药学学报

No.	Tentative identification	Formula	Source
1	Taurodeoxycholic acid	C₂₆H₄₅NO₆S	CB
2	Glycochenodeoxycholic acid	C₂₆H₄₃NO₅	CB
3	Tetrahydroxycholestan-26-oic acid	C₂₇H₄₆O₆	CB
4	Ursodeoxycholic acid	C₂₄H₄₀O₄	CB
5	Hyodeoxycholic acid	C₂₄H₄₀O₄	CB
6	Ketodeoxycholic acid	C₂₄H₃₈O₄	CB
7	Chenodeoxycholic acid	C₂₄H₄₀O₄	CB
8	Deoxycholic acid	C₂₄H₄₀O₄	CB
9	Methyl cholate	C₂₅H₄₂O₅	CB
10	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
11	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
12	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
13	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
14	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
15	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
16	3α, 6β, 7α, 12α-tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
17	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
18	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
19	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
20	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
21	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
22	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
23	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
24	Cholic acid-sulfate	C₂₄H₄₀O₈S	SG
25	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
26	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
27	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
28	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
29	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
30	Glycocholic acid	C₂₆H₄₃NO₆	CB, SG
31	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
32	Taurochenodeoxycholic acid	C₂₆H₄₅NO₆S	CB, SG
33	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
34	Cholic acid	C₂₄H₄₀O₅	CB, SG
35	Glycodeoxycholic acid	C₂₆H₄₃NO₅	CB, SG

No.	Tentative identification	Formula	Source
1	Taurodeoxycholic acid	C₂₆H₄₅NO₆S	CB
2	Glycochenodeoxycholic acid	C₂₆H₄₃NO₅	CB
3	Tetrahydroxycholestan-26-oic acid	C₂₇H₄₆O₆	CB
4	Ursodeoxycholic acid	C₂₄H₄₀O₄	CB
5	Hyodeoxycholic acid	C₂₄H₄₀O₄	CB
6	Ketodeoxycholic acid	C₂₄H₃₈O₄	CB
7	Chenodeoxycholic acid	C₂₄H₄₀O₄	CB
8	Deoxycholic acid	C₂₄H₄₀O₄	CB
9	Methyl cholate	C₂₅H₄₂O₅	CB
10	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
11	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
12	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
13	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
14	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
15	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
16	3α, 6β, 7α, 12α-tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
17	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
18	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
19	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
20	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
21	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
22	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
23	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
24	Cholic acid-sulfate	C₂₄H₄₀O₈S	SG
25	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
26	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
27	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
28	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
29	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
30	Glycocholic acid	C₂₆H₄₃NO₆	CB, SG
31	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
32	Taurochenodeoxycholic acid	C₂₆H₄₅NO₆S	CB, SG
33	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
34	Cholic acid	C₂₄H₄₀O₅	CB, SG
35	Glycodeoxycholic acid	C₂₆H₄₃NO₅	CB, SG

No.	Compound	Formula	Exact mass	Adduct ion (negative)	MS/MS (negative)	Adduct ion (positive)	MS/MS (positive)	Ref.
1	Notoginsenic acid β-sophoroside	C₂₂H₃₂O₁₃	504.184 3	[M+HCOO]^-	549, 503, 341, 179	[M+Na]⁺	527, 505, 365	[4, 32]
2	Notoginsenoside J/isomer	C₄₂H₇₄O₁₆	834.497 7	[M+HCOO]^-	879, 833, 785, 671	[M+Na]⁺	857, 835, 677, 439, 421	[4, 6, 32]
3	Notoginsenoside J/isomer	C₄₂H₇₄O₁₆	834.497 7	[M+HCOO]^-	879, 833, 785, 671	[M+Na]⁺	857, 835, 677, 439, 421	[4, 6, 32]
4	Ginsenoside Rg1	C₄₂H₇₂O₁₄	800.492 2	[M+HCOO]^-	845, 799, 637, 475	[M+Na]⁺	823, 801, 441, 423, 405	[4, 5, 32]
5	Notoginsenoside R1	C₄₇H₈₀O₁₈	932.534 5	[M-H]^-	931, 799, 769, 637, 475	[M+Na]⁺	955, 801, 770, 477, 459, 441, 423, 405	[4-6, 32]
6	Notoginsenoside R3/N	C₄₈H₈₂O₁₉	962.545 0	[M+HCOO]^-	1 107, 961, 799, 637, 475	[M+Na]⁺	985, 423, 405, 365	[4, 32]
7	Notoginsenoside R3/N	C₄₈H₈₂O₁₉	962.545 0	[M+HCOO]^-	1 107, 961, 799, 637, 475	[M+Na]⁺	985, 423, 405, 365	[4, 32]
8	Ginsenoside Re	C₄₈H₈₂O₁₈	946.550 1	[M-H]^-	945, 783, 621, 459	[M+Na]⁺	969, 423, 405	[4-6, 32]
9	Notoginsenoside R2/isomer	C₄₁H₇₀O₁₃	770.481 6	[M+HCOO]^-	815, 769, 637, 475	[M+Na]⁺	793, 643, 423, 405	[4, 32]
10	Notoginsenoside R2/isomer	C₄₁H₇₀O₁₃	770.481 6	[M+HCOO]^-	815, 769, 637, 475	[M+Na]⁺	793, 643, 423, 405	[4, 32]
11	Ginsenoside Rg2	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 637, 475	[M+Na]⁺	807, 441, 423, 405	[4, 6, 32]
12	Ginsenoside F2	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 621	[M+Na]⁺	807, 425, 407	[4, 32]
13	Ginsenoside Rg3	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 621, 603, 459	[M+Na]⁺	807, 365	[4, 6, 32]
14	Ginsenoside Rh3	C₃₆H₆₀O₇	604.433 9	[M-H]^-	603, 441	[M+Na]⁺	627, 465, 447	[6, 32]
15	Ginsenoside Rb1	C₅₄H₉₂O₂₃	1 108.602 9	[M-H]^-	1 107, 945, 783, 765	[M+Na]⁺	1 131, 425, 407	[4-6, 32]
16	Ginsenoside Rh1	C₃₆H₆₂O₉	638.439 4	[M+HCOO]^-	683, 637, 475, 391, 179, 161	[M+Na]⁺	661, 441, 423, 405	[4, 6, 32]
17	Ginsenoside Rd	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 783, 621, 459	[M+Na]⁺	969, 443, 425, 407	[4, 6, 32]
18	Ginsenoside K	C₄₈H₈₂O₁₈	946.550 1	[M-H]^-	945, 783, 621, 459	[M+Na]⁺	969, 443, 425, 407	[4, 5, 32]
19	Notoginsenoside G/isomer	C₄₈H₈₀O₁₉	960.529 4			[M+Na]⁺	983, 439, 421	[32]
20	Notoginsenoside G/isomer	C₄₈H₈₀O₁₉	960.529 4			[M+Na]⁺	983, 439, 421	[32]
21	Malonylginsenoside Rb1/isomer	C₅₇H₉₄O₂₆	1 194.603 3			[M+Na]⁺	1 217, 1 173, 425, 407	[32]
22	Malonylginsenoside Rb1/isomer	C₅₇H₉₄O₂₆	1 194.603 3			[M+Na]⁺	1 217, 1 173, 425, 407	[32]
23	Malonylginsenoside Rg1	C₄₅H₇₄O₁₇	886.492 6			[M+Na]⁺	909, 865, 441, 423, 405	[32]
24	Ginsenoside Rb2	C₅₃H₉₀O₂₂	1 078.592 4			[M+Na]⁺	1 101, 425, 407	[32]
25	Ginsenoside Rb3	C₅₃H₉₀O₂₂	1 078.592 4			[M+Na]⁺	1 101, 425, 407	[32]
26	Ginsenoside Rh2	C₃₆H₆₂O₈	622.444 5	[M-H]^-	621, 459			[6]
27	Ginsenoside Rf	C₄₂H₇₂O₁₄	800.492 2	[M+HCOO]^-	845, 799, 637, 475			[4, 6]
28	Ginsenoside F1	C₃₆H₆₂O₉	638.439 4	[M+HCOO]^-	683, 637, 475, 391, 179, 161			[4, 31]
29	Ginsenoside Rc	C₅₃H₉₀O₂₂	1 078.592 4	[M-H]^-	1 077, 945, 783, 621, 603, 459			[6]
30	Notoginsenoside K/isomer	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 783, 621, 459			[4, 6]
31	Notoginsenoside ST-5	C₄₇H₈₀O₁₈	932.534 5	[M+HCOO]^-	977, 931			[4]
32	Notoginsenoside A/Koryoginsenoside Rg2	C₅₄H₉₂O₂₄	1 124.597 9	[M-H]^-	1 123, 961, 799			[6]
33	Notoginsenoside A/Koryoginsenoside Rg2	C₅₄H₉₂O₂₄	1 124.597 9	[M-H]^-	1 123, 961, 799			[6]
34	Gypenoside Ⅷ	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 851, 673			[4]
35	Gypenoside Ⅸ	C₄₇H₈₀O₁₇	916.539 6	[M-H]^-	915			[4]
36	Notoginsenoside H	C₄₇H₈₀O₁₉	948.529 4	[M+HCOO]^-	993, 947, 785, 767, 635			[6]
37	Yesanchinoside E	C₅₄H₉₂O₂₃	1 108.602 9	[M-H]^-	1 107, 945, 783, 765			[4]
38	Taurine	C₂H₇NO₃S	125.014 7	[M-H]^-	124, 106, 79	[M+H]⁺	126, 108	[5, 6]
39	Taurocholic acid	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 432, 391, 124, 79	[M+Na]⁺	538, 516, 498, 480, 462, 373, 355	[5, 31, 32]
40	Taurochenodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8	[M-H]^-	498, 480, 355	[M+Na]⁺	522, 500, 482, 464, 354, 254	[4, 6, 32]
41	Taurodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8	[M-H]^-	498, 480, 355	[M+H]⁺	500, 482, 357, 339	[4, 6]
42	Cholic acid	C₂₄H₄₀O₅	408.287 6	[M-H]^-	407, 389, 361, 345, 343, 327	[M+Na]⁺	431, 426, 391, 373, 355, 273, 254	[4-6, 32]
43	Ursodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	393, 375, 357	[4, 6, 32]
44	Chenodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 373	[M+Na]⁺	415, 375, 357	[4-6, 32]
45	Deoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	357, 161	[4, 5]
46	Hyodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	415, 375, 357	[4, 6]
47	Glycocholic acid	C₂₆H₄₃NO₆	465.309 0	[M-H]^-	464, 446, 402, 382, 353	[M+H]⁺	466, 448, 430	[4-6]
48	Glycodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1	[M-H]^-	448, 430, 402, 386	[M+H]⁺	450, 432, 414, 339	[4-6]
49	Gallodesoxycholic acid	C₂₄H₄₀O₄	392.292 7			[M+H]⁺	393, 357	[32]
50	Glycoursodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1			[M+H]⁺	450, 432, 414, 339	[6]
51	Glycohyodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1			[M+H]⁺	450, 432, 414, 339	[6]
52	Taurohyodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8			[M+H]⁺	500, 482, 357	[6]
53	Tauroursodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8			[M+H]⁺	500, 482, 357	[6]
54	Glycochenodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1	[M-H]^-	448, 404, 355			[4]
55	Ketodeoxycholic acid	C₂₄H₃₈O₄	390.277 0	[M-H]^-	389, 371, 309			[4]
56	Homodeoxycholic acid/isomer	C₂₅H₄₀O₅	420.287 6	[M-H]^-	419, 373, 297, 283			[31]
57	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 387, 359, 325			[4]
58	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
59	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
60	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
61	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
62	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
63	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
64	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
65	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
66	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
67	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 480, 456, 358			[4]
68	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 480, 456, 358			[4]
69	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 359, 343			[4]
70	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 343, 289, 251			[4]
71	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 343, 289, 251			[4]
72	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 456, 358, 328			[4]
73	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 456, 358, 328			[4]
74	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-holenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 480, 358, 353			[4]
75	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353, 329			[4]
76	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353, 329			[4]
77	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353			[4]
78	Cholic acid-sulfate	C₂₄H₄₀O₈S	488.244 4	[M-H]^-	487, 452, 408			[4]
79	Methyl cholate	C₂₅H₄₂O₅	422.303 2	[M-H]^-	421, 375, 273			[4]
80	Tetrahydroxycholestan-26-oic acid	C₂₇H₄₆O₆	466.329 4	[M-H]^-	465, 401, 383, 263			[4]
81	Tetradecanoic acid	C₁₄H₂₈O₂	228.208 9	[M-H]^-	227, 199, 181			[31]
82	N-Palmitoyltaurine/isomer	C₁₈H₃₇NO₄S	363.244 3	[M+HCOO]^-	362, 316, 124, 79			[31]
83	Pentadecanoiic acid	C₁₅H₃₀O₂	242.224 6	[M-H]^-	241, 223			[31]
84	Oleic acid	C₁₈H₃₄O₂	282.255 9	[M-H]^-	281, 263			[31]
85	Stearic acid	C₁₈H₃₆O₂	284.271 53	[M-H]^-	283, 265			[31]
86	Malic acid	C₄H₆O₅	134.021 5	[M-H]^-	133, 89			[6]
87	Citric acid	C₆H₈O₇	192.027 0	[M-H]^-	191, 147			[6]
88	Lutein	C₄₀H₅₆O₂	568.428 0			[M+Na]⁺	591, 551, 532	[32]
89	Oleanolic acid	C₃₀H₄₈O₃	456.360 3			[M+H]⁺	457, 439, 411, 393	[32]
90	Muscone	C₁₆H₃₀O	238.229 67			[M+H]⁺	239, 95	[5]

No.	Compound	Formula	Exact mass	Adduct ion (negative)	MS/MS (negative)	Adduct ion (positive)	MS/MS (positive)	Ref.
1	Notoginsenic acid β-sophoroside	C₂₂H₃₂O₁₃	504.184 3	[M+HCOO]^-	549, 503, 341, 179	[M+Na]⁺	527, 505, 365	[4, 32]
2	Notoginsenoside J/isomer	C₄₂H₇₄O₁₆	834.497 7	[M+HCOO]^-	879, 833, 785, 671	[M+Na]⁺	857, 835, 677, 439, 421	[4, 6, 32]
3	Notoginsenoside J/isomer	C₄₂H₇₄O₁₆	834.497 7	[M+HCOO]^-	879, 833, 785, 671	[M+Na]⁺	857, 835, 677, 439, 421	[4, 6, 32]
4	Ginsenoside Rg1	C₄₂H₇₂O₁₄	800.492 2	[M+HCOO]^-	845, 799, 637, 475	[M+Na]⁺	823, 801, 441, 423, 405	[4, 5, 32]
5	Notoginsenoside R1	C₄₇H₈₀O₁₈	932.534 5	[M-H]^-	931, 799, 769, 637, 475	[M+Na]⁺	955, 801, 770, 477, 459, 441, 423, 405	[4-6, 32]
6	Notoginsenoside R3/N	C₄₈H₈₂O₁₉	962.545 0	[M+HCOO]^-	1 107, 961, 799, 637, 475	[M+Na]⁺	985, 423, 405, 365	[4, 32]
7	Notoginsenoside R3/N	C₄₈H₈₂O₁₉	962.545 0	[M+HCOO]^-	1 107, 961, 799, 637, 475	[M+Na]⁺	985, 423, 405, 365	[4, 32]
8	Ginsenoside Re	C₄₈H₈₂O₁₈	946.550 1	[M-H]^-	945, 783, 621, 459	[M+Na]⁺	969, 423, 405	[4-6, 32]
9	Notoginsenoside R2/isomer	C₄₁H₇₀O₁₃	770.481 6	[M+HCOO]^-	815, 769, 637, 475	[M+Na]⁺	793, 643, 423, 405	[4, 32]
10	Notoginsenoside R2/isomer	C₄₁H₇₀O₁₃	770.481 6	[M+HCOO]^-	815, 769, 637, 475	[M+Na]⁺	793, 643, 423, 405	[4, 32]
11	Ginsenoside Rg2	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 637, 475	[M+Na]⁺	807, 441, 423, 405	[4, 6, 32]
12	Ginsenoside F2	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 621	[M+Na]⁺	807, 425, 407	[4, 32]
13	Ginsenoside Rg3	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 621, 603, 459	[M+Na]⁺	807, 365	[4, 6, 32]
14	Ginsenoside Rh3	C₃₆H₆₀O₇	604.433 9	[M-H]^-	603, 441	[M+Na]⁺	627, 465, 447	[6, 32]
15	Ginsenoside Rb1	C₅₄H₉₂O₂₃	1 108.602 9	[M-H]^-	1 107, 945, 783, 765	[M+Na]⁺	1 131, 425, 407	[4-6, 32]
16	Ginsenoside Rh1	C₃₆H₆₂O₉	638.439 4	[M+HCOO]^-	683, 637, 475, 391, 179, 161	[M+Na]⁺	661, 441, 423, 405	[4, 6, 32]
17	Ginsenoside Rd	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 783, 621, 459	[M+Na]⁺	969, 443, 425, 407	[4, 6, 32]
18	Ginsenoside K	C₄₈H₈₂O₁₈	946.550 1	[M-H]^-	945, 783, 621, 459	[M+Na]⁺	969, 443, 425, 407	[4, 5, 32]
19	Notoginsenoside G/isomer	C₄₈H₈₀O₁₉	960.529 4			[M+Na]⁺	983, 439, 421	[32]
20	Notoginsenoside G/isomer	C₄₈H₈₀O₁₉	960.529 4			[M+Na]⁺	983, 439, 421	[32]
21	Malonylginsenoside Rb1/isomer	C₅₇H₉₄O₂₆	1 194.603 3			[M+Na]⁺	1 217, 1 173, 425, 407	[32]
22	Malonylginsenoside Rb1/isomer	C₅₇H₉₄O₂₆	1 194.603 3			[M+Na]⁺	1 217, 1 173, 425, 407	[32]
23	Malonylginsenoside Rg1	C₄₅H₇₄O₁₇	886.492 6			[M+Na]⁺	909, 865, 441, 423, 405	[32]
24	Ginsenoside Rb2	C₅₃H₉₀O₂₂	1 078.592 4			[M+Na]⁺	1 101, 425, 407	[32]
25	Ginsenoside Rb3	C₅₃H₉₀O₂₂	1 078.592 4			[M+Na]⁺	1 101, 425, 407	[32]
26	Ginsenoside Rh2	C₃₆H₆₂O₈	622.444 5	[M-H]^-	621, 459			[6]
27	Ginsenoside Rf	C₄₂H₇₂O₁₄	800.492 2	[M+HCOO]^-	845, 799, 637, 475			[4, 6]
28	Ginsenoside F1	C₃₆H₆₂O₉	638.439 4	[M+HCOO]^-	683, 637, 475, 391, 179, 161			[4, 31]
29	Ginsenoside Rc	C₅₃H₉₀O₂₂	1 078.592 4	[M-H]^-	1 077, 945, 783, 621, 603, 459			[6]
30	Notoginsenoside K/isomer	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 783, 621, 459			[4, 6]
31	Notoginsenoside ST-5	C₄₇H₈₀O₁₈	932.534 5	[M+HCOO]^-	977, 931			[4]
32	Notoginsenoside A/Koryoginsenoside Rg2	C₅₄H₉₂O₂₄	1 124.597 9	[M-H]^-	1 123, 961, 799			[6]
33	Notoginsenoside A/Koryoginsenoside Rg2	C₅₄H₉₂O₂₄	1 124.597 9	[M-H]^-	1 123, 961, 799			[6]
34	Gypenoside Ⅷ	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 851, 673			[4]
35	Gypenoside Ⅸ	C₄₇H₈₀O₁₇	916.539 6	[M-H]^-	915			[4]
36	Notoginsenoside H	C₄₇H₈₀O₁₉	948.529 4	[M+HCOO]^-	993, 947, 785, 767, 635			[6]
37	Yesanchinoside E	C₅₄H₉₂O₂₃	1 108.602 9	[M-H]^-	1 107, 945, 783, 765			[4]
38	Taurine	C₂H₇NO₃S	125.014 7	[M-H]^-	124, 106, 79	[M+H]⁺	126, 108	[5, 6]
39	Taurocholic acid	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 432, 391, 124, 79	[M+Na]⁺	538, 516, 498, 480, 462, 373, 355	[5, 31, 32]
40	Taurochenodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8	[M-H]^-	498, 480, 355	[M+Na]⁺	522, 500, 482, 464, 354, 254	[4, 6, 32]
41	Taurodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8	[M-H]^-	498, 480, 355	[M+H]⁺	500, 482, 357, 339	[4, 6]
42	Cholic acid	C₂₄H₄₀O₅	408.287 6	[M-H]^-	407, 389, 361, 345, 343, 327	[M+Na]⁺	431, 426, 391, 373, 355, 273, 254	[4-6, 32]
43	Ursodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	393, 375, 357	[4, 6, 32]
44	Chenodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 373	[M+Na]⁺	415, 375, 357	[4-6, 32]
45	Deoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	357, 161	[4, 5]
46	Hyodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	415, 375, 357	[4, 6]
47	Glycocholic acid	C₂₆H₄₃NO₆	465.309 0	[M-H]^-	464, 446, 402, 382, 353	[M+H]⁺	466, 448, 430	[4-6]
48	Glycodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1	[M-H]^-	448, 430, 402, 386	[M+H]⁺	450, 432, 414, 339	[4-6]
49	Gallodesoxycholic acid	C₂₄H₄₀O₄	392.292 7			[M+H]⁺	393, 357	[32]
50	Glycoursodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1			[M+H]⁺	450, 432, 414, 339	[6]
51	Glycohyodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1			[M+H]⁺	450, 432, 414, 339	[6]
52	Taurohyodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8			[M+H]⁺	500, 482, 357	[6]
53	Tauroursodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8			[M+H]⁺	500, 482, 357	[6]
54	Glycochenodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1	[M-H]^-	448, 404, 355			[4]
55	Ketodeoxycholic acid	C₂₄H₃₈O₄	390.277 0	[M-H]^-	389, 371, 309			[4]
56	Homodeoxycholic acid/isomer	C₂₅H₄₀O₅	420.287 6	[M-H]^-	419, 373, 297, 283			[31]
57	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 387, 359, 325			[4]
58	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
59	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
60	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
61	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
62	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
63	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
64	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
65	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
66	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
67	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 480, 456, 358			[4]
68	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 480, 456, 358			[4]
69	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 359, 343			[4]
70	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 343, 289, 251			[4]
71	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 343, 289, 251			[4]
72	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 456, 358, 328			[4]
73	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 456, 358, 328			[4]
74	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-holenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 480, 358, 353			[4]
75	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353, 329			[4]
76	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353, 329			[4]
77	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353			[4]
78	Cholic acid-sulfate	C₂₄H₄₀O₈S	488.244 4	[M-H]^-	487, 452, 408			[4]
79	Methyl cholate	C₂₅H₄₂O₅	422.303 2	[M-H]^-	421, 375, 273			[4]
80	Tetrahydroxycholestan-26-oic acid	C₂₇H₄₆O₆	466.329 4	[M-H]^-	465, 401, 383, 263			[4]
81	Tetradecanoic acid	C₁₄H₂₈O₂	228.208 9	[M-H]^-	227, 199, 181			[31]
82	N-Palmitoyltaurine/isomer	C₁₈H₃₇NO₄S	363.244 3	[M+HCOO]^-	362, 316, 124, 79			[31]
83	Pentadecanoiic acid	C₁₅H₃₀O₂	242.224 6	[M-H]^-	241, 223			[31]
84	Oleic acid	C₁₈H₃₄O₂	282.255 9	[M-H]^-	281, 263			[31]
85	Stearic acid	C₁₈H₃₆O₂	284.271 53	[M-H]^-	283, 265			[31]
86	Malic acid	C₄H₆O₅	134.021 5	[M-H]^-	133, 89			[6]
87	Citric acid	C₆H₈O₇	192.027 0	[M-H]^-	191, 147			[6]
88	Lutein	C₄₀H₅₆O₂	568.428 0			[M+Na]⁺	591, 551, 532	[32]
89	Oleanolic acid	C₃₀H₄₈O₃	456.360 3			[M+H]⁺	457, 439, 411, 393	[32]
90	Muscone	C₁₆H₃₀O	238.229 67			[M+H]⁺	239, 95	[5]

片仔癀的物质基础及药理作用研究进展

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杨艳全 , 孙建国 , 阿基业 , 王广基 ^* , 彭英 ^*

药学学报 | 综述 2023,58(8): 2155-2167

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药学学报 |综述 2023 , 58 (8) : 2155 -2167

片仔癀的物质基础及药理作用研究进展

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杨艳全, 孙建国, 阿基业, 王广基^*, 彭英^*

作者信息

中国药科大学, 江苏省药物代谢动力学重点实验室, 江苏南京 210009

通讯作者:

*王广基, Tel: 86-25-83271176, E-mail: guangjiwang@hotmail.com;

彭英, Tel: 13770828062, E-mail: pengy2014@126.com

Research progress on the material basis and pharmacological effects of Pien Tze Huang

Yan-quan YANG, Jian-guo SUN, Ji-ye A, Guang-ji WANG^*, Ying PENG^*

Affiliations

Key Lab of Drug Metabolism and Pharmacokinetics, China Pharmaceutical University, Nanjing 210009, China

出版时间: 2023-08-12 doi: 10.16438/j.0513-4870.2022-1120

文章导航

摘要

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片仔癀药用历史悠久, 且是现今唯一一个工艺和配方“双绝密”的品种, 具有清热解毒、消肿止痛、凉血化瘀之功效。目前, 已有研究者对片仔癀及其主方中三七、牛黄、蛇胆和麝香等名贵药材中的部分化合物进行了分析鉴定, 并对这些化学成分进行了活性筛选和药代动力学、药理学相关研究。发现片仔癀在急慢性肝炎、溃疡、结直肠癌、肝癌等疾病的治疗上效果显著。本文旨在对近些年研究者们在片仔癀的物质基础、药理作用和临床应用等方面的研究成果进行系统的论述, 以期为片仔癀下一步研究的展开提供思路。

关键词

片仔癀 / 物质基础 / 化学成分 / 药理作用

Abstract

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The medicinal history of Pien Tze Huang is long, and it is the only "double top secret" variety of technology and formula at present. It has the effects of clearing heat and detoxifying, detumescence and pain, cooling blood and removing blood stasis. At present, researchers have analyzed and identified some compounds in Pien Tze Huang and its precious medicinal materials, such as Panax notoginseng, calculus bovis, snake gall and musk, and conducted activity screening, pharmacokinetics and pharmacological related studies on these chemical components. It was found that Pien Tze Huang had a significant effect on the treatment of acute and chronic hepatitis, ulcer, colon cancer, liver cancer and other diseases. The purpose of this paper is to systematically discuss the research achievements of researchers in recent years on the material basis, pharmacological effects and clinical application of Pien Tze Huang, with a view to providing ideas for the further research of Pien Tze Huang.

Key words

Pien Tze Huang / material basis / chemical compositions / pharmacological effect

引用本文

杨艳全, 孙建国, 阿基业, 王广基, 彭英. 片仔癀的物质基础及药理作用研究进展. 药学学报, 2023 , 58 (8) : 2155 -2167 . DOI: 10.16438/j.0513-4870.2022-1120

Yan-quan YANG, Jian-guo SUN, Ji-ye A, Guang-ji WANG, Ying PENG. Research progress on the material basis and pharmacological effects of Pien Tze Huang[J]. Acta Pharmaceutica Sinica, 2023 , 58 (8) : 2155 -2167 . DOI: 10.16438/j.0513-4870.2022-1120

正文

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1 概述

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片仔癀是一种是由天然麝香(Moschus)、天然牛黄(Calculus Bovis)、三七[Panax notoginseng (Burk.) F. H. Chen] 和蛇胆(snake gall) 等名贵中药材制成的中成药。其质量标准收载于卫生部颁布的中药成方制剂第18册, 包括两个显色反应及三七药材的薄层鉴别^[1]。在药典中对片仔癀的质量要求包括对三七皂苷R1、人参皂苷Rb1和Rg1对照品、胆酸、去氧胆酸、胆红素的薄层鉴别和麝香酮的含量测定^[2]。片仔癀在我国的药用历史悠久, 最早可追溯至明朝年间, 距今有近五百年的历史。长久以来, 片仔癀因其在热毒血瘀所致急慢性肝炎、痈疽疔疮、跌打损伤、无名肿痛及各种炎症上的显著疗效而形成了极佳的口碑, 后来随着华侨下南洋而流传世界各地, 被国内外中药界誉为“国宝名药”。如今更是已成为海上丝绸之路上的“中国符号”, 连续多年位居中国中成药单品种出口创汇前列。

片仔癀处方属于国家级保密配方, 是唯一一个工艺和配方“双绝密”的品种, 已公开的组方包括三七(85%)、牛黄(5%)、蛇胆(7%) 和麝香(3%) 等^{[2, 3]}。其中, 牛黄、蛇胆清热解毒, 为君药; 麝香活血通经, 消肿止痛, 为臣药; 三七散瘀消肿止痛, 为佐药。目前, 虽已有研究者对这4种名贵药材的化学成分进行了表征, 然而片仔癀作为复方中药, 其中的化学成分尚未得到全面、系统的解析。检索文献发现已有研究者对片仔癀中的部分化学成分进行了初步的鉴定, 并筛选出了一些活性化合物^[4-6]。也有研究者通过相关的药理学研究表明, 片仔癀具有治疗急慢性肝炎、溃疡、外伤、脑保护和抗肿瘤等作用^[7-11]。另外, 片仔癀在治疗结直肠癌(colorectal cancer, CRC)、肝癌(hepatocellular carcinoma, HCC) 及各种炎症上的效果也已在多项临床研究中得到了验证。

本文通过查阅相关文献, 对近年来研究者们在片仔癀的物质基础、药理活性和临床应用等方面最新的研究成果进行系统的论述, 以期能够为片仔癀下一步研究的展开提供思路。

2 片仔癀的物质基础

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2.1 主方

片仔癀属于国家一级中药保护品种, 其配方属于国家级绝密配方, 并且享有永久保护期。目前, 片仔癀公开的组方包括三七、牛黄、蛇胆和麝香等4种名贵药材。

2.1.1 牛黄

牛黄为片仔癀组方中的君药, 其首载于《神农本草经》, 曰“牛黄, 味苦, 平。主惊痫寒热, 热盛狂, 除邪, 逐鬼, 生平泽。”除此之外, 牛黄在历代医家中均有记载。如《名医别录》中言: 主治小儿百病, 诸痫, 热口不开, 大人狂癫。《药性论》: 君, 味甘。能辟邪魅, 安魂定魄, 小儿夜啼, 主卒中恶。

牛黄是牛科动物牛的干燥胆结石, 表面黄红色至棕黄色, 有的表面挂有一层黑色光亮的薄膜, 习称“乌金衣”^[2]。天然牛黄作为一味名贵的传统中药材, 在临床上的使用极其广泛, 但受限于资源的短缺, 牛黄的代用品人工牛黄、培植牛黄和体外培育牛黄等也就应运而生。人工牛黄是根据天然牛黄已知的成分, 以牛胆粉、胆酸、胆红素、猪去氧胆酸、牛磺酸、胆固醇和一些无机盐类等为原料与淀粉混合得到^[12], 在化学成分上与天然牛黄仍有较大差异, 临床疗效也明显不如天然牛黄^[13]。体内培植牛黄是通过外科手术在活牛胆中植入特定的异物核心(致黄因子), 并注射一种促进牛黄产生的菌液, 在异物和菌的刺激下形成牛黄, 由于其产生的环境与天然牛黄相同, 所以其化学成分和药理活性与天然牛黄无明显差异^[14]。但由于其生产周期较长, 并且受到医学伦理的质疑, 所以在市面上流通较少。体外培育牛黄是模拟体内牛黄结石的原理和形成环境, 采用生化和物理方法, 使正常牛胆汁形成牛胆红素钙结石所得到, 其化学成分和药理活性与天然牛黄相近^[15]。目前尚未在天然牛黄中发现可区分于体培牛黄的专属性成分, 但Xia等^[16]研究发现天然牛黄中的共价胆红素显著高于体外培育牛黄, 而体外培育牛黄中结合胆红素比例明显高于天然牛黄且没有游离胆红素, 这也是造成二者药理活性差异的原因之一。

目前, 牛黄的化学成分经多位研究者研究, 现基本已解析清楚, 主要可分为胆汁酸、胆汁色素、胆甾醇、脂肪酸、黏蛋白、氨基酸等物质^[17]。牛黄中的胆汁酸可分为游离型胆汁酸(猪去氧胆酸、熊去氧胆酸、鹅去氧胆酸等) 和结合型胆汁酸, 其中, 结合型胆汁酸又可分为甘氨酸结合型胆汁酸(甘氨熊脱氧胆酸、甘氨脱氧胆酸、甘氨胆酸等) 和牛磺酸结合型胆汁酸(牛磺去氧胆酸、牛磺鹅脱氧胆酸、牛磺胆酸等)^[17]。

2.1.2 蛇胆

蛇胆与牛黄清热解毒, 共同作为片仔癀中的君药。蛇胆为蛇体内贮存胆汁的胆囊, 内含丰富的胆汁酸和胆汁酸盐类, 如牛磺鹅去氧胆酸、牛磺胆酸、牛磺去氧胆酸和甘氨胆酸等^[18]。蛇胆始载于《明医别录》, 具有清热明目、祛风除湿、抗炎、平喘、祛痰、抑菌等功能。在片仔癀中蛇胆与牛黄均是胆汁酸的主要提供者, 但有报道指出二者提供的胆汁酸种类含量有较大不同, 见表 1^[4], 表明二者在片仔癀主方中的作用无法相互替代。

2.1.3 麝香

麝香活血通经, 消肿止痛, 为片仔癀组方中的臣药。麝香为鹿科动物林麝、马麝或原麝成熟雄体香囊中的干燥分泌物^[2], 始载于《神农本草经》: 主辟恶气, 温疟, 痫痓, 去三虫。麝香鹿在过去的半个世纪里急剧下降, 在已发现的7种麝香鹿中有6种濒临灭绝, 我国在2003年将麝科的所有种类调整为国家一级保护野生动物。为确保天然麝香的可持续利用, 中国首批仅允许安宫牛黄丸、六神丸、八宝丹、片仔癀等4种中成药使用天然麝香, 其他中成药使用人工麝香。人工麝香是国家重大科研成果和保密品种, 其制作方法不得而知^[19]。

天然麝香中的化学成分主要可分为大环酮类(如麝香酮)、甾体类(如雄酮)、吡啶类(如羟基麝香吡啶A) 以及多肽蛋白质类和一些脂肪酸类等^[20]。Liang等^[21]采用GC-MS对天然麝香与人工麝香的特征性成分进行鉴别, 发现麝香吡啶(muscopyridine, C₁₆H₂₅N) 和3-甲基十三环酮(3-methylcyclotridecanone, C₁₄H₂₆O) (图 1) 是天然麝香区别于人工麝香的专属成分。Li等^[22]通过对小鼠进行急性和亚急性炎症的抗炎实验, 发现人工麝香和天然麝香在抗炎方面效果相当。He^[23]研究也指出人工麝香和天然麝香对大鼠中枢神经均具有显著性影响(P < 0.05), 但以天然麝香更为明显。

目前, 麝香的评价主要以麝香酮的含量作为标准, 但麝香酮以外的甾体类、多肽类、大环酮类等也逐渐被认为是麝香内的活性成分, 所以在对麝香进行质量评价时, 多活性组分的含量测定已成为业内共识。

2.1.4 三七

三七散瘀消肿止痛, 为片仔癀组方中的佐药。三七是五加科植物三七的干燥根及根茎, 始载于《本草纲目》, 明代李时珍称其为“金不换”。性温, 可止血、定痛, 主治跌扑瘀肿、胸痹绞痛、症瘕、血瘀经闭、痛经、疮痈肿痛等。清朝药学著作《本草纲目拾遗》中记载: “人参补气第一, 三七补血第一, 味同而功亦等, 故称人参三七, 为中药中之最珍贵者。”

三七的主要化学成分为皂苷、环肽类、黄酮类、甾醇类、三七素、氨基酸及挥发油类等^[24], 其中一般认为皂苷类为三七的主要活性成分。根据皂苷的母核结构可以将其分为原人参二醇型皂苷、原人参三醇型皂苷、齐墩果酸型皂苷和C17位侧链变异型皂苷等^[6]。在三七的根、茎、叶中已提取出210余种皂苷类成分, 这些皂苷以20(S)-原人参二醇型(人参皂苷Rb1、Rb2、Rd等) 和20(S)-原人参三醇型皂苷(三七皂苷R1、人参皂苷Re、Rf、Rg1等) 为主^[24]。

2.2 化学成分鉴定

目前, 对片仔癀组方中的三七、牛黄、蛇胆、麝香等各单味药中的化学成分已研究得较为透彻。但片仔癀作为复方中药, 其中的化学成分仍未得到全面、系统的解析, 而片仔癀中各成分的全面解析和阐述是在体外建立其质量标准和研究体内药效基础的前提。

几十年来, 研究者们通过各种检测方式对片仔癀中的化学成分进行鉴别。如气相色谱法^[25]、紫外分光光度法^[26]、薄层色谱法^[27]、高效液相色谱法^[28]、混合胶束毛细管电动色谱法^[29]等。然而使用这些方法仅可对片仔癀中少量的化学成分进行鉴定, 而若想对整个组方中的几种药材进行定性鉴别则至少需要两种或以上的方法。令人欣喜的是, 随着时代的不断发展, 各种中药复方化学成分的鉴定检测方式也在不断更新换代。

Huang等^{[6, 30]}均采用超高效液相色谱串联三重四极杆质谱法(UPLC-QQQ-MS) 从片仔癀中分别鉴定得到13种和39种化合物。Jia等^[31]通过使用TripleTOF 5600+质谱仪(配有电喷雾离子源), 采用直接注射-多级质谱全扫描法(DI-MS/MS^ALL) 分析片仔癀样品提取物。从中初步鉴定出52种化合物, 包括16个皂苷类化合物、24个胆汁酸类化合物、9个脂肪酸类化合物、2个糖类化合物以及1个其他类化合物。同时发现片仔癀中的多数化合物均可在负离子模式下得到良好的响应值, 而来自于麝香的大环酮类化合物则在正离子模式下响应较好。Tang等^[32]运用UPLC-MS技术并结合自建数据库分析片仔癀的化学成分, 鉴定出化合物35种, 包括26种皂苷类、7种胆汁酸类和2种其他类。Li等^[4]建立了一种在线加压溶剂提取方法, 用水作为提取溶剂, 通过升温和加压的方式来提高水对药材中化学成分的溶解和提取能力, 实现了快速、高效的提取。通过这种提取方式, 采用在线加压溶剂提取-超高效液相色谱-离子阱-飞行时间质谱(online PLE-UHPLC-IT-TOF-MS) 法从片仔癀中共检测到73个化学成分, 其中36个来源于三七, 15个来源于蛇胆, 9个来源于牛黄, 11个可能来源于牛黄与蛇胆, 另有2个结构无法确定。现将近些年在片仔癀中鉴定出的化学成分汇总为表 2^{[4-6, 31, 32]}。

2.3 活性化合物研究

片仔癀作为一种中药复方, 与西药相比尤其不同的一点是其在给药后发挥药效的并不单是某一个化学成分, 而是包括皂苷、胆汁酸、类固醇、多肽类等在内的数十种活性化学成分的共同作用。如Huang等^[6]对片仔癀中的27种化合物进行体外抗炎活性评价, 发现有9种皂苷、11种胆汁酸、牛磺酸和麝香酮对肿瘤坏死因子-α (tumor necrosis factor-α, TNF-α) 的产生均具有显著的抑制作用, IC₅₀值为12.34~147.24 μmol·L^-1。

在片仔癀中的数百种化学成分中有多种化学成分被研究者们证实具有较好的药理活性, 其中以皂苷类和胆汁酸类成分研究较多。有研究表明片仔癀中的多种胆汁酸对某些疾病具有较好的药理活性。如熊去氧胆酸可以提高胆固醇胆结石患者胆囊平滑肌的体外收缩能力^[33], 同时它也是原发性胆汁性胆管炎的一线用药, 并具有良好的安全性^{[34, 35]}。牛磺熊去氧胆酸在多种神经退行性疾病模型中具有神经保护作用等^[36]。Liu等^[37]发现鹅去氧胆酸可以通过由白血病细胞线粒体功能障碍引起的活性氧/p38丝裂原活化蛋白激酶/二酰甘油O酰基转移酶同源物1 (reactive oxygen species/p38 mitogen activated protein kinases /diacylglycerol-O-acyltransferase homolog 1, ROS/p38 MAPK/DGAT1) 通路协同促进脂滴积累和脂质过氧化, 并抑制M2巨噬细胞极化, 从而抑制急性髓性白血病进展。同时胆汁酸也是一种信号分子, 它们通过肝细胞、肠细胞和免疫系统细胞中的几种核受体和膜受体作用于脂质代谢和免疫反应, 如法尼醇X受体、孕烷X受体、小异二聚体伴侣受体和G蛋白偶联受体5等^[38]。片仔癀中的皂苷类可抑制外伤性颅内出血^[39]、缓解静脉血栓的症状^[40]、治疗在缺血再灌注后继发的心、脑、肾、肠道、神经等组织的损伤^[41-43], 其中, 人参皂苷Rb1作为一种抗氧化和抗炎剂, 可以保护神经系统和心血管系统。研究表明, Rb1可以通过调节线粒体能量代谢、线粒体分裂和融合、氧化应激和活性氧释放、线粒体自噬和线粒体膜电位来发挥这些作用^{[44, 45]}。人参皂苷Rb2具有抗糖尿病及其并发症作用、心脏保护作用和抗直肠癌的作用、神经保护作用^{[46, 47]}。另外, 猪去氧胆酸、牛磺胆酸、牛磺熊去氧胆酸、甘胆酸、人参皂苷Rg1、Rg2、Rh1、三七皂苷R1、麝香酮等化合物的药理活性也均有报道^[6]。

2.4 药代动力学研究

片仔癀的使用历史极其悠久, 但是相关的药代动力学研究却较为稀少。Xu等^[48]开发了一种UPLC-MS/MS方法, 用于同时检测大鼠口服片仔癀后血浆中的三七皂苷R1、人参皂苷Re、Rg1、Rb1、Rd和麝香酮, 并进行了方法学验证, 成功应用于片仔癀的药代动力学, 但对片仔癀中各成分的药代动力学行为并未进行详细叙述。除此之外, 未检索到其他片仔癀复方直接相关的药代动力学研究。因此, 现对已在片仔癀中被明确鉴定的部分化学成分相关的药代动力学研究作出简要论述, 以期能够为后来的相关研究提供参考。

Li等^[49]对14组大鼠(n = 5) 进行麝香酮的血浆和脑的药代动力学研究, 按125 mg·kg^-1的剂量对大鼠进行灌胃, 采用大鼠心脏采血方式, 并在最后开颅取脑, 发现大鼠口服麝香酮后在血浆和脑中的药代动力学行为符合二房式模型, 血中t_{max (吸收)} = 0.42 h, 脑组织t_{max (吸收)} = 0.54 h, 血和脑组织中的消除速率常数分别为0.45 h^-1和0.56 h^-1, 可知麝香酮在体内的吸收和消除速度均较快, 可以较快产生药效同时又不会产生蓄积。Zhao等^[50]研究了大鼠口服(50 mg·kg^-1) 和静脉给药(10 mg·kg^-1) 后人参皂苷Rb1、Rb2和Rb3的药代动力学行为, 发现口服的生物利用度都很差, Rb1、Rb2和Rb3分别为0.78%、0.08%和0.52%, 通过口服后t_max发现Rb3的吸收最快, Rb1的吸收最慢, 通过静脉给药后的t_1/2表明三种人参皂苷在体内消除均较为缓慢, 而Rb3的t_1/2是24.9 h ± 12.6 h, 三者中最慢。Li等^[51]研究了三七皂苷R1在正常和心肌缺血模型大鼠的体内药动学行为, 将48只SD雄性大鼠等分成正常组和垂体后叶诱导急性心肌缺血模型, 两组都分为三七皂苷R1高、中、低(200、100、50 mg·kg^-1) 剂量组, 灌胃给药后发现与正常大鼠比较, 模型大鼠高低剂量AUC_0-t和AUC_0-∞显著增加(P < 0.01), 消除半衰期显著延长(P < 0.01)。

需要注意的是, 片仔癀复方中的化学成分具有复杂和多样性, 并且部分化学成分之间的相互作用也可能会使相关化合物在体内的药代动力学行为产生变化, 如麝香酮对人参皂苷具有促进吸收作用^[52]。故而单体化合物的研究仅可提供参考价值, 片仔癀在体内的药代动力学行为仍需要进一步的研究。

2.5 代谢物研究

片仔癀中含有上百种化学成分, 一些化学物质在经过体内菌群或者酶的代谢后, 会产生一种或数种代谢物, 有些代谢物无药理活性, 但同时也有一些代谢物可能会有较强的药理活性, 这要求研究者不得不对片仔癀给药后的各种化学成分的一系列代谢物进行鉴定和解析。然而片仔癀在这一方面的研究却较为稀少, 但有部分研究者曾对某些已在片仔癀中得到确证的化学成分的代谢产物进行了研究。

Kim等^[53]采用液相色谱结合三重四极杆质谱技术, 对大鼠灌胃给予人参皂苷Re后的尿液和粪便中的化合物及其代谢物进行鉴定, 发现人参皂苷Re主要转化为人参皂苷Rg1, 除此之外产生了人参皂苷Rg2、Rh1和F1。Lee等^[54]发现人参皂苷Rg1通过肠道微生物群代谢为人参皂苷Rh1、F1和20(S)-原人参三醇, 这些人参皂苷可有效抑制脂多糖(lipopolysaccharide, LPS) 刺激的巨噬细胞中的核因子κB (nuclear factor kappa-B, NF-κB) 活化, 且20(S)-原人参三醇可以非常有效地抑制LPS刺激的巨噬细胞炎症。Shen等^[55]发现人参皂苷Rb1与混合的肠道细菌进行厌氧培养时, Rb1产生了五种代谢物, 即Rd、F2、CpdK和稀有的绞股蓝皂苷XVII、绞股蓝皂苷XXV, 其中人参皂苷F2为主要代谢物。Marschall等^[56]进行了熊去氧胆酸在人体中的代谢物研究, 让10名健康受试者以每人750 mg·d^-1的剂量口服熊去氧胆酸10天, 在开始服药的前一天和最后一天收集了24 h的尿液样本, 采用气相色谱-质谱法和快速原子轰击质谱法进行分析, 发现N-乙酰氨基葡糖偶联物占熊去氧胆酸尿代谢物的50%以上。

3 片仔癀的药理作用

收起

3.1 抗结直肠癌

结直肠癌是全球死亡率排名第三的癌症^[11], 严重威胁着人们的生命健康安全。白细胞介素-6/信号传导转录激活因子3 (interleukin-6/signal transducer and activator of transcription 3, IL-6/STAT3) 是已知在CRC中发生故障的最关键的细胞信号转导途径之一^[57]。作为STAT3信号转导的靶基因, 细胞因子信号抑制因子-3 (suppressor of cytokine signaling-3, SOCS3) 可通过IL-6的刺激被快速诱导, 但随后通过竞争性结合糖蛋白130和两面神激酶限制IL-6介导的STAT3磷酸化^[58]。STAT3的异常激活和SOCS的表达降低与致癌作用密切相关。研究表明, 片仔癀可以显著呈剂量依赖性地抑制IL-6介导的HT-29细胞中STAT3磷酸化水平和转录活性的增加, 从而抑制癌细胞增殖并诱导癌细胞凋亡^[59]。Shen等^[60]的研究表明片仔癀处理抑制Caco-2细胞中细胞周期蛋白-D1 (cyclin-D1) 和细胞周期蛋白依赖性激酶4 (cyclin-dependent-kinases 4, CDK4) 的mRNA和蛋白质表达, 阻断了G1/S细胞周期进程, 从而使癌细胞的增殖受阻。除此之外, 血管生成在癌症进展和转移中也具有重要作用, 肿瘤细胞诱导新血管的生成, 从中获取营养以支持肿瘤的持续生长并为肿瘤转移提供条件^[61]。Shen等^[62]首次证明片仔癀通过抑制导致肿瘤血管生成的多种细胞内信号通路来抑制CRC的生长, 这可能部分解释了其抗癌活性。另外, 有越来越多的证据表明, 被称为癌症干细胞(cancer stem cell, CSC) 的一小部分细胞在肿瘤发展和耐药性中至关重要, 会导致癌症复发和转移^[63]。Wei等^[64]研究片仔癀对从HT-29细胞系中作为侧群(side population, SP) 分离的CSC的影响。结果表明, 片仔癀显著且呈剂量依赖性地降低了CRC干细胞样SP细胞的百分比, 降低了HT-29 SP细胞的活力和成球能力。而且, 片仔癀处理后的HT-29 SP细胞中的ATP结合盒B亚家族成员1和ATP结合盒转运蛋白G2的mRNA水平显著受到抑制^[65], 表明片仔癀处理降低了CSC的多药耐药性。

除了以上这些, 研究者们还在片仔癀抗CRC的其他机制上做了大量研究。Lin等^[66]使用各种人类CRC细胞系评估了片仔癀对癌细胞迁移和血管内皮生长因子-C (vascularendothelial growth factor-C, VEGF-C) 表达的影响, 证明片仔癀通过下调VEGF-C抑制淋巴管生成, 以此来抑制CRC的转移。Chen等^[10]的研究表明, 片仔癀通过抑制Wnt/β-连环蛋白信号传导来下调增殖细胞核抗原和cyclin-D1的表达, 从而抑制了CRC的增殖活性, 他们还发现片仔癀在药理学上提高了抗PD-1/PD-L1免疫疗法的抗肿瘤功效, 即片仔癀对免疫治疗的协同增强作用。除此之外, 一些研究还表明片仔癀可以通过抑制CRC细胞上皮间质转化来治疗癌症^[67]。

3.2 抗肝癌

肝癌是全球癌症相关死亡的主要原因之一, 目前主要通过手术、化疗和靶向药物来进行治疗。然而, 由于耐药性和非特异性细胞毒性的发展, 这些治疗方案存在着明显的限制。近些年, 研究者们对片仔癀的抗HCC作用进行了较多的研究。

Qi等^[68]探讨了片仔癀对BEL-7402肝癌细胞系增殖和凋亡的影响, 发现片仔癀的治疗显著下调了抗凋亡基因Bcl-2和促增殖因子cyclin-D1和CDK4的表达, 进而抑制了BEL-7402的细胞活力、融合和克隆形成, 诱导细胞周期停滞和促进细胞凋亡。Fan等^[9]对HCC异种移植Balb/c小鼠进行片仔癀治疗, 然后使用蛋白质组学检测和IPA软件分析肿瘤组织中的分化磷酸化蛋白, 在片仔癀处理的小鼠中鉴定出84种上调和11种下调的磷酸化蛋白。其中, 20条信号通路与炎症(包括IL-6和TNFR1/2通路)、癌症生长(包括p53和FAK通路) 和细胞周期(包括G2/M和G1/S检查点调节通路) 相关。这表明片仔癀在HCC中的抗肿瘤活性可能是通过调节炎症相关的细胞因子分泌、癌症生长途径和诱导G2/M停滞来实现的。Luo等^[69]通过将SK-Hep-1细胞通过尾静脉注射到B-NDG小鼠体内, 构建的肺转移小鼠模型用于评估片仔癀的抗转移功能, 结果表明片仔癀显著抑制了血小板衍生生长因子受体β (platelet-derived growth factor receptor β, PDGFR β)、YES关联蛋白(YES-associated protein, YAP)、结缔组织生长因子2 (connective tissue growth factor 2, CCN2) 和N-钙黏蛋白的表达, 进而得出片仔癀可能是通过抑制PDGFRB/YAP/CCN2轴来抑制HCC细胞的迁移、侵袭和上皮间质转化。

3.3 抗炎

“癀”在福建文化中意为热毒肿痛, 片仔癀对此病医治有奇效, 几个世纪以来片仔癀一直在中国和东南亚被用以治疗各种炎症性疾病, 如肝炎、结肠炎、关节炎等。

Lian等^[70]为探究片仔癀在非酒精性脂肪肝炎中的作用机制, 使用蛋氨酸-胆碱缺乏饮食和高脂肪饮食诱导了两种非酒精性脂肪肝炎小鼠模型。给药后发现片仔癀可以通过改善肝脏重量和脂肪变性以及降低丙氨酸转氨酶(alanine transaminase, ALT) 和天冬氨酸转氨酶(aspartate transaminase, AST) 血清水平来发挥保肝作用。在机制上, 片仔癀通过阻止NF-κB抑制蛋白α的降解来抑制促炎转录因子NF-κB的活化来发挥作用。Liu等^[71]使用刀豆球蛋白A诱导自身免疫性肝炎模型, 该模型中M1型巨噬细胞显著增加而M2型巨噬细胞则被抑制, M1/M2比例失衡, 大量TNF-α、IL-12、IL-1β等炎性因子被分泌, ALT、AST水平升高。对于片仔癀给药组, 以上指标均得到明显改善(P < 0.05)。此外, 该研究提到片仔癀对肝炎的治疗也有可能是通过肠道菌群而发生作用。

Li等^[72]使用硫酸葡聚糖钠盐(dextran sulfate sodium, DSS) 建立了小鼠结肠炎模型, 并通过观察临床表现评估了片仔癀对溃疡性结肠炎(ulcerative colitis, UC) 的治疗效果, 发现片仔癀明显减轻了DSS引起的结肠炎症状, 包括体重减轻、直肠出血和大便稠度等。并且UC小鼠中炎症生物标志物血清淀粉酶A的血清水平、结肠组织中IL-6的表达以及IL-6诱导的STAT3磷酸化水平也被片仔癀显著抑制。Deng等^[73]使用雄性DBA/1J小鼠建立胶原诱导关节炎(collagen-induced arthritis, CIA) 动物模型, 给予不同剂量的片仔癀治疗4周, 发现片仔癀可以减轻CIA小鼠后爪红斑肿胀, 改善关节病理状况, 减少血清和关节中IL-1β、IL-6和IL-17的产生。除此之外, 有研究者发现片仔癀对肠道黏膜炎, 以及对自身免疫性脑脊髓炎、脑缺血再灌注损伤的神经炎症也有较好的治疗作用^{[74, 75]}。

3.4 其他作用

除抗结直肠癌、肝癌以及各种炎症外, 也有研究者对片仔癀的其他药理作用进行了研究。Zhu等^[76]使用CCl₄-诱导小鼠模型, 建立用片仔癀处理的肝纤维化小鼠的片仔癀组和未经任何处理的肝纤维化小鼠的对照组, 发现片仔癀可以显著抑制炎症细胞浸润和胶原沉积, 并且片仔癀治疗组的ALT、AST和血清白蛋白在第8周显著下降(P < 0.05), 这表明片仔癀可以通过增强免疫过程来减轻肝损伤和纤维化。与之相应的, Zheng等^[77]的研究也验证了这个结论。Yan等^[78]以剂量依赖性方式研究了片仔癀对高浓度葡萄糖损伤的表皮成纤维细胞的抗细胞凋亡作用, 然后比较了系统给药和局部给药途径对链脲佐菌素诱导的糖尿病小鼠切除创面的影响。发现片仔癀降低了细胞中的ROS水平, 通过ROS/Bcl-2/Bax/Caspase-3途径防止细胞损伤和凋亡, 通过刺激1型胶原蛋白分泌、减少成纤维细胞凋亡、增强肌成纤维细胞分化促进伤口闭合。另外, 一些研究表明, 片仔癀对脑缺血损伤、肝损伤、卵巢癌和乳腺癌等病症也有较好的治疗作用^[79-81]。

