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Article(id=1308841094142587331, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840985296204417, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-1447, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1764691200000, receivedDateStr=2025-12-03, revisedDate=1767801600000, revisedDateStr=2026-01-08, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981633934, onlineDateStr=2026-09-21, pubDate=1778515200000, pubDateStr=2026-05-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981633934, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981633934, creator=13701087609, updateTime=1789981633934, updator=13701087609, issue=Issue{id=1308840985296204417, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='5', pageStart='1435', pageEnd='1880', issueExtLink='null', onlineDate='null', pubDate='1778515200000', pubDateStr='2026-05-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981607984, creator='13701087609', updateTime=1789984207975, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851890515968861, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840985296204417, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851890515968862, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840985296204417, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=1757, endPage=1763, ext={EN=ArticleExt(id=1308841094322942404, articleId=1308841094142587331, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new guaiane-type sesquiterpenoid from the roots of Lindera glauca, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Nine sesquiterpenoids were isolated from the dichloromethane fraction of the 95% ethanol extract from the roots of Lindera glauca by using a combination of separation techniques, including silica gel, ODS and Sephadex LH-20 column chromatographies, as well as semi-preparative HPLC. Based on a comprehensive analysis of modern spectroscopic data, such as IR, UV, NMR, HRESIMS and ECD, the structures of isolated compounds were identified as glaucatotone M (1), glaucatotone K (2), glaucatotone G (3), pseudoguaianelactone C (4), pseudoguaianelactone B (5), elema-1,3,11(13)-trien-12-oic acid (6), α-costic acid (7), 3β-hydroxycostic acid (8) and rupestonic acid I (9), respectively. Compound 1 was a new guaiane-type sesquiterpenoid, and compounds 6 and 7 were first reported from the genus Lindera. The inhibitory activity of compounds 1-7 and 9 against both the proliferation of TNF-α-induced rheumatoid arthritis fibroblast-like synoviocytes cell line MH7A and the release of pro-inflammatory cytokines (IL-6 and IL-1β) were evaluated. The results showed that compound 1 had a significant inhibitory effect against TNF-α-induced MH7A cell proliferation and reduced the production of IL-6 and IL-1β effectively.

, authors=Yu-jia TAO, Hang-jie REN, Gang LI, Qi SHI, Lu-ping QIN*, Hua-qiang LI*, authorsList=Yu-jia TAO, Hang-jie REN, Gang LI, Qi SHI, Lu-ping QIN, Hua-qiang LI, authorCompany=null, correspAuthors=Lu-ping QIN, Hua-qiang LI, 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=1308841098743738829, articleId=1308841094142587331, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=山胡椒根中一个新的愈创木烷型倍半萜, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、ODS和Sephadex LH-20等柱色谱以及半制备型HPLC等多种分离技术, 从山胡椒根95%乙醇提取物的二氯甲烷萃取相中分离得到了9个倍半萜类成分。结合IR、UV、NMR、HRESIMS和ECD等现代波谱学技术进行结构鉴定, 确定其结构分别为glaucatotone M (1)、glaucatotone K (2)、glaucatotone G (3)、pseudoguaianelactone C (4)、pseudoguaianelactone B (5)、elema-1,3,11(13)-trien-12-oic acid (6)、α-costic acid (7)、3β-hydroxycostic acid (8) 和rupestonic acid I (9)。其中, 化合物1为一个新的愈创木烷型倍半萜类化合物, 化合物6和7为首次从山胡椒属植物中分离得到。评价化合物1~7和9对TNF-α诱导的类风湿性关节炎滑膜成纤维细胞系MH7A细胞增殖和炎症因子IL-6、IL-1β释放的抑制活性, 结果显示, 化合物1对TNF-α诱导的MH7A细胞的增殖表现出了较为显著的抑制效果, 且能够有效降低IL-6和IL-1β的生成量。

, authors=陶玉佳, 任航洁, 李刚, 施琦, 秦路平*, 李华强*, authorsList=陶玉佳, 任航洁, 李刚, 施琦, 秦路平, 李华强, authorCompany=null, correspAuthors=秦路平, 李华强, authorNote=

作者贡献:

陶玉佳为本文第一作者, 负责成分分离、结构鉴定和论文的撰写及修改; 任航洁协助样品分离纯化; 李刚参与化合物ECD计算; 施琦负责实验药理部分的工作; 秦路平和李华强负责实验设计指导和稿件修改。

, correspAuthorsNote=
秦路平, E-mail:
李华强, E-mail:
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Acta Pharm Sin (药学学报), 2025, 60: 3655-3664., articleTitle=null, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1308841098945065422, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, xref=null, ext=[AuthorCompanyExt(id=1308841098953454031, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, companyId=1308841098945065422, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=School of Pharmaceutical Sciences, Zhejiang Chinese Medical University, Hangzhou 311403, China), AuthorCompanyExt(id=1308841098961842640, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, companyId=1308841098945065422, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=浙江中医药大学药学院, 浙江 杭州 311403)])], figs=[ArticleFig(id=1308841103223255545, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=EN, label=null, caption=null, figureFileSmall=4fd8MOqkbME0l54rzt5rkA==, figureFileBig=6My7maOfSCvKR6Ig/YBRdg==, tableContent=null), ArticleFig(id=1308841103281975802, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=CN, label=Fig.1, caption=Chemical structures of compounds 1-9, figureFileSmall=4fd8MOqkbME0l54rzt5rkA==, figureFileBig=6My7maOfSCvKR6Ig/YBRdg==, tableContent=null), ArticleFig(id=1308841103466525179, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=EN, label=null, caption=null, figureFileSmall=rCCg6NDs/Uu6hg0G0y9vVQ==, figureFileBig=HDdj2yA2WGVPnuM9vKlcMQ==, tableContent=null), ArticleFig(id=1308841103546216956, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=CN, label=Fig.2, caption=Key 1H-1H COSY, HMBC and NOESY correlations of compound 1, figureFileSmall=rCCg6NDs/Uu6hg0G0y9vVQ==, figureFileBig=HDdj2yA2WGVPnuM9vKlcMQ==, tableContent=null), ArticleFig(id=1308841103655268861, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=EN, label=null, caption=null, figureFileSmall=v0ef44C8rbZBqccWG+HBpA==, figureFileBig=Fcy6DxXTTNkQL/GadJozyA==, tableContent=null), ArticleFig(id=1308841103709794814, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=CN, label=Fig.3, caption=Experimental and calculated ECD spectra of compound 1, figureFileSmall=v0ef44C8rbZBqccWG+HBpA==, figureFileBig=Fcy6DxXTTNkQL/GadJozyA==, tableContent=null), ArticleFig(id=1308841103768515071, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=EN, label=null, caption=null, figureFileSmall=Df+Us7MzVmJ2WPJN+opEcg==, figureFileBig=/Jl9GEnFmF0hPWvhxszDrg==, tableContent=null), ArticleFig(id=1308841103823041024, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=CN, label=Fig.4, caption=The effect of compound 1 on the levels of inflammatory cytokine of TNF-α-induced MH7A cells. The levels of IL-6 (A) and IL-1β (B) were determined by ELISA kits. n = 3, $ \overline{x} $ ± s. **P < 0.01, ***P < 0.001 vs MTX: 5 μmol·L-1. The "ns" indicates no significant difference vs MTX: 5 μmol·L-1, figureFileSmall=Df+Us7MzVmJ2WPJN+opEcg==, figureFileBig=/Jl9GEnFmF0hPWvhxszDrg==, tableContent=null), ArticleFig(id=1308841103902732801, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
No.δHδC
12.96, m49.8, CH
21.34, dt (13.1, 7.5)
2.44, dt (13.1, 7.8)		39.5, CH2
34.49, dd (7.8, 2.2)79.2, CH
4143.2, C
5134.4, C
64.87, d (10.6)84.8, CH
72.87, ddd (10.6, 3.3, 1.7)47.1, CH
81.58, m
2.13, m		25.3, CH2
91.73, m
1.85, overlapped		36.2, CH2
101.85, overlapped36.9, CH
11141.2, C
12172.3, C
135.60, d (3.4)
6.14, d (3.4)		119.8, CH2
140.84, d (6.9)13.1, CH3
151.87, m12.4, CH3
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1H NMR (600 MHz) and 13C NMR (150 MHz) data of compound 1 (CD3OD)

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No.δHδC
12.96, m49.8, CH
21.34, dt (13.1, 7.5)
2.44, dt (13.1, 7.8)		39.5, CH2
34.49, dd (7.8, 2.2)79.2, CH
4143.2, C
5134.4, C
64.87, d (10.6)84.8, CH
72.87, ddd (10.6, 3.3, 1.7)47.1, CH
81.58, m
2.13, m		25.3, CH2
91.73, m
1.85, overlapped		36.2, CH2
101.85, overlapped36.9, CH
11141.2, C
12172.3, C
135.60, d (3.4)
6.14, d (3.4)		119.8, CH2
140.84, d (6.9)13.1, CH3
151.87, m12.4, CH3
), ArticleFig(id=1308841104057922051, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841094142587331, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
CompoundInhibition rate/%
5 μmol·L-110 μmol·L-1
133.42 ± 0.5840.46 ± 0.59
210.33 ± 0.961.92 ± 0.77
3--
411.55 ± 0.87-
516.82 ± 1.514.03 ± 1.05
65.35 ± 0.2811.57 ± 0.39
76.82 ± 0.989.18 ± 0.81
9--
MTX44.16 ± 0.51/
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Inhibitory activity of compounds 1-7 and 9 on TNF-α-induced proliferation of MH7A cells. MTX: Methotrexate. n = 3, $ \overline{x} $ ± s. "-" indicates no activity

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CompoundInhibition rate/%
5 μmol·L-110 μmol·L-1
133.42 ± 0.5840.46 ± 0.59
210.33 ± 0.961.92 ± 0.77
3--
411.55 ± 0.87-
516.82 ± 1.514.03 ± 1.05
65.35 ± 0.2811.57 ± 0.39
76.82 ± 0.989.18 ± 0.81
9--
MTX44.16 ± 0.51/
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山胡椒根中一个新的愈创木烷型倍半萜
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陶玉佳 , 任航洁 , 李刚 , 施琦 , 秦路平 * , 李华强 *
药学学报 | 研究论文 2026,61(5): 1757-1763
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药学学报 |研究论文 2026 , 61 (5) : 1757 -1763
山胡椒根中一个新的愈创木烷型倍半萜
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陶玉佳, 任航洁, 李刚, 施琦, 秦路平* , 李华强*
作者信息
  • 浙江中医药大学药学院, 浙江 杭州 311403
通讯作者:
秦路平, E-mail:
李华强, E-mail:
作者简介:

作者贡献:

陶玉佳为本文第一作者, 负责成分分离、结构鉴定和论文的撰写及修改; 任航洁协助样品分离纯化; 李刚参与化合物ECD计算; 施琦负责实验药理部分的工作; 秦路平和李华强负责实验设计指导和稿件修改。

A new guaiane-type sesquiterpenoid from the roots of Lindera glauca
Yu-jia TAO, Hang-jie REN, Gang LI, Qi SHI, Lu-ping QIN* , Hua-qiang LI*
Affiliations
  • School of Pharmaceutical Sciences, Zhejiang Chinese Medical University, Hangzhou 311403, China
出版时间: 2026-05-12 doi: 10.16438/j.0513-4870.2025-1447
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摘要
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采用硅胶、ODS和Sephadex LH-20等柱色谱以及半制备型HPLC等多种分离技术, 从山胡椒根95%乙醇提取物的二氯甲烷萃取相中分离得到了9个倍半萜类成分。结合IR、UV、NMR、HRESIMS和ECD等现代波谱学技术进行结构鉴定, 确定其结构分别为glaucatotone M (1)、glaucatotone K (2)、glaucatotone G (3)、pseudoguaianelactone C (4)、pseudoguaianelactone B (5)、elema-1,3,11(13)-trien-12-oic acid (6)、α-costic acid (7)、3β-hydroxycostic acid (8) 和rupestonic acid I (9)。其中, 化合物1为一个新的愈创木烷型倍半萜类化合物, 化合物6和7为首次从山胡椒属植物中分离得到。评价化合物1~7和9对TNF-α诱导的类风湿性关节炎滑膜成纤维细胞系MH7A细胞增殖和炎症因子IL-6、IL-1β释放的抑制活性, 结果显示, 化合物1对TNF-α诱导的MH7A细胞的增殖表现出了较为显著的抑制效果, 且能够有效降低IL-6和IL-1β的生成量。

山胡椒  /  化学成分  /  倍半萜  /  结构鉴定  /  类风湿性关节炎

Nine sesquiterpenoids were isolated from the dichloromethane fraction of the 95% ethanol extract from the roots of Lindera glauca by using a combination of separation techniques, including silica gel, ODS and Sephadex LH-20 column chromatographies, as well as semi-preparative HPLC. Based on a comprehensive analysis of modern spectroscopic data, such as IR, UV, NMR, HRESIMS and ECD, the structures of isolated compounds were identified as glaucatotone M (1), glaucatotone K (2), glaucatotone G (3), pseudoguaianