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Article(id=1308840380477563358, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840287129141340, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-1399, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1763913600000, receivedDateStr=2025-11-24, revisedDate=1765209600000, revisedDateStr=2025-12-09, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981463783, onlineDateStr=2026-09-21, pubDate=1775923200000, pubDateStr=2026-04-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981463783, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981463783, creator=13701087609, updateTime=1789981463783, updator=13701087609, issue=Issue{id=1308840287129141340, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='4', pageStart='1001', pageEnd='1434', issueExtLink='null', onlineDate='null', pubDate='1775923200000', pubDateStr='2026-04-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981441528, creator='13701087609', updateTime=1789984228828, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851977992368434, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840287129141340, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851977992368435, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840287129141340, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=1311, endPage=1320, ext={EN=ArticleExt(id=1308840382348222943, articleId=1308840380477563358, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=C21 steroidal components from Cynanchum wallichii Wight and their anti-hepatocellular carcinoma activity, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

By comprehensively applying various separation techniques such as silica gel, ODS, and Sephadex LH-20 column chromatography, as well as preparative HPLC, fourteen C21 steroidal compounds were isolated from the chloroform extract of Cynanchum wallichii Wight. The structures of these compounds were identified through spectroscopic techniques including mass spectrometry (MS), nuclear magnetic resonance spectroscopy (NMR), ultraviolet spectroscopy (UV), and infrared spectroscopy (IR) methods as cynanotonin E (1), qingyangshengenin (2), qinyangshengenin-3-O-β-D-cymaropyranoside-(1→4)-β-D-cymaropyranoside (3), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosy-(1→4)-β-D-digitoxopyranoside (4), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (5), 12-O-benzoylsarcostin-3-O-β-D-oleandropyranosy-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl (6), 12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl (7), caudatin-3-O-β-D-digitoxopyranoside (8), caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (9), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (10), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (11), otophylloside B (12), otophylloside E (13) and otophylloside F (14). Among them, compound 1 is a new compound. The cytotoxic activities of compounds 1-14 against human hepatocellular carcinoma HepG2 cells were tested using the MTS method. The results indicated that all compounds exhibited good inhibitory activities against the proliferation of HepG2 cells, with IC50 values ranging from 4.3 ± 1.25 - 26.3 ± 1.65 μmol·L-1. Among them, the inhibitory activities of compounds 1, 3 and 6-14 were all stronger than that of the positive control cisplatin (DDP, IC50: 15.9 ± 1.25 μmol·L-1).

, authors=Zhong-hai DAO, De-qiong NIU, Zhi-feng XIAO, Jin-run DONG*, authorsList=Zhong-hai DAO, De-qiong NIU, Zhi-feng XIAO, Jin-run DONG, authorCompany=null, correspAuthors=Jin-run DONG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2026 Acta Pharmaceutica Sinica. All rights reserved., copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, fund=null), CN=ArticleExt(id=1308840383119974884, articleId=1308840380477563358, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=昆明杯冠藤中C21甾体成分及其抗肝癌活性研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

综合运用硅胶柱色谱、葡聚糖凝胶Sephadex LH-20柱色谱、制备薄层色谱和高效液相色谱等多种技术, 从昆明杯冠藤(Cynanchum wallichii Wight) 氯仿提取物中分离得到14个C21甾体类化合物。通过质谱、核磁共振波谱、紫外、红外等波谱技术对化合物进行了结构鉴定。分别鉴定为cynanotonin E (1)、qingyangshengenin (2)、qinyangshengenin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (3)、qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (4)、qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (5)、12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl (6)、12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (7)、caudatin-3-O-β-D-digitoxopyranoside (8)、caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (9)、caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (10)、caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (11)、otophylloside B (12)、otophylloside E (13) 和otophylloside F (14), 其中化合物1为新化合物。采用MTS法测试化合物1~14对人肝癌细胞HepG2的细胞毒活性, 结果表明, 所有化合物均表现出较好的抑制HepG2细胞增殖活性, 其IC50值范围为4.3 ± 1.25~26.3 ± 1.65 μmol·L-1, 其中化合物1、3和6~14的抑制活性强于阳性对照顺铂(DDP, IC50: 15.9 ± 1.25 μmol·L-1)。

, authors=刀中海, 牛德琼, 肖智锋, 董锦润*, authorsList=刀中海, 牛德琼, 肖智锋, 董锦润, authorCompany=null, correspAuthors=董锦润, authorNote=

作者贡献:

刀中海是本文的第一作者, 负责药材成分分离及肿瘤细胞毒活性测定; 牛德琼和肖智锋协助分离纯化和活性测定; 董锦润是本文的通讯作者, 设计和组织了整个实验, 负责结构鉴定及修改稿件。

, correspAuthorsNote=
董锦润, E-mail:
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Fitoterapia, 2015, 101: 107-116., articleTitle=null, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1308840383409381861, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, xref=null, ext=[AuthorCompanyExt(id=1308840383417770470, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, companyId=1308840383409381861, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=College of Biology and Food Engineering, Southwest Forestry University, Kunming 650224, China), AuthorCompanyExt(id=1308840383426159079, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, companyId=1308840383409381861, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=西南林业大学生物与食品工程学院, 云南 昆明 650224)])], figs=[ArticleFig(id=1308840386873876998, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, language=EN, label=null, caption=null, figureFileSmall=u/4kDw85/rIXSEqapiBerQ==, figureFileBig=RLM4Po9oUmPgQUJ7hFoB2w==, tableContent=null), ArticleFig(id=1308840386945180167, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, language=CN, label=Fig.1, caption=Structures of compounds 1-14, figureFileSmall=u/4kDw85/rIXSEqapiBerQ==, figureFileBig=RLM4Po9oUmPgQUJ7hFoB2w==, tableContent=null), ArticleFig(id=1308840387129729544, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, language=EN, label=null, caption=null, figureFileSmall=7A2Y185+DKrcA5M/m4SSJg==, figureFileBig=qyLwoaV3hcR5n+Dlw+TUjA==, tableContent=null), ArticleFig(id=1308840387188449801, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, language=CN, label=Fig.2, caption=Key 1H-1H COSY and HMBC correlations of compounds 1, figureFileSmall=7A2Y185+DKrcA5M/m4SSJg==, figureFileBig=qyLwoaV3hcR5n+Dlw+TUjA==, tableContent=null), ArticleFig(id=1308840387251364362, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
No.δH (J in Hz)δCNo.δH (J in Hz)δC
11.10 m; 1.85 m39.8 (CH2)D-Digit
21.58 m; 1.84 m30.2 (CH2)1″4.97 dd (9.6, 2.0)97.0 (CH)
33.57 m79.3 (CH)2″1.69 m; 1.96 m38.9 (CH2)
42.22 m; 2.35 m39.8 (CH2)3″4.24 d (3.2)74.1 (CH)
5140.2 (C)4″3.32 m83.6 (CH)
65.35 d (4.8)119.7 (CH)5″3.96 m69.5 (CH)
71.97 m; 2.14 m35.5 (CH2)6″1.3 d (6.1)18.5 (CH3)
875.0 (C)D-Cym
91.58 m45.1 (CH)1‴4.79 m100.6 (CH)
1038.1 (C)2‴1.61 m; 2.14 m36.2 (CH2)
111.76 m; 1.96 m25.5 (CH2)3‴3.84 m79.2 (CH)
124.75 dd (11.7, 4.3)74.4 (CH)4‴3.29 m83.8 (CH)
1359.1 (C)5‴3.00 m68.4 (CH)
1490.0 (C)6‴1.27 s18.5 (CH3)
151.74 m; 1.93 m34.3 (CH2)OMe3.45 d (8.5)58.5 (OCH3)
161.72 m; 2.85 m33.5 (CH2)D-Cym
1793.0 (C)1″″4.77 m101.3 (CH)
181.65 s10.6 (CH3)2″″1.90 m; 2.24 m37.4 (CH2)
191.15 s18.7 (CH3)3″″3.92 m74.4 (CH)
20212.1 (C)4″″3.51 dd (9.6, 2.9)78.5 (CH)
212.04 s27.8 (CH3)5″″4.20 m70.0 (CH)
p-OH-Benzoyl6″″1.42 d (6.2)18.4 (CH3)
1′166.8 (C)OMe3.46 s58.1 (OCH3)
2′122.1 (C)
3′7.79 (d, 8.8)132.8 (CH)
4′6.80 (dd, 8.9, 3.0)116.3 (CH)
5′164.0 (C)
6′6.80 dd (8.9, 3.0)116.3 (CH)
7′7.79 d (8.8)132.8 (CH)
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1H NMR (400 MHz) and 13C NMR (150 MHz) data of compound 1 in CD3OD

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No.δH (J in Hz)δCNo.δH (J in Hz)δC
11.10 m; 1.85 m39.8 (CH2)D-Digit
21.58 m; 1.84 m30.2 (CH2)1″4.97 dd (9.6, 2.0)97.0 (CH)
33.57 m79.3 (CH)2″1.69 m; 1.96 m38.9 (CH2)
42.22 m; 2.35 m39.8 (CH2)3″4.24 d (3.2)74.1 (CH)
5140.2 (C)4″3.32 m83.6 (CH)
65.35 d (4.8)119.7 (CH)5″3.96 m69.5 (CH)
71.97 m; 2.14 m35.5 (CH2)6″1.3 d (6.1)18.5 (CH3)
875.0 (C)D-Cym
91.58 m45.1 (CH)1‴4.79 m100.6 (CH)
1038.1 (C)2‴1.61 m; 2.14 m36.2 (CH2)
111.76 m; 1.96 m25.5 (CH2)3‴3.84 m79.2 (CH)
124.75 dd (11.7, 4.3)74.4 (CH)4‴3.29 m83.8 (CH)
1359.1 (C)5‴3.00 m68.4 (CH)
1490.0 (C)6‴1.27 s18.5 (CH3)
151.74 m; 1.93 m34.3 (CH2)OMe3.45 d (8.5)58.5 (OCH3)
161.72 m; 2.85 m33.5 (CH2)D-Cym
1793.0 (C)1″″4.77 m101.3 (CH)
181.65 s10.6 (CH3)2″″1.90 m; 2.24 m37.4 (CH2)
191.15 s18.7 (CH3)3″″3.92 m74.4 (CH)
20212.1 (C)4″″3.51 dd (9.6, 2.9)78.5 (CH)
212.04 s27.8 (CH3)5″″4.20 m70.0 (CH)
p-OH-Benzoyl6″″1.42 d (6.2)18.4 (CH3)
1′166.8 (C)OMe3.46 s58.1 (OCH3)
2′122.1 (C)
3′7.79 (d, 8.8)132.8 (CH)
4′6.80 (dd, 8.9, 3.0)116.3 (CH)
5′164.0 (C)
6′6.80 dd (8.9, 3.0)116.3 (CH)
7′7.79 d (8.8)132.8 (CH)
), ArticleFig(id=1308840387406553612, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308840380477563358, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compd.IC50/μmol·L-1Compd.IC50/μmol·L-1
19.2 ± 1.43911.8 ± 1.33
226.3 ± 1.651012.5 ± 2.15
312.7 ± 1.021111.3 ± 1.67
419.2 ± 0.95126.5 ± 1.53
523.6 ± 2.11134.3 ± 1.25
614.6 ± 1.42147.8 ± 1.27
712.1 ± 2.01DDP15.9 ± 1.25
814.5 ± 1.03
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The cytotoxicity of compounds 1-14 against HepG2 cells. n = 3, $ \stackrel{-}{x} $ ± s. DDP: Cisplatin

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Compd.IC50/μmol·L-1Compd.IC50/μmol·L-1
19.2 ± 1.43911.8 ± 1.33
226.3 ± 1.651012.5 ± 2.15
312.7 ± 1.021111.3 ± 1.67
419.2 ± 0.95126.5 ± 1.53
523.6 ± 2.11134.3 ± 1.25
614.6 ± 1.42147.8 ± 1.27
712.1 ± 2.01DDP15.9 ± 1.25
814.5 ± 1.03
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昆明杯冠藤中C21甾体成分及其抗肝癌活性研究
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刀中海 , 牛德琼 , 肖智锋 , 董锦润 *
药学学报 | 研究论文 2026,61(4): 1311-1320
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药学学报 |研究论文 2026 , 61 (4) : 1311 -1320
昆明杯冠藤中C21甾体成分及其抗肝癌活性研究
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刀中海, 牛德琼, 肖智锋, 董锦润*
作者信息
  • 西南林业大学生物与食品工程学院, 云南 昆明 650224
通讯作者:
董锦润, E-mail:
作者简介:

作者贡献:

刀中海是本文的第一作者, 负责药材成分分离及肿瘤细胞毒活性测定; 牛德琼和肖智锋协助分离纯化和活性测定; 董锦润是本文的通讯作者, 设计和组织了整个实验, 负责结构鉴定及修改稿件。

C21 steroidal components from Cynanchum wallichii Wight and their anti-hepatocellular carcinoma activity
Zhong-hai DAO, De-qiong NIU, Zhi-feng XIAO, Jin-run DONG*
Affiliations
  • College of Biology and Food Engineering, Southwest Forestry University, Kunming 650224, China
出版时间: 2026-04-12 doi: 10.16438/j.0513-4870.2025-1399
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摘要
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综合运用硅胶柱色谱、葡聚糖凝胶Sephadex LH-20柱色谱、制备薄层色谱和高效液相色谱等多种技术, 从昆明杯冠藤(Cynanchum wallichii Wight) 氯仿提取物中分离得到14个C21甾体类化合物。通过质谱、核磁共振波谱、紫外、红外等波谱技术对化合物进行了结构鉴定。分别鉴定为cynanotonin E (1)、qingyangshengenin (2)、qinyangshengenin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (3)、qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (4)、qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (5)、12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl (6)、12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (7)、caudatin-3-O-β-D-digitoxopyranoside (8)、caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (9)、caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (10)、caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (11)、otophylloside B (12)、otophylloside E (13) 和otophylloside F (14), 其中化合物1为新化合物。采用MTS法测试化合物1~14对人肝癌细胞HepG2的细胞毒活性, 结果表明, 所有化合物均表现出较好的抑制HepG2细胞增殖活性, 其IC50值范围为4.3 ± 1.25~26.3 ± 1.65 μmol·L-1, 其中化合物1、3和6~14的抑制活性强于阳性对照顺铂(DDP, IC50: 15.9 ± 1.25 μmol·L-1)。

鹅绒藤属  /  昆明杯冠藤  /  C21甾体  /  结构鉴定  /  细胞毒活性

By comprehensively applying various separation techniques such as silica gel, ODS, and Sephadex LH-20 column chromatography, as well as preparative HPLC, fourteen C21 steroidal compounds were isolated from the chloroform extract of Cynanchum wallichii Wight. The structures of these compounds were identified through spectroscopic techniques including mass spectrometry (MS), nuclear magnetic resonance spectroscopy (NMR), ultraviolet spectroscopy (UV), and infrared spectroscopy (IR) methods as cynanotonin E (1), qingyangshengenin (2), qinyangshengenin-3-O-β-D-cymaropyranoside-(1→4)-β-D-cymaropyranoside (3), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosy-(1→4)-β-D-digitoxopyranoside (4), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (5), 12-O-benzoylsarcostin-3-O-β-D-oleandropyranosy-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl (6), 12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl (7), caudatin-3-O-β-D-digitoxopyranoside (8), caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (9), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (10), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (11), otophylloside B (12), otophylloside E (13) and otophylloside F (14). Among them, compound 1 is a new compound. The cytotoxic activities of compounds 1-14 against human hepatocellular carcinoma HepG2 cells were tested using the MTS method. The results indicated that all compounds exhibited good inhibitory activities against the proliferation of HepG2 cells, with IC50 values ranging from 4.3 ± 1.25 - 26.3 ± 1.65 μmol·L-1. Among them, the inhibitory activities of compounds 1, 3 and 6-14 were all stronger than that of the positive control cisplatin (DDP, IC50: 15.9 ± 1.25 μmol·L-1).

Cynanchum  /  Cynanchum wallichii Wight  /  C21 steroidal compound  /  structural identification  /  cytotoxic activity
刀中海, 牛德琼, 肖智锋, 董锦润. 昆明杯冠藤中C21甾体成分及其抗肝癌活性研究. 药学学报, 2026 , 61 (4) : 1311 -1320 . DOI: 10.16438/j.0513-4870.2025-1399
Zhong-hai DAO, De-qiong NIU, Zhi-feng XIAO, Jin-run DONG. C21 steroidal components from Cynanchum wallichii Wight and their anti-hepatocellular carcinoma activity[J]. Acta Pharmaceutica Sinica, 2026 , 61 (4) : 1311 -1320 . DOI: 10.16438/j.0513-4870.2025-1399
正文
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昆明杯冠藤(Cynanchum wallichii Wight.) 为萝藦科(Asclepiadaceae) 鹅绒藤属(Cynanchum Linn.) 多年生草质藤本中药。别名昆明白前、青洋参、断节参等。生于山坡草地、村边和路旁、灌木丛或山谷等处, 产于云南、贵州、广西和四川等省区, 并分布于印度[1]。是我国独具特色的民族中药材, 药用历史悠久, 民间常用其根作滋补强壮药, 并用于治疗跌打损伤、风湿关节炎、病后体虚以及肾虚腰痛等[2, 3]。被纳入云南特色中成药“虎力散”的核心组方[4]。目前关于昆明杯冠藤化学成分研究报道较少, 主要为苯乙酮、C21甾体类化学成分, 其中C21甾体类化合物是其主要活性成分, 具有抗炎、抗肿瘤、抗抑郁等多种药理活性[5-11]。C21甾体类化合物的结构多样性主要体现在苷元类型差异, 目前已鉴定出断节参苷元(wallicosid)、加加明(gagamine)、青阳参苷元(qingyangshengenin)、去乙酰萝摩苷元(deacylmetaplexigenin) 及告达亭(caudatin) 等主要苷元类型[12, 13]。为了深入研究昆明杯冠藤主要的C21甾体类成分及其生物活性, 本实验对其甲醇提取物的氯仿萃取部位进行系统的提取分离, 从中分离得到14个C21甾体皂苷类化合物(图1), cynanotonin E (1)、qingyangshengenin (2)、qinyangshengenin-3-O-β- D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (3)、qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (4)、qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (5)、12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl (6)、12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (7)、caudatin-3-O-β-D-digitoxopyranoside (8)、caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (9)、caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (10)、caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (11)、otophylloside B (12)、otophylloside E (13) 和otophylloside F (14), 其中化合物1为新的C21甾体皂苷类化合物。采用MTS法测试了14个化合物对人肝癌细胞HepG2的细胞毒活性, 结果表明, 所有化合物均表现出较好的抑制HepG2细胞增殖活性, 其IC50值为4.3 ± 1.25~26.3 ± 1.65 μmol·L-1, 其中化合物1, 3和6~14的抑制活性都强于阳性对照顺铂(DDP, IC50: 15.9 ± 1.25 μmol·L-1)。
结果与讨论
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1　化合物1结构鉴定
白色无定形粉末, [α]$ {}_{\mathrm{D}}^{26.2} $ +4.0 (0.16, MeOH)。Liberman-Buchard和Keller-Kiliani反应呈阳性, 提示化合物1可能为甾体2-去氧吡喃糖苷类化合物。高分辨电喷雾质谱HRESIMS显示准分子离子峰[M+K]+的m/z为957.424 5, 故化合物1的分子式为C48H70O17。在红外光谱中显示有羟基(3 440 cm-1), 羰基(1 708 cm-1) 和双键(1 663 cm-1) 的振动吸收。13C NMR和DEPT谱(表1) 显示化合物1共有48个碳, 分别为6个甲基、2个甲氧基、10个亚甲基、20个次甲基(包括1个sp3次甲基, 5个sp2次甲基, 14个氧化的次甲基) 以及10个季碳(包括3个sp2季碳、1个酯羰基、1个酮羰基、2个sp3季碳、3个氧化的季碳)。综合以上的数据可以推测化合物1为典型的带3个去氧糖的C21甾体苷。通过比较1H NMR及13C NMR谱图, 发现化合物1的苷元部分与文献[14]中的青阳参苷元的数据基本一致, 也为青阳参苷元。在90~110 ppm处, 13C NMR显示化合物1含有3个糖端基碳的共振信号: δC 97.0, δC 100.6, δC 101.3。HSQC实验指明1H NMR中相应的3个端基质子的共振信号: H-1″ (δH 4.97, dd, J = 2.0, 9.6 Hz), H-1‴ (δH 4.79, m), H-1″″ (δH 4.77, m), 因此推断化合物1为三糖苷。通过将化合物1的1H NMR及13C NMR数据与文献[15, 16]进行比对, 结合TLC检测结果, 对其在弱酸性条件下的水解产物与加拿大麻吡喃糖(cymarose) 和毛地黄毒吡喃糖(digitoxose) 对照品进行对照分析, 结果表明, 该化合物中的3个糖基由2个加拿大麻吡喃糖和1个毛地黄毒吡喃糖组成, 且糖链中的糖均以β-苷键连接。进一步将糖的旋光OR值与文献[16]比较(digitoxose: [α]$ {}_{\mathrm{D}}^{20} $ +43.5, 文献为D-digitoxose [α]$ {}_{\mathrm{D}}^{20} $ +40.5; cymarose: [α]$ {}_{\mathrm{D}}^{20} $ +56.0, 文献为D-cymarose [α]$ {}_{\mathrm{D}}^{20} $ +46.2), 确定三个糖的绝对构型为D型。图2给出了化合物1主要的1H-1H COSY和HMBC相关信号。尤其在HMBC谱中, 质子H-1″ (δH 4.97, dd, J = 9.6, 2.0 Hz) 与苷元的C-3位(δC 79.3) 远程相关, 说明化合物1的内侧糖基与苷元的C-3位上的羟基相连。进一步通过HMBC谱确定了化合物1的三个糖基之间的连接顺序: H-1″与C-3, H-1‴与C-4″ (δC 83.6), H-1″″与C-4‴ (δC 83.8) 有较强的相关性, 说明糖链通过内侧的毛地黄毒吡喃糖基与苷元的C-3位连接, 糖链内的糖基通过1, 4-糖苷键(1→4) 进行连接。综上所述, 化合物1的结构推断为青阳参苷元-3-O-β-D-加拿大麻吡喃糖-(1→4)-β-D-加拿大麻吡喃糖-(1→4)-β-D-毛地黄毒吡喃糖苷, 命名为cynanotonin E (1)。
2　化合物的细胞毒作用
采用MTS法测定化合物1~14对人肝癌细胞HepG2的细胞毒活性, 结果见表2。发现所有化合物均表现出较好的细胞毒活性, 其IC50值从4.3 ± 1.25~26.3 ± 1.65 μmol·L-1不等, 除了化合物2、4和5, 化合物1、3和6~14表现出显著的抑制HepG2细胞增殖活性, 它们的抑制效果比阳性对照顺铂(DDP, IC50: 15.9 ± 1.25 μmol·L-1) 更强。通过比较化合物之间的活性差异, 发现化合物C-3位连的糖基数量对化合物的细胞毒活性有较大的影响, 含3个糖基的化合物活性明显增强。
实验部分
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超导核磁共振仪AVANCEIII-400 MHz和AV-600 MHz (δ为ppm, J为Hz, 四甲基硅烷TMS作为内标)、傅里叶变换中红外光谱仪Tensor-27、液相离子阱色谱质谱联用仪(HCT/Esquire), 德国Bruker公司; 全自动数字旋光仪(日本Jasco P-1020); 液相四极杆飞行时间质谱仪(APIQSTAR Pulsa)、多功能酶标仪(MULTISKAN FC), 美国赛默飞公司; 紫外可见分光光度仪(ShimadzuUV2401PC, 日本岛津公司); 高效液相色谱(1100, 美国安捷伦公司); 反相材料RP-18 (日本Fuji公司); LH-20葡聚糖凝胶为进口分装; 柱色谱硅胶、薄层色谱硅胶(青岛海洋化工); 显色剂: 10%硫酸-无水乙醇溶液, 喷洒后适当加热; 细胞株(人肝癌细胞HepG2, 美国ATCC公司); 胎牛血清(美国Hyclone公司, SH30406.05); DMEM培养基(美国Gibco公司)。
昆明杯冠藤药材购买于云南省昆明市新螺蛳湾中药材市场, 并由昆明植物研究所裴盛基研究员鉴定为昆明杯冠藤(Cynanchum wallichii Wight) 的干燥块根。凭证样品(KUN No. 0776921) 存放于西南林业大学生物与食品工程学院生物化学实验室。
1　提取与分离
