药学学报

No.	δ_H	δ_C
1	7.29 (1H, d, 1.8)	140.8
2	6.27 (1H, dd, 3.0, 1.8)	110.2
3	5.97 (1H, d, 3.0)	104.7
4		156.6
5	2.61 (2H, t, 7.6)	28.1
6	1.63 (2H, m)	28.1
7	1.33 (2H, overlap)	29.1
8	1.33 (2H, overlap)	29.0
9	1.39 (2H, m)	28.9
10	1.55 (2H, m),	28.4
11	2.32 (2H, t, 7.0)	19.7
12	-	85.2
13	-	65.3
14	-	78.6
15	-	72.1
16	5.50 (1H, d, 10.8)	108.8
17	6.03 (1H, dt, 10.8, 7.5)	146.7
18	2.44 (2H, m)	30.0
19	2.17 (2H, m)	33.0
20	5.81 (1H, ddt, 17.1, 10.3, 6.5)	137.8
21	5.05 (1H, dd, 17.1, 1.8) 4.99 (1H, dd, 10.3, 1.8)	115.3

No.	δ_H	δ_C
1	7.29 (1H, d, 1.8)	140.8
2	6.27 (1H, dd, 3.0, 1.8)	110.2
3	5.97 (1H, d, 3.0)	104.7
4		156.6
5	2.61 (2H, t, 7.6)	28.1
6	1.63 (2H, m)	28.1
7	1.33 (2H, overlap)	29.1
8	1.33 (2H, overlap)	29.0
9	1.39 (2H, m)	28.9
10	1.55 (2H, m),	28.4
11	2.32 (2H, t, 7.0)	19.7
12	-	85.2
13	-	65.3
14	-	78.6
15	-	72.1
16	5.50 (1H, d, 10.8)	108.8
17	6.03 (1H, dt, 10.8, 7.5)	146.7
18	2.44 (2H, m)	30.0
19	2.17 (2H, m)	33.0
20	5.81 (1H, ddt, 17.1, 10.3, 6.5)	137.8
21	5.05 (1H, dd, 17.1, 1.8) 4.99 (1H, dd, 10.3, 1.8)	115.3

Compound	MIC/μg·mL^-1
1	> 128	> 128	> 128	> 128	> 128
2	> 128	> 128	64	> 128	> 128
3	> 128	> 128	128	> 128	> 128
4	> 128	> 128	> 128	> 128	> 128
5	> 128	> 128	128	> 128	> 128
6	> 128	> 128	128	> 128	> 128
7	> 128	> 128	128	> 128	> 128
8	> 128	> 128	> 128	> 128	> 128
9	> 128	> 128	> 128	> 128	> 128
10	> 128	> 128	> 128	> 128	> 128
11	> 128	> 128	> 128	> 128	> 128
12	> 128	> 128	> 128	> 128	> 128
13	> 128	> 128	> 128	128	> 128
Ciprofloxacin	0.25	0.5	0.25	-	-
Vancomycin	-	2	1	-	-
Fluconazole	-	-	-	4	4

Compound	MIC/μg·mL^-1
1	> 128	> 128	> 128	> 128	> 128
2	> 128	> 128	64	> 128	> 128
3	> 128	> 128	128	> 128	> 128
4	> 128	> 128	> 128	> 128	> 128
5	> 128	> 128	128	> 128	> 128
6	> 128	> 128	128	> 128	> 128
7	> 128	> 128	128	> 128	> 128
8	> 128	> 128	> 128	> 128	> 128
9	> 128	> 128	> 128	> 128	> 128
10	> 128	> 128	> 128	> 128	> 128
11	> 128	> 128	> 128	> 128	> 128
12	> 128	> 128	> 128	> 128	> 128
13	> 128	> 128	> 128	128	> 128
Ciprofloxacin	0.25	0.5	0.25	-	-
Vancomycin	-	2	1	-	-
Fluconazole	-	-	-	4	4

蕉木的化学成分研究

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刘庭亮 ¹^,² , 王甜甜 ³ , 郑文琳 ¹^,² , 吴嘉正 ¹^,² , 杜世云 ² , 贺震旦 ² , 吴炎 ²^,⁴^,^*

药学学报 | 研究论文 2026,61(5): 1769-1776

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药学学报 |研究论文 2026 , 61 (5) : 1769 -1776

蕉木的化学成分研究

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刘庭亮¹^,², 王甜甜³, 郑文琳¹^,², 吴嘉正¹^,², 杜世云², 贺震旦², 吴炎²^,⁴^,^*

作者信息

¹深圳大学医学部药学院, 广东深圳 518060

²深圳技术大学药学院, 广东深圳 518118

³河南大学药学院, 河南开封 475004

⁴暨南大学, 教育部中药现代化与创新药物研究国际合作联合实验室, 广东广州 510632

通讯作者:

吴炎，E-mail: wuyan1219@yeah.net

作者简介:

作者贡献:

刘庭亮是本文的第一作者, 负责蕉木化学成分的分离纯化、结构解析和论文初稿撰写; 王甜甜对提取分离和结构鉴定提供了一定帮助; 郑文琳负责抗菌活性测定; 吴嘉正在数据整理方面提供了一定的帮助; 杜世云负责论文的审阅和提出写作的建议; 贺震旦负责论文的审阅和提供必要的科研资源支持; 吴炎负责实验的整体设计与指导工作、提供必要的科研资源支持、指导论文的修改完善和论文的审阅。

Chemical constituents from Meiogyne hainanensis

Ting-liang LIU¹^,², Tian-tian WANG³, Wen-lin ZHENG¹^,², Jia-zheng WU¹^,², Shi-yun DU², Zhen-dan HE², Yan WU²^,⁴^,^*

Affiliations

¹School of Pharmacy, Shenzhen University Medical School, Shenzhen University, Shenzhen 518060, China

²College of Pharmacy, Shenzhen Technology University, Shenzhen 518118, China

³School of Pharmacy, Henan University, Kaifeng 475004, China

⁴International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China, Jinan University, Guangzhou 510632, China

出版时间: 2026-05-12 doi: 10.16438/j.0513-4870.2025-1429

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摘要

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采用硅胶、凝胶柱色谱及半制备液相等色谱分离技术, 从蕉木[Meiogyne hainanensis (Merr.) N. T. Ban] 枝叶的提取物中分离得到13个化合物。通过核磁、紫外及质谱等方法鉴定化合物结构, 分别为蕉木聚炔N (chienhainanin N, 1)、(S)-15, 16-didehydrocoriolic acid methyl ester (2)、13(S)-羟基-9Z, 11E, 15E-十八碳三烯酸(3)、(S)-coriolic acid (4)、13-氧代-9Z, 11E-十八碳二烯酸(5)、13-氧代-9E, 11E-十八碳二烯酸(6)、9-氧代-10E, 12Z-十八碳二烯酸(7)、9-氧代-10E, 12E-十八碳二烯酸(8)、α-生育酚(9)、托可醌(10)、α-tocospiro A (11)、17³-脱镁叶绿素乙酯(12)、mustakone (13), 其中化合物1为新化合物, 化合物2、3、5~8、10~12为首次从番荔枝科植物中分离得到, 化合物4、9和13为首次从鹿茸木属植物中分离得到。采用肉汤微量稀释法评价化合物的抗菌活性, 结果发现化合物2、3、5~7对耐甲氧西林金葡菌有一定的抑制作用, 最低抑菌浓度(minimum inhibitory concentration, MIC) 分别为64、128、128、128和128 μg·mL^-1; 化合物13对新型隐球菌有一定的抑制作用, MIC值为128 μg·mL^-1。

关键词

蕉木 / 番荔枝科 / 鹿茸木属 / 化学成分 / 抗菌活性

Abstract

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Thirteen compounds were isolated from the twigs and leaves of Meiogyne hainanensis (Merr.) N. T. Ban by silica gel column chromatography, sephadex LH-20, and preparative HPLC. Their structures were respectively determined as chienhainanin N (1), (S)-15, 16-didehydrocoriolic acid methyl ester (2), 13-hydroxy-9Z, 11E, 15E-octadecatrienoic acid (3), (S)-coriolic acid (4), 13-oxo-(9Z, 11E)-octadecadienic acid (5), 13-oxo-(9E, 11E)-octadecadienic acid (6), 9-oxo-(10E, 12Z)-octadecadienic acid (7), 9-oxo-(10E, 12E)-octadecadienic acid (8), α-tocopherol (9), vitamin E quinone (10), α-tocospiro A (11), 17c-ethoxypheaophorbide A (12), mustakone (13) by spectral data analysis. Among them, compound 1 is a new compound, compounds 2, 3, 5-8, 10-12 are isolated from Annonaceae plants for the first time, and compounds 4, 9 and 13 are isolated from the genus Meiogyne for the first time. Their antimicrobial activities were evaluated by the broth microdilution method. Compounds 2, 3, 5-7 showed weak antimicrobial effect against MRSA with MIC values from 64 to128 μg·mL^-1, respectively. Compound 13 showed weak antimicrobial effects against Cryptococcus neoformans with the MIC value of 128 μg·mL^-1.

Key words

Meiogyne hainanensis / Annonaceae / Meiogyne / chemical constituent / antimicrobial activity

引用本文

刘庭亮, 王甜甜, 郑文琳, 吴嘉正, 杜世云, 贺震旦, 吴炎. 蕉木的化学成分研究. 药学学报, 2026 , 61 (5) : 1769 -1776 . DOI: 10.16438/j.0513-4870.2025-1429

Ting-liang LIU, Tian-tian WANG, Wen-lin ZHENG, Jia-zheng WU, Shi-yun DU, Zhen-dan HE, Yan WU. Chemical constituents from Meiogyne hainanensis[J]. Acta Pharmaceutica Sinica, 2026 , 61 (5) : 1769 -1776 . DOI: 10.16438/j.0513-4870.2025-1429

正文

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蕉木[Meiogyne hainanensis (Merr.) N. T. Ban] 为番荔枝科(Annonaceae) 鹿茸木属(Meiogyne) 植物, 产于我国海南、广东和广西等省区, 生于山谷水旁密林中^[1]。目前, 关于蕉木的化学成分和药理活性研究较少。本课题组在前期的研究中, 从蕉木中分离得到了一系列结构新颖且抗菌活性显著的聚炔类成分^[2]。在对该植物化学成分的深入研究中, 进一步从其枝叶的乙醇提取物中分离得到13个化合物, 包括1个聚炔类化合物(1), 7个脂肪酸衍生物(2~8), 3个生育酚衍生物(9~11), 1个卟啉衍生物(12) 和1个倍半萜类化合物(13), 化合物结构见图1。其中化合物1为新化合物, 化合物2、3、5~8、10~12为首次从番荔枝科植物中分离得到, 化合物4、9和13为首次从鹿茸木属植物中分离得到。采用肉汤微量稀释法对分离得到的化合物进行抗菌活性评价, 结果表明化合物2、3、5~7对耐甲氧西林金葡菌有一定的抑制作用, 化合物13对新型隐球菌有一定的抑制作用。

结果与讨论

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1　结构鉴定

化合物1为淡黄色油状物, 易溶于氯仿。HR-ESI-MS谱中显示分子离子峰m/z 295.205 8 [M+H]⁺ (计算值为C₂₁H₂₇O⁺, 295.205 6), 提示化合物的分子式为C₂₁H₂₆O, 不饱和度为9。UV光谱显示在208 (4.78)、214 (4.85)、240 (3.92)、253 (4.24)、267 (4.43) 和283 (4.33) nm处有最大吸收, 紫外图谱在225~300 nm之间呈锯齿状, 提示化合物1为聚炔类化合物^{[3, 4]}。¹H NMR谱(表1) 显示有8个双键氢信号[δ_H 7.29 (1H, d, J = 1.8 Hz), 6.27 (1H, dd, J = 3.0, 1.8 Hz), 6.03 (1H, dt, J = 10.8, 7.5 Hz), 5.97 (1H, d, J = 3.0 Hz), 5.81 (1H, ddt, J = 17.1, 10.3, 6.5 Hz), 5.50 (1H, d, J = 10.8 Hz), 5.05 (1H, dd, J = 17.1, 1.8 Hz), 4.99 (1H, dd, J = 10.3, 1.8 Hz)] 和9个亚甲基的氢信号[δ_H 2.61 (2H, t, J = 7.6 Hz), 2.44 (2H, m), 2.32 (2H, t, J = 7.0 Hz), 2.17 (2H, m), 1.63 (2H, m), 1.55 (2H, m), 1.39 (2H, m), 1.33 (2H, overlap), 1.33 (2H, overlap)]。¹³C NMR谱结合DEPT谱提示该化合物有21个碳信号, 包括: 8个双键碳信号(δ_C 156.6, 146.7, 140.8, 137.8, 115.3, 110.2, 108.8, 104.7)、4个叁键季碳信号(δ_C 85.2, 78.6, 72.1, 65.3) 和9个亚甲基碳信号(δ_C 33.0, 30.0, 29.1, 29.0, 28.9, 28.4, 28.1, 28.1, 19.7)。通过与文献^{[2, 5]}数据比对, 进一步确证化合物1为聚炔类化合物。¹H-¹H COSY谱(图2) 中可观察到H-1 (δ_H 7.29) 至H-3 (δ_H 5.97)、H-5 (δ_H 2.61) 至H-11 (δ_H 2.32) 及H-16 (δ_H 5.50) 至H-21 (δ_H 5.05/4.99) 的3组自旋耦合系统。HMBC谱(图2) 中, 通过H-1 (δ_H 7.29) 与C-4 (δ_C 156.6) 相关, H-2 (δ_H 6.27) 与C-4 (δ_C 156.6) 相关, H-3 (δ_H 5.97) 与C-1 (δ_C 140.8)、C-2 (δ_C 110.2)、C-4 (δ_C 156.6) 相关, H-5 (δ_H 2.61) 与C-3 (δ_C 104.7)、C-4 (δ_C 156.6)、C-7 (δ_C 29.1) 相关和H-6 (δ_H 1.63) 与C-4 (δ_C 156.6) 相关, 推断C-5与C-4, C-3与C-4相连, 结合C-1的化学位移(140.8)、C-4的化学位移(156.6) 和分子式信息可知C-4与C-1通过氧原子相连形成呋喃环; 通过H-10 (δ_H 1.55) 与C-8 (δ_C 29.0)、C-12 (δ_C 85.2) 相关, H-11 (δ_H 2.32) 与C-9 (δ_C 28.9)、C-12 (δ_C 85.2)、C-13 (δ_C 65.3)、C-14 (δ_C 78.6)、C-15 (δ_C 72.1) 相关和H-18 (δ_H 2.44) 与C-15 (δ_C 72.1)、C-16 (δ_C 108.8) 相关, 可知C-11与C-12相连, C-15与C-16相连。H-16 (δ_H 5.50) 与H-17 (δ_H 6.03) 之间耦合常数J_{16, 17} = 10.8 Hz, 可知此处双键为顺式结构, 最终确定化合物的结构。综上所述, 化合物1结构为(Z)-2-(heptadeca-12, 16-dien-8, 10-diyn-1-yl) furan。经检索, 化合物1为一未报道的新化合物, 命名为蕉木聚炔N (chienhainanin N)。

2　抗菌活性评价

采用肉汤微量稀释法测试化合物1~13的抗菌活性, 以P. aeruginosa (ATCC27853)、E. faecalis (ATCC29212)、MRSA (ATCC43300)、C. neoformans (ATCC32045) 和C. albicans (ATCC10231) 为测试菌株, 万古霉素、环丙沙星和氟康唑为阳性对照药物。结果如表2, 化合物2、3、5~7对耐甲氧西林金葡菌有一定的抑制作用, 最低抑菌浓度(minimum inhibitory concentration, MIC) 分别为64、128、128、128和128 μg·mL^-1, 化合物13对新型隐球菌有一定的抑制作用, MIC值为128 μg·mL^-1。

3　讨论

本研究从蕉木枝叶中分离鉴定到了13个化合物, 其中化合物1为新化合物, 化合物2、3、5~8、10~12为首次从番荔枝科植物中分离得到, 化合物4、9和13为首次从鹿茸木属植物中分离得到。化合物2、3、5~7对耐甲氧西林金葡菌有一定的抑制作用, 化合物13对新型隐球菌有一定的抑制作用。蕉木原归属于番荔枝科蕉木属(Chieniodendron), 近期被修订为番荔枝科鹿茸木属(Meiogyne)。相关研究报道显示^{[6, 7]}, 鹿茸木属的Meiogyne cylindrocarpa (Burck) Heusden和Meiogyne baillonii (Guillaumin) Heusden两种植物中含有多种聚炔类化合物。本课题组在对蕉木的研究中, 也分离得到了多种聚炔类化合物, 这也从化学分类学角度为此次分类修订的正确性提供了佐证。本研究为蕉木的进一步研究和开发利用奠定了物质基础。

实验部分

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Bruker Avance 400型核磁共振仪(德国Bruker公司); 海能P810全自动旋光仪(济南海能仪器股份有限公司); Thermo Scientific Evolution One紫外-可见分光光度计、Orbitrap Exploris 120型高分辨质谱仪(美国ThermoFisher公司); Agilent 1260 Infinity Ⅱ/Vanquish Core型高效液相色谱仪(美国Agilent公司/美国ThermoFisher公司); Agilent 1260 Infinity Ⅱ型制备型高效液相色谱仪(美国Agilent公司); 通微EasySep^®-3050型半制备高效液相色谱仪(上海通微分析技术有限公司); BUCHI Rotavapor R-100型旋转蒸发仪(瑞士BUCHI公司); BCE224-1CCN万分之一分析天平[赛多利斯科学仪器(北京) 有限公司]; THZ-98AB型恒温振荡器(上海一恒科学仪器有限公司); GF₂₅₄薄层色谱硅胶板(烟台银龙硅胶有限公司); 正相柱色谱硅胶(100~200、200~300目; 青岛海洋化工公司分厂); ODS柱色谱填料(Spherical C18 Monomeric, 120A, 50 μm, 加拿大SILICYCLE公司); 凝胶柱色谱填料(Toyopearl HW-40F, 日本TOSOH公司); 分析型HPLC色谱柱(Global Chromatography C18, 250 mm × 4.6 mm, 10 μm, 上海通微分析技术有限公司; Cosmosil 5C18-MS-Ⅱ, 250 mm × 4.6 mm, 5 μm, 日本Nacalai Tesque公司) 和手性HPLC色谱柱(ChromegaChiral CC4, 250 mm × 4.6 mm, 5 μm, 美国PerkinElmer公司); 半制备型HPLC色谱柱(Global Chromatography C18, 250 mm × 10 mm, 10 μm, 上海通微分析技术有限公司) 和(Cosmosil 5C18-MS-Ⅱ, 250 mm × 10 mm, 5 μm, 日本Nacalai Tesque公司); 制备型HPLC色谱柱(Global Chromatography C18, 250 mm × 20 mm, 10 μm, 上海通微分析技术有限公司; Cosmosil 5C18-MS-Ⅱ, 250 mm × 20 mm, 5 μm, 日本Nacalai Tesque公司); 营养琼脂培养基平板和马铃薯葡萄糖琼脂平板(广东环凯生物科技有限公司); CAMHB肉汤培养基和YM培养基(青岛海博生物技术有限公司); ATCC29212粪肠球菌、ATCC43300金黄色葡萄球菌金黄色亚种、ATCC27853铜绿假单胞菌、ATCC32045新型隐球菌和ATCC10231白色念珠菌(合肥万物生物科技有限公司); 环丙沙星、盐酸万古霉素和氟康唑(上海阿拉丁生化科技股份有限公司, 批号C129896、V105495和E129360)。所用化学试剂均为色谱纯(安耐吉化学公司) 或分析纯(成都金山化学试剂有限公司)。

蕉木植物材料于2023年5月采集于中国云南省昆明市, 经深圳技术大学药学院吴炎副教授鉴定为番荔枝科鹿茸木属植物蕉木[Meiogyne hainanensis (Merr.) N. T. Ban], 植物标本(No. 2023050001) 保存于深圳技术大学中药标本室。

1　提取分离

蕉木[Meiogyne hainanensis (Merr.) N. T. Ban] 枝叶53 kg, 粉碎成粗粉, 用95%乙醇80 L渗漉提取, 合并渗漉液并减压浓缩至无醇味, 得到的总浸膏约5.5 kg。浸膏用100~200目硅胶拌样后依次用石油醚、二氯甲烷、乙酸乙酯洗脱, 得到石油醚萃取部位350 g、二氯甲烷萃取部位549 g和乙酸乙酯萃取部位574 g。

石油醚萃取物进一步经硅胶柱色谱分离, 以石油醚-乙酸乙酯为洗脱剂(100∶0~0∶100), 经薄层色谱(TLC) 分析并合并相似流分, 得到15个主流分Fr.1~Fr.15。流分Fr.12 (2 g) 经半制备液相(乙腈-水, 95∶5, 4 mL·min^-1) 纯化得到化合物10 (t_R = 23 min; 4.3 mg)。

二氯甲烷萃取物进一步经硅胶柱色谱分离, 以石油醚-乙酸乙酯为洗脱剂(100∶1~0∶100), 得到24个主流分Fr.1~Fr.24。流分Fr.5 (8 g) 经半制备液相(甲醇-水, 95∶5, 4 mL·min^-1) 纯化得到化合物9 (t_R = 39 min; 18.8 mg); 流分Fr.6 (5 g) 经半制备液相(甲醇-水, 90∶10, 4 mL·min^-1) 纯化得到化合物11 (t_R = 49 min; 4.3 mg)。流分Fr.8 (25 g) 经Sephadex LH-20柱(甲醇) 分离后得到5个亚流分Fr.8A~Fr.8E, 其中流分Fr.8C (17 g) 经ODS (甲醇-水, 70∶30~100∶0) 分离, 获得11个流分Fr.8Ca~Fr.8Ck, Fr.8Cb进一步经半制备液相(甲醇-水, 60∶40, 4 mL·min^-1) 纯化, 得到化合物13 (t_R = 30 min; 13.3 mg)。

流分Fr.15 (38 g) 与Fr.16 (57 g) 合并后经硅胶柱色谱(石油醚-乙酸乙酯, 15∶1~1∶1) 分离, 得到6个亚流分Fr.15A~Fr.15F。流分Fr.15C (5 g) 经制备液相(乙腈-水, 80∶20, 16 mL·min^-1) 分离得到6个流分Fr.15Ca~Fr.15Cf, 流分Fr.15Cb经制备液相(乙腈-水, 65∶35, 16 mL·min^-1) 纯化后, 再经半制备液相(乙腈-水, 50∶50, 4 mL·min^-1) 纯化, 得到化合物2 (t_R = 39 min; 3.5 mg)。流分Fr.15D (40 g) 经ODS (甲醇-水, 40∶60~100∶0) 分离, 得到20个流分Fr.15Da~Fr.15Dt。流分Fr.15Dm经制备液相(乙腈-水, 50∶50, 16 mL·min^-1) 纯化, 得到化合物3 (t_R = 26 min; 39.7 mg); 流分Fr.15Dn经制备液相(乙腈-水, 55∶45, 16 mL·min^-1) 纯化, 得到化合物4 (t_R = 27 min; 90.3 mg)、5 (t_R=35 min; 12.5 mg)、6 (t_R = 37 min; 11.5 mg)、7 (t_R = 38 min; 34.7 mg)、8 (t_R = 43 min; 21.3 mg)。流分Fr.15Do经制备液相(乙腈-水, 55∶45, 16 mL·min^-1) 分离得到7个流分Fr.15Do1~Fr.15Do7, 流分Fr.15Do3经半制备液相(乙腈-水, 55∶45, 4 mL·min^-1) 纯化得到化合物1 (t_R = 38 min; 1.2 mg)。流分Fr.15E (41 g) 经ODS (甲醇-水, 70∶30~100∶0) 分离, 得到8个流分Fr.15Ea~Fr.15Eh, Fr.15Eh经制备液相(乙腈-水, 95∶5, 16 mL·min^-1) 纯化得到化合物12 (t_R = 21 min; 29.8 mg)。

2　结构鉴定

化合物1 淡黄色油状物; HR-ESI-MS m/z 295.205 8 [M+H]⁺ (计算值为C₂₁H₂₇O⁺, 295.205 6), 分子式: C₂₁H₂₆O。UV (CH₃CN) λ_max (log ε) 208 (4.78), 214 (4.85), 240 (3.92), 253 (4.24), 267 (4.43), 283 (4.33)。¹H NMR (CDCl₃, 400 MHz) 和¹³C NMR (CDCl₃, 100 MHz) 数据见表1。

化合物2 淡黄色油状物; [α]

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+5.50° (c 0.350, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 309.23 [M+H]⁺, 分子式: C₁₉H₃₂O₃。UV (CH₃OH) λ_max (log ε) 192 (3.33), 197 (3.35), 199 (3.29), 235 (3.61); ¹H NMR (CDCl₃, 400 MHz) δ_H 6.51 (1H, dd, J = 15.2, 11.0 Hz, H-11), 5.97 (1H, dd, J = 11.0, 10.8 Hz, H-10), 5.69 (1H, dd, J = 15.2, 6.4 Hz, H-12), 5.57 (1H, dt, J = 10.8, 7.6 Hz, H-16), 5.43 (1H, dt, J = 10.8, 7.6 Hz, H-9), 5.36 (1H, dt, J = 10.8, 7.6 Hz, H-15), 4.21 (1H, m, H-13), 3.66 (3H, s, H-1′), 2.31 (4H, overlap, H-2, H-14), 2.17 (2H, m, H-8), 2.07 (2H, m, H-17), 1.60 (2H, m, H-3), 1.37 (2H, m, H-7), 1.31 (6H, overlap, H-4, H-5, H-6), 0.97 (3H, t, J = 7.5 Hz, H-18); ¹³C NMR (CDCl₃, 100 MHz) δ_C 174.5 (C-1), 34.2 (C-2), 25.0 (C-3), 29.2 (C-4/5/6), 29.2 (C-4/5/6), 29.1 (C-4/5/6), 29.6 (C-7), 27.8 (C-8), 133.0 (C-9), 127.9 (C-10), 126.0 (C-11), 135.2 (C-12), 72.3 (C-13), 35.4 (C-14), 123.9 (C-15), 135.4 (C-16), 20.9 (C-17), 14.4 (C-18), 51.6 (C-1′)。以上波谱数据与文献^[8]报道数据基本一致, 故鉴定化合物2为(S)-15, 16-didehydrocoriolic acid methyl ester。

化合物3 淡黄色油状物; [α]

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+3.51° (c 0.993, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 293.21 [M-H]^－, 分子式: C₁₈H₃₀O₃。UV (CH₃OH) λ_max (log ε) 192 (3.90), 196 (3.90), 201 (4.05), 234 (4.26)。¹H NMR (CD₃OD, 400 MHz) δ_H 6.40 (1H, dd, J = 15.2, 11.0 Hz, H-11), 5.87 (1H, dd, J = 11.0, 10.8 Hz, H-10), 5.54 (1H, dd, J = 15.2, 6.5 Hz, H-12), 5.31 (3H, overlap, H-9, H-15, H-16), δ_H 4.02 (1H, m, H-13), 2.18 (4H, overlap, H-2, H-14), 2.09 (2H, m, H-8), 1.96 (2H, m, H-17), 1.50 (2H, m, H-3), 1.29 (2H, m, H-7), 1.24 (6H, overlap, H-4, H-5, H-6), 0.86 (3H, t, J = 7.5 Hz, H-18); ¹³C NMR (CD₃OD, 100 MHz) δ_C 177.7 (C-1), 34.9 (C-2), 26.0 (C-3), 30.2 (C-4/5/6), 30.2 (C-4/5/6), 30.1 (C-4/5/6), 30.7 (C-7), 28.6 (C-8), 133.0 (C-9), 129.3 (C-10), 126.6 (C-11), 136.6 (C-12), 73.2 (C-13), 36.2 (C-14), 125.5 (C-15), 134.5 (C-16), 21.7 (C-17), 14.6 (C-18)。以上波谱数据与文献^[9]报道数据基本一致, 故鉴定化合物3为13(S)-羟基-9Z, 11E, 15E-十八碳三烯酸。

化合物4 淡黄色油状物; [α]

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+1.85° (c 1.806, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 295.23 [M-H]^－, 分子式: C₁₈H₃₂O₃。UV (CH₃OH) λ_max (log ε) 191 (3.83), 194 (3.82), 196 (3.88), 198 (3.93), 233 (4.34), 277 (2.78)。¹H NMR (CD₃OD, 400 MHz) δ_H 6.26 (1H, dd, J = 15.2, 11.0 Hz, H-11), 5.75 (1H, dd, J = 11.0, 10.8 Hz, H-10), 5.39 (1H, dd, J = 15.2, 6.7 Hz, H-12), 5.17 (1H, dt, J = 10.8, 7.7 Hz, H-9), 3.85 (1H, m, H-13), 2.04 (2H, t, J = 7.4 Hz, H-2), 1.96 (2H, m, H-8), 1.36 (2H, m, H-3), 1.27 (2H, m, H-14), 1.17 (2H, m, H-7), 1.10 (12H, overlap, H-4, H-5, H-6, H-15, H-16, H-17), 0.68 (3H, t, J = 7.0 Hz, H-18); ¹³C NMR (CD₃OD, 100 MHz) δ_C 177.6 (C-1), 34.9 (C-2), 26.0 (C-3), 30.2 (C-4/5/6), 30.2 (C-4/5/6), 30.1 (C-4/5/6), 30.7 (C-7), 28.6 (C-8), 132.8 (C-9), 129.4 (C-10), 126.4 (C-11), 137.3 (C-12), 73.3 (C-13), 38.4 (C-14), 26.3 (C-15), 32.9 (C-16), 23.7 (C-17), 14.5 (C-18)。以上波谱数据与文献^[8]报道数据基本一致, 故鉴定化合物4为(S)-coriolic acid。

化合物5 淡黄色油状物; HR-ESI-MS m/z 295.23 [M+H]⁺, 分子式为: C₁₈H₃₀O₃。UV (CH₃OH) λ_max (log ε) 191 (3.65), 194 (3.51), 197 (3.47), 199 (3.63), 202 (3.63), 214 (3.56), 280 (3.99)。¹H NMR (CD₃OD, 400 MHz) δ_H 7.57 (1H, dd, J = 15.2, 11.6 Hz, H-11), 6.20 (2H, overlap, H-10, H-12), 5.97 (1H, dt, J = 10.8, 7.6 Hz, H-9), 2.61 (2H, t, J = 7.4 Hz, H-14), 2.35 (2H, m, H-8), 2.27 (2H, t, J = 7.2 Hz, H-2), 1.60 (4H, overlap, H-3, H-15), 1.46 (2H, m, H-7), 1.34 (10H, overlap, H-4, H-5, H-6, H-16, H-17), 0.91 (3H, t, J = 7.2 Hz, H-18); ¹³C NMR (CD₃OD, 100 MHz) δ_C 177.7 (C-1), 34.9 (C-2), 26.0 (C-3), 30.0 (C-4/5/6), 30.1 (C-4/5/6), 30.1 (C-4/5/6), 30.3 (C-7), 29.1 (C-8), 143.9 (C-9), 128.2 (C-10), 139.0 (C-11), 130.4 (C-12), 203.8 (C-13), 41.5 (C-14), 25.3 (C-15), 32.6 (C-16), 23.5 (C-17), 14.3 (C-18)。以上波谱数据与文献^{[10, 11]}报道数据基本一致, 故鉴定化合物5为13-氧代-9Z, 11E-十八碳二烯酸。

化合物6 淡黄色油状物; HR-ESI-MS m/z 295.23 [M+H]⁺, 分子式: C₁₈H₃₀O₃。UV (CH₃OH) λ_max (log ε) 191 (3.67), 194 (3.63), 197 (3.57), 201 (3.70), 214 (3.64), 275 (3.94)。¹H NMR (CD₃OD, 400 MHz) δ_H 7.23 (1H, dd, J = 15.6, 9.6 Hz, H-11), 6.27 (2H, overlap, H-9, H-10), 6.12 (1H, d, J = 15.6 Hz, H-12), 2.59 (2H, t, J = 7.4 Hz, H-14), 2.28 (2H, t, J = 7.2 Hz, H-2), 2.21 (2H, m, H-8), 1.60 (4H, overlap, H-3, H-15), 1.47 (2H, m, H-7), 1.34 (10H, overlap, H-4, H-5, H-6, H-16, H-17), 0.91 (3H, t, J = 7.2 Hz, H-18); ¹³C NMR (CD₃OD, 100 MHz) δ_C 177.7 (C-1), 34.9 (C-2), 26.0 (C-3), 30.1 (C-4), 30.1 (C-5), 30.2 (C-6), 29.8 (C-7), 34.1 (C-8), 147.3 (C-9), 130.3 (C-10), 145.3 (C-11), 128.8 (C-12), 203.9 (C-13), 41.0 (C-14), 25.3 (C-15), 32.6 (C-16), 23.5 (C-17), 14.3 (C-18)。以上波谱数据与文献^{[12, 13]}报道数据基本一致, 故鉴定化合物6为13-氧代-9E, 11E-十八碳二烯酸。

化合物7 淡黄色油状物; HR-ESI-MS m/z 295.23 [M+H]⁺, 分子式: C₁₈H₃₀O₃。UV (CH₃OH) λ_max (log ε) 191 (3.57), 194 (3.57), 198 (3.63), 201 (3.73), 214 (3.58), 281 (4.20)。¹H NMR (CD₃OD, 400 MHz) δ_H 7.54 (1H, dd, J = 15.2, 11.2 Hz, H-11), 6.17 (2H, overlap, H-10, H-12), 5.94 (1H, dt, J = 10.7, 7.6 Hz, H-13), 2.58 (2H, t, J = 7.3 Hz, H-8), 2.31 (2H, m, H-14), 2.24 (2H, t, J = 7.2 Hz, H-2), 1.57 (4H, overlap, H-3, H-7), 1.42 (2H, m, H-15), 1.30 (10H, overlap, H-4, H-5, H-6, H-16, H-17), 0.88 (3H, t, J = 6.8 Hz, H-18); ¹³C NMR (CD₃OD, 100 MHz) δ_C 177.6 (C-1), 34.9 (C-2), 26.0 (C-3), 30.1 (C-4), 30.1 (C-5), 30.1 (C-6), 25.5 (C-7), 41.5 (C-8), 203.7 (C-9), 130.4 (C-10), 138.9 (C-11), 128.2 (C-12), 144.0 (C-13), 29.2 (C-14), 30.2 (C-15), 32.5 (C-16), 23.5 (C-17), 14.4 (C-18)。以上波谱数据与文献^[10]报道数据基本一致, 故鉴定化合物7为9-氧代-10E, 12Z-十八碳二烯酸。

化合物8 淡黄色油状物; HR-ESI-MS m/z 295.23 [M+H]⁺, 分子式: C₁₈H₃₀O₃。UV (CH₃OH) λ_max (log ε) 191 (3.65), 194 (3.46), 196 (3.59), 199 (3.60), 203 (3.59), 214 (3.53), 275 (4.16)。¹H NMR (CD₃OD, 400 MHz) δ_H 7.22 (1H, dd, J = 15.6, 9.2 Hz, H-11), 6.25 (2H, overlap, H-12, H-13), 6.10 (1H, d, J = 15.6 Hz, H-10), 2.58 (2H, t, J = 7.4 Hz, H-8), 2.26 (2H, t, J = 7.4 Hz, H-2), 2.19 (2H, m, H-14), 1.58 (4H, overlap, H-3, H-7), 1.45 (2H, m, H-15), 1.32 (10H, overlap, H-4, H-5, H-6, H-16, H-17), 0.90 (3H, t, J = 6.8 Hz, H-18); ¹³C NMR (CD₃OD, 100 MHz) δ_C 177.7 (C-1), 35.0 (C-2), 26.0 (C-3), 30.2 (C-4/5/6), 30.2 (C-4/5/6), 30.1 (C-4/5/6), 25.5 (C-7), 41.0 (C-8), 203.8 (C-9), 128.8 (C-10), 145.3 (C-11), 130.2 (C-12), 147.4 (C-13), 34.1 (C-14), 29.5 (C-15), 32.5 (C-16), 23.5 (C-17), 14.4 (C-18)。以上波谱数据与文献^[14]报道数据基本一致, 故鉴定化合物8为9-氧代-10E, 12E-十八碳二烯酸。

化合物9 淡黄色油状物; [α]

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+1.81° (c 0.710, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 431.38 [M+H]⁺, 分子式: C₂₉H₅₀O₂。UV (CH₃OH) λ_max (log ε) 193 (3.78), 205 (4.52), 292 (3.48)。¹H NMR (CDCl₃, 400 MHz) δ_H 2.61 (2H, t, J = 6.8 Hz, H-4), 2.17 (3H, s, H-7a), 2.12 (3H, s, H-5a), 2.12 (3H, s, H-8a), 1.79 (2H, m, H-3), 1.53 (3H, overlap, H-1′, H-12′), 1.39 (4H, overlap, H-2′, H-4′, H-8′), 1.28 (8H, overlap, H-3′, H-6′, H-9′, H-10′), 1.24 (3H, s, H-2a), 1.15 (2H, m, H-11′), 1.08 (4H, overlap, H-5′, H-7′), 0.88 (3H, d, J = 6.8 Hz, H-12′a), 0.88 (3H, d, J = 6.8 Hz, H-13′), 0.85 (6H, overlap, H-4′a, H-8′a); ¹³C NMR (CDCl₃, 100 MHz) δ_C 74.7 (C-2), 23.9 (C-2a), 31.7 (C-3), 20.9 (C-4), 118.7 (C-5), 11.4 (C-5a), 144.7 (C-6), 121.2 (C-7), 12.3 (C-7a), 122.8 (C-8), 11.9 (C-8a), 145.7 (C-9), 117.5 (C-10), 40.0 (C-1′), 21.2 (C-2′), 37.6 (C-3′), 33.0 (C-4′), 19.9 (C-4′a), 37.6 (C-5′), 24.6 (C-6′), 37.6 (C-7′), 32.9 (C-8′), 19.8 (C- 8′a), 37.4 (C-9′), 24.9 (C-10′), 39.5 (C-11′), 28.1 (C-12′), 22.9 (C-12′a), 22.8 (C-13′)。以上波谱数据与文献^[15]报道数据基本一致, 故鉴定化合物9为α-生育酚。

化合物10 黄色油状物; [α]

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+1.71° (c 1.374, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 447.38 [M+H]⁺, 分子式: C₂₉H₅₀O₃。UV (CH₃OH) λ_max (log ε) 195 (3.76), 202 (4.07), 263 (4.24), 268 (4.25)。¹H NMR (CDCl₃, 400 MHz) δ_H 2.52 (2H, m, H-2′), 2.00 (3H, s, H-7a), 1.97 (3H, s, H-5a), 1.97 (3H, s, H-8a), 1.47 (5H, overlap, H-3, H-1′, H-12′), 1.35 (4H, overlap, H-4, H-4′, H-8′), 1.25 (8H, overlap, H-3′, H-6′, H-9′, H-10′), 1.21 (3H, s, H-2a), 1.11 (2H, m, H-11′), 1.06 (4H, overlap, H-5′, H-7′), 0.83 (6H, overlap, H-12′a, H-13′), 0.81 (6H, overlap, H-4′a, H-8′a); ¹³C NMR (CDCl₃, 100 MHz) δ_C 72.7 (C-2), 26.7 (C-2a), 40.3 (C-3), 21.5 (C-4), 140.6 (C-5), 12.4 (C-5a), 187.7 (C-6), 140.5 (C-7), 12.0 (C-7a), 140.3 (C-8), 12.4 (C-8a), 187.3 (C-9), 144.6 (C-10), 42.4 (C-1′), 21.4 (C-2′), 37.7 (C-3′), 32.9 (C-4′), 19.8 (C-4′a), 37.5 (C-5′), 24.6 (C-6′), 37.5 (C-7′), 32.9 (C-8′), 19.8 (C-8′a), 37.4 (C-9′), 24.9 (C-10′), 39.5 (C-11′), 28.1 (C-12′), 22.8 (C-12′a), 22.7 (C-13′)。以上波谱数据与文献^[16]报道数据基本一致, 故鉴定化合物10为托可醌。

化合物11 淡黄色油状物; [α]

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+36.28° (c 0.430, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 463.38 [M+H]⁺, 分子式: C₂₉H₅₀O₄。UV (CH₃OH) λ_max (log ε) 192 (3.77), 194 (3.77), 196 (3.77), 199 (3.71), 202 (3.66), 234 (3.95)。¹H NMR (CDCl₃, 400 MHz) δ_H 2.43 (1H, m, H-7), 2.02 (3H, s, H-3a), 1.90 (1H, m, H-8), 1.83 (3H, s, H-6a), 1.82 (3H, s, H-5a), 1.78 (1H, m, H-7), 1.70 (1H, m, H-8), 1.60 (2H, m, H-10), 1.52 (1H, m, H-21), 1.38 (2H, overlap, H-13, H-17), 1.33 (2H, m, H-11), 1.26 (8H, overlap, H-12, H-15, H-18, H-19), 1.15 (2H, m, H-20), 1.09 (4H, overlap, H-14, H-16), 1.05 (3H, s, H-9a), 0.86 (3H, d, J = 6.8 Hz, H-21a), 0.86 (3H, d, J = 6.8 Hz, H-22), 0.83 (6H, overlap, H-13a, H-17a); ¹³C NMR (CDCl₃, 100 MHz) δ_C 205.1 (C-1), 92.3 (C-2), 207.3 (C-3), 25.0 (C-3a), 89.2 (C-4), 163.2 (C-5), 11.9 (C-5a), 139.5 (C-6), 8.8 (C-6a), 33.0 (C-7), 36.3 (C-8), 87.2 (C-9), 25.6 (C-9a), 41.6 (C-10), 22.6 (C-11), 37.7 (C-12), 33.0 (C-13), 19.9 (C-13a), 37.6 (C-14), 24.9 (C- 15), 37.6 (C-16), 32.9 (C-17), 19.8 (C-17a), 37.4 (C-18), 24.6 (C-19), 39.5 (C-20), 28.1 (C-21), 22.9 (C-21a), 22.8 (C-22)。以上波谱数据与文献^[17]报道数据基本一致, 故鉴定化合物11为α-tocospiro A。

化合物12 黑绿色胶状物; [α]

$ {}_{\mathrm{D}}^{20} $

+15.50° (c 0.745, CH₃CN; 1 g·100 mL^-1); HR-ESI-MS m/z 621.31 [M+H]⁺, 分子式: C₃₇H₄₀O₅N₄。UV (CH₃CN) λ_max (log ε) 193 (4.32), 268 (4.00), 324 (4.16), 408 (4.80)。¹H NMR (CDCl₃, 400 MHz) δ_H 9.35 (1H, s, H-10), 9.16 (1H, s, H-5), 8.56 (1H, s, H-20), 7.84 (1H, dd, J= 18.0, 11.6 Hz, H-3a), 6.30 (1H, s, H-13b), 6.20 (1H, d, J = 18.0 Hz, H-3b), 6.10 (1H, d, J = 11.6 Hz, H-3b), 4.50 (1H, m, H-18), 4.25 (1H, d, J = 8.0 Hz, H-17), 4.07 (2H, m, H-17d), 3.93 (3H, s, H-13d), 3.66 (3H, s, H-12a), 3.49 (2H, m, H-8a), 3.35 (3H, s, H-2a), 3.06 (3H, s, H-7a), 2.67 (1H, m, H-17a), 2.53 (1H, m, H-17b), 2.36 (1H, m, H-17a), 2.25 (1H, m, H-17b), 1.86 (3H, d, J = 7.2 Hz, H-18a), 1.63 (3H, t, J = 7.2 Hz, H-8b), 1.15 (3H, t, J = 7.2 Hz, H-17e); ¹³C NMR (CDCl₃, 100 MHz) δ_C 142.1 (C-1), 131.9 (C-2), 12.2 (C-2a), 136.2 (C-3), 129.1 (C-3a), 122.7 (C-3b), 136.1 (C-4), 97.5 (C-5), 155.6 (C-6), 136.5 (C-7), 11.2 (C-7a), 145.1 (C-8), 19.4 (C-8a), 17.4 (C-8b), 151.0 (C-9), 104.4 (C-10), 138.0 (C-11), 129.1 (C-12), 12.1 (C-12a), 129.0 (C-13), 189.8 (C-13a), 64.9 (C-13b), 169.8 (C-13c), 53.0 (C-13d), 149.8 (C-14), 105.3 (C-15), 161.4 (C-16), 51.3 (C-17), 30.0 (C-17a), 31.4 (C-17b), 173.1 (C-17c), 60.6 (C-17d), 14.2 (C-17e), 50.3 (C-18), 23.2 (C-18a), 172.3 (C-19), 93.2 (C-20)。以上波谱数据与文献^[18]报道数据基本一致, 故鉴定化合物12为17³-脱镁叶绿素乙酯。

化合物13 无色油状物; [α]

$ {}_{\mathrm{D}}^{20} $

-2.80° (c 0.665, CH₃OH; 1 g·100 mL^-1); HR-ESI-MS m/z 219.17 [M+H]⁺, 分子式: C₁₅H₂₂O。UV (CH₃OH) λ_max (log ε) 194 (3.34), 196 (3.36), 204 (3.58), 258 (3.53)。¹H NMR (CDCl₃, 400 MHz) δ_H 5.73 (1H, s, H-3), 2.68 (1H, d, J = 6.8 Hz, H-1), 2.66 (1H, s, H-6), 2.00 (3H, s, H-14), 1.98 (1H, d, J = 6.8 Hz, H-5), 1.87 (1H, m, H-9), 1.73 (3H, overlap, H-7, H-8, H-9), 1.61 (1H, m, H-8), 1.51 (1H, m, H-11), 0.97 (3H, s, H-15), 0.85 (6H, overlap, H-12, H-13); ¹³C NMR (CDCl₃, 100 MHz) δ_C 56.7 (C-1), 204.2 (C-2), 121.5 (C-3), 170.2 (C-4), 56.1 (C-5), 54.6 (C-6), 45.5 (C-7), 22.1 (C-8), 36.8 (C-9), 57.4 (C-10), 31.9 (C-11), 19.6 (C-12), 20.1 (C-13), 20.4 (C-14), 23.8 (C-15)。以上波谱数据与文献^[19]报道数据基本一致, 故鉴定化合物13为mustakone。

3　抗菌活性测定

化合物的抗菌活性测试参照CLSI相关规定, 采用肉汤微量稀释法^{[2, 20]}。

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2026年第61卷第5期

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doi: 10.16438/j.0513-4870.2025-1429

接收时间：2025-12-01
首发时间：2026-09-21
出版时间：2026-05-12

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收稿日期：2025-12-01
修回日期：2026-01-05

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¹深圳大学医学部药学院, 广东深圳 518060

²深圳技术大学药学院, 广东深圳 518118

³河南大学药学院, 河南开封 475004

⁴暨南大学, 教育部中药现代化与创新药物研究国际合作联合实验室, 广东广州 510632

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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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