批号: 110852-200806) 均购自中国食品药品检定研究院; 11-羰基-β-乳香酸(批号: HS16311R2)、3α-乙酰氧基-羊毛脂-8, 24-二烯-21-酸(批号: HS15151B1) 均购自宝鸡辰光生物科技有限公司; 二氢丹参酮Ⅰ (批号: MUST-15020102) 购自成都曼斯特生物科技有限公司; Z-藁本内酯(批号: A26GB158725)、丹参素(批号: H09N10S102463)、丹酚酸A (批号: J26IB221287)、丹酚酸B (批号: S29GB162878)、丹参酮Ⅰ (批号: K30D10B107208)、丹参酮Ⅱ_A (批号: J10GB151070)、3-乙酰-11-羰基-β-乳香酸(批号: J20GB152181)、α-乳香酸(批号: F16IB207144)、β-乳香酸(批号: N17GB168325) 均购自上海源叶生物科技有限公司; 2-甲氧基-8, 12-环氧吉马烷-1(10)7, 11-三烯-6-酮(MCS134, 批号: 231640) 购自美国TargetMol公司; 2-甲氧基-5-乙酰基-呋喃吉马烷-1(10)-烯-6-酮(FSA) 为实验室自制, 纯度≥ 95%; 乙腈为色谱级(德国Merck公司); 甲酸色谱级(美国ThermoFisher Scientific公司); 屈臣氏蒸馏水购自南京禾苗生物科技有限公司; 无水乙醇(分析纯, 批号: 20240122, 无锡市亚盛化工有限公司); 链脲佐菌素(streptozotocin, STZ; 批号: S0130, 美国Sigma公司); 柠檬酸钠缓冲液(0.1 mmol·L^-1, pH 4.5, 批号: C-1013, 北京索莱宝公司)。

实验动物 SPF级雄性SD大鼠, 体重180~220 g, 购于上海斯莱克实验动物有限责任公司, 动物许可证号为SCXK (沪) 2022-0004, 南京中医药大学实验动物中心屏障环境内分笼饲养, 室温控制在22 ℃左右, 相对湿度40%~70%, 保持采光通风良好, 大鼠正常活动。本实验获得南京中医药大学动物实验伦理委员会审核批准(伦理批准号为202310A023), 实验过程中普通饲料和垫料均购自南京中医药大学实验动物中心; 高脂饲料(配方: 维持基础料43.6%, 猪油17.5%, 蔗糖12%, 全脂奶粉10%, 酪蛋白10%, 实验动物预混料2%, 微晶纤维素1.9%, 磷酸氢钙2%, 石粉1%) 购自书玉生物科技有限公司。

对照品溶液的制备 精密称取Z-藁本内酯、阿魏酸、丹参素、丹酚酸A、丹酚酸B、隐丹参酮、丹参酮Ⅰ、二氢丹参酮Ⅰ、丹参酮Ⅱ_A、11-羰基-β-乳香酸、3-乙酰-11-羰基-β-乳香酸、α-乳香酸、β-乳香酸、3α-乙酰氧基-羊毛脂-8, 24-二烯-21-酸、MCS134、FSA, 用甲醇配制成浓度为1 mg·mL^-1的单一对照品溶液; 分别吸取0.05 mL单一对照品溶液于同一10 mL量瓶中, 用甲醇定容, 制成各成分浓度均为0.005 mg·mL^-1的混合对照品溶液。

活络效灵丹提取物制备 按1∶1∶1∶1的配比称取适量当归、丹参、乳香、没药饮片, 加入6倍量纯水浸泡0.5 h, 水蒸气蒸馏法回流提取8 h, 静置1 h, 收集挥发油, 经无水硫酸钠干燥, 水提液趁热过滤, 滤液置于旋转蒸发仪中浓缩, 剩余药渣加入10倍量80%乙醇, 回流提取1 h, 提取3次, 滤液置于旋转蒸发仪中浓缩至无醇味, 与水提液合并浓缩至相当于药材0.8 g·mL^-1, 加入干燥后的挥发油混合均匀, 待用。

活络效灵丹供试品溶液制备 吸取活络效灵丹提取物0.05 mL, 加入0.95 mL色谱级乙腈, 涡旋混匀, 于4 ℃下13 000 r·min^-1离心15 min, 取上清液经0.22 μm孔径滤膜过滤, 4 ℃冰箱保存待测。

糖尿病周围神经病变模型大鼠造模及给药 12只SD大鼠适应性喂养一周, 随机分为空白组与模型组, 每组6只, 空白组喂养普通饲料, 模型组大鼠喂养高脂饲料3周后, 注射小剂量1% STZ建立糖尿病(diabetes mellitus, DM) 大鼠: 大鼠禁食12 h后, 避光环境下单侧腹腔注射35 mg·kg^-1的STZ, 72 h后测大鼠尾静脉空腹血糖≥ 11.1 mmol·L^-1视为DM造模成功。DM大鼠继续以高脂饲料喂养3周, 检测大鼠机械痛阈值(mechanical withdrawal threshold, MWT), 采用Up and down法检测^[8]: 将大鼠置于底部为多孔钢丝的笼中自由活动30~60 min适应环境, 从2.0 g的von Frey纤维针开始, 垂直刺激大鼠后肢足底中部, 至纤维丝弯曲为S形, 持续6 s以上, 重复3次, 每次间隔1~3 min, 当大鼠出现舔咬、抬脚或缩回, 视为阳性表现, 根据动物反应, 选用克数更大或更小的纤维丝进行下一次刺激, 直至产生6个有效测定数据。测得大鼠机械痛阈值下降10%的判定为DPN大鼠造模成功^{[9, 10]}。

血浆样本的制备 提前禁食12 h, 给药前取自身空白血浆0.5 mL, 随即按生药量6.25 g·kg^-1灌胃给予活络效灵丹提取物, 给药1 h后经眼底静脉丛取血0.5 mL于含肝素钠的离心管内静置2 h, 于4 ℃、4 000 r·min^-1离心10 min, 取上清液, -80 ℃冰箱存放备用。

血浆样本的预处理 取各组血浆样品于冰上化冻, 吸取100 μL血浆加入400 μL预冷乙腈, 涡旋混匀60 s, 4 ℃、13 000 r·min^-1离心15 min, 取上清液离心浓缩至干, 残留物加入50 μL预冷乙腈复溶, 4 ℃、13 000 r·min^-1离心15 min, 取上清用于入血成分检测分析。

液相条件 Waters ACQUITY UPLC BEH C₁₈色谱柱(100 mm × 2.1 mm, 1.7 μm); 流动相: 0.1%甲酸水(A)-乙腈(B); 柱温: 40 ℃; 流速: 0.3 mL·min^-1, 进样量: 2 μL; 梯度洗脱: 0~3 min, 5%~20% B; 3~7 min, 20%~30% B; 7~13 min, 30%~80% B; 13~15 min, 80%~87% B; 15~17 min, 87%~90% B; 17~18 min, 90%~95% B; 18~19 min, 95%~5% B; 19~20 min, 5% B。

质谱条件 开启动态背景扣除(DBS) 功能, 采用电喷雾离子源(ESI), 正、负离子模式扫描, 正离子电喷雾电压: 5.5 kV, 负离子电喷雾电压: -4.5 kV; 离子源温度: 550 ℃; 去簇电压: 80 V (正离子)/-80 V (负离子); 碰撞能量: 35 V (正离子)/-35 V (负离子); 质量扫描范围m/z 80~1 000; 喷雾气和辅助气: 55 psi (1 psi ≈ 6.895 kPa); 气帘气35 psi。

数据处理 采用Graphpad Prism 8软件对大鼠FBG及MWT进行统计分析, 数据用均值±标准差(

$ \stackrel{-}{x} $

± s) 表示, 组间各指标比较采用Unpaired student's t检验, P < 0.05表示具有统计学意义。质谱原始数据导入PeakView^TM 1.2软件(美国AB Sciex公司), 根据精确分子量及二级质谱裂解碎片, 结合对照品质谱图、参考文献及PubChem数据库进行比对, 结合化合物特有的质谱裂解规律鉴定体外成分及入血原型成分。借助Molecule Profiler^TM软件(美国AB Sciex公司), 通过多重质量亏损功能, 与空白样本比较, 在小于5×10^-6的误差范围预测代谢产物准分子离子峰, 根据参考文献结合质谱裂解规律鉴定代谢产物。

活络效灵丹入血成分靶点预测及疾病靶点筛选 将DPN大鼠体内鉴定出的17个成分输入PubChem数据库(https://pubchem.ncbi.nlm.nih.gov/) 搜索下载结构文件, 选择Swiss Target Prediction数据库(http://www.swisstargetprediction.ch/) 中probability值> 0的靶点, 合并删除重复值, 得到成分靶点。在GeneCards数据库(https://www.genecards.org/)、OMIM数据库(https://www.omim.org/)、DrugBank数据库(https://go.drugbank.com/) 中, 以关键词“diabetic peripheral neuropathy”进行搜索, 保留GeneCards数据库前25%的靶点, 整合所有靶点并去重, 得到疾病靶点。使用Venny 2.1作图工具(https://bioinfogp.cnb.csic.es/tools/-venny/) 将成分靶点与疾病靶点取交集, 得到活络效灵丹治疗DPN的潜在靶点。

蛋白互作网络(protein-protein interaction, PPI) 与“成分-靶点”网络图构建 将潜在靶点输入STRING数据库(https://string-db.org/), 物种选择“Homo sapiens”, 构建PPI互作网络图, 导入Cytoscape 3.10.1软件进行分析, 根据度值(degree)、中介中心性(betweenness centrality, BC)、接近中心性(closeness centrality, CC) 筛选出核心靶点; 运用Cytoscape 3.10.1软件构建“成分-靶点”网络图, 根据度值筛选核心成分。

GO和KEGG通路富集分析 将核心靶点导入DAVID数据库(https://david.ncifcrf.gov/) 进行GO生物功能富集分析和KEGG通路富集分析, 设置阈值P < 0.05进行筛选, 将结果导入微生信平台绘图。

结果

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1 糖尿病周围神经病变大鼠模型制备

造模后, 空白组(CON组) 大鼠体重稳定上升, 毛色鲜亮, 精神状态良好; 模型组(MOD组) 大鼠体重减轻, 毛色发黄、脱毛, 多饮、多食、多尿, 空腹血糖值显著上升, 机械痛阈值明显下降, 与空白组相比具有显著性差异(P < 0.01), 提示DPN大鼠造模成功。结果如图 1所示。

2 活络效灵丹体外化学成分鉴定

在活络效灵丹提取物中共鉴定出83种化合物, 其中萜类52种、苯酞类11种、有机酸类15种、香豆素类4种、酚类1种, 正负离子模式下的总离子流图如图 2所示, 主要鉴定信息见表 1。

2.1 萜类化合物

活络效灵丹提取物中共鉴定出52种萜类化合物, 包括19种倍半萜类、20种二萜类及13种三萜类化合物, 主要来自丹参、乳香、没药。二萜类化合物在正离子模式下的信号响应较高, 准分子离子峰主要以[M+H]⁺形式呈现, 其中丹参中的二萜醌类主要丢失H₂O、CH₃和CO等中性分子^[11]。

例如化合物61 (t_R = 14.04 min), 正离子模式下准分子离子峰为m/z 295.132 7 [M+H]⁺, 推断化合物的分子式为C₁₉H₁₈O₃ (误差为-0.6×10^-6), 二级质谱图中出现的碎片离子为m/z 280.110 4、277.125 9、266.094 9、262.100 8、249.127 6, 其中碎片离子m/z 280.110 4为该化合物失去1分子CH₃所形成, 进一步脱去1分子H₂O形成m/z 262.100 8 [M+H-CH₃-H₂O]⁺的碎片离子; 母离子失去醛基形成m/z 266.094 9 [M+H-CHO]⁺, 脱去1分子H₂O产生m/z 277.125 9 [M+H-H₂O]⁺, 继续脱去1分子CO得到m/z 249.127 6 [M+H-H₂O-CO]⁺, 结合文献^[12]数据及与对照品比对, 确定该化合物为丹参酮Ⅱ_A, 可能的裂解途径见图 3A。

三萜类化合物主要构型有齐墩果烷型及乌苏烷型, 母核结构不易开裂, 裂解方式主要为脱去H₂O、乙酰基及CH₃COOH等侧链取代基。以化合物75 (t_R = 16.45 min) 为例, 正离子模式下准分子离子峰为m/z 513.357 3, 推断化合物分子式为C₃₂H₄₈O₅ (误差为-0.3×10^-6), 主要的二级碎片离子为m/z 497.812 6、495.347 9、470.005 9、453.339 3、437.328 0, 碎片离子m/z 497.812 6、495.347 9、470.005 9、453.339 3分别为分子离子峰失去1分子O、H₂O、乙酰基及CH₃COOH形成的碎片离子, m/z 453.339 3进一步脱去O形成m/z 437.328 0 [M+H-CH₃COOH-O]⁺。结合裂解规律及与文献^[13]、对照品比对, 鉴定该化合物为3-乙酰基-11-酮基-β-乳香酸, 可能的裂解途径见图 3B。

2.2 苯酞类化合物

鉴定出11种苯酞类化合物, 主要存在于当归中, 分为简单苯酞与苯酞二聚体。苯酞类化合物在裂解时易脱去H₂O、CO、CO₂, 或失去侧链上的烯烃结构^[14]。

以化合物42 (t_R = 12.17 min) 为例, 正离子模式下该化合物准分子离子峰为m/z 191.106 6, 判断化合物的分子式为C₁₂H₁₄O₂ (误差为-0.1×10^-6), 二级质谱的主要碎片离子有m/z 173.096 3、163.111 6、145.100 8、117.070 0、105.069 8、91.054 5等, 分子离子峰丢失2分子CH₂形成m/z 163.111 6的碎片离子, m/z 173.096 3、145.100 8、117.070 0、105.069 8为准分子离子峰连续丢失1分子H₂O、1分子CO、2分子CH₂、1分子C₃H₄形成的碎片离子, 在m/z 105.069 8的基础上丢失1分子CH₂产生m/z 91.054 5 [M+H-H₂O-CO-C₄H₆]⁺。结合参考文献^[15]并与对照品比对, 判定该化合物为Z-藁本内酯, 其裂解途径见图 3C。

2.3 有机酸类化合物

共鉴定出15种有机酸类化合物, 主要来源于当归、丹参, 其裂解规律为容易丢失CO、CO₂、COOH、H₂O等小分子。例如化合物6 (t_R = 5.06 min), 正离子模式下显示准分子离子峰为m/z 195.065 2, 判断化合物的分子式为C₁₀H₁₀O₄ (误差为-0.6×10^-6), 主要的二级质谱的碎片离子包括m/z 177.055 0、149.059 2、134.036 5, 其中碎片离子m/z 177.055 0是由准分子离子峰脱去1分子H₂O所形成, 继而丢失1分子CO形成m/z 149.059 2 [M+H-H₂O-CO]⁺, 在此基础上丢失1分子CH₃形成m/z 134.036 5 [M+H-H₂O-CO-CH₃]⁺。依据参考文献^[16]结合对照品比对, 推断该化合物为阿魏酸, 可能的裂解途径见图 3D。

2.4 其他类化合物

除上述3种化合物外, 还在活络效灵丹提取物中检测出4种香豆素类化合物及1种酚类化合物, 其中香豆素类化合物来源于当归, 酚类化合物来源于乳香。

3 活络效灵丹入血成分分析

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3.1 活络效灵丹入血原型成分分析

各组血浆处理后检测得到正负离子模式下的总离子流图, 见图 2; 处理质谱数据, 结合体外成分质谱信息及文献查阅, 分别扣除各组空白血浆中的内源性成分, 于空白给药组(SL组) 中鉴定出15种原型成分, 在模型给药组(BL组) 中鉴定出17种原型成分, 具体信息见表 2。共检测出9个相同的原型成分, 主要为有机酸类、苯酞类及萜类化合物, 其中有机酸类来自当归、丹参中的阿魏酸与异阿魏酸, 苯酞类主要来源于当归中的洋川芎内酯F, 萜类来源于丹参中的丹参酮Ⅱ_B、隐丹参酮、二氢丹参酮I, 乳香中的3-乙酰基-11-酮基-β-乳香酸及没药中的myrrhanolide B。鉴定出的成分大多为药材中的特征性成分, 提示这些成分可能为活络效灵丹改善DPN的功效物质。可能因为不同状态大鼠药物吸收程度存在差异, 检测出SL组及BL组的原型成分种类不同, SL组中还检测出丹参醛、丹参素等成分, BL组中鉴定出SL组中没有的Z-藁本内酯、MCS134及11-羰基-β-乳香酸等成分。

3.2 活络效灵丹入血代谢产物鉴定

在SL组大鼠体内检测出29个代谢产物, BL组大鼠体内检测出32个代谢产物, 多发生羟基化、脱氢化、氧化等I相代谢反应与甲基化、硫酸化等Ⅱ相代谢反应, 具体代谢产物信息见表 2。

在BL组大鼠体内检测到代谢产物M2、M3及M5, 在SL组大鼠体内检测到代谢产物M2及M5。化合物M2 (t_R = 2.38 min), 负离子模式下准分子离子峰为m/z 277.001 9 [M-H]^-, 比原型成分丹参素的准分子离子峰m/z 197.044 9增加80, 预测分子式为C₉H₁₀O₈S (误差为-1.6×10^-6), 二级裂解产生m/z 197.045 8 [M-H-SO₃]^-、179.035 0 [M-H-SO₃-H₂O]^-、135.045 2 [M-H-SO₃-H₂O-CO]^-等碎片离子, 推测M2是丹参素的硫酸化产物^[17]。化合物M3 (t_R = 2.92 min) 及M5 (t_R = 3.35 min), 准分子离子峰分别为m/z 181.050 3与m/z 211.060 9, 判断分子式分别为C₉H₁₀O₄ (误差为-1.9×10^-6) 与C₁₀H₁₂O₅ (误差为-1.3×10^-6), M3裂解产生m/z 163.040 2 [M-H-H₂O]^-、135.045 3 [M-H-HCOOH]^-、119.050 5 [M-H-HCOOH-CH₂]^-、107.050 3 [M-H-HCOOH-CO]^-等碎片离子, M5的二级质谱特征碎片包括m/z 193.050 7 [M-H-H₂O]^-、178.027 2 [M-H-H₂O-CH₃]^-、149.024 4 [M-H-H₂O-CO₂]^-、134.037 5 [M-H-H₂O-CH₃-CO₂]^-, 推测M3是丹参素的去羟基化产物, M5是丹参素的甲基化产物^[18]。具体代谢途径见图 4。

4 活络效灵丹入血成分治疗糖尿病周围神经病变的网络药理学分析

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4.1 活络效灵丹入血成分靶点预测及疾病靶点筛选

Swiss Target Prediction数据库预测的靶点经去重后得到入血成分对应靶点447个; GeneCards等数据库获取的靶点筛选去重后得到疾病靶点2 285个。对成分靶点与疾病靶点取交集, 得到160个活络效灵丹的潜在作用靶点。

4.2 PPI与“成分-靶点”图构建

将潜在靶点输入STRING数据库获得蛋白间相互作用关系, 导入Cytoscape 3.10.1软件分析并构建PPI互作网络图(图 5A), 取度值、BC、CC均值以上的靶点作为核心靶点, 得到TNF、IL6、PPARG等27个核心靶点; 将成分与交集靶点导入Cytoscape 3.10.1软件绘制“成分-靶点”图(图 5B), 该网络图共有节点177个, 边339条, 其中度值排名为前5的活性成分为3-乙酰基-11-酮基-β-乳香酸、11-酮基-β-乳香酸、丹参酮Ⅱ_B、洋川芎内酯F、阿魏酸, 可能为活络效灵丹治疗DPN的核心成分。

4.3 GO和KEGG通路富集分析

核心靶点在DAVID数据库中进行GO与KEGG富集分析, 筛选得到活络效灵丹入血成分治疗DPN的GO分析结果中生物过程(biological process, BP) 条目219个, 主要参与RNA聚合酶Ⅱ启动子转录的正调控、磷酸化、ERK1和ERK2级联的正向调控等; 细胞组分(cellular component, CC) 条目38个, 主要包括细胞质膜、细胞质、细胞核等; 分子功能(molecular function, MF) 条目41个, 主要涉及蛋白结合、相同蛋白结合、ATP结合、酶结合等(图 6A)。KEGG富集分析得到134条通路, 结果显示, 活络效灵丹治疗DPN主要涉及AGE-RAGE信号通路、PI3K/Akt信号通路、丝裂原活化蛋白激酶MAPK信号通路、白介素IL-17信号通路、肿瘤坏死因子TNF信号通路等(图 6B)。

讨论

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活络效灵丹为临床常用祛瘀止痛的方剂, 方中当归能补血止痛, 为生血活血之主药, 丹参能凉血消痈、祛瘀生新, 乳香与没药相须为用, 发挥活血生肌、止痛散瘀的作用^[5]。本研究采用UPLC-Q-TOF-MS/MS技术检测活络效灵丹提取物的体外成分, 共鉴定出83个化学成分: 24个来源于当归, 23个来源于丹参, 18个来源于乳香, 22个来源于没药, 其中, 当归与丹参有4个相同的成分。

中药复方中的成分非常复杂, 一般认为药物经口服后, 真正吸收入血的才可能是中药发挥药效的成分。本实验在空白给药组与模型给药组大鼠体内检测到9种共有的入血原型成分, 在SL组大鼠体内检测出15种原型成分与29种代谢产物, BL组大鼠体内检测出17种原型成分及32种代谢产物, 与SL组相比, 原型成分及代谢产物种类增多, 可能由于正常动物与病理状态的动物体内微环境不同, 且DPN病程较长, 机体气血受损, 持续高血糖环境下促进AGEs形成, 炎症反应与氧化应激损伤加重, 导致外周神经系统的微血管环境改变与代谢功能紊乱, 血液循环减慢, 进而使得机体在正常状态与病理状态下对药物吸收与代谢效率存在差异^{[19, 20]}。

网络药理学预测得到排名前5的核心成分为3-乙酰基-11-酮基-β-乳香酸、11-酮基-β-乳香酸、丹参酮Ⅱ_B、洋川芎内酯F及阿魏酸, 其中阿魏酸能通过抑制神经炎症、促进坐骨神经修复以发挥镇痛作用^[21]; 11-酮基-β-乳香酸能显著降低STZ诱导的糖尿病大鼠血糖与血脂水平, 改善胰腺受损情况^[22]; 丹参酮Ⅱ_B可以通过抑制NF-κB信号通路以发挥抗炎作用^[23]; 洋川芎内酯F可能是通过改善线粒体功能障碍与调节巨噬细胞极化以缓解动脉粥样硬化^[24]; 3-乙酰基-11-酮基-β-乳香酸能减轻1型糖尿病大鼠的高血糖, 抑制STZ诱导的氧化应激、炎症反应及细胞凋亡^[25]。结果显示, 活络效灵丹可能是作用于TNF、IL6、PPARG、SRC、CTNNB1、CASP3等27个核心靶点, 通过调控AGE-RAGE、PI3K/Akt等信号通路发挥治疗DPN的作用, 其中TNF是一种促炎细胞因子, 表达后导致细胞凋亡并激活炎症级联反应, 引发炎症组织损伤与疼痛行为, 并伴有痛觉过敏^{[26, 27]}; IL6是活化后的小胶质细胞释放的炎症因子, 与小胶质细胞之间存在正向反馈, 导致神经性疼痛时间增加, 且可能发展为痛觉过敏或痛觉异常^[28]。PPARG是一种内源性抗炎因子, 主要通过抑制NF-κB信号通路以改善炎症, 通常用于调节巨噬细胞浸润及降低炎症部位促炎分子产生以发挥抗炎镇痛作用^[29]。

综上所述, 本研究鉴定了活络效灵丹的体外成分及正常大鼠和DPN大鼠的入血原型成分与代谢产物, 分析了各类化合物的质谱裂解规律, 通过网络药理学筛选活络效灵丹治疗DPN的核心成分与核心靶点, 预测其可能的作用机制, 推测其核心成分为活络效灵丹治疗DPN的潜在功效物质, 为后续质量标准、功效物质基础及作用机制研究提供了科学依据。

基金

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国家自然科学基金项目资助(82274086)
国家自然科学基金区域创新发展联合基金重点项目(U23A20502)
国家中医药管理局高水平中医药重点学科建设项目(zyyzdxk-2023083)
江苏省高校优秀科技创新团队项目(2021)

参考文献

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2025年第60卷第4期

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doi: 10.16438/j.0513-4870.2024-1123

接收时间：2024-11-12
首发时间：2025-10-29
出版时间：2025-04-12

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收稿日期：2024-11-12
修回日期：2025-01-25

基金

国家自然科学基金项目资助(82274086)

国家自然科学基金区域创新发展联合基金重点项目(U23A20502)

国家中医药管理局高水平中医药重点学科建设项目(zyyzdxk-2023083)

江苏省高校优秀科技创新团队项目(2021)

作者信息

通讯作者:

宿树兰, Tel: 13809043258, E-mail: sushulan1974@163.com

段金廒, Tel: 86-25-85811291, E-mail: dja@njucm.edu.cn

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2种不同金属材料的力学参数

科 Family	属数 Number of genus	种数 Number of species	占总种数比例 Percentage of total species (%)	属 Genus	种数 Number of species	占总种数比例 Percentage of total species (%)
鹅膏菌科Amanitaceae	2	11	5.26	鹅膏菌属 Amanita	10	4.78
小菇科 Mycenaceae	2	12	5.74	丝盖伞属 Inocybe	5	2.39
多孔菌科 Polyporaceae	8	14	6.70	蜡蘑属 Laccaria	5	2.39
红菇科 Russulaceae	3	23	11.00	小皮伞属 Marasmius	6	2.87
				小菇属 Mycena	11	5.26
				光柄菇属 Pluteus	5	2.39
				红菇属 Russula	17	8.13
				栓菌属 Trametes	5	2.39

