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Article(id=1190373736009273900, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190332325088039709, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-0167, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1739894400000, receivedDateStr=2025-02-19, revisedDate=1741017600000, revisedDateStr=2025-03-04, acceptedDate=null, acceptedDateStr=null, onlineDate=1761736814738, onlineDateStr=2025-10-29, pubDate=1746979200000, pubDateStr=2025-05-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1761736814738, onlineIssueDateStr=2025-10-29, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1761736814738, creator=13701087609, updateTime=1761736814738, updator=13701087609, issue=Issue{id=1190332325088039709, tenantId=1146029695717560320, journalId=1189982191388893191, year='2025', volume='60', issue='5', pageStart='1183', pageEnd='1572', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=1, specialIssue=null, createTime=1761726941606, creator=13701087609, updateTime=1761813457266, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1190695198163354009, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190332325088039709, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1190695198163354010, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190332325088039709, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1479, endPage=1484, ext={EN=ArticleExt(id=1190373736604865069, articleId=1190373736009273900, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Isolation and characterization of four undescribed lanostane tetracyclic triterpenoids from Ganoderma lucidum, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Four previously undescribed lanostane tetracyclic triterpenoids baoslingzhines T-W (1-4) were isolated from Ganoderma lucidum. Their structures including relative and absolute configurations were assigned by spectroscopic methods and ECD calculations.

, correspAuthors=Yong-xian CHENG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2025 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, authorCompany=null, fund=null, authors=null, authorsList=Xin-ping TANG, Yun-yun LIU, Yong-xian CHENG), CN=ArticleExt(id=1190374114188694112, articleId=1190373736009273900, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=赤芝中4个新的羊毛脂甾烷型三萜的分离与鉴定, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用多种色谱技术从中药赤芝中分离得到4个化合物。经一维(1D)、二维(2D) 核磁共振波谱(nuclear magnetic resonance spectroscopy, NMR) 等方法鉴定其均为新的羊毛脂甾烷型三萜, 并采用量子化学计算方法确定其绝对构型, 命名为baoslingzhines T~W (1~4)。

, correspAuthors=程永现, authorNote=null, correspAuthorsNote=
*程永现，Tel: 86-755-86172799, E-mail:
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Nat Prod Res, 2005, 19: 461-465., articleTitle=null, refAbstract=null)], funds=[Fund(id=1190694623292047567, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190373736009273900, awardId=82030115, language=CN, fundingSource=国家自然科学基金项目(82030115), fundOrder=null, country=null)], companyList=[AuthorCompany(id=1190694616639881380, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190373736009273900, xref=null, ext=[AuthorCompanyExt(id=1190694616648269989, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190373736009273900, companyId=1190694616639881380, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=1. 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No. 1 2
δH (J in Hz) δC, type δH (J in Hz) δC, type
1 2.03, overlap 35.6, CH2 Ha: 2.76, dt (13.6, 3.7) 30.8, CH2
Hb: 1.33, td (13.6, 3.7)
2 Ha: 2.80, m 34.1, CH2 Ha: 1.98, m 24.3, CH2
Hb: 2.35, m Hb: 1.61, dq (15.1, 3.7)
3 220.0, C 4.64, t (3.7) 79.1, CH
4 48.4, C 37.8, C
5 2.31, d (13.0) 56.5, CH 1.44, m 47.7, CH
6 4.29, d (13.0) 72.8, CH Ha: 1.71, m 18.1, CH2
Hb: 1.49, m
7 200.2, C Ha: 2.38, m 30.5, CH2
Hb: 2.27, m
8 138.4, C 164.7, C
9 164.2, C 141.2, C
10 41.5, C 38.9, C
11 Ha: 2.20, m 29.5, CH2 200.6, C
Hb: 1.37, m
12 1.87, overlap 31.4, CH2 Ha: 2.86, d (16.6) 52.8, CH2
Hb: 2.41, d (16.6)
13 36.0, C 48.2, C
14 48.5, C 54.1, C
15 Ha: 2.08, m 32.5, CH2 5.21, dd (9.6, 5.6) 76.5, CH
Hb: 1.54, m
16 Ha: 2.45, m 24.4, CH2 Ha: 2.13, m 36.6, CH2
Hb: 2.41, m Hb: 1.79, m
17 1.56, m 50.5, CH 1.96, m 49.9, CH
18 0.72, s 16.5, CH3 0.95, s 17.3, CH3
19 1.19, s 19.7, CH3 1.15, s 19.3, CH3
20 1.46, m 37.4, CH 1.47, m 37.1, CH
21 0.99, d (6.4) 18.9, CH3 0.94, d (6.5) 18.4, CH3
22 Ha: 1.60, m 36.0, CH2 Ha: 1.52, m 35.6, CH2
Hb: 1.20, m Hb: 1.19, m
23 Ha: 2.25, m 26.5, CH2 Ha: 2.24, m 26.4, CH2
Hb: 2.12, m Hb: 2.12, m
24 6.75, t (7.5) 143.8, CH 6.74, td (7.4, 1.5) 143.5, CH
25 129.1 C 129.2 C
26 172.3, C 172.0, C
27 1.81, s 12.5, CH3 1.82, br s 12.5, CH3
28 1.31, s 31.3, CH3 0.91, s 28.4, CH3
29 1.41, s 20.4, CH3 0.96, s 22.4, CH3
30 1.06, s 24.9, CH3 1.31, s 20.4, CH3
3-OCOCH3 172.5, C
3-OCOCH3 2.03, s 21.1, CH3
15-OCOCH3 172.5, C
15-OCOCH3 2.07, s 21.2, CH3
), ArticleFig(id=1190694622767759564, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190373736009273900, language=CN, label=Table 1, caption=

1H (500 MHz) and 13C NMR (150 MHz) spectral data of 1 and 2 (in CD3OD)

, figureFileSmall=null, figureFileBig=null, tableContent=
No. 1 2
δH (J in Hz) δC, type δH (J in Hz) δC, type
1 2.03, overlap 35.6, CH2 Ha: 2.76, dt (13.6, 3.7) 30.8, CH2
Hb: 1.33, td (13.6, 3.7)
2 Ha: 2.80, m 34.1, CH2 Ha: 1.98, m 24.3, CH2
Hb: 2.35, m Hb: 1.61, dq (15.1, 3.7)
3 220.0, C 4.64, t (3.7) 79.1, CH
4 48.4, C 37.8, C
5 2.31, d (13.0) 56.5, CH 1.44, m 47.7, CH
6 4.29, d (13.0) 72.8, CH Ha: 1.71, m 18.1, CH2
Hb: 1.49, m
7 200.2, C Ha: 2.38, m 30.5, CH2
Hb: 2.27, m
8 138.4, C 164.7, C
9 164.2, C 141.2, C
10 41.5, C 38.9, C
11 Ha: 2.20, m 29.5, CH2 200.6, C
Hb: 1.37, m
12 1.87, overlap 31.4, CH2 Ha: 2.86, d (16.6) 52.8, CH2
Hb: 2.41, d (16.6)
13 36.0, C 48.2, C
14 48.5, C 54.1, C
15 Ha: 2.08, m 32.5, CH2 5.21, dd (9.6, 5.6) 76.5, CH
Hb: 1.54, m
16 Ha: 2.45, m 24.4, CH2 Ha: 2.13, m 36.6, CH2
Hb: 2.41, m Hb: 1.79, m
17 1.56, m 50.5, CH 1.96, m 49.9, CH
18 0.72, s 16.5, CH3 0.95, s 17.3, CH3
19 1.19, s 19.7, CH3 1.15, s 19.3, CH3
20 1.46, m 37.4, CH 1.47, m 37.1, CH
21 0.99, d (6.4) 18.9, CH3 0.94, d (6.5) 18.4, CH3
22 Ha: 1.60, m 36.0, CH2 Ha: 1.52, m 35.6, CH2
Hb: 1.20, m Hb: 1.19, m
23 Ha: 2.25, m 26.5, CH2 Ha: 2.24, m 26.4, CH2
Hb: 2.12, m Hb: 2.12, m
24 6.75, t (7.5) 143.8, CH 6.74, td (7.4, 1.5) 143.5, CH
25 129.1 C 129.2 C
26 172.3, C 172.0, C
27 1.81, s 12.5, CH3 1.82, br s 12.5, CH3
28 1.31, s 31.3, CH3 0.91, s 28.4, CH3
29 1.41, s 20.4, CH3 0.96, s 22.4, CH3
30 1.06, s 24.9, CH3 1.31, s 20.4, CH3
3-OCOCH3 172.5, C
3-OCOCH3 2.03, s 21.1, CH3
15-OCOCH3 172.5, C
15-OCOCH3 2.07, s 21.2, CH3
), ArticleFig(id=1190694622876811469, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190373736009273900, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
No. 3 4
δH (J in Hz) δC, type δH (J in Hz) δC, type
1 Ha: 1.61, m 36.4, CH2 Ha: 2.38, m 37.6, CH2
Hb: 1.22, m Hb: 1.71, td (14.5, 4.3)
2 Ha: 2.86, td (14.6, 5.8) 35.7, CH2 Ha: 2.85, td (14.5, 5.5) 35.7, CH2
Hb: 2.50, m Hb: 2.39, m
3 2.30, m 219.1, C 218.8, C
4 49.0, C 48.3, C
5 1.54, dd (12.0, 3.7) 52.3, CH 1.53, m 51.7, CH
6 Ha: 2.26, m 24.6, CH2 Ha: 2.27, m 26.4, CH2
Hb: 2.11, m Hb: 2.15, m
7 5.56, d (6.8) 121.2, CH 6.80, d (6.2) 124.8, CH
8 144.1, C 137.1, C
9 145.9, C 146.0, C
10 38.4, C 38.6, C
11 5.46, d (6.4) 118.5, CH 5.46, d (6.2) 117.3, CH
12 Ha: 2.25, m 39.0, CH2 Ha: 2.45, m 37.8, CH2
Hb: 2.23, m Hb: 2.35, m
13 44.9, C 43.6, C
14 51.5, C 56.7, C
15 Ha: 1.69, m 32.5, CH2 219.0, C
Hb: 1.44, m
16 Ha: 2.03, m 28.9, CH2 Ha: 2.68, m 42.5, CH2
Hb: 1.38, m Hb: 1.90, m
17 1.66, m 52.5, CH 1.91, m 46.7, CH
18 0.65, s 16.3, CH3 0.72, s 16.3, CH3
19 1.23 s 22.4, CH3 1.23, s 22.3, CH3
20 1.48, m 37.4, CH 2.33, m 36.8, CH
21 0.98, d (6.5) 18.8, CH3 1.05, d (6.6) 18.8, CH3
22 Ha: 2.36, m 37.8, CH2 Ha: 2.30, m 35.8, CH2
Hb: 1.72, m Hb: 1.26, m
23 Ha: 2.37, m 26.3, CH2 Ha: 2.26, m 24.5, CH2
Hb: 2.24, m Hb: 2.18, m
24 6.87, t (7.7) 147.1, CH 6.76, t (7.6) 143.6, CH
25 133.3, C 129.1, C
26 170.0, C 171.9, C
27 4.31, s 56.9, CH3 1.82, s 12.5, CH3
28 1.14, s 25.8, CH3 1.07, s 25.8, CH3
29 1.06, s 22.8, CH3 1.14, s 22.7, CH3
30 0.91, s 25.9, CH3 1.10, s 22.8, CH3
), ArticleFig(id=1190694622998446286, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190373736009273900, language=CN, label=Table 2, caption=

1H (500 MHz) and 13C NMR (150 MHz) spectral data of 3 and 4 (in CD3OD)

, figureFileSmall=null, figureFileBig=null, tableContent=
No. 3 4
δH (J in Hz) δC, type δH (J in Hz) δC, type
1 Ha: 1.61, m 36.4, CH2 Ha: 2.38, m 37.6, CH2
Hb: 1.22, m Hb: 1.71, td (14.5, 4.3)
2 Ha: 2.86, td (14.6, 5.8) 35.7, CH2 Ha: 2.85, td (14.5, 5.5) 35.7, CH2
Hb: 2.50, m Hb: 2.39, m
3 2.30, m 219.1, C 218.8, C
4 49.0, C 48.3, C
5 1.54, dd (12.0, 3.7) 52.3, CH 1.53, m 51.7, CH
6 Ha: 2.26, m 24.6, CH2 Ha: 2.27, m 26.4, CH2
Hb: 2.11, m Hb: 2.15, m
7 5.56, d (6.8) 121.2, CH 6.80, d (6.2) 124.8, CH
8 144.1, C 137.1, C
9 145.9, C 146.0, C
10 38.4, C 38.6, C
11 5.46, d (6.4) 118.5, CH 5.46, d (6.2) 117.3, CH
12 Ha: 2.25, m 39.0, CH2 Ha: 2.45, m 37.8, CH2
Hb: 2.23, m Hb: 2.35, m
13 44.9, C 43.6, C
14 51.5, C 56.7, C
15 Ha: 1.69, m 32.5, CH2 219.0, C
Hb: 1.44, m
16 Ha: 2.03, m 28.9, CH2 Ha: 2.68, m 42.5, CH2
Hb: 1.38, m Hb: 1.90, m
17 1.66, m 52.5, CH 1.91, m 46.7, CH
18 0.65, s 16.3, CH3 0.72, s 16.3, CH3
19 1.23 s 22.4, CH3 1.23, s 22.3, CH3
20 1.48, m 37.4, CH 2.33, m 36.8, CH
21 0.98, d (6.5) 18.8, CH3 1.05, d (6.6) 18.8, CH3
22 Ha: 2.36, m 37.8, CH2 Ha: 2.30, m 35.8, CH2
Hb: 1.72, m Hb: 1.26, m
23 Ha: 2.37, m 26.3, CH2 Ha: 2.26, m 24.5, CH2
Hb: 2.24, m Hb: 2.18, m
24 6.87, t (7.7) 147.1, CH 6.76, t (7.6) 143.6, CH
25 133.3, C 129.1, C
26 170.0, C 171.9, C
27 4.31, s 56.9, CH3 1.82, s 12.5, CH3
28 1.14, s 25.8, CH3 1.07, s 25.8, CH3
29 1.06, s 22.8, CH3 1.14, s 22.7, CH3
30 0.91, s 25.9, CH3 1.10, s 22.8, CH3
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赤芝中4个新的羊毛脂甾烷型三萜的分离与鉴定
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唐新萍 1, 2 , 刘云云 2 , 程永现 1, 2, *
药学学报 | 研究论文 2025,60(5): 1479-1484
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药学学报 | 研究论文 2025, 60(5): 1479-1484
赤芝中4个新的羊毛脂甾烷型三萜的分离与鉴定
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唐新萍1, 2, 刘云云2, 程永现1, 2, *
作者信息
  • 1.云南中医药大学中药学院, 云南 昆明 650500
  • 2.深圳大学医学部药学院, 中医药守正创新研究院, 广东省中药有效成分与微生物组学重点实验室, 广东 深圳 518060

通讯作者:

*程永现，Tel: 86-755-86172799, E-mail:
Isolation and characterization of four undescribed lanostane tetracyclic triterpenoids from Ganoderma lucidum
Xin-ping TANG1, 2, Yun-yun LIU2, Yong-xian CHENG1, 2, *
Affiliations
  • 1. School of Traditional Chinese Medicine, Yunnan University of Chinese Medicine, Kunming 650500, China
  • 2. Guangdong Provincial Key Laboratory of Chinese Medicine Ingredients and Gut Microbiomics, Institute for Inheritance-Based Innovation of Chinese Medicine, Shenzhen University Medical School, Shenzhen University, Shenzhen 518060, China
出版时间: 2025-05-12 doi: 10.16438/j.0513-4870.2025-0167
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摘要
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利用多种色谱技术从中药赤芝中分离得到4个化合物。经一维(1D)、二维(2D) 核磁共振波谱(nuclear magnetic resonance spectroscopy, NMR) 等方法鉴定其均为新的羊毛脂甾烷型三萜, 并采用量子化学计算方法确定其绝对构型, 命名为baoslingzhines T~W (1~4)。

多孔菌科赤芝  /  分离鉴定  /  羊毛脂甾烷型三萜

Four previously undescribed lanostane tetracyclic triterpenoids baoslingzhines T-W (1-4) were isolated from Ganoderma lucidum. Their structures including relative and absolute configurations were assigned by spectroscopic methods and ECD calculations.

Ganoderma lucidum  /  isolation and characterization  /  lanostane tetracyclic triterpenoid
唐新萍, 刘云云, 程永现. 赤芝中4个新的羊毛脂甾烷型三萜的分离与鉴定. 药学学报, 2025 , 60 (5) : 1479 -1484 . DOI: 10.16438/j.0513-4870.2025-0167
Xin-ping TANG, Yun-yun LIU, Yong-xian CHENG. Isolation and characterization of four undescribed lanostane tetracyclic triterpenoids from Ganoderma lucidum[J]. Acta Pharmaceutica Sinica, 2025 , 60 (5) : 1479 -1484 . DOI: 10.16438/j.0513-4870.2025-0167
正文
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灵芝是一种著名的药食同源真菌, 在中国已有2000年使用历史, 被用于预防和治疗各种人类疾病, 是活性化合物的重要来源[1]。赤芝[Ganoderma lucidum (Leyss. Ex Fr.) Karst.] 和紫芝(Ganoderma sinense Zhao, Xu et Zhang) 是灵芝科灵芝属的两个成员[2], 始载于《神农本草经》, 有“益心气、安神、增智慧、好颜色、利关节、坚筋骨”等功效, 被列为上品[3, 4]。近年来, 研究表明灵芝中主要含有多糖、三萜类、杂萜类、核苷类、呋喃类、甾醇、生物碱类及氨基酸类等多种化学成分[5-9], 且具备多种药理活性[10-13], 包括降血糖、降血脂、抗肿瘤、抗氧化、保护心血管系统、保肝护肝、调节免疫、神经保护等。灵芝三萜是灵芝中一类主要的活性成分, 现代药理学研究表明三萜类成分具有抗炎、抗肿瘤、抗菌等作用。此外, 灵芝三萜的神经保护、抗氧化等作用也日益成为研究热点。灵芝相较其他药物, 具有不良反应小的优势, 进一步挖掘其化学成分对灵芝药物研发和应用均具有重要意义。本实验从保山产赤芝中分离鉴定出4个新化合物, 结构见图 1。
结果与讨论
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化合物1, 黄色固体, 13C NMR、DEPT谱(表 1) 及HRESIMS (m/z 485.325 8 [M+H]+, calcd. for 485.326 2) 确定其分子式为C30H44O5, 不饱和度为9。1H NMR谱(表 1) 显示7个甲基[δH 1.81 (3H, s, H-27), 1.41 (3H, s, H-29), 1.31 (3H, s, H-28), 1.19 (3H, s, H-19), 1.06 (3H, s, H-30), 0.99 (3H, d, J = 6.4 Hz, H-21), 0.72 (3H, s, H-18)] 和1个烯质子[δH 6.75 (1H, t, J = 7.5 Hz, H-24)]。13C NMR、DEPT谱(表 1) 显示30个碳原子, 包括7个甲基、8个亚甲基、5个次甲基, 其中1个为sp2杂化[δC 143.8 (C-24)] 和1个被氧化[δC 72.8 (C-6)]、10个季碳, 其中3个酮基[δC 220.0 (C-3), 200.2 (C-7), 172.3 (C-26)], 3个烯碳[δC 164.2 (C-9), 138.4 (C-8), 129.1 (C-25)] 和4个sp3杂化, 上述核磁共振波谱数据表明化合物1为羊毛脂甾烷型三萜。详细分析其1D和2D NMR数据, 发现化合物1与12α-hydroxy-3, 7-dioxo-5α-lanosta-8, 24(E)-dien-26-oic acid[14]的结构相似, 区别在于羟基的位置由C-11位转移到C-6位。1H-1H COSY谱(图 2) 中H2-11/H2-12的相关和HMBC谱(图 2) 中H-6/C-5, C-7 (δC 200.2), C-8 (δC 138.4), C-10的相关及H-5的峰型由dd (J = 14.0, 3.2 Hz) 转变为d (J = 13.0 Hz) 证明了上述结论。
对于化合物1的相对构型, 主要由ROESY相关和耦合常数确定。ROESY谱(图 3) 中H3-19/H-6, H3-18, H3-18/H-20和H-17/H3-30的相关表明H-6, H3-19, H3-18在同一朝向, 定义为β构型, H3-30和H-17在上述质子相反面, 为α构型。此外, 在ROESY谱中观察到H2-23/H3-27的相关, 表明Δ24, 25为E型。H-5耦合常数J = 13.0 Hz表明H-5和H-6为反式。结合H3-21 [δH 0.99 (d, J = 6.4 Hz)] 的化学位移确定了C-20的绝对构型为20R (20R: δH 0.90)[15]。为确定其绝对构型, 分别计算了(5R, 6R, 10S, 13R, 14R, 17R, 20R)-1和(5S, 6S, 10R, 13S, 14S, 17S, 20R)-1两种构型。结果表明, 1的实测ECD曲线与(5R, 6R, 10S, 13R, 14R, 17R, 20R)-1构型的ECD曲线拟合很好(图 4)。因此, 确定了1的绝对构型为5R, 6R, 10S, 13R, 14R, 17R, 20R。至此, 化合物1的结构得以鉴定, 并命名为baoslingzhine T。
化合物2, 黄色固体。根据13C NMR谱和HRESIMS数据(m/z 571.362 0 [M+H]+, calcd. for 571.362 9), 确定其分子式为C34H50O7。仔细分析化合物2的1D NMR数据(表 1), 发现2与ganoderic acid W[16]的核磁共振波谱数据相似。在13C NMR谱中两者显著的区别在于2缺失了一个含氧次甲基信号[δH/δC 4.11/66.5 (CH-7)], 伴随着C-7周围的碳信号发生了不同程度的改变, 包括C-5 (δC 40.1 in CDCl3→δC 47.7 in CD3OD) 的化学位移向低场方向移动和C-6 (δC 27.4 in CDCl3→δC 18.1 in CD3OD) 的化学位移向高场方向移动。该变化推断化合物2的C-7位羟基被还原为亚甲基, 1H-1H COSY谱(图 2) 中H-5/H2-6/H2-7的相关和HMBC谱(图 2) 中H2-7/C-8 (δC 164.7), C-9 (δC 141.2) 和H3-19/C-5, C-9, C-10的相关证实了这一推断。此外, 13C NMR谱中两者另一显著的区别在于2出现了一个酮基信号[δC 200.6 (C-11)], 伴随着C-8 (δC 133.9 in CDCl3→δC 164.7 in CD3OD) 的化学位移向低场方向移动, 结合其特征性UV吸收(253 nm), 表明C-11位的亚甲基被氧化为酮基, 并与Δ8, 9形成了α, β不饱和酮, HMBC谱(图 2) 中H2-12/C-9, C-11的相关证实了这一推断。因此, 确定了化合物2的平面结构。ROESY谱(图 3) 中H3-30/H-17, H-5和H-5/H3-28的相关表明H3-30, H-17, H-5和H3-28相邻, 且在同一朝向, 为α构型。ROESY谱中H3-19/H3-29, H-3和H-15/H3-18, H-20的相关表明H3-19, H3-29, H-3, H-15和H3-18为β构型。此外, 在ROESY谱中还观察到H3-27/H2-23的相关, 确定了Δ24, 25的构型为E型。同样, 结合H3-21 [δH 0.94 (d, J = 6.5 Hz)] 的化学位移确定了C-20的绝对构型为20R[15]。最后, 根据实测与计算ECD曲线比较(图 4) 确定了化合物2的绝对构型为3R, 5R, 10S, 13R, 14R, 17R, 20R, 并命名为baoslingzhine U。
化合物3, 黄色固体, 根据13C NMR谱和HRESIMS数据(m/z 469.330 8 [M+H]+, calcd for 469.331 2) 确定该化合物的分子式为C30H44O4, 不饱和度为9。化合物3与lucidenic acid S[17]的1D NMR数据(表 2) 相似, 除了C-27 (δC 65.3 in CDCl3→δC 56.9 in CD3OD) 的化学位移向高场方向移动, 推断3为lucidenic acid S双键异构体, Δ24, 25构型由Z向E型的转变对C-27产生了屏蔽效应。ROESY谱(图 3) 中H2-27/H2-23的相关证明了上述推测。最后, ECD实测与计算曲线比对(图 4) 确定了化合物3的绝对构型为5R, 10S, 13R, 14R, 17R, 20R, 并命名为baoslingzhine V。
化合物4, 黄色固体, 根据13C NMR谱和HRESIMS的数据确定了该化合物的分子式为C30H42O4。详细分析1H和13C NMR谱(表 2), 发现化合物4和ganoderic acid SZ[18]数据相似, 除了4缺失了一个亚甲基和出现了一个额外的酮基信号[δC 219.0 (C-15)], 推断化合物4的C-15位的亚甲基被氧化为酮基。1H-1H COSY谱(图 2) 中H2-16/H-17的相关和HMBC谱(图 2) 中H3-30/C-13, C-14, C-15 (δC 219.0) 和H2-16/C-14, C-15的相关证明了上述推测。ROESY谱(图 3) 中H3-30/H-5, H-17和H3-18/H3-19, H-20的相关确定了化合物4的相对构型为5R*, 10S*, 13R*, 14R*, 17R*。H3-21 [δH 1.02 (d, J = 6.5 Hz)] 的化学位移确定了C-20的绝对构型为20R[15]。最后, ECD计算(图 4) 确定了化合物4的绝对构型为5R, 10S, 13R, 14R, 17R, 20R, 并命名为baoslingzhine W。
实验部分
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Anton Paar MCP-100 digital polarimeter型全自动数字旋光仪(Anton Paar公司); 圆二色谱仪(应用光物理公司); SP 5030型半制备高效液相色谱仪(北京赛谱锐思科技有限公司); AB SCIEX triple TOF X500R高分辨质谱仪(AB SCIEX公司); Bruker AV-500 MHz及AV-600 MHz核磁共振波谱仪(以TMS为内标, 德国Bruker公司); MCI gel CHP 20P填料(70~150 μm, 日本三菱公司); YMC gel ODS-A-HG填料(12 nm S-50 μm, 日本YMC公司); 半制备SEP Basic C18色谱柱(120A 5 μm, 10 mm × 250 mm, 北京赛谱锐思科技有限公司)。
灵芝药材于2018年4月购自云南省保山市滇滩镇胜利村, 为栽培灵芝。由中国科学院昆明植物研究所杨祝良教授鉴定为赤芝的干燥子实体, 样品标本(CHYX0619) 已存放在广东省深圳市深圳大学药学院。
1 提取分离
取赤芝干燥子实体500.0 kg, 粉碎后用80%乙醇回流提取(2 × 3 000 L × 3 h), 合并回流液, 减压浓缩, 得粗浸膏(约24.6 kg)。将总浸膏用温水混悬, 加等体积乙酸乙酯萃取4次, 合并乙酸乙酯液减压浓缩, 得乙酸乙酯部位浸膏(11.5 kg)。其经MCI gel CHP 20P反相色谱柱以甲醇-水系统(40%~100%) 梯度洗脱, TLC监测合并相同部分, 得到17个组分Fr.A~Q。
Fr.M (736.0 g), 经MCI Gel CHP-20P柱层析, 甲醇-水(30%~100%) 梯度洗脱, 得8个组分(Fr.M.1~Fr.M.8)。Fr.M.5 (220.0 g) 经Sephadex LH-20柱, 甲醇洗脱得4个亚组分(Fr.M.5.1~Fr.M.5.4)。Fr.M.5.1 (117.0 g) 经RP-18柱(甲醇-水, 40%~100%) 梯度分离得到8段(Fr.M.5.1.1~Fr.M.5.1.8)。Fr.M.5.1.3 (22.9 g) 经RP-18柱(甲醇-水, 50%~100%) 梯度洗脱得到7部分(Fr.M.5.1.3.1~Fr.M.5.1.3.7)。Fr.M.5.1.3.4 (2.9 g) 经Sephadex LH-20柱, 甲醇(100%) 洗脱得3个亚组分(Fr.M.5.1.3.4.1~Fr.M.5.1.3.4.3)。Fr.M.5.1.3.4.2 (606.8 mg) 经Sephadex LH-20柱, 甲醇洗脱得2个亚组分(Fr.M.5.1.3.4.2.1和Fr.M.5.1.3.4.2.2)。Fr.M.5.1.3.4.2.1 (268.4 mg) 经半制备HPLC (乙腈-水, 75%, 水中含0.05% TFA, 流速: 3.0 mL·min-1) 纯化得到化合物2 (tR = 27.15 min, 3.89 mg)。Fr.M.5.1.3.5 (4.9 g) 经Sephadex LH-20柱, 甲醇洗脱得3个亚组分(Fr.M.5.1.3.5.1~Fr.M.5.1.3.5.3)。Fr.M.5.1.3.5.3 (254.0 mg) 经半制备HPLC (乙腈-水, 80%, 水中含0.05% TFA, 流速: 3.0 mL·min-1) 纯化得到化合物1 (tR = 20.50 min, 1.82 mg)和4 (tR = 24.14 min, 3.06 mg)。Fr.M.5.1.5 (19.0 g) 经Sephadex LH-20柱, 甲醇洗脱得2个亚组分(Fr.M.5.1.5.1和Fr.M.5.1.5.2)。Fr.M.5.1.5.1 (9.7 g) 经RP-18柱(甲醇-水, 50%~100%) 梯度洗脱得到6个组分(Fr.M.5.1.5.1.1~Fr.M.5.1.5.1.6)。Fr.M.5.1.5.1.2 (2.5 g) 经Sephadex LH-20柱, 甲醇洗脱得2个组分(Fr.M.5.1.5.1.2.1和Fr.M.5.1.5.1.2.2)。Fr.M.5.1.5.1.2.2 (592.8 mg) 经半制备HPLC (乙腈-水, 72%, 水中含0.05% TFA, 流速为3.0 mL·min-1) 纯化得到化合物3 (tR = 34.93 min, 3.29 mg)。
2 理化数据
化合物1, 黄色固体, 溶于甲醇。[α]$ {}_{\mathrm{D}}^{25} $ +80.4 (c 0.17, MeOH); UV (MeOH) λmax (log ε): 249 (3.25), 218 (3.56), 203 (3.38) nm; CD (MeOH) λmax (Δε): 278 (+3.41), 233 (-3.49), 210 (+5.12), 203 (+3.47) nm; HRESIMS m/z 485.325 8 [M+H]+ (calcd. for C30H45O5, 485.326 2); 1H和13C NMR数据见表 1。
化合物2, 黄色固体, 溶于甲醇。[α]$ {}_{\mathrm{D}}^{25} $ +71.1 (c 0.30, MeOH); UV (MeOH) λmax (log ε): 253 (3.46), 217 (3.68) nm; CD (MeOH) λmax (Δε): 293 (-0.35), 257 (+36.29), 220 (-11.64), 202 (-0.65) nm; HRESIMS m/z 571.362 0 [M+H]+ (calcd. for C34H51O7, 571.362 9); 1H和13C NMR数据见表 1。
化合物3, 黄色固体, 溶于甲醇。[α]$ {}_{\mathrm{D}}^{25} $ +47.2 (c 0.24, MeOH); UV (MeOH) λmax (log ε): 243 (3.71), 233 (3.74), 216 (3.77) nm; CD (MeOH) λmax (Δε): 273 (+2.52), 259 (+2.18), 234 (+2.71), 223 (+5.87), 209 (+1.86), 201 (+2.66) nm; HRESIMS m/z 469.330 8 [M+H]+ (calcd. for C30H45O4, 469.331 2); 1H和13C NMR数据见表 2。
化合物4, 黄色固体, 溶于甲醇。[α]$ {}_{\mathrm{D}}^{25} $ +55.0 (c 0.20, MeOH); UV (MeOH) λmax (log ε): 249 (3.16), 217 (3.47), 202 (3.29) nm; CD (MeOH) λmax (Δε): 284 (+4.14), 232 (-3.89), 210 (+5.84), 205 (+3.83), 201 (+4.24) nm; HRESIMS m/z 467.315 2 [M+H]+ (calcd. for C30H43O4, 467.315 6); 1H和13C NMR数据见表 2。
作者贡献: 唐新萍是本文的第一作者, 负责对化合物提取分离以及撰写文章; 刘云云为本文的第二作者, 负责结构鉴定和修改文章; 程永现为本文的通讯作者, 负责实验的指导和设计, 并对文章进行审阅和定稿。
利益冲突: 所有作者均声明没有利益冲突。
基金
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  • 国家自然科学基金项目(82030115)
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参考文献 引证文献
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2025年第60卷第5期
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doi: 10.16438/j.0513-4870.2025-0167
  • 接收时间：2025-02-19
  • 首发时间：2025-10-29
  • 出版时间：2025-05-12
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  • 收稿日期：2025-02-19
  • 修回日期：2025-03-04
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国家自然科学基金项目(82030115)
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    1.云南中医药大学中药学院, 云南 昆明 650500
    2.深圳大学医学部药学院, 中医药守正创新研究院, 广东省中药有效成分与微生物组学重点实验室, 广东 深圳 518060

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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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