4 片仔癀的临床应用

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4.1 抗炎

片仔癀作为中国古方, 在中国已使用多年, 传统上片仔癀在临床上被用于清热解毒及治疗肝炎、痈疽疔疮、无名肿痛等疾病。Zhang等^[82]对171位接受片仔癀治疗的肝炎患者进行了临床观察。171位患者中, 甲肝41例, 乙肝43例, 甲乙混合肝炎33例, 慢性肝炎40例, 其他肝炎14例。对照组52例中, 甲肝24例, 乙肝4例, 甲乙混合肝炎8例, 慢性肝炎10例, 其他肝炎6例。观察结果显示, 片仔癀对各类肝炎的疗效显著、安全可靠。片仔癀对各类肝炎的治疗效果也在几十年来的多项临床研究中得到了证实^{[83, 84]}。另外, 一些临床研究表明片仔癀对胆囊炎、关节炎等疾病也有着明显的临床疗效^{[85, 86]}。

4.2 抗肿瘤

目前, 随着中医药在抗肿瘤领域研究的不断深入, 复方斑蝥丸、槐耳颗粒、六神丸、西黄丸等多种中成药逐渐被用于肿瘤治疗。片仔癀也是其中之一, 其对CRC、HCC等癌症的治疗效果现已在多项临床研究中得到证实。

Gu等^[87]对25例晚期CRC患者经用片仔癀治疗后做出的疗效观察报告, 表明片仔癀对晚期CRC的治疗确有疗效。Lin等^[88]对47例经中医辨证为毒热瘀结型晚期结肠癌患者随机分为治疗组(片仔癀联合奥沙利铂、5-Fu、亚叶酸钙) 24例和对照组(奥沙利铂、5-Fu、亚叶酸钙) 23例, 观察近期疗效。发现治疗组相较于对照组, 有效率更高、不良反应发生率更低(P < 0.05)。Guo等^[89]将182例原发性HCC患者分为试验组(n = 92) 和对照组(n = 90), 对照组使用伽马刀立体定向放疗治疗, 试验组使用放疗和片仔癀联合治疗。生存分析显示, 试验组的生存期显著高于对照组, 且不良反应显著低于对照组。Huang等^[90]的临床研究也再次验证了片仔癀对原发性HCC的治疗作用。

5 总结与展望

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片仔癀作为我国唯一一个工艺和配方“双绝密”的品种, 其地位是毋庸置疑的。在过去的几十年中, 它的各种药理作用和临床疗效均已在多项临床和非临床研究中得到验证。尤其是在CRC、HCC、脑损伤以及各类炎症的治疗上效果显著。然而即便如此, 片仔癀仍不得不去面对的一个问题是, 它其中所包含的各类化学成分仍未得到完全的解析和说明, 尤其是麝香相关化学成分, 只在片仔癀中鉴定出极少一部分。而片仔癀中各成分的全面解析和阐述是在体外建立其质量标准和研究体内药效机制的前提, 故而对片仔癀进行严谨详细的化学成分鉴定是必不可少的。除此之外, 片仔癀中含有天然麝香和天然牛黄, 而天然麝香和天然牛黄正面临着资源短缺问题。目前, 有研究者试图探讨在片仔癀中使用人工麝香和体外培育牛黄来代替天然麝香和天然牛黄的可能性, 然而使用人造麝香、牛黄和使用天然麝香、牛黄所制成的片仔癀之间的化学成分和药理作用之间的具有哪些差异仍是尚未解决的问题。另外, 片仔癀相关的药代动力学研究仍较为匮乏, 需要更多的相关研究来阐明其在体内的吸收、分布、代谢和排泄特征, 以更好地解释其药效并对临床用药做出指导。总体来说, 片仔癀在CRC、HCC、缺血性损伤和各类炎症的治疗上具有极大的潜力, 然而在其物质基础和药理作用机制等方面仍需更深入的研究。

作者贡献: 杨艳全负责文章的撰写工作; 孙建国和阿基业负责相关资料的搜集和文章的审核; 王广基和彭英负责指导文章的写作与修改。

利益冲突: 所有作者均声明不存在利益冲突。

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2023年第58卷第8期

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doi: 10.16438/j.0513-4870.2022-1120

接收时间：2022-10-18
首发时间：2025-11-21
出版时间：2023-08-12

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收稿日期：2022-10-18
修回日期：2023-01-18

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中国药科大学, 江苏省药物代谢动力学重点实验室, 江苏南京 210009

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*王广基, Tel: 86-25-83271176, E-mail: guangjiwang@hotmail.com;

彭英, Tel: 13770828062, E-mail: pengy2014@126.com

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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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TxT

No.	Tentative identification	Formula	Source
1	Taurodeoxycholic acid	C₂₆H₄₅NO₆S	CB
2	Glycochenodeoxycholic acid	C₂₆H₄₃NO₅	CB
3	Tetrahydroxycholestan-26-oic acid	C₂₇H₄₆O₆	CB
4	Ursodeoxycholic acid	C₂₄H₄₀O₄	CB
5	Hyodeoxycholic acid	C₂₄H₄₀O₄	CB
6	Ketodeoxycholic acid	C₂₄H₃₈O₄	CB
7	Chenodeoxycholic acid	C₂₄H₄₀O₄	CB
8	Deoxycholic acid	C₂₄H₄₀O₄	CB
9	Methyl cholate	C₂₅H₄₂O₅	CB
10	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
11	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
12	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
13	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
14	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
15	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
16	3α, 6β, 7α, 12α-tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
17	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
18	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
19	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	SG
20	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	SG
21	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
22	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
23	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	SG
24	Cholic acid-sulfate	C₂₄H₄₀O₈S	SG
25	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
26	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
27	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
28	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	CB, SG
29	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
30	Glycocholic acid	C₂₆H₄₃NO₆	CB, SG
31	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
32	Taurochenodeoxycholic acid	C₂₆H₄₅NO₆S	CB, SG
33	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	CB, SG
34	Cholic acid	C₂₄H₄₀O₅	CB, SG
35	Glycodeoxycholic acid	C₂₆H₄₃NO₅	CB, SG

No.

Tentative identification

Formula

Source

Taurodeoxycholic acid

C₂₆H₄₅NO₆S

Glycochenodeoxycholic acid

C₂₆H₄₃NO₅

Tetrahydroxycholestan-26-oic acid

C₂₇H₄₆O₆

Ursodeoxycholic acid

C₂₄H₄₀O₄

Hyodeoxycholic acid

C₂₄H₄₀O₄

Ketodeoxycholic acid

C₂₄H₃₈O₄

Chenodeoxycholic acid

C₂₄H₄₀O₄

Deoxycholic acid

C₂₄H₄₀O₄

Methyl cholate

C₂₅H₄₂O₅

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

3α, 6β, 7α, 12α-tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

Cholic acid-sulfate

C₂₄H₄₀O₈S

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

CB, SG

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

CB, SG

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

CB, SG

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

CB, SG

3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer

C₂₄H₃₈O₅

CB, SG

Glycocholic acid

C₂₆H₄₃NO₆

CB, SG

3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer

C₂₄H₃₈O₅

CB, SG

Taurochenodeoxycholic acid

C₂₆H₄₅NO₆S

CB, SG

3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer

C₂₄H₃₈O₅

CB, SG

Cholic acid

C₂₄H₄₀O₅

CB, SG

Glycodeoxycholic acid

C₂₆H₄₃NO₅

CB, SG

No.	Compound	Formula	Exact mass	Adduct ion (negative)	MS/MS (negative)	Adduct ion (positive)	MS/MS (positive)	Ref.
1	Notoginsenic acid β-sophoroside	C₂₂H₃₂O₁₃	504.184 3	[M+HCOO]^-	549, 503, 341, 179	[M+Na]⁺	527, 505, 365	[4, 32]
2	Notoginsenoside J/isomer	C₄₂H₇₄O₁₆	834.497 7	[M+HCOO]^-	879, 833, 785, 671	[M+Na]⁺	857, 835, 677, 439, 421	[4, 6, 32]
3	Notoginsenoside J/isomer	C₄₂H₇₄O₁₆	834.497 7	[M+HCOO]^-	879, 833, 785, 671	[M+Na]⁺	857, 835, 677, 439, 421	[4, 6, 32]
4	Ginsenoside Rg1	C₄₂H₇₂O₁₄	800.492 2	[M+HCOO]^-	845, 799, 637, 475	[M+Na]⁺	823, 801, 441, 423, 405	[4, 5, 32]
5	Notoginsenoside R1	C₄₇H₈₀O₁₈	932.534 5	[M-H]^-	931, 799, 769, 637, 475	[M+Na]⁺	955, 801, 770, 477, 459, 441, 423, 405	[4-6, 32]
6	Notoginsenoside R3/N	C₄₈H₈₂O₁₉	962.545 0	[M+HCOO]^-	1 107, 961, 799, 637, 475	[M+Na]⁺	985, 423, 405, 365	[4, 32]
7	Notoginsenoside R3/N	C₄₈H₈₂O₁₉	962.545 0	[M+HCOO]^-	1 107, 961, 799, 637, 475	[M+Na]⁺	985, 423, 405, 365	[4, 32]
8	Ginsenoside Re	C₄₈H₈₂O₁₈	946.550 1	[M-H]^-	945, 783, 621, 459	[M+Na]⁺	969, 423, 405	[4-6, 32]
9	Notoginsenoside R2/isomer	C₄₁H₇₀O₁₃	770.481 6	[M+HCOO]^-	815, 769, 637, 475	[M+Na]⁺	793, 643, 423, 405	[4, 32]
10	Notoginsenoside R2/isomer	C₄₁H₇₀O₁₃	770.481 6	[M+HCOO]^-	815, 769, 637, 475	[M+Na]⁺	793, 643, 423, 405	[4, 32]
11	Ginsenoside Rg2	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 637, 475	[M+Na]⁺	807, 441, 423, 405	[4, 6, 32]
12	Ginsenoside F2	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 621	[M+Na]⁺	807, 425, 407	[4, 32]
13	Ginsenoside Rg3	C₄₂H₇₂O₁₃	784.497 3	[M+HCOO]^-	829, 783, 621, 603, 459	[M+Na]⁺	807, 365	[4, 6, 32]
14	Ginsenoside Rh3	C₃₆H₆₀O₇	604.433 9	[M-H]^-	603, 441	[M+Na]⁺	627, 465, 447	[6, 32]
15	Ginsenoside Rb1	C₅₄H₉₂O₂₃	1 108.602 9	[M-H]^-	1 107, 945, 783, 765	[M+Na]⁺	1 131, 425, 407	[4-6, 32]
16	Ginsenoside Rh1	C₃₆H₆₂O₉	638.439 4	[M+HCOO]^-	683, 637, 475, 391, 179, 161	[M+Na]⁺	661, 441, 423, 405	[4, 6, 32]
17	Ginsenoside Rd	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 783, 621, 459	[M+Na]⁺	969, 443, 425, 407	[4, 6, 32]
18	Ginsenoside K	C₄₈H₈₂O₁₈	946.550 1	[M-H]^-	945, 783, 621, 459	[M+Na]⁺	969, 443, 425, 407	[4, 5, 32]
19	Notoginsenoside G/isomer	C₄₈H₈₀O₁₉	960.529 4			[M+Na]⁺	983, 439, 421	[32]
20	Notoginsenoside G/isomer	C₄₈H₈₀O₁₉	960.529 4			[M+Na]⁺	983, 439, 421	[32]
21	Malonylginsenoside Rb1/isomer	C₅₇H₉₄O₂₆	1 194.603 3			[M+Na]⁺	1 217, 1 173, 425, 407	[32]
22	Malonylginsenoside Rb1/isomer	C₅₇H₉₄O₂₆	1 194.603 3			[M+Na]⁺	1 217, 1 173, 425, 407	[32]
23	Malonylginsenoside Rg1	C₄₅H₇₄O₁₇	886.492 6			[M+Na]⁺	909, 865, 441, 423, 405	[32]
24	Ginsenoside Rb2	C₅₃H₉₀O₂₂	1 078.592 4			[M+Na]⁺	1 101, 425, 407	[32]
25	Ginsenoside Rb3	C₅₃H₉₀O₂₂	1 078.592 4			[M+Na]⁺	1 101, 425, 407	[32]
26	Ginsenoside Rh2	C₃₆H₆₂O₈	622.444 5	[M-H]^-	621, 459			[6]
27	Ginsenoside Rf	C₄₂H₇₂O₁₄	800.492 2	[M+HCOO]^-	845, 799, 637, 475			[4, 6]
28	Ginsenoside F1	C₃₆H₆₂O₉	638.439 4	[M+HCOO]^-	683, 637, 475, 391, 179, 161			[4, 31]
29	Ginsenoside Rc	C₅₃H₉₀O₂₂	1 078.592 4	[M-H]^-	1 077, 945, 783, 621, 603, 459			[6]
30	Notoginsenoside K/isomer	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 783, 621, 459			[4, 6]
31	Notoginsenoside ST-5	C₄₇H₈₀O₁₈	932.534 5	[M+HCOO]^-	977, 931			[4]
32	Notoginsenoside A/Koryoginsenoside Rg2	C₅₄H₉₂O₂₄	1 124.597 9	[M-H]^-	1 123, 961, 799			[6]
33	Notoginsenoside A/Koryoginsenoside Rg2	C₅₄H₉₂O₂₄	1 124.597 9	[M-H]^-	1 123, 961, 799			[6]
34	Gypenoside Ⅷ	C₄₈H₈₂O₁₈	946.550 1	[M+HCOO]^-	991, 945, 851, 673			[4]
35	Gypenoside Ⅸ	C₄₇H₈₀O₁₇	916.539 6	[M-H]^-	915			[4]
36	Notoginsenoside H	C₄₇H₈₀O₁₉	948.529 4	[M+HCOO]^-	993, 947, 785, 767, 635			[6]
37	Yesanchinoside E	C₅₄H₉₂O₂₃	1 108.602 9	[M-H]^-	1 107, 945, 783, 765			[4]
38	Taurine	C₂H₇NO₃S	125.014 7	[M-H]^-	124, 106, 79	[M+H]⁺	126, 108	[5, 6]
39	Taurocholic acid	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 432, 391, 124, 79	[M+Na]⁺	538, 516, 498, 480, 462, 373, 355	[5, 31, 32]
40	Taurochenodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8	[M-H]^-	498, 480, 355	[M+Na]⁺	522, 500, 482, 464, 354, 254	[4, 6, 32]
41	Taurodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8	[M-H]^-	498, 480, 355	[M+H]⁺	500, 482, 357, 339	[4, 6]
42	Cholic acid	C₂₄H₄₀O₅	408.287 6	[M-H]^-	407, 389, 361, 345, 343, 327	[M+Na]⁺	431, 426, 391, 373, 355, 273, 254	[4-6, 32]
43	Ursodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	393, 375, 357	[4, 6, 32]
44	Chenodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 373	[M+Na]⁺	415, 375, 357	[4-6, 32]
45	Deoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	357, 161	[4, 5]
46	Hyodeoxycholic acid	C₂₄H₄₀O₄	392.292 7	[M-H]^-	391, 345, 327	[M+H]⁺	415, 375, 357	[4, 6]
47	Glycocholic acid	C₂₆H₄₃NO₆	465.309 0	[M-H]^-	464, 446, 402, 382, 353	[M+H]⁺	466, 448, 430	[4-6]
48	Glycodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1	[M-H]^-	448, 430, 402, 386	[M+H]⁺	450, 432, 414, 339	[4-6]
49	Gallodesoxycholic acid	C₂₄H₄₀O₄	392.292 7			[M+H]⁺	393, 357	[32]
50	Glycoursodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1			[M+H]⁺	450, 432, 414, 339	[6]
51	Glycohyodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1			[M+H]⁺	450, 432, 414, 339	[6]
52	Taurohyodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8			[M+H]⁺	500, 482, 357	[6]
53	Tauroursodeoxycholic acid	C₂₆H₄₅NO₆S	499.296 8			[M+H]⁺	500, 482, 357	[6]
54	Glycochenodeoxycholic acid	C₂₆H₄₃NO₅	449.314 1	[M-H]^-	448, 404, 355			[4]
55	Ketodeoxycholic acid	C₂₄H₃₈O₄	390.277 0	[M-H]^-	389, 371, 309			[4]
56	Homodeoxycholic acid/isomer	C₂₅H₄₀O₅	420.287 6	[M-H]^-	419, 373, 297, 283			[31]
57	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 387, 359, 325			[4]
58	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
59	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
60	3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer	C₂₄H₄₀O₆	424.282 5	[M-H]^-	423, 405, 325			[4]
61	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
62	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
63	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
64	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
65	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
66	Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer	C₂₆H₄₅NO₈S	531.286 6	[M-H]^-	530, 512			[4]
67	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 480, 456, 358			[4]
68	Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 480, 456, 358			[4]
69	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 359, 343			[4]
70	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 343, 289, 251			[4]
71	3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer	C₂₄H₃₈O₅	406.271 9	[M-H]^-	405, 343, 289, 251			[4]
72	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 456, 358, 328			[4]
73	Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer	C₂₆H₄₃NO₇S	513.276 0	[M-H]^-	512, 456, 358, 328			[4]
74	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-holenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 480, 358, 353			[4]
75	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353, 329			[4]
76	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353, 329			[4]
77	Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer	C₂₆H₄₅NO₇S	515.291 7	[M-H]^-	514, 496, 353			[4]
78	Cholic acid-sulfate	C₂₄H₄₀O₈S	488.244 4	[M-H]^-	487, 452, 408			[4]
79	Methyl cholate	C₂₅H₄₂O₅	422.303 2	[M-H]^-	421, 375, 273			[4]
80	Tetrahydroxycholestan-26-oic acid	C₂₇H₄₆O₆	466.329 4	[M-H]^-	465, 401, 383, 263			[4]
81	Tetradecanoic acid	C₁₄H₂₈O₂	228.208 9	[M-H]^-	227, 199, 181			[31]
82	N-Palmitoyltaurine/isomer	C₁₈H₃₇NO₄S	363.244 3	[M+HCOO]^-	362, 316, 124, 79			[31]
83	Pentadecanoiic acid	C₁₅H₃₀O₂	242.224 6	[M-H]^-	241, 223			[31]
84	Oleic acid	C₁₈H₃₄O₂	282.255 9	[M-H]^-	281, 263			[31]
85	Stearic acid	C₁₈H₃₆O₂	284.271 53	[M-H]^-	283, 265			[31]
86	Malic acid	C₄H₆O₅	134.021 5	[M-H]^-	133, 89			[6]
87	Citric acid	C₆H₈O₇	192.027 0	[M-H]^-	191, 147			[6]
88	Lutein	C₄₀H₅₆O₂	568.428 0			[M+Na]⁺	591, 551, 532	[32]
89	Oleanolic acid	C₃₀H₄₈O₃	456.360 3			[M+H]⁺	457, 439, 411, 393	[32]
90	Muscone	C₁₆H₃₀O	238.229 67			[M+H]⁺	239, 95	[5]

No.

Compound

Formula

Exact mass

Adduct ion (negative)

MS/MS (negative)

Adduct ion (positive)

MS/MS (positive)

Ref.

Notoginsenic acid β-sophoroside

C₂₂H₃₂O₁₃

504.184 3

[M+HCOO]^-

549, 503, 341, 179

[M+Na]⁺

527, 505, 365

[4, 32]

Notoginsenoside J/isomer

C₄₂H₇₄O₁₆

834.497 7

[M+HCOO]^-

879, 833, 785, 671

[M+Na]⁺

857, 835, 677, 439, 421

[4, 6, 32]

Notoginsenoside J/isomer

C₄₂H₇₄O₁₆

834.497 7

[M+HCOO]^-

879, 833, 785, 671

[M+Na]⁺

857, 835, 677, 439, 421

[4, 6, 32]

Ginsenoside Rg1

C₄₂H₇₂O₁₄

800.492 2

[M+HCOO]^-

845, 799, 637, 475

[M+Na]⁺

823, 801, 441, 423, 405

[4, 5, 32]

Notoginsenoside R1

C₄₇H₈₀O₁₈

932.534 5

[M-H]^-

931, 799, 769, 637, 475

[M+Na]⁺

955, 801, 770, 477, 459, 441, 423, 405

[4-6, 32]

Notoginsenoside R3/N

C₄₈H₈₂O₁₉

962.545 0

[M+HCOO]^-

1 107, 961, 799, 637, 475

[M+Na]⁺

985, 423, 405, 365

[4, 32]

Notoginsenoside R3/N

C₄₈H₈₂O₁₉

962.545 0

[M+HCOO]^-

1 107, 961, 799, 637, 475

[M+Na]⁺

985, 423, 405, 365

[4, 32]

Ginsenoside Re

C₄₈H₈₂O₁₈

946.550 1

[M-H]^-

945, 783, 621, 459

[M+Na]⁺

969, 423, 405

[4-6, 32]

Notoginsenoside R2/isomer

C₄₁H₇₀O₁₃

770.481 6

[M+HCOO]^-

815, 769, 637, 475

[M+Na]⁺

793, 643, 423, 405

[4, 32]

Notoginsenoside R2/isomer

C₄₁H₇₀O₁₃

770.481 6

[M+HCOO]^-

815, 769, 637, 475

[M+Na]⁺

793, 643, 423, 405

[4, 32]

Ginsenoside Rg2

C₄₂H₇₂O₁₃

784.497 3

[M+HCOO]^-

829, 783, 637, 475

[M+Na]⁺

807, 441, 423, 405

[4, 6, 32]

Ginsenoside F2

C₄₂H₇₂O₁₃

784.497 3

[M+HCOO]^-

829, 783, 621

[M+Na]⁺

807, 425, 407

[4, 32]

Ginsenoside Rg3

C₄₂H₇₂O₁₃

784.497 3

[M+HCOO]^-

829, 783, 621, 603, 459

[M+Na]⁺

807, 365

[4, 6, 32]

Ginsenoside Rh3

C₃₆H₆₀O₇

604.433 9

[M-H]^-

603, 441

[M+Na]⁺

627, 465, 447

[6, 32]

Ginsenoside Rb1

C₅₄H₉₂O₂₃

1 108.602 9

[M-H]^-

1 107, 945, 783, 765

[M+Na]⁺

1 131, 425, 407

[4-6, 32]

Ginsenoside Rh1

C₃₆H₆₂O₉

638.439 4

[M+HCOO]^-

683, 637, 475, 391, 179, 161

[M+Na]⁺

661, 441, 423, 405

[4, 6, 32]

Ginsenoside Rd

C₄₈H₈₂O₁₈

946.550 1

[M+HCOO]^-

991, 945, 783, 621, 459

[M+Na]⁺

969, 443, 425, 407

[4, 6, 32]

Ginsenoside K

C₄₈H₈₂O₁₈

946.550 1

[M-H]^-

945, 783, 621, 459

[M+Na]⁺

969, 443, 425, 407

[4, 5, 32]

Notoginsenoside G/isomer

C₄₈H₈₀O₁₉

960.529 4

[M+Na]⁺

983, 439, 421

[32]

Notoginsenoside G/isomer

C₄₈H₈₀O₁₉

960.529 4

[M+Na]⁺

983, 439, 421

[32]

Malonylginsenoside Rb1/isomer

C₅₇H₉₄O₂₆

1 194.603 3

[M+Na]⁺

1 217, 1 173, 425, 407

[32]

Malonylginsenoside Rb1/isomer

C₅₇H₉₄O₂₆

1 194.603 3

[M+Na]⁺

1 217, 1 173, 425, 407

[32]

Malonylginsenoside Rg1

C₄₅H₇₄O₁₇

886.492 6

[M+Na]⁺

909, 865, 441, 423, 405

[32]

Ginsenoside Rb2

C₅₃H₉₀O₂₂

1 078.592 4

[M+Na]⁺

1 101, 425, 407

[32]

Ginsenoside Rb3

C₅₃H₉₀O₂₂

1 078.592 4

[M+Na]⁺

1 101, 425, 407

[32]

Ginsenoside Rh2

C₃₆H₆₂O₈

622.444 5

[M-H]^-

621, 459

[6]

Ginsenoside Rf

C₄₂H₇₂O₁₄

800.492 2

[M+HCOO]^-

845, 799, 637, 475

[4, 6]

Ginsenoside F1

C₃₆H₆₂O₉

638.439 4

[M+HCOO]^-

683, 637, 475, 391, 179, 161

[4, 31]

Ginsenoside Rc

C₅₃H₉₀O₂₂

1 078.592 4

[M-H]^-

1 077, 945, 783, 621, 603, 459

[6]

Notoginsenoside K/isomer

C₄₈H₈₂O₁₈

946.550 1

[M+HCOO]^-

991, 945, 783, 621, 459

[4, 6]

Notoginsenoside ST-5

C₄₇H₈₀O₁₈

932.534 5

[M+HCOO]^-

977, 931

[4]

Notoginsenoside A/Koryoginsenoside Rg2

C₅₄H₉₂O₂₄

1 124.597 9

[M-H]^-

1 123, 961, 799

[6]

Notoginsenoside A/Koryoginsenoside Rg2

C₅₄H₉₂O₂₄

1 124.597 9

[M-H]^-

1 123, 961, 799

[6]

Gypenoside Ⅷ

C₄₈H₈₂O₁₈

946.550 1

[M+HCOO]^-

991, 945, 851, 673

[4]

Gypenoside Ⅸ

C₄₇H₈₀O₁₇

916.539 6

[M-H]^-

915

[4]

Notoginsenoside H

C₄₇H₈₀O₁₉

948.529 4

[M+HCOO]^-

993, 947, 785, 767, 635

[6]

Yesanchinoside E

C₅₄H₉₂O₂₃

1 108.602 9

[M-H]^-

1 107, 945, 783, 765

[4]

Taurine

C₂H₇NO₃S

125.014 7

[M-H]^-

124, 106, 79

[M+H]⁺

126, 108

[5, 6]

Taurocholic acid

C₂₆H₄₅NO₇S

515.291 7

[M-H]^-

514, 496, 432, 391, 124, 79

[M+Na]⁺

538, 516, 498, 480, 462, 373, 355

[5, 31, 32]

Taurochenodeoxycholic acid

C₂₆H₄₅NO₆S

499.296 8

[M-H]^-

498, 480, 355

[M+Na]⁺

522, 500, 482, 464, 354, 254

[4, 6, 32]

Taurodeoxycholic acid

C₂₆H₄₅NO₆S

499.296 8

[M-H]^-

498, 480, 355

[M+H]⁺

500, 482, 357, 339

[4, 6]

Cholic acid

C₂₄H₄₀O₅

408.287 6

[M-H]^-

407, 389, 361, 345, 343, 327

[M+Na]⁺

431, 426, 391, 373, 355, 273, 254

[4-6, 32]

Ursodeoxycholic acid

C₂₄H₄₀O₄

392.292 7

[M-H]^-

391, 345, 327

[M+H]⁺

393, 375, 357

[4, 6, 32]

Chenodeoxycholic acid

C₂₄H₄₀O₄

392.292 7

[M-H]^-

391, 373

[M+Na]⁺

415, 375, 357

[4-6, 32]

Deoxycholic acid

C₂₄H₄₀O₄

392.292 7

[M-H]^-

391, 345, 327

[M+H]⁺

357, 161

[4, 5]

Hyodeoxycholic acid

C₂₄H₄₀O₄

392.292 7

[M-H]^-

391, 345, 327

[M+H]⁺

415, 375, 357

[4, 6]

Glycocholic acid

C₂₆H₄₃NO₆

465.309 0

[M-H]^-

464, 446, 402, 382, 353

[M+H]⁺

466, 448, 430

[4-6]

Glycodeoxycholic acid

C₂₆H₄₃NO₅

449.314 1

[M-H]^-

448, 430, 402, 386

[M+H]⁺

450, 432, 414, 339

[4-6]

Gallodesoxycholic acid

C₂₄H₄₀O₄

392.292 7

[M+H]⁺

393, 357

[32]

Glycoursodeoxycholic acid

C₂₆H₄₃NO₅

449.314 1

[M+H]⁺

450, 432, 414, 339

[6]

Glycohyodeoxycholic acid

C₂₆H₄₃NO₅

449.314 1

[M+H]⁺

450, 432, 414, 339

[6]

Taurohyodeoxycholic acid

C₂₆H₄₅NO₆S

499.296 8

[M+H]⁺

500, 482, 357

[6]

Tauroursodeoxycholic acid

C₂₆H₄₅NO₆S

499.296 8

[M+H]⁺

500, 482, 357

[6]

Glycochenodeoxycholic acid

C₂₆H₄₃NO₅

449.314 1

[M-H]^-

448, 404, 355

[4]

Ketodeoxycholic acid

C₂₄H₃₈O₄

390.277 0

[M-H]^-

389, 371, 309

[4]

Homodeoxycholic acid/isomer

C₂₅H₄₀O₅

420.287 6

[M-H]^-

419, 373, 297, 283

[31]

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

424.282 5

[M-H]^-

423, 405, 387, 359, 325

[4]

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

424.282 5

[M-H]^-

423, 405, 325

[4]

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

424.282 5

[M-H]^-

423, 405, 325

[4]

3α, 6β, 7α, 12α-Tetrahydroxy bile acid/isomer

C₂₄H₄₀O₆

424.282 5

[M-H]^-

423, 405, 325

[4]

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

531.286 6

[M-H]^-

530, 512

[4]

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

531.286 6

[M-H]^-

530, 512

[4]

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

531.286 6

[M-H]^-

530, 512

[4]

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

531.286 6

[M-H]^-

530, 512

[4]

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

531.286 6

[M-H]^-

530, 512

[4]

Tauro-3α, 7α, 12α, 23R-tetrahydroxy-5β-cholenoic acid/isomer

C₂₆H₄₅NO₈S

531.286 6

[M-H]^-

530, 512

[4]

Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

513.276 0

[M-H]^-

512, 480, 456, 358

[4]

Tauro-Δ8-3β, 7α, 12α-trihydroxy-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

513.276 0

[M-H]^-

512, 480, 456, 358

[4]

3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer

C₂₄H₃₈O₅

406.271 9

[M-H]^-

405, 359, 343

[4]

3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer

C₂₄H₃₈O₅

406.271 9

[M-H]^-

405, 343, 289, 251

[4]

3α, 12α-Dihydroxy-7-oxo-5β-cholic acid/isomer

C₂₄H₃₈O₅

406.271 9

[M-H]^-

405, 343, 289, 251

[4]

Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

513.276 0

[M-H]^-

512, 456, 358, 328

[4]

Tauro-3α, 7α-dihydroxy-12-oxo-5β-cholenoic acid/isomer

C₂₆H₄₃NO₇S

513.276 0

[M-H]^-

512, 456, 358, 328

[4]

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-holenoic acid/isomer

C₂₆H₄₅NO₇S

515.291 7

[M-H]^-

514, 496, 480, 358, 353

[4]

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

515.291 7

[M-H]^-

514, 496, 353, 329

[4]

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

515.291 7

[M-H]^-

514, 496, 353, 329

[4]

Taurocholic acid/tauro-3α, 7α, 12α-trihydroxy-5α-cholenoic acid/isomer

C₂₆H₄₅NO₇S

515.291 7

[M-H]^-

514, 496, 353

[4]

Cholic acid-sulfate

C₂₄H₄₀O₈S

488.244 4

[M-H]^-

487, 452, 408

[4]

Methyl cholate

C₂₅H₄₂O₅

422.303 2

[M-H]^-

421, 375, 273

[4]

Tetrahydroxycholestan-26-oic acid

C₂₇H₄₆O₆

466.329 4

[M-H]^-

465, 401, 383, 263

[4]

Tetradecanoic acid

C₁₄H₂₈O₂

228.208 9

[M-H]^-

227, 199, 181

[31]

N-Palmitoyltaurine/isomer

C₁₈H₃₇NO₄S

363.244 3

[M+HCOO]^-

362, 316, 124, 79

[31]

Pentadecanoiic acid

C₁₅H₃₀O₂

242.224 6

[M-H]^-

241, 223

[31]

Oleic acid

C₁₈H₃₄O₂

282.255 9

[M-H]^-

281, 263

[31]

Stearic acid

C₁₈H₃₆O₂

284.271 53

[M-H]^-

283, 265

[31]

Malic acid

C₄H₆O₅

134.021 5

[M-H]^-

133, 89

[6]

Citric acid

C₆H₈O₇

192.027 0

[M-H]^-

191, 147

[6]

Lutein

C₄₀H₅₆O₂

568.428 0

[M+Na]⁺

591, 551, 532

[32]

Oleanolic acid

C₃₀H₄₈O₃

456.360 3

[M+H]⁺

457, 439, 411, 393

[32]

Muscone

C₁₆H₃₀O

238.229 67

[M+H]⁺

239, 95

[5]