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No.	t_R/min	Compound	Formula	m/z	Adduct	Error/×10^-6	MS/MS
1	1.00	Gallic acid	C₇H₆O₅	169.014 0	[M-H]^-	-1.5	125.024 6, 107.014 0
2	2.42	Caffeic acid	C₉H₈O₄	179.034 8	[M-H]^-	-1.2	135.045 0, 117.032 4, 107.049 9
3	2.43	Danshensu	C₉H₁₀O₅	197.045 2	[M-H]^-	-2.0	179.034 7, 135.046 1, 123.046 0, 109.029 5
4	2.56	Coumarate	C₉H₈O₃	165.054 6	[M+H]⁺	-0.2	119.085 6, 91.054 1
5	3.84	Vanillic acid	C₈H₈O₄	169.049 6	[M+H]⁺	0.3	125.060 1, 111.007 1, 95.066 8
6	5.06	Ferulic acid	C₁₀H₁₀O₄	195.065 2	[M+H]⁺	-0.6	177.055 0, 149.059 2, 134.036 5
7	5.07	6-Methoxycoumarin	C₁₀H₈O₃	177.054 7	[M+H]⁺	0.4	149.060 0, 145.028 7, 134.036 0, 117.033 8
8	5.09	Isoferulic acid	C₁₀H₁₀O₄	193.050 1	[M-H]^-	-2.9	178.027 1, 134.037 4
9	5.39	3, 4-Dicaffeoylquinic acid	C₂₅H₂₄O₁₂	515.119 1	[M-H]^-	-0.8	353.087 1, 191.055 7, 179.034 1
10	5.51	Salvianolic acid D	C₂₀H₁₈O₁₀	417.081 6	[M-H]^-	-2.8	197.045 3, 135.044 9
11	6.16	7-Hydroxycoumarin	C₉H₆O₃	163.039 0	[M+H]⁺	0.2	135.044 7, 117.034 0
12	6.16	Rosmarinic acid	C₁₈H₁₆O₈	359.076 5	[M-H]^-	-1.9	179.035 3, 161.026 3
13	6.17	Isomer of umbelliferide	C₉H₆O₃	161.023 9	[M-H]^-	-3.0	133.028 7, 117.039 1
14	6.28	Azelaic acid	C₉H₁₆O₄	187.097 2	[M-H]^-	-2.0	125.096 7, 123.081 4
15	6.51	Isomer of senkyunolide I	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 8, 179.106 3, 165.090 5
16	6.54	Senkyunolide I	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 8, 189.090 5, 179.078 9
17	6.78	Salvianolic acid B	C₃₆H₃₀O₁₆	717.143 0	[M-H]^-	-4.3	519.093 3, 339.049 5, 321.040 2, 295.061 8
18	6.98	Senkyunolide F	C₁₂H₁₄O₃	207.101 7	[M+H]⁺	0.4	189.091 3, 179.106 0, 123.044 3
19	6.99	Senkyunolide H	C₁₂H₁₆O₄	225.112 1	[M+H]⁺	-0.3	207.101 5, 189.091 1, 179.106 9, 165.089 5, 161.095 7, 117.069 4
20	7.09	New osthol lactone	C₁₂H₁₈O₂	195.137 9	[M+H]⁺	-0.5	177.127 3, 159.117 1, 117.070 0
21	7.42	Salvianolic acid A	C₂₆H₂₂O₁₀	493.113 0	[M-H]^-	-2.0	313.071 8, 295.062 9, 203.034 9, 185.024 7, 159.045 2, 109.030 3
22	9.04	Myrrhanolide B	C₁₅H₁₈O₄	261.112 6	[M-H]^-	-2.5	201.092 1, 187.076 4, 175.112 7
23	9.29	Coniferyl ferulate	C₂₀H₂₀O₆	355.117 0	[M-H]^-	-4.8	311.128 1, 296.104 6
24	9.44	Atractylenolide Ⅲ	C₁₅H₂₀O₃	249.148 5	[M+H]⁺	0.0	135.080 6, 107.084 8
25	9.50	Myrrhterpenoid H	C₁₆H₂₀O₄	277.143 6	[M+H]⁺	0.4	245.120 1, 121.066 8
26	9.63	Commipholinone	C₁₄H₁₆O₃	233.117 5	[M+H]⁺	1.1	119.085 4, 105.069 9
27	9.76	Commiterpene D	C₁₈H₂₂O₅	319.154 3	[M+H]⁺	1.0	227.107 9, 156.093 4
28	9.89	9, 10-Secoisohydro-xyaconido lactone	C₁₅H₁₈O₃	247.132 9	[M+H]⁺	0.2	159.081 8, 91.055 0
29	10.02	Isopimpinellin	C₁₃H₁₀O₅	247.059 4	[M+H]⁺	-3.1	189.091 0, 161.095 7, 133.064 9
30	10.59	MCS134	C₁₆H₂₂O₃	285.147 5	[M+Na]⁺	4.9	187.038 6, 171.116 7, 159.116 4, 145.101 3
31	10.89	Przewaquinone A	C₁₉H₁₈O₄	311.127 8	[M+H]⁺	0.0	283.132 4, 237.056 3
32	10.91	Nortanshinone	C₁₇H₁₂O₄	281.080 3	[M+H]⁺	-1.8	253.086 2, 225.092 4
33	11.06	Tanshinone Ⅱ_B	C₁₉H₁₈O₄	311.127 8	[M+H]⁺	0.0	293.117 1, 283.132 9, 275.106 7, 250.106 9, 247.111 0
34	11.06	1S-Hydroxy-anhydride of 16R cryptotanshinone	C₁₉H₂₀O₅	327.122 5	[M-H]^-	-4.0	283.133 4, 239.143 7
35	11.38	Senkyunolide A	C₁₂H₁₆O₂	193.122 2	[M+H]⁺	-0.5	147.117 8, 137.061 0, 119.084 9, 105.070 0, 93.070 7
36	11.47	Tanshialdehyde	C₁₉H₁₆O₄	309.112 2	[M+H]⁺	0.2	265.123 2, 250.098 6, 235.076 3
37	11.49	Canangaterpene Ⅵ	C₁₄H₂₂O₂	223.169 0	[M+H]⁺	-1.0	119.085 7, 91.054 6
38	11.91	N-Butylphthalide	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.1	173.097 3, 145.100 8
39	12.05	FSA	C₁₈H₂₄O₅	321.169 5	[M+H]⁺	-0.4	185.096 7, 168.095 3, 159.083 4, 145.076 3, 131.086 0
40	12.06	Commiterpene B	C₁₈H₂₂O₄	303.159 4	[M+H]⁺	1.0	211.112 5, 181.065 7
41	12.09	Dihydrotanshinone I	C₁₈H₁₄O₃	279.101 4	[M+H]⁺	-0.5	261.094 1, 233.099 0, 205.103 5
42	12.17	Z-Ligustilide	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.1	173.096 3, 163.111 6, 145.100 8, 117.070 0, 105.069 8, 91.054 5
43	12.27	(1E)-8, 12-Epoxy-germacra-1, 7, 10, 11-tetraen-6-one	C₁₅H₁₈O₂	231.138 1	[M+H]⁺	0.7	145.065 1, 105.070 0, 91.054 4
44	12.37	2-Methoxy-furanogermacra-1(10), 4-diene	C₁₆H₂₀O₃	261.148 3	[M+H]⁺	-0.5	175.112 3, 161.135 2, 91.053 9
45	12.39	Danshenxinkun B	C₁₈H₁₆O₃	281.117 1	[M+H]⁺	-0.6	253.158 7, 235.113 9
46	12.46	Epicurzerenone	C₁₅H₂₀O₂	233.153 4	[M+H]⁺	-0.9	145.102 5, 131.087 3, 95.086 0
47	12.92	9-Methymyrrhone	C₁₆H₁₈O₃	259.132 8	[M+H]⁺	-0.3	211.074 5, 189.092 1, 174.101 8, 161.060 2
48	12.96	Myrrhone	C₁₅H₁₆O₂	229.122 2	[M+H]⁺	-0.5	159.086 6, 145.066 9
49	13.03	Tanshinone I	C₁₈H₁₂O₃	277.085 7	[M+H]⁺	-1.0	262.063 2, 249.096 1, 221.096 3
50	13.08	Cryptotanshinone	C₁₉H₂₀O₃	297.148 3	[M+H]⁺	-0.6	282.126 4, 279.140 0, 268.111 1, 251.144 4, 237.097 3, 227.071 4
51	13.17	Rel-3R-methoxy-4S-furanogermacra-1E, 10(15)-dien-6-one	C₁₆H₂₀O₃	261.148 4	[M+H]⁺	-0.4	175.076 7, 161.060 4, 145.085 2, 131.086 1
52	13.18	Myrrhterpenoid J	C₁₆H₂₀O₃	261.148 4	[M+H]⁺	-0.6	229.125 3, 201.110 2, 196.088 8
53	13.36	Incensole oxide	C₂₀H₃₄O₃	323.257 8	[M+H]⁺	-0.7	163.147 1, 149.133 0, 121.102 3
54	13.46	Methylenetanshinquinone	C₁₈H₁₄O₃	279.101 4	[M+H]⁺	-0.5	261.096 7, 233.099 6, 205.103 1
55	13.66	Levistolide A	C₂₄H₂₈O₄	381.205 7	[M+H]⁺	-0.7	191.110 8, 173.096 4, 149.059 5, 145.100 8, 135.043 8, 117.070 0
56	13.75	Angelicide	C₂₄H₂₈O₄	381.205 7	[M+H]⁺	-0.7	335.200 6, 191.112 2
57	13.81	Olibanumol I	C₂₉H₄₆O₂	427.356 5	[M+H]⁺	-1.2	163.147 7, 149.131 9
58	13.82	Senkyunolide P	C₂₄H₂₈O₄	381.205 8	[M+H]⁺	-0.6	335.201 5, 279.136 7, 191.113 4
59	13.85	Dehydromiltirone	C₁₉H₂₀O₂	281.153 3	[M+H]⁺	-1.1	266.130 4, 253.158 5
60	13.90	Alismol	C₁₅H₂₄O	221.189 9	[M+H]⁺	-0.6	147.116 7, 107.085 4, 103.054 0
61	14.04	Tanshinone Ⅱ_A	C₁₉H₁₈O₃	295.132 7	[M+H]⁺	-0.6	280.110 4, 277.125 9, 266.094 9, 262.100 8, 249.127 6
62	14.19	(-)-α-Cubebene	C₁₅H₂₄	205.194 8	[M+H]⁺	-1.2	105.070 8, 91.057 8
63	14.22	Dihydro-cryptotanshinone	C₁₉H₂₂O₃	299.163 9	[M+H]⁺	-1.0	281.153 8, 253.158 9
64	14.30	Miltirone	C₁₉H₂₂O₂	283.169 1	[M+H]⁺	-0.7	268.145 3, 265.159 0
65	14.46	Lupan-20(29)-ene-3α, 30-diol	C₃₀H₅₀O₂	443.387 6	[M+H]⁺	-1.8	297.247 6, 217.195 1
66	14.68	11-Oxo-24-norursa-3, 9(11), 12-triene	C₂₉H₄₄O	409.346 2	[M+H]⁺	-0.6	219.174 8, 175.148 2
67	14.69	Tsugaric acid A	C₃₂H₅₀O₄	499.377 3	[M+H]⁺	-1.8	439.358 2, 369.273 4, 329.276 2, 255.212 5
68	14.76	11-Carbonyl-β-boswellic acid	C₃₀H₄₆O₄	469.330 6	[M-H]^-	-3.7	407.331 2, 391.300 0
69	14.79	Lupeolic acid	C₃₀H₄₆O₄	455.351 7	[M+H]⁺	-0.7	437.341 9, 271.241 6
70	15.01	Boscartol C	C₂₀H₃₂O₂	305.247 2	[M+H]⁺	-0.9	175.147 0, 159.116 5, 145.101 2
71	15.23	Incensole	C₂₀H₃₄O₂	307.263 0	[M+H]⁺	-0.6	123.118 1, 109.102 8, 95.088 4
72	15.36	Boscartin X	C₂₂H₃₆O₄	365.268 2	[M+H]⁺	-1.2	305.248 5, 175.147 1, 151.111 6, 121.101 2
73	15.79	β-Hydroxyman-subin-13(17)-ene-11-ketone	C₂₂H₃₄O₂	331.262 9	[M+H]⁺	-0.8	189.163 6, 121.101 0
74	16.36	α-Boswellic acid	C₃₀H₄₈O₃	455.350 8	[M-H]^-	-5.0	437.351 8, 409.350 9, 361.063 9
75	16.45	3-Acetyl-11-keto-β-boswellic acid	C₃₂H₄₈O₅	513.357 3	[M+H]⁺	-0.3	497.812 6, 495.347 9, 470.005 9, 453.339 3, 437.328 0
76	16.51	Verticiol	C₂₀H₃₄O	291.267 9	[M+H]⁺	-1.2	107.085 3, 93.069 9, 81.070 5
77	16.53	3α-Acetyl-9, 11-deoxy-β-boswellic acid	C₃₂H₄₈O₄	497.362 2	[M+H]⁺	-0.7	437.342 1, 391.335 8
78	16.67	β-Boswellic acid	C₃₀H₄₈O₃	455.350 8	[M-H]^-	-5.0	409.310 5, 367.391 6, 283.712 5
79	16.91	Cycloartenol	C₃₀H₅₀O	427.392 8	[M+H]⁺	-1.5	189.163 6, 173.131 8
80	17.44	Commiphorane G2	C₂₂H₃₄O	315.268 0	[M+H]⁺	-0.8	145.100 5, 105.069 9
81	17.70	Epilupeol	C₃₀H₄₈O	425.377 0	[M+H]⁺	-1.9	187.147 5, 135.116 7
82	17.72	Lupenone	C₃₀H₄₈O	425.376 7	[M+H]⁺	-2.3	203.179 2, 189.163 1, 147.116 6, 105.069 5, 81.070 0
83	17.85	Incensole acetate	C₂₂H₃₆O₃	349.273 4	[M+H]⁺	-0.9	203.179 9, 163.148 2

No.

t_R/min

Compound

Formula

m/z

Adduct

Error/×10^-6

MS/MS

1.00

Gallic acid

C₇H₆O₅

169.014 0

[M-H]^-

-1.5

125.024 6, 107.014 0

2.42

Caffeic acid

C₉H₈O₄

179.034 8

[M-H]^-

-1.2

135.045 0, 117.032 4, 107.049 9

2.43

Danshensu

C₉H₁₀O₅

197.045 2

[M-H]^-

-2.0

179.034 7, 135.046 1, 123.046 0, 109.029 5

2.56

Coumarate

C₉H₈O₃

165.054 6

[M+H]⁺

-0.2

119.085 6, 91.054 1

3.84

Vanillic acid

C₈H₈O₄

169.049 6

[M+H]⁺

0.3

125.060 1, 111.007 1, 95.066 8

5.06

Ferulic acid

C₁₀H₁₀O₄

195.065 2

[M+H]⁺

-0.6

177.055 0, 149.059 2, 134.036 5

5.07

6-Methoxycoumarin

C₁₀H₈O₃

177.054 7

[M+H]⁺

0.4

149.060 0, 145.028 7, 134.036 0, 117.033 8

5.09

Isoferulic acid

C₁₀H₁₀O₄

193.050 1

[M-H]^-

-2.9

178.027 1, 134.037 4

5.39

3, 4-Dicaffeoylquinic acid

C₂₅H₂₄O₁₂

515.119 1

[M-H]^-

-0.8

353.087 1, 191.055 7, 179.034 1

5.51

Salvianolic acid D

C₂₀H₁₈O₁₀

417.081 6

[M-H]^-

-2.8

197.045 3, 135.044 9

6.16

7-Hydroxycoumarin

C₉H₆O₃

163.039 0

[M+H]⁺

0.2

135.044 7, 117.034 0

6.16

Rosmarinic acid

C₁₈H₁₆O₈

359.076 5

[M-H]^-

-1.9

179.035 3, 161.026 3

6.17

Isomer of umbelliferide

C₉H₆O₃

161.023 9

[M-H]^-

-3.0

133.028 7, 117.039 1

6.28

Azelaic acid

C₉H₁₆O₄

187.097 2

[M-H]^-

-2.0

125.096 7, 123.081 4

6.51

Isomer of senkyunolide I

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 8, 179.106 3, 165.090 5

6.54

Senkyunolide I

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 8, 189.090 5, 179.078 9

6.78

Salvianolic acid B

C₃₆H₃₀O₁₆

717.143 0

[M-H]^-

-4.3

519.093 3, 339.049 5, 321.040 2, 295.061 8

6.98

Senkyunolide F

C₁₂H₁₄O₃

207.101 7

[M+H]⁺

0.4

189.091 3, 179.106 0, 123.044 3

6.99

Senkyunolide H

C₁₂H₁₆O₄

225.112 1

[M+H]⁺

-0.3

207.101 5, 189.091 1, 179.106 9, 165.089 5, 161.095 7, 117.069 4

7.09

New osthol lactone

C₁₂H₁₈O₂

195.137 9

[M+H]⁺

-0.5

177.127 3, 159.117 1, 117.070 0

7.42

Salvianolic acid A

C₂₆H₂₂O₁₀

493.113 0

[M-H]^-

-2.0

313.071 8, 295.062 9, 203.034 9, 185.024 7, 159.045 2, 109.030 3

9.04

Myrrhanolide B

C₁₅H₁₈O₄

261.112 6

[M-H]^-

-2.5

201.092 1, 187.076 4, 175.112 7

9.29

Coniferyl ferulate

C₂₀H₂₀O₆

355.117 0

[M-H]^-

-4.8

311.128 1, 296.104 6

9.44

Atractylenolide Ⅲ

C₁₅H₂₀O₃

249.148 5

[M+H]⁺

0.0

135.080 6, 107.084 8

9.50

Myrrhterpenoid H

C₁₆H₂₀O₄

277.143 6

[M+H]⁺

0.4

245.120 1, 121.066 8

9.63

Commipholinone

C₁₄H₁₆O₃

233.117 5

[M+H]⁺

1.1

119.085 4, 105.069 9

9.76

Commiterpene D

C₁₈H₂₂O₅

319.154 3

[M+H]⁺

1.0

227.107 9, 156.093 4

9.89

9, 10-Secoisohydro-xyaconido lactone

C₁₅H₁₈O₃

247.132 9

[M+H]⁺

0.2

159.081 8, 91.055 0

10.02

Isopimpinellin

C₁₃H₁₀O₅

247.059 4

[M+H]⁺

-3.1

189.091 0, 161.095 7, 133.064 9

10.59

MCS134

C₁₆H₂₂O₃

285.147 5

[M+Na]⁺

4.9

187.038 6, 171.116 7, 159.116 4, 145.101 3

10.89

Przewaquinone A

C₁₉H₁₈O₄

311.127 8

[M+H]⁺

0.0

283.132 4, 237.056 3

10.91

Nortanshinone

C₁₇H₁₂O₄

281.080 3

[M+H]⁺

-1.8

253.086 2, 225.092 4

11.06

Tanshinone Ⅱ_B

C₁₉H₁₈O₄

311.127 8

[M+H]⁺

0.0

293.117 1, 283.132 9, 275.106 7, 250.106 9, 247.111 0

11.06

1S-Hydroxy-anhydride of 16R cryptotanshinone

C₁₉H₂₀O₅

327.122 5

[M-H]^-

-4.0

283.133 4, 239.143 7

11.38

Senkyunolide A

C₁₂H₁₆O₂

193.122 2

[M+H]⁺

-0.5

147.117 8, 137.061 0, 119.084 9, 105.070 0, 93.070 7

11.47

Tanshialdehyde

C₁₉H₁₆O₄

309.112 2

[M+H]⁺

0.2

265.123 2, 250.098 6, 235.076 3

11.49

Canangaterpene Ⅵ

C₁₄H₂₂O₂

223.169 0

[M+H]⁺

-1.0

119.085 7, 91.054 6

11.91

N-Butylphthalide

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.1

173.097 3, 145.100 8

12.05

FSA

C₁₈H₂₄O₅

321.169 5

[M+H]⁺

-0.4

185.096 7, 168.095 3, 159.083 4, 145.076 3, 131.086 0

12.06

Commiterpene B

C₁₈H₂₂O₄

303.159 4

[M+H]⁺

1.0

211.112 5, 181.065 7

12.09

Dihydrotanshinone I

C₁₈H₁₄O₃

279.101 4

[M+H]⁺

-0.5

261.094 1, 233.099 0, 205.103 5

12.17

Z-Ligustilide

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.1

173.096 3, 163.111 6, 145.100 8, 117.070 0, 105.069 8, 91.054 5

12.27

(1E)-8, 12-Epoxy-germacra-1, 7, 10, 11-tetraen-6-one

C₁₅H₁₈O₂

231.138 1

[M+H]⁺

0.7

145.065 1, 105.070 0, 91.054 4

12.37

2-Methoxy-furanogermacra-1(10), 4-diene

C₁₆H₂₀O₃

261.148 3

[M+H]⁺

-0.5

175.112 3, 161.135 2, 91.053 9

12.39

Danshenxinkun B

C₁₈H₁₆O₃

281.117 1

[M+H]⁺

-0.6

253.158 7, 235.113 9

12.46

Epicurzerenone

C₁₅H₂₀O₂

233.153 4

[M+H]⁺

-0.9

145.102 5, 131.087 3, 95.086 0

12.92

9-Methymyrrhone

C₁₆H₁₈O₃

259.132 8

[M+H]⁺

-0.3

211.074 5, 189.092 1, 174.101 8, 161.060 2

12.96

Myrrhone

C₁₅H₁₆O₂

229.122 2

[M+H]⁺

-0.5

159.086 6, 145.066 9

13.03

Tanshinone I

C₁₈H₁₂O₃

277.085 7

[M+H]⁺

-1.0

262.063 2, 249.096 1, 221.096 3

13.08

Cryptotanshinone

C₁₉H₂₀O₃

297.148 3

[M+H]⁺

-0.6

282.126 4, 279.140 0, 268.111 1, 251.144 4, 237.097 3, 227.071 4

13.17

Rel-3R-methoxy-4S-furanogermacra-1E, 10(15)-dien-6-one

C₁₆H₂₀O₃

261.148 4

[M+H]⁺

-0.4

175.076 7, 161.060 4, 145.085 2, 131.086 1

13.18

Myrrhterpenoid J

C₁₆H₂₀O₃

261.148 4

[M+H]⁺

-0.6

229.125 3, 201.110 2, 196.088 8

13.36

Incensole oxide

C₂₀H₃₄O₃

323.257 8

[M+H]⁺

-0.7

163.147 1, 149.133 0, 121.102 3

13.46

Methylenetanshinquinone

C₁₈H₁₄O₃

279.101 4

[M+H]⁺

-0.5

261.096 7, 233.099 6, 205.103 1

13.66

Levistolide A

C₂₄H₂₈O₄

381.205 7

[M+H]⁺

-0.7

191.110 8, 173.096 4, 149.059 5, 145.100 8, 135.043 8, 117.070 0

13.75

Angelicide

C₂₄H₂₈O₄

381.205 7

[M+H]⁺

-0.7

335.200 6, 191.112 2

13.81

Olibanumol I

C₂₉H₄₆O₂

427.356 5

[M+H]⁺

-1.2

163.147 7, 149.131 9

13.82

Senkyunolide P

C₂₄H₂₈O₄

381.205 8

[M+H]⁺

-0.6

335.201 5, 279.136 7, 191.113 4

13.85

Dehydromiltirone

C₁₉H₂₀O₂

281.153 3

[M+H]⁺

-1.1

266.130 4, 253.158 5

13.90

Alismol

C₁₅H₂₄O

221.189 9

[M+H]⁺

-0.6

147.116 7, 107.085 4, 103.054 0

14.04

Tanshinone Ⅱ_A

C₁₉H₁₈O₃

295.132 7

[M+H]⁺

-0.6

280.110 4, 277.125 9, 266.094 9, 262.100 8, 249.127 6

14.19

(-)-α-Cubebene

C₁₅H₂₄

205.194 8

[M+H]⁺

-1.2

105.070 8, 91.057 8

14.22

Dihydro-cryptotanshinone

C₁₉H₂₂O₃

299.163 9

[M+H]⁺

-1.0

281.153 8, 253.158 9

14.30

Miltirone

C₁₉H₂₂O₂

283.169 1

[M+H]⁺

-0.7

268.145 3, 265.159 0

14.46

Lupan-20(29)-ene-3α, 30-diol

C₃₀H₅₀O₂

443.387 6

[M+H]⁺

-1.8

297.247 6, 217.195 1

14.68

11-Oxo-24-norursa-3, 9(11), 12-triene

C₂₉H₄₄O

409.346 2

[M+H]⁺

-0.6

219.174 8, 175.148 2

14.69

Tsugaric acid A

C₃₂H₅₀O₄

499.377 3

[M+H]⁺

-1.8

439.358 2, 369.273 4, 329.276 2, 255.212 5

14.76

11-Carbonyl-β-boswellic acid

C₃₀H₄₆O₄

469.330 6

[M-H]^-

-3.7

407.331 2, 391.300 0

14.79

Lupeolic acid

C₃₀H₄₆O₄

455.351 7

[M+H]⁺

-0.7

437.341 9, 271.241 6

15.01

Boscartol C

C₂₀H₃₂O₂

305.247 2

[M+H]⁺

-0.9

175.147 0, 159.116 5, 145.101 2

15.23

Incensole

C₂₀H₃₄O₂

307.263 0

[M+H]⁺

-0.6

123.118 1, 109.102 8, 95.088 4

15.36

Boscartin X

C₂₂H₃₆O₄

365.268 2

[M+H]⁺

-1.2

305.248 5, 175.147 1, 151.111 6, 121.101 2

15.79

β-Hydroxyman-subin-13(17)-ene-11-ketone

C₂₂H₃₄O₂

331.262 9

[M+H]⁺

-0.8

189.163 6, 121.101 0

16.36

α-Boswellic acid

C₃₀H₄₈O₃

455.350 8

[M-H]^-

-5.0

437.351 8, 409.350 9, 361.063 9

16.45

3-Acetyl-11-keto-β-boswellic acid

C₃₂H₄₈O₅

513.357 3

[M+H]⁺

-0.3

497.812 6, 495.347 9, 470.005 9, 453.339 3, 437.328 0

16.51

Verticiol

C₂₀H₃₄O

291.267 9

[M+H]⁺

-1.2

107.085 3, 93.069 9, 81.070 5

16.53

3α-Acetyl-9, 11-deoxy-β-boswellic acid

C₃₂H₄₈O₄

497.362 2

[M+H]⁺

-0.7

437.342 1, 391.335 8

16.67

β-Boswellic acid

C₃₀H₄₈O₃

455.350 8

[M-H]^-

-5.0

409.310 5, 367.391 6, 283.712 5

16.91

Cycloartenol

C₃₀H₅₀O

427.392 8

[M+H]⁺

-1.5

189.163 6, 173.131 8

17.44

Commiphorane G2

C₂₂H₃₄O

315.268 0

[M+H]⁺

-0.8

145.100 5, 105.069 9

17.70

Epilupeol

C₃₀H₄₈O

425.377 0

[M+H]⁺

-1.9

187.147 5, 135.116 7

17.72

Lupenone

C₃₀H₄₈O

425.376 7

[M+H]⁺

-2.3

203.179 2, 189.163 1, 147.116 6, 105.069 5, 81.070 0

17.85

Incensole acetate

C₂₂H₃₆O₃

349.273 4

[M+H]⁺

-0.9

203.179 9, 163.148 2

No.	t_R /min	Formula	m/z	Adduct	Error/×10^-6	MS/MS	Compound	Phase	SL	BL
1	1.89	C₉H₈O₃	165.054 7	[M+H]⁺	0.3	119.050 9, 91.054 9	Coumarate	-	+	+
2	2.41	C₉H₁₀O₅	197.044 9	[M-H]^-	-3.4	179.034 4, 135.045 6, 123.045 3, 109.030 2	Danshensu	-	+	-
3	3.49	C₁₀H₁₀O₄	193.049 8	[M-H]^-	-4.4	178.025 6, 134.037 9	Isoferulic acid	-	+	+
4	6.34	C₁₀H₁₀O₄	195.065 1	[M+H]⁺	-0.6	177.163 5, 149.050 9, 134.033 9	Ferulic acid	-	+	+
5	6.96	C₁₂H₁₄O₃	207.101 5	[M+H]⁺	-0.4	189.090 9, 179.106 8, 123.044 8	Senkyunolide F	-	+	+
6	8.15	C₁₅H₁₈O₃	247.132 8	[M+H]⁺	-0.5	159.080 7, 91.054 2	9,10-Secoiso-hydroxyaconido lactone	-	-	+
7	8.90	C₁₅H₁₈O₄	261.113 3	[M-H]^-	0.1	201.092 8, 187.079 4	Myrrhanolide B	-	+	+
8	9.60	C₁₆H₂₀O₃	261.148 5	[M+H]⁺	0.0	175.112 1, 161.095 6, 91.054 3	2-Methoxy-furanogermacra-1(10),4-diene	-	+	-
9	9.87	C₁₅H₂₀O₃	249.148 5	[M+H]⁺	0.1	135.648 5, 107.084 1	Atractylenolide Ⅲ	-	+	-
10	10.14	C₁₄H₁₆O₃	233.117 4	[M+H]⁺	0.6	119.085 1, 105.069 3	Commipholinone	-	-	+
11	10.77	C₁₅H₁₆O₂	229.122 1	[M+H]⁺	-0.8	159.080 5, 145.101 1	Myrrhone	-	-	+
12	11.00	C₁₉H₁₈O₄	311.127 5	[M+H]⁺	-1.1	293.116 0, 283.131 1, 275.099 7, 250.095 3, 247.119 6	Tanshinone Ⅱ_B	-	+	+
13	11.39	C₁₉H₁₆O₄	309.112 0	[M+H]⁺	-0.4	265.122 3, 250.098 9, 235.111 6	Tanshialdehyde	-	+	-
14	11.44	C₁₈H₁₄O₃	279.101 7	[M+H]⁺	0.3	261.092 1, 233.095 9, 205.100 4	Dihydrotanshinone I	-	+	+
15	11.68	C₁₉H₂₀O₃	297.148 5	[M+H]⁺	-0.2	251.142 6, 237.091 1, 227.105 4	Cryptotanshinone	-	+	+
16	11.87	C₁₂H₁₄O₂	191.106 7	[M+H]⁺	0.0	173.098 6, 163.112 1, 145.062 5, 117.069 1, 105.067 9, 91.054 1	Z-Ligustilide	-	-	+
17	12.43	C₁₆H₂₂O₃	263.163 6	[M+H]⁺	-2.0	187.074 9, 171.117 6, 159.077 6, 145.100 6	MCS134	-	-	+
18	14.19	C₃₀H₄₆O₃	455.351 5	[M+H]⁺	-1.0	437.341 3, 271.204 3	Lupeolic acid	-	+	-