取昆明杯冠藤干燥根茎20公斤粉碎, 使用95%甲醇在80 ℃水浴条件下回流提取(每次10倍量溶剂, 提取3次, 每次2 h)。合并提取液并减压回收溶剂, 得到浸膏共2 kg。加适量水使浸膏分散, 依次用石油醚、氯仿进行萃取(10 L×3次), 减压回收得氯仿萃取物400 g。取氯仿萃取部位用硅胶柱色谱进行分离, 依次用氯仿-甲醇(80∶1、50∶1、20∶1和5∶1) 洗脱, 根据薄层色谱结果, 合并洗脱液得到4个组分(Fr.1~Fr.4)。将Fr.2 (60 g) 上正相硅胶柱分离, 经氯仿-甲醇(60∶1) 洗脱, 得到5个组分(Fr2.1~Fr2.5)。将Fr2.1组分(45 g) 上反相ODS柱色谱分离, 甲醇-水(40∶60~100∶0) 系统梯度洗脱, 得到11个组分(Fr2.1.1~Fr2.1.11)。Fr2.1.9 (10 g) 上正相硅胶柱色谱, 经氯仿-丙酮(15∶1) 梯度洗脱, 得到6个组分(Fr2.1.9.1~Fr2.1.9.6)。将Fr2.1.9.4 (4 g) 上反相ODS柱色谱分离, 甲醇-水(20∶80~100∶0) 系统梯度洗脱, 经点板确认, 得到3个组分(Fr2.1.9.4.1~Fr2.1.9.4.3), 选取Fr2.1.9.4.2经半制备-HPLC (乙腈-水, 60∶40, 流速3 mL·min-1) 后得到化合物6 (tR = 15.4 min; 8 mg), 7 (tR = 22.5 min; 7 mg), 8 (tR = 11.0 min; 10 mg), 9 (tR = 34.5 min; 50 mg)。再选取Fr2.1.10经半制备- HPLC (乙腈-水, 55∶45, 流速3 mL·min-1) 富集纯化, 得到化合物10 (tR = 18.3 min; 50 mg)、11 (tR = 24.5 min; 15 mg) 和12 (tR = 36.4 min; 1 g)。将Fr2.3段(30 g) 上反相ODS柱色谱分离, 经甲醇-水(40∶60~100∶0) 系统梯度洗脱, 共得到15个组分(Fr2.3.1~Fr2.3.15)。Fr2.3.7组分(3 g) 上薄层层析硅胶柱进一步分离, 得到化合物2 (200 mg)。将Fr2.3.12和Fr2.3.13组分分别上硅胶柱色谱分离, 经氯仿-甲醇(35∶1) 洗脱, 分别得到6个组分(Fr2.3.12.1~Fr2.3.12.6) 及(Fr2.3.13.1~Fr2.3.13.6)。Fr2.3.12.2经半制备-HPLC (乙腈-水, 50∶50, 流速3 mL·min-1) 富集纯化得到化合物3 (tR = 26.2 min; 6 mg) 和4 (tR = 37.5 min; 500 mg)。对Fr2.3.13.4进行薄层层析硅胶柱进一步分离, 得到5个组分(Fr2.3.13.4.1~Fr2.3.13.4.5), 其中Fr2.3.13.4.3段经半制备-HPLC纯化(乙腈-水, 40∶60, 流速3 mL·min-1) 后得到化合物1 (tR = 16.0 min; 20 mg) 和5 (tR = 25.7 min; 5 mg)。将Fr2.3.15进行薄层层析硅胶柱进一步分离, 得到5个组分(Fr2.3.15.1~Fr2.3.15.5)。其中Fr2.3.15.1 (250 mg) 经半制备-HPLC纯化(乙腈-水, 45∶55, 流速3 mL·min-1), 得到化合物13 (tR = 17.8 min; 10 mg) 和14 (tR = 27.5 min; 20 mg)。
2　化合物的理化常数
化合物1  白色无定形粉末; [α]$ {}_{\mathrm{D}}^{26.2} $ +4.0 (0.16, MeOH); UV (MeOH) λmax (log ε): 203(4.26), 259 (4.23), 368 (2.08); IR (KBr) vmax: 3 440, 2 930, 1 708, 1 663, 1 399, 1 276, 1 194, 1 058和719 cm-1; ESIMS m/z 957 [M+K]+, HRESIMS m/z 957.424 5 [M+K]+ (calcd. for C48H70KO17, 957.424 7), 1H NMR (400 MHz, CD3OD) 和13C NMR (150 MHz, CD3OD) 数据, 见表1。
化合物2  白色无定形粉末, 分子式为C28H36O8; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 7.81 (1H, d, J = 8.8 Hz, H-3′/7′), 6.82 (1H, d, J = 8.7 Hz, H-4′/6′), 5.33 (1H, s, H-6), 4.76 (1H, dd, J = 5.3, 10.2 Hz, H-12), 3.30 (1H, m, H-3), 2.07 (3H, s, H-21), 1.64 (3H, s, H-18), 1.15 (3H, s, H-19); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 31.7 (C-2), 72.6 (C-3), 42.9 (C-4), 140.7 (C-5), 119.3 (C-6), 35.2 (C-7), 75.0 (C-8), 45.1 (C-9), 38.0 (C-10), 25.5 (C-11), 74.1 (C-12), 59.1 (C-13), 90.0 (C-14), 34.3 (C-15), 33.5 (C-16), 93.1 (C-17), 10.6 (C-18), 18.6 (C-19), 212.1 (C-20), 27.8 (C-21), 166.8 (C-1′), 122.4 (C-2′), 132.8 (C-3′), 116.1 (C-4′), 163.6 (C-5′), 116.1 (C-6′), 132.8 (C-7′)。以上波谱数据与文献[17]报道对比, 确定化合物2为qingyangshengenin。
化合物3  白色无定形粉末, 分子式为C42H60O14; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 7.81 (1H, d, J = 8.8 Hz, H-3′/7′), 6.82 (1H, d, J = 8.7 Hz, H-4′/6′), 5.36 (1H, s, H-6), 4.78 (1H, dd, J = 4.3, 11.8 Hz, H-1″), 4.77 (1H, dd, J = 5.3, 10.2 Hz, H-12), 4.76 (1H, dd, J = 4.3, 11.8 Hz, H-1‴), 3.84 (1H, m, H-3″), 3.84 (1H, m, H-3‴), 3.59 (1H, m, H-3), 3.59 (1H, m, H-5″), 3.45 (3H, s, OCH3), 3.43 (1H, m, H-5‴), 3.42 (3H, s, OCH3), 3.21 (1H, dd, J = 3.2, 9.6 Hz, H-4″), 3.18 (1H, dd, J = 3.2, 9.6 Hz, H-4‴), 2.10 (3H, s, H-21), 1.64 (3H, s, H-18), 1.23 (3H, d, J = 6.2 Hz, H-6″), 1.22 (3H, d, J = 6.2 Hz, H-6‴), 1.14 (3H, s, H-19); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.1 (C-9), 38.2 (C-10), 25.5 (C-11), 74.1 (C-12), 59.1 (C-13), 90.0 (C-14), 34.3 (C-15), 33.5 (C-16), 93.1 (C-17), 10.6 (C-18), 18.6 (C-19), 212.1 (C-20), 27.8 (C-21), 166.8 (C-1′), 122.3 (C-2′), 132.8 (C-3′), 116.2 (C-4′), 163.7 (C-5′), 116.2 (C-6′), 132.8 (C-7′), 97.2 (C-1″), 36.6 (C-2″), 79.2 (C-3″), 74.5 (C-4″), 71.3 (C-5″), 18.7 (C-6″), 58.4 (OCH3), 101.2 (C-1‴), 35.6 (C-2‴), 78.6 (C-3‴), 74.1 (C-4‴), 70.0 (C-5‴), 18.5 (C-6‴), 58.1 (OCH3)。以上波谱数据与文献[18]报道对比, 确定化合物3为qinyangshengenin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside。
化合物4  白色无定形粉末, 分子式为C48H70O17; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 7.72 (1H, d, J = 8.8 Hz, H-3′/7′), 6.74 (1H, d, J = 8.7 Hz, H-4′/6′), 5.35 (1H, s, H-6), 4.96 (1H, d, J = 9.6 Hz, H-1″), 4.85 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.80 (1H, dd, J = 5.3, 10.2 Hz, H-12), 4.60 (1H, d, J = 9.2 Hz, H-1″″), 4.23 (1H, d, J = 2.8 Hz, H-3″), 3.85 (1H, m, H-3‴), 3.83 (1H, m, H-5‴), 3.82 (1H, m, H-5″), 3.56 (1H, m, H-3), 3.54 (3H, s, OCH3), 3.51 (1H, m, H-3″″), 3.43 (3H, s, OCH3), 3.34 (1H, m, H-5″″), 3.28 (1H, m, H-4‴), 3.20 (1H, m, H-4″), 3.20 (1H, m, H-4″″), 2.10 (3H, s, H-21), 1.63 (3H, s, H-18), 1.30 (3H, d, J = 6.0 Hz, H-6″″), 1.21 (3H, d, J = 6.0 Hz, H-6‴), 1.19 (3H, d, J = 6.3 Hz, H-6″), 1.15 (3H, s, H-19); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.1 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.1 (C-9), 38.2 (C-10), 25.5 (C-11), 74.1 (C-12), 59.1 (C-13), 90.0 (C-14), 34.3 (C-15), 33.5 (C-16), 93.1 (C-17), 10.6 (C-18), 18.6 (C-19), 212.1 (C-20), 27.8 (C-21), 166.8 (C-1′), 122.1 (C-2′), 132.8 (C-3′), 116.2 (C-4′), 163.6 (C-5′), 116.3 (C-6′), 132.8 (C-7′), 97.0 (C-1″), 38.8 (C-2″), 68.3 (C-3″), 83.6 (C-4″), 69.5 (C-5″), 18.6 (C-6″), 100.6 (C-1‴), 36.3 (C-2‴), 78.4 (C-3‴), 83.8 (C-4‴), 70.0 (C-5‴), 18.5 (C-6‴), 58.6 (OCH3), 102.8 (C-1″″), 37.4 (C-2″″), 81.6 (C-3″″), 76.9 (C-4″″), 73.2 (C-5″″), 18.5 (C-6″″), 57.4 (OCH3)。以上波谱数据与文献[18]报道对比, 确定化合物4为qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside。
化合物5  白色无定形粉末, 分子式为C55H82O20; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 7.81 (1H, d, J = 8.8 Hz, H-3′/7′), 6.81 (1H, d, J = 8.7 Hz, H-4′/6′), 5.35 (1H, s, H-6), 4.96 (1H, d, J = 9.6 Hz, H-1″), 4.85 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.85 (1H, dd, J = 1.8, 9.6 Hz, H-1″″), 4.60 (1H, d, J = 9.2 Hz, H-1‴″), 4.58 (1H, dd, J = 5.3, 10.2 Hz, H-12), 4.23 (1H, d, J = 2.8 Hz, H-3″), 3.85 (1H, m, H-3‴), 3.85 (1H, m, H-3″″), 3.83 (1H, m, H-5‴), 3.83 (1H, m, H-5″″), 3.82 (1H, m, H-5″), 3.56 (1H, m, H-3), 3.54 (3H, s, OCH3), 3.51 (1H, m, H-3‴″), 3.43 (3H, s, OCH3), 3.34 (1H, m, H-5‴″), 3.28 (1H, m, H-4‴), 3.28 (1H, m, H-4″″), 3.20 (1H, m, H-4″), 3.20 (1H, m, H-4‴″), 2.10 (3H, s, H-21), 1.63 (3H, s, H-18), 1.30 (3H, d, J = 6.0 Hz, H-6‴″), 1.21 (3H, d, J = 6.0 Hz, H-6‴), 1.21 (3H, d, J = 6.0 Hz, H-6″″), 1.19 (3H, d, J = 6.3 Hz, H-6″), 1.15 (3H, s, H-19); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.1 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.1 (C-9), 38.2 (C-10), 25.5 (C-11), 74.1 (C-12), 59.1 (C-13), 90.0 (C-14), 34.3 (C-15), 33.5 (C-16), 93.1 (C-17), 10.6 (C-18), 18.6 (C-19), 212.1 (C-20), 27.8 (C-21), 166.8 (C-1′), 122.2 (C-2′), 132.8 (C-3′), 116.2 (C-4′), 163.8 (C-5′), 116.2 (C-6′), 132.8 (C-7′), 97.0 (C-1″), 38.8 (C-2″), 68.3 (C-3″), 83.6 (C-4″), 69.5 (C-5″), 18.6 (C-6″), 99.7 (C-1‴), 36.3 (C-2‴), 78.4 (C-3‴), 83.8 (C-4‴), 70.0 (C-5‴), 18.5 (C-6‴), 58.6 (OCH3), 100.6 (C-1″″), 36.3 (C-2‴), 78.4 (C-3″″), 83.8 (C-4″″), 70.0 (C-5″″), 18.5 (C-6″″), 58.0 (OCH3), 102.7 (C-1‴″), 37.4 (C-2‴″), 81.6 (C-3‴″), 76.9 (C-4‴″), 73.2 (C-5‴″), 18.5 (C-6‴″), 57.6 (OCH3)。以上波谱数据与文献[19]报道对比, 确定化合物5为qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside。
化合物6  白色无定形粉末, 分子式为C49H72O16; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 7.85 (1H, d, J = 7.2 Hz, H-3′/7′), 7.51 (1H, m, H-5′), 7.39 (1H, d, J = 8.0 Hz, H-4′/6′), 5.35 (1H, s, H-6), 4.73 (1H, dd, J = 1.6, 9.6 Hz, H-1″), 4.69 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.59 (1H, d, J = 9.2 Hz, H-1″″), 4.50 (1H, dd, J = 5.3, 10.2 Hz, H-12), 3.89 (1H, m, H-5‴), 3.86 (1H, m, H-3″), 3.85 (1H, m, H-3‴), 3.82 (1H, m, H-5″), 3.54 (3H, s, OCH3), 3.54 (3H, s, OCH3), 3.50 (1H, m, H-3), 3.50 (1H, m, H-3″″), 3.42 (3H, s, OCH3), 3.42 (3H, s, OCH3), 3.30 (1H, m, H-5″″), 3.26 (1H, m, H-4″), 3.23 (1H, m, H-4‴), 3.18 (1H, m, H-4″″), 2.10 (3H, s, H-21), 1.63 (3H, s, H-18), 1.30 (3H, d, J = 6.0 Hz, H-6″″), 1.29 (3H, d, J = 6.4 Hz, H-6‴), 1.18 (3H, d, J = 6.3 Hz, H-6″), 1.15 (3H, s, H-19); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.1 (C-5), 119.8 (C-6), 35.2 (C-7), 75.0 (C-8), 45.1 (C-9), 38.2 (C-10), 25.5 (C-11), 74.1 (C-12), 59.1 (C-13), 90.0 (C-14), 34.3 (C-15), 33.5 (C-16), 93.1 (C-17), 10.6 (C-18), 18.6 (C-19), 212.3 (C-20), 27.8 (C-21), 166.7 (C-1′), 131.5 (C-2′), 129.6 (C-3′), 130.5 (C-4′), 134.3 (C-5′), 130.5 (C-6′), 129.6 (C-7′), 97.2 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 58.5 (OCH3), 101.2 (C-1‴), 36.4 (C-2‴), 78.6 (C-3‴), 83.9 (C-4‴), 70.0 (C-5‴), 18.6 (C-6‴), 58.4 (OCH3), 102.8 (C-1″″), 37.4 (C-2″″), 76.9 (C-3″″), 81.7 (C-4″″), 73.2 (C-5″″), 18.5 (C-6″″), 57.4 (OCH3)。以上波谱数据与文献[20]报道对比, 确定化合物6为12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside。
化合物7  白色无定形粉末, 分子式为C48H72O16; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 7.60 (1H, d, J = 7.2 Hz, H-3′/7′), 7.58 (1H, m, H-5′), 7.37 (1H, d, J = 8.0 Hz, H-4′/6′), 5.35 (1H, s, H-6), 4.96 (1H, d, J = 9.6 Hz, H-1″), 4.85 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.60 (1H, d, J = 9.2 Hz, H-1″″), 4.52 (1H, dd, J = 5.3, 10.2 Hz, H-12), 4.23 (1H, d, J = 2.8 Hz, H-3″), 3.85 (1H, m, H-3‴), 3.83 (1H, m, H-5‴), 3.82 (1H, m, H-5″), 3.54 (3H, s, OCH3), 3.51 (1H, m, H-3″″), 3.43 (3H, s, OCH3), 3.34 (1H, m, H-5″″), 3.28 (1H, m, H-4‴), 3.20 (1H, m, H-4″), 3.20 (1H, m, H-4″″), 2.10 (3H, s, H-21), 1.63 (3H, s, H-18), 1.30 (3H, d, J = 6.0 Hz, H-6″″), 1.21 (3H, d, J = 6.0 Hz, H-6‴), 1.19 (3H, d, J = 6.3 Hz, H-6″), 1.15 (3H, s, H-19); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.1 (C-5), 119.8 (C-6), 35.2 (C-7), 75.0 (C-8), 45.1 (C-9), 38.2 (C-10), 25.5 (C-11), 74.1 (C-12), 59.1 (C-13), 90.0 (C-14), 34.3 (C-15), 33.5 (C-16), 93.1 (C-17), 10.6 (C-18), 18.6 (C-19), 212.3 (C-20), 27.8 (C-21), 166.7 (C-1′), 131.5 (C-2′), 129.6 (C-3′), 130.5 (C-4′), 134.3 (C-5′), 130.5 (C-6′), 129.6 (C-7′), 97.0 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 100.6 (C-1‴), 36.4 (C-2‴), 78.6 (C-3‴), 83.8 (C-4‴), 70.0 (C-5‴), 18.5 (C-6‴), 58.7 (OCH3), 102.8 (C-1″″), 37.4 (C-2″″), 76.9 (C-3″″), 81.7 (C-4″″), 73.2 (C-5″″), 18.4 (C-6″″), 58.5 (OCH3)。以上波谱数据与文献[21]报道对比, 确定化合物7为12-O-benzoylsarcostin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside。