19	14.61	C₃₀H₄₆O₄	469.331 7	[M-H]^-	-1.4	407.222 2, 391.952 6	11-Carbonyl-β-boswellicacid	-	-	+
20	15.85	C₁₅H₂₄O	221.189 9	[M+H]⁺	-0.5	147.117 7, 107.085 8, 103.055 2	Alismol	-	-	+
21	16.32	C₃₂H₄₈O₅	513.357 2	[M+H]⁺	-0.5	495.354 1, 453.340 2	3α-Acetyl-9,11-deoxy-β-boswellic acid	-	+	+
22	16.40	C₃₀H₄₈O	425.376 2	[M+H]⁺	-3.7	203.178 6, 189.164 1, 147.116 3, 105.069 3, 81.069 3	Lupenone	-	+	-
23	17.60	C₁₄H₂₂O₂	223.169 0	[M+H]⁺	-1.3	119.086 0, 91.053 7	Canangaterpene Ⅵ	-	-	+
M1	2.29	C₁₈H₁₄O₃	279.101 0	[M+H]⁺	-1.9	279.100 2, 205.087 4	Reduction of tanshinone I	I	-	+
M2	2.38	C₉H₁₀O₈S	277.001 9	[M-H]^-	-1.6	197.045 8, 179.035 0, 135.045 2	Sulfate danshensu	Ⅱ	+	+
M3	2.92	C₉H₁₀O₄	181.050 3	[M-H]^-	-1.9	163.040 2, 135.045 3, 119.050 5, 107.050 3	Dehydroxyl danshensu	I	-	+
M4	3.32	C₁₂H₁₆O₂	193.122 4	[M+H]⁺	0.3	165.127 3, 123.079 7	Dedihydroxylation of senkyunolide I/H	I	+	+
M5	3.35	C₁₀H₁₂O₅	211.060 9	[M-H]^-	-1.3	193.050 7, 178.027 2, 149.024 4, 134.037 5	Methyl danshensu	Ⅱ	+	+
M6	3.90	C₁₅H₂₂O	219.174 0	[M+H]⁺	-1.5	145.101 2, 105.069 5	Dehydrogenation of alismol	I	+	+
M7	4.99	C₁₂H₁₄O₂	191.106 7	[M+H]⁺	0.0	173.095 1, 145.100 7, 135.080 6	Dehydrogenation of senkyunolide A	I	+	+
M8	5.10	C₁₂H₁₄O₃	207.101 7	[M+H]⁺	0.7	189.092 0, 165.055 3, 161.094 7, 133.101 2	Ketone formation of senkyunolide A	I	+	+
M9	5.17	C₁₅H₂₂O₄	267.159 0	[M+H]⁺	-0.3	249.147 9, 231.137 6, 203.142 5, 185.132 1, 119.085 6, 105.069 9	Internal hydrolysis of atractylenolide Ⅲ	I	+	+
M10	5.53	C₁₅H₂₀O₄	265.143 6	[M+H]⁺	0.4	247.133 8, 229.123 6, 105.069 9	Oxidation of atractylenolide Ⅲ	I	+	+
M11	5.89	C₁₅H₁₈O₄	263.128 2	[M+H]⁺	1.5	245.117 1, 203.118 5, 175.111 1	Ketone formation of atractylenolide Ⅲ	I	+	+
M12	6.95	C₁₂H₁₄O₃	207.101 4	[M+H]⁺	-0.6	189.091 8, 179.108 4, 161.096 9, 133.101 2, 121.100 6, 107.085 4	Hydroxyl Z-ligustilide	I	+	+
M13	7.06	C₁₂H₁₈O₂	195.137 4	[M+H]⁺	-2.7	177.127 5, 153.051 1, 149.132 5, 139.110 4	Hydrogenation of senkyunolide A	I	+	-
M14	7.10	C₁₁H₁₂O₄	209.080 9	[M+H]⁺	0.4	165.067 5, 121.065 4, 109.063 5	Methyl ferulic acid	Ⅱ	+	-
M15	7.65	C₁₂H₁₆O₂	193.122 1	[M+H]⁺	-0.8	165.125 7, 147.114 2, 119.085 1, 107.086 2, 93.068 9	Hydrogenation of Z-ligustilide	I	+	+
M16	8.90	C₁₅H₁₈O₄	263.128 1	[M+H]⁺	1.0	245.123 3, 217.127 0	Demethylation and methylene to ketone of MCS134	I	+	+
M17	8.98	C₁₂H₁₆O₃	209.117 0	[M+H]⁺	-1.3	153.089 4, 121.062 6, 107.085 4	Dehydroxyl senkyunolide I/H	I	+	-
M18	9.08	C₁₁H₁₂O₃	193.085 9	[M+H]⁺	0.0	175.073 8, 151.109 4, 147.076 7	Demethylation and methylene to ketone of senkyunolide A	I	+	+
M19	9.16	C₁₆H₂₂O₃	263.164 2	[M+H]⁺	0.0	189.096 0, 161.062 1	Methyl atractylenolide Ⅲ	Ⅱ	-	+
M20	9.32	C₁₆H₂₀O₅	293.138 6	[M+H]⁺	0.7	275.127 8, 247.132 0, 187.111 5	Demethylation to carboxylic acid of MCS134	I	+	+
M21	9.54	C₁₉H₂₀O₄	313.143 6	[M+H]⁺	0.6	271.093 3, 269.152 4, 267.138 1, 254.094 1, 253.085 6, 249.109 4	Hydroxyl cryptotanshinone	I	+	-
M22	9.82	C₁₉H₁₆O₄	309.112 4	[M+H]⁺	0.8	265.121 9, 223.075 4	Hydroxylation and oxidation of tanshinone Ⅱ_A	I	+	-
M23	9.99	C₁₂H₁₂O₂	189.090 9	[M+H]⁺	-0.5	171.080 5, 161.092 0, 143.085 9, 115.053 4	Dehydrogenation of Z-ligustilide	I	+	+
M24	10.10	C₁₂H₁₄O₂	191.106 6	[M+H]⁺	-0.4	173.093 2, 163.086 2, 107.087 3	Dehydrogenation of senkyunolide F	I	+	+
M25	10.11	C₁₈H₁₂O₃	293.080 9	[M+H]⁺	0.1	293.079 6, 249.091 4	Hydroxyl tanshinone I	I	+	+
M26	10.43	C₁₅H₂₀O₂	233.153 3	[M+H]⁺	-1.5	119.085 9, 91.053 7	Dehydrogenation of atractylenolide Ⅲ	I	-	+
M27	10.47	C₁₅H₂₄O₂	237.184 4	[M+H]⁺	-2.1	163.112 2, 123.116 5, 119.086 2	Oxidation of alismol	I	-	+
M28	10.79	C₁₅H₂₂O₃	251.164 0	[M+H]⁺	-0.8	233.152 3, 205.157 6, 187.149 8, 159.119 6, 133.101 4, 105.069 7	Hydrogenation of atractylenolide Ⅲ	I	+	+
M29	10.99	C₁₉H₁₈O₄	311.127 2	[M+H]⁺	-1.8	293.115 2, 267.138 8, 265.086 5, 247.115 5	Hydroxylation and dehydrogenation of cryptotanshinone	I	+	-
M30	11.29	C₃₀H₄₆O₄	471.346 8	[M+H]⁺	-0.2	453.334 6, 409.356 9	Deacetylation of 3-acetyl-11-keto-β-boswellic acid	I	+	+
M31	11.39	C₁₉H₁₆O₄	309.112 4	[M+H]⁺	0.9	291.101 0, 281.117 0	Dehydrogenation of tanshinone Ⅱ_B	I	+	+
M32	11.66	C₁₉H₂₀O₃	297.148 4	[M+H]⁺	-0.3	251.144 0, 237.090 8	Hydrogenation of tanshinone Ⅱ_A	I	+	+
M33	12.64	C₁₂H₁₆O₃	209.117 0	[M+H]⁺	-1.0	191.106 8, 173.132 8, 165.067 8	Oxidation of senkyunolide A	I	-	+
M34	12.68	C₁₃H₁₆O₃	221.117 1	[M+H]⁺	-0.8	193.124 7, 137.059 6	Methyl senkyunolide F	Ⅱ	+	+
M35	12.83	C₃₀H₄₈O₄	471.345 9	[M-H]^-	-4.4	471.346 5, 393.314 7	Hydrogenation of 11-carbonyl-β-boswellic acid	I	-	+
M36	14.01	C₃₀H₄₆O₅	485.325 4	[M-H]^-	-3.8	485.326 9, 423.326 8	Hydroxyl 11-carbonyl-β-boswellic acid	I	+	+
M37	14.57	C₃₂H₄₈O₆	529.350 8	[M+H]⁺	-2.9	511.342 2, 469.333 7, 423.326 3	Hydroxyl 3-acetyl-11-keto-β-boswellic acid	I	-	+
M38	16.38	C₃₂H₄₈O₄	497.361 5	[M+H]⁺	-2.1	479.364 3, 437.340 8	Dehydroxyl 3-acetyl-11-keto-β-boswellic acid	I	-	+

No.

t_R
/min

Formula

m/z

Adduct

Error/×10^-6

MS/MS

Compound

Phase

1.89

C₉H₈O₃

165.054 7

[M+H]⁺

0.3

119.050 9, 91.054 9

Coumarate

2.41

C₉H₁₀O₅

197.044 9

[M-H]^-

-3.4

179.034 4, 135.045 6, 123.045 3, 109.030 2

Danshensu

3.49

C₁₀H₁₀O₄

193.049 8

[M-H]^-

-4.4

178.025 6, 134.037 9

Isoferulic acid

6.34

C₁₀H₁₀O₄

195.065 1

[M+H]⁺

-0.6

177.163 5, 149.050 9, 134.033 9

Ferulic acid

6.96

C₁₂H₁₄O₃

207.101 5

[M+H]⁺

-0.4

189.090 9, 179.106 8, 123.044 8

Senkyunolide F

8.15

C₁₅H₁₈O₃

247.132 8

[M+H]⁺

-0.5

159.080 7, 91.054 2

9,10-Secoiso-hydroxyaconido lactone

8.90

C₁₅H₁₈O₄

261.113 3

[M-H]^-

0.1

201.092 8, 187.079 4

Myrrhanolide B

9.60

C₁₆H₂₀O₃

261.148 5

[M+H]⁺

0.0

175.112 1, 161.095 6, 91.054 3

2-Methoxy-furanogermacra-1(10),4-diene

9.87

C₁₅H₂₀O₃

249.148 5

[M+H]⁺

0.1

135.648 5, 107.084 1

Atractylenolide Ⅲ

10.14

C₁₄H₁₆O₃

233.117 4

[M+H]⁺

0.6

119.085 1, 105.069 3

Commipholinone

10.77

C₁₅H₁₆O₂

229.122 1

[M+H]⁺

-0.8

159.080 5, 145.101 1

Myrrhone

11.00

C₁₉H₁₈O₄

311.127 5

[M+H]⁺

-1.1

293.116 0, 283.131 1, 275.099 7, 250.095 3, 247.119 6

Tanshinone Ⅱ_B

11.39

C₁₉H₁₆O₄

309.112 0

[M+H]⁺

-0.4

265.122 3, 250.098 9, 235.111 6

Tanshialdehyde

11.44

C₁₈H₁₄O₃

279.101 7

[M+H]⁺

0.3

261.092 1, 233.095 9, 205.100 4

Dihydrotanshinone I

11.68

C₁₉H₂₀O₃

297.148 5

[M+H]⁺

-0.2

251.142 6, 237.091 1, 227.105 4

Cryptotanshinone

11.87

C₁₂H₁₄O₂

191.106 7

[M+H]⁺

0.0

173.098 6, 163.112 1, 145.062 5, 117.069 1, 105.067 9, 91.054 1

Z-Ligustilide

12.43

C₁₆H₂₂O₃

263.163 6

[M+H]⁺

-2.0

187.074 9, 171.117 6, 159.077 6, 145.100 6

MCS134

14.19

C₃₀H₄₆O₃

455.351 5

[M+H]⁺

-1.0

437.341 3, 271.204 3

Lupeolic acid

14.61

C₃₀H₄₆O₄

469.331 7

[M-H]^-

-1.4

407.222 2, 391.952 6

11-Carbonyl-β-boswellicacid

15.85

C₁₅H₂₄O

221.189 9

[M+H]⁺

-0.5

147.117 7, 107.085 8, 103.055 2

Alismol

16.32

C₃₂H₄₈O₅

513.357 2

[M+H]⁺

-0.5

495.354 1, 453.340 2

3α-Acetyl-9,11-deoxy-β-boswellic
acid

16.40

C₃₀H₄₈O

425.376 2

[M+H]⁺

-3.7

203.178 6, 189.164 1, 147.116 3, 105.069 3, 81.069 3

Lupenone

17.60

C₁₄H₂₂O₂

223.169 0

[M+H]⁺

-1.3

119.086 0, 91.053 7

Canangaterpene Ⅵ

2.29

C₁₈H₁₄O₃

279.101 0

[M+H]⁺

-1.9

279.100 2, 205.087 4

Reduction of tanshinone I

2.38

C₉H₁₀O₈S

277.001 9

[M-H]^-

-1.6

197.045 8, 179.035 0, 135.045 2

Sulfate danshensu

Ⅱ

2.92

C₉H₁₀O₄

181.050 3

[M-H]^-

-1.9

163.040 2, 135.045 3, 119.050 5, 107.050 3

Dehydroxyl danshensu

3.32

C₁₂H₁₆O₂

193.122 4

[M+H]⁺

0.3

165.127 3, 123.079 7

Dedihydroxylation of senkyunolide I/H

3.35

C₁₀H₁₂O₅

211.060 9

[M-H]^-

-1.3

193.050 7, 178.027 2, 149.024 4, 134.037 5

Methyl danshensu

Ⅱ

3.90

C₁₅H₂₂O

219.174 0

[M+H]⁺

-1.5

145.101 2, 105.069 5

Dehydrogenation of alismol

4.99

C₁₂H₁₄O₂

191.106 7

[M+H]⁺

0.0

173.095 1, 145.100 7, 135.080 6

Dehydrogenation of senkyunolide A

5.10

C₁₂H₁₄O₃

207.101 7

[M+H]⁺

0.7

189.092 0, 165.055 3, 161.094 7, 133.101 2

Ketone formation of senkyunolide A

5.17

C₁₅H₂₂O₄

267.159 0

[M+H]⁺

-0.3

249.147 9, 231.137 6, 203.142 5, 185.132 1, 119.085 6, 105.069 9

Internal hydrolysis of atractylenolide Ⅲ

M10

5.53

C₁₅H₂₀O₄

265.143 6

[M+H]⁺

0.4

247.133 8, 229.123 6, 105.069 9

Oxidation of atractylenolide Ⅲ

M11

5.89

C₁₅H₁₈O₄

263.128 2

[M+H]⁺

1.5

245.117 1, 203.118 5, 175.111 1

Ketone formation of atractylenolide Ⅲ

M12

6.95

C₁₂H₁₄O₃

207.101 4

[M+H]⁺

-0.6

189.091 8, 179.108 4, 161.096 9, 133.101 2, 121.100 6, 107.085 4

Hydroxyl Z-ligustilide

M13

7.06

C₁₂H₁₈O₂

195.137 4

[M+H]⁺

-2.7

177.127 5, 153.051 1, 149.132 5, 139.110 4

Hydrogenation of senkyunolide A

M14

7.10

C₁₁H₁₂O₄

209.080 9

[M+H]⁺

0.4

165.067 5, 121.065 4, 109.063 5

Methyl ferulic acid

Ⅱ

M15

7.65

C₁₂H₁₆O₂

193.122 1

[M+H]⁺

-0.8

165.125 7, 147.114 2, 119.085 1, 107.086 2, 93.068 9

Hydrogenation of Z-ligustilide

M16

8.90

C₁₅H₁₈O₄

263.128 1

[M+H]⁺

1.0

245.123 3, 217.127 0

Demethylation and methylene to ketone of MCS134

M17

8.98

C₁₂H₁₆O₃

209.117 0

[M+H]⁺

-1.3

153.089 4, 121.062 6, 107.085 4

Dehydroxyl senkyunolide I/H

M18

9.08

C₁₁H₁₂O₃

193.085 9

[M+H]⁺

0.0

175.073 8, 151.109 4, 147.076 7

Demethylation and methylene to ketone of senkyunolide A

M19

9.16

C₁₆H₂₂O₃

263.164 2

[M+H]⁺

0.0

189.096 0, 161.062 1

Methyl atractylenolide Ⅲ

Ⅱ

M20

9.32

C₁₆H₂₀O₅

293.138 6

[M+H]⁺

0.7

275.127 8, 247.132 0, 187.111 5

Demethylation to carboxylic acid of MCS134

M21

9.54

C₁₉H₂₀O₄

313.143 6

[M+H]⁺

0.6

271.093 3, 269.152 4, 267.138 1, 254.094 1, 253.085 6, 249.109 4

Hydroxyl cryptotanshinone

M22

9.82

C₁₉H₁₆O₄

309.112 4

[M+H]⁺

0.8

265.121 9, 223.075 4

Hydroxylation and oxidation of tanshinone Ⅱ_A

M23

9.99

C₁₂H₁₂O₂

189.090 9

[M+H]⁺

-0.5

171.080 5, 161.092 0, 143.085 9, 115.053 4

Dehydrogenation of Z-ligustilide

M24

10.10

C₁₂H₁₄O₂

191.106 6

[M+H]⁺

-0.4

173.093 2, 163.086 2, 107.087 3

Dehydrogenation of senkyunolide F

M25

10.11

C₁₈H₁₂O₃

293.080 9

[M+H]⁺

0.1

293.079 6, 249.091 4

Hydroxyl tanshinone I

M26

10.43

C₁₅H₂₀O₂

233.153 3

[M+H]⁺

-1.5

119.085 9, 91.053 7

Dehydrogenation of atractylenolide Ⅲ

M27

10.47

C₁₅H₂₄O₂

237.184 4

[M+H]⁺

-2.1

163.112 2, 123.116 5, 119.086 2

Oxidation of alismol

M28

10.79

C₁₅H₂₂O₃

251.164 0

[M+H]⁺

-0.8

233.152 3, 205.157 6, 187.149 8, 159.119 6, 133.101 4, 105.069 7

Hydrogenation of atractylenolide Ⅲ

M29

10.99

C₁₉H₁₈O₄

311.127 2

[M+H]⁺

-1.8

293.115 2, 267.138 8, 265.086 5, 247.115 5

Hydroxylation and dehydrogenation of cryptotanshinone

M30

11.29

C₃₀H₄₆O₄

471.346 8

[M+H]⁺

-0.2

453.334 6, 409.356 9

Deacetylation of 3-acetyl-11-keto-β-boswellic acid

M31

11.39

C₁₉H₁₆O₄

309.112 4

[M+H]⁺

0.9

291.101 0, 281.117 0

Dehydrogenation of tanshinone Ⅱ_B

M32

11.66

C₁₉H₂₀O₃

297.148 4

[M+H]⁺

-0.3

251.144 0, 237.090 8

Hydrogenation of tanshinone Ⅱ_A

M33

12.64

C₁₂H₁₆O₃

209.117 0

[M+H]⁺

-1.0

191.106 8, 173.132 8, 165.067 8

Oxidation of senkyunolide A

M34

12.68

C₁₃H₁₆O₃

221.117 1

[M+H]⁺

-0.8

193.124 7, 137.059 6

Methyl senkyunolide F

Ⅱ

M35

12.83

C₃₀H₄₈O₄

471.345 9

[M-H]^-

-4.4

471.346 5, 393.314 7

Hydrogenation of 11-carbonyl-β-boswellic acid

M36

14.01

C₃₀H₄₆O₅

485.325 4

[M-H]^-

-3.8

485.326 9, 423.326 8

Hydroxyl 11-carbonyl-β-boswellic acid

M37

14.57

C₃₂H₄₈O₆

529.350 8

[M+H]⁺

-2.9

511.342 2, 469.333 7, 423.326 3

Hydroxyl 3-acetyl-11-keto-β-boswellic acid

M38

16.38

C₃₂H₄₈O₄

497.361 5

[M+H]⁺

-2.1

479.364 3, 437.340 8

Dehydroxyl 3-acetyl-11-keto-β-boswellic acid