化合物8  白色无定形粉末, 分子式为C34H52O10; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.84 (1H, s, H-2′), 5.35 (1H, d, J = 2.7 Hz, H-6), 4.98 (1H, d, J = 11.3 Hz, H-1″), 4.85 (1H, dd, J = 5.4, 10.1 Hz, H-12), 4.69 (1H, dd, J = 4.2, 11.6 Hz, H-3″), 3.84 (1H, m, H-3), 3.75 (1H, m, H-4″), 3.13 (1H, m, H-5″), 2.26 (3H, s, H-7′), 2.24 (1H, m, H-4′), 2.10 (3H, s, H-21), 1.63 (3H, s, H-18), 1.17 (3H, d, J = 5.8 Hz, H-6″), 1.14 (3H, s, H-19), 0.95 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.2 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 74.9 (C-8), 45.2 (C-9), 38.1 (C-10), 25.4 (C-11), 73.2 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.0 (C-17), 10.5 (C-18), 18.7 (C-19), 211.6 (C-20), 27.6 (C-21), 167.5 (C-1′), 114.2 (C-2′), 167.5(C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.3 (C-7′), 97.1 (C-1″), 39.8 (C-2″), 75.6 (C-3″), 70.8(C-4″), 74.4 (C-5″), 18.6 (C-6″)。以上波谱数据与文献[22]报道对比, 确定化合物8为caudatin-3-O-β-D-digitoxopyranoside。
化合物9  白色无定形粉末, 分子式为C42H66O13; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.86 (1H, s, H-2′), 5.34 (1H, d, J = 2.7 Hz, H-6), 4.89 (1H, m, H-1″), 4.84 (1H, dd, J = 5.4, 10.1 Hz, H-12), 4.59 (1H, dd, J = 2.0, 9.9 Hz, H-1‴), 3.86 (1H, m, H-3), 3.82 (1H, m, H-3″), 3.80 (1H, m, H-5″), 3.42 (3H, s, OCH3), 3.42 (3H, s, OCH3), 3.27 (1H, m, H-5‴), 3.25 (1H, m, H-4″), 3.19 (1H, m, H-3‴), 2.97 (1H, d, J = 9.0 Hz, H-4‴), 2.26 (3H, s, H-7′), 2.24 (1H, m, H-4′), 2.12 (3H, s, H-21), 1.62 (3H, s, H-18), 1.27 (3H, d, J = 6.3 Hz, H-6″), 1.21 (3H, d, J = 6.2 Hz, H-6‴), 1.13 (3H, s, H-19), 0.93 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.1 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.2 (C-9), 38.1 (C-10), 25.4 (C-11), 73.3 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.0 (C-17), 10.4 (C-18), 18.4 (C-19), 211.6 (C-20), 27.6 (C-21), 167.5 (C-1′), 114.3 (C-2′), 167.4 (C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.7 (C-7′), 97.2 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 58.5 (OCH3), 102.8 (C-1‴), 37.4 (C-2‴), 76.9 (C-3‴), 81.7 (C-4‴), 73.2 (C-5‴), 18.5 (C-6‴), 57.4 (OCH3)。以上波谱数据与文献[23]报道对比, 确定化合物9为caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside。
化合物10  白色无定形粉末, 分子式为C42H66O13; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.54 (1H, s, H-2′), 5.34 (1H, d, J = 2.6 Hz, H-6), 4.96 (1H, m, H-1″), 4.87 (1H, dd, J = 5.2, 10.2 Hz, H-12), 4.50 (1H, dd, J =2.0, 9.9 Hz, H-1‴), 3.85 (1H, m, H-3), 3.82 (1H, m, H-3″), 3.80 (1H, m, H-5″), 3.42 (3H, s, OCH3), 3.42 (3H, s, OCH3), 3.27 (1H, m, H-5‴), 3.25 (1H, m, H-4″), 3.19 (1H, m, H-3‴), 2.97 (1H, d, J = 9.0 Hz, H-4‴), 2.26 (3H, s, H-7′), 2.24 (1H, m, H-4′), 2.12 (3H, s, H-21), 1.55 (3H, s, H-18), 1.27 (3H, d, J = 6.3 Hz, H-6″), 1.21 (3H, d, J = 6.2 Hz, H-6‴), 1.14 (3H, s, H-19), 1.10 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.1 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.2 (C-9), 38.1 (C-10), 25.4 (C-11), 73.3 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.0 (C-17), 10.4 (C-18), 18.4 (C-19), 211.6 (C-20), 27.6 (C-21), 167.5 (C-1′), 114.3 (C-2′), 167.5 (C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.7 (C-7′), 97.2 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 58.5 (OCH3), 101.2 (C-1‴), 37.4 (C-2‴), 76.9 (C-3‴), 81.7 (C-4‴), 73.2 (C-5‴), 18.5 (C-6‴), 57.4 (OCH3)。以上波谱数据与文献[24]报道对比, 确定化合物10为caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside。
化合物11  白色无定形粉末, 分子式为C41H64O13; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.45 (1H, s, H-2′), 5.25 (1H, d, J = 2.6 Hz, H-6), 4.87 (1H, dd, J = 5.2, 10.2 Hz, H-12), 4.86 (1H, m, H-1″), 4.86 (1H, dd, J =2.0, 9.9 Hz, H-1‴), 4.13 (1H, m, H-3″), 4.12 (1H, m, H-5″), 4.12 (1H, m, H-3‴), 3.67 (1H, m, H-3), 3.50 (1H, m, H-5‴), 3.50 (3H, s, OCH3), 3.21 (1H, m, H-4″), 3.12 (1H, d, J = 9.0 Hz, H-4‴), 2.24 (1H, m, H-4′), 2.14 (3H, s, H-21), 2.12 (3H, s, H-7′), 1.60 (3H, s, H-18), 1.20 (3H, d, J = 6.3 Hz, H-6″), 1.19 (3H, d, J = 6.2 Hz, H-6‴), 1.14 (3H, s, H-19), 1.10 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.1 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.2 (C-9), 38.1 (C-10), 25.4 (C-11), 73.3 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.0 (C-17), 10.4 (C-18), 18.4 (C-19), 211.6 (C-20), 27.6 (C-21), 167.5 (C-1′), 114.3 (C-2′), 167.5 (C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.7 (C-7′), 97.0 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 100.6 (C-1‴), 37.4 (C-2‴), 76.9 (C-3‴), 81.7 (C-4‴), 73.2 (C-5‴), 18.5 (C-6‴), 57.4 (OCH3)。以上波谱数据与文献[24]报道对比, 确定化合物11为caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside。
化合物12  白色无定形粉末, 分子式为C49H78O16; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.54 (1H, s, H-2′), 5.34 (1H, d, J = 2.0 Hz, H-6), 4.86 (1H, dd, J = 1.6, 9.6 Hz, H-1″), 4.79 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.60 (1H, d, J = 9.2 Hz, H-1″″), 4.48 (1H, dd, J = 4.1, 11.6 Hz, H-12), 3.89 (1H, m, H-5‴), 3.86 (1H, m, H-3″), 3.85 (1H, m, H-3‴), 3.82 (1H, m, H-5″), 3.54 (3H, s, OCH3), 3.53 (1H, m, H-3), 3.50 (1H, m, H-3″″), 3.42 (3H, s, OCH3), 3.42 (3H, s, OCH3), 3.30 (1H, m, H-5″″), 3.26 (1H, m, H-4″), 3.23 (1H, m, H-4‴), 3.18 (1H, m, H-4″″), 2.40 (1H, m, H-4′), 2.17 (3H, s, H-21), 2.11 (3H, s, H-7′), 1.50 (3H, s, H-18), 1.30 (3H, d, J = 6.0 Hz, H-6″″), 1.29 (3H, d, J = 6.4 Hz, H-6‴), 1.18 (3H, d, J = 6.3 Hz, H-6″), 1.14 (3H, s, H-19), 1.07 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.2 (C-9), 38.1 (C-10), 25.4 (C-11), 73.3 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.0 (C-17), 10.4 (C-18), 18.4 (C-19), 211.6 (C-20), 27.6 (C-21), 167.4 (C-1′), 114.3 (C-2′), 167.4 (C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.7 (C-7′), 97.2 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 58.5(OCH3), 101.2 (C-1‴), 36.4 (C-2‴), 78.6 (C-3‴), 83.9 (C-4‴), 70.0 (C-5‴), 18.6 (C-6‴), 58.4 (OCH3), 102.8 (C-1″″), 37.4 (C-2″″), 76.9 (C-3″″), 81.7 (C-4″″), 73.2 (C-5″″), 18.5 (C-6″″), 57.4 (OCH3)。以上波谱数据与文献[25]报道对比, 确定化合物12为otophylloside B。
化合物13  白色无定形粉末, 分子式为C48H76O16; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.54 (1H, s, H-2′), 5.37 (1H, d, J = 2.0 Hz, H-6), 4.86 (1H, dd, J = 1.6, 9.6 Hz, H-1″), 4.79 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.60 (1H, d, J = 9.2 Hz, H-1″″), 4.48 (1H, dd, J = 4.1, 11.6 Hz, H-12), 4.26 (1H, m, H-3‴), 3.87 (1H, m, H-3″), 3.87 (1H, m, H-5‴), 3.81 (1H, m, H-5″), 3.54 (1H, m, H-3), 3.46 (3H, s, OCH3), 3.43 (3H, s, OCH3), 3.40 (1H, m, H-5″″), 3.26 (1H, m, H-4″), 3.22 (1H, m, H-4‴), 3.20 (1H, m, H-3″″), 3.19 (1H, m, H-4″″), 2.40 (1H, m, H-4′), 2.17 (3H, s, H-21), 2.12 (3H, s, H-7′), 1.51 (3H, s, H-18), 1.39 (3H, d, J = 6.0 Hz, H-6″″), 1.29 (3H, d, J = 6.4 Hz, H-6‴), 1.18 (3H, d, J = 6.3 Hz, H-6″), 1.15 (3H, s, H-19), 1.08 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.2 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 74.9 (C-8), 45.2 (C-9), 38.1 (C-10), 25.4 (C-11), 73.3 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.0 (C-17), 10.4 (C-18), 18.4 (C-19), 211.6 (C-20), 27.6 (C-21), 167.5 (C-1′), 114.3 (C-2′), 167.4 (C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.7 (C-7′), 97.2 (C-1″), 36.4 (C-2″), 78.5 (C-3″), 83.8 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 58.7(OCH3), 100.6 (C-1‴), 36.4 (C-2‴), 78.6 (C-3‴), 83.9 (C-4‴), 70.0 (C-5‴), 18.5 (C-6‴), 102.8 (C-1″″), 37.4 (C-2″″), 76.9 (C-3″″), 81.7 (C-4″″), 73.2 (C-5″″), 18.5 (C-6″″), 57.4 (OCH3)。以上波谱数据与文献[26]报道对比, 确定化合物13为otophylloside E。
化合物14  白色无定形粉末, 分子式为C48H76O16; 1H NMR (CD3OD, 400 MHz, J in Hz) δH: 5.54 (1H, s, H-2′), 5.35 (1H, d, J = 2.0 Hz, H-6), 4.96 (1H, d, J = 9.6 Hz, H-1″), 4.85 (1H, dd, J = 1.8, 9.6 Hz, H-1‴), 4.60 (1H, d, J = 9.2 Hz, H-1″″), 4.48 (1H, dd, J = 4.1, 11.6 Hz, H-12), 4.23 (1H, d, J = 2.8 Hz, H-3″), 3.85 (1H, m, H-3‴), 3.83 (1H, m, H-5‴), 3.82 (1H, m, H-5″), 3.54 (3H, s, OCH3), 3.53 (1H, m, H-3), 3.51 (1H, m, H-3″″), 3.43 (3H, s, OCH3), 3.34 (1H, m, H-5″″), 3.28 (1H, m, H-4‴), 3.20 (1H, m, H-4″), 3.20 (1H, m, H-4″″), 2.40 (1H, m, H-4′), 2.16 (3H, s, H-21), 2.12 (3H, s, H-7′), 1.51 (3H, s, H-18), 1.30 (3H, d, J = 6.0 Hz, H-6″″), 1.21 (3H, d, J = 6.0 Hz, H-6‴), 1.19 (3H, d, J = 6.3 Hz, H-6″), 1.15 (3H, s, H-19), 1.07 (3H, dd, J = 6.8, 8.7 Hz, H-5′/H-6′); 13C NMR (CD3OD, 150 MHz) δC: 39.8 (C-1), 30.1 (C-2), 79.3 (C-3), 39.8 (C-4), 140.2 (C-5), 119.7 (C-6), 35.2 (C-7), 75.0 (C-8), 45.2 (C-9), 38.0 (C-10), 25.4 (C-11), 73.3 (C-12), 58.7 (C-13), 89.9 (C-14), 34.2 (C-15), 33.2 (C-16), 93.1 (C-17), 10.4 (C-18), 18.4 (C-19), 211.6 (C-20), 27.6 (C-21), 167.5 (C-1′), 114.3 (C-2′), 167.5 (C-3′), 39.3 (C-4′), 21.3 (C-5′), 21.3 (C-6′), 16.7 (C-7′), 97.0 (C-1″), 36.6 (C-2″), 78.5 (C-3″), 83.9 (C-4″), 69.8 (C-5″), 18.6 (C-6″), 100.6 (C-1‴), 36.4 (C-2‴), 78.6 (C-3‴), 83.8 (C-4‴), 70.0 (C-5‴), 18.5 (C-6‴), 58.7 (OCH3), 102.8 (C-1″″), 37.4 (C-2″″), 76.9 (C-3″″), 81.7 (C-4″″), 73.2 (C-5″″), 18.4 (C-6″″), 58.5 (OCH3)。以上波谱数据与文献[26]报道对比, 确定化合物14为otophylloside F。
3　化合物1的酸水解实验
取2 mg化合物1, 溶解在2 mL甲醇与二氧六环混合液中(甲醇-二氧六环, 1∶1), 加入2 mL HCl (2 mol·L-1), 在60 ℃水浴中加热搅拌2 h, TLC检测确认反应完全后, 加入4 mL水稀释, 并用饱和NaHCO3调节pH到中性。接着用2倍体积的氯仿进行萃取, 得到水部位(糖) 和氯仿部位(苷元), 分别浓缩得到相应反应产物。对于水部位的反应产物, 用氯仿-甲醇(10∶1) 溶解, 以加拿大麻吡喃糖标准品和毛地黄毒吡喃糖标准品为对照, 进行TLC鉴别。当展开剂为氯仿-甲醇(9∶1) 时, 加拿大麻吡喃糖和毛地黄毒吡喃糖的Rf值分别为: 0.45和0.22, 当展开剂为丙酮-石油醚(2∶3) 时, 其Rf值分别为: 0.32和0.16。显色剂为10%的硫酸-乙醇溶液。对于氯仿部位(苷元) 则通过HPLC进行分离纯化, 最后通过1D NMR和2D NMR验证苷元的结构。
4　细胞毒活性测试
采用MTS法测定化合物对人肝癌细胞株(HepG2) 的细胞毒性。取对数生长期的细胞, 用含10%胎牛血清的DMEM培养液配成单个细胞悬液, 调整细胞密度为每毫升1×104个后, 将细胞接种到96孔板, 每孔体积100 μL, 培养于37 ℃、5% CO2的培养箱内。培养24 h后加入待测化合物溶液, 化合物用DMSO溶解, 分设空白组、化合物组和阳性对照组, 每孔终体积200 μL, 每种处理均设3个复孔。培养48 h后, 弃培养上清, 每孔加MTS溶液20 μL和培养液100 μL, 设3个空白复孔(MTS溶液20 μL和培养液100 μL的混合液), 继续孵育2~4 h, 使反应充分进行。选择492 nm波长, 多功能酶标仪读取各孔光吸收值, 记录结果。实验设顺铂(DDP) 为阳性化合物, 数据处理后以浓度为横坐标, 细胞存活率为纵坐标绘制细胞生长曲线, 应用两点法(Reed and Muench法) 计算化合物的IC50值。

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2026年第61卷第4期
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doi: 10.16438/j.0513-4870.2025-1399
  • 接收时间：2025-11-24
  • 首发时间：2026-09-21
  • 出版时间：2026-04-12
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  • 收稿日期：2025-11-24
  • 修回日期：2025-12-09
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    西南林业大学生物与食品工程学院, 云南 昆明 650224

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董锦润, E-mail:
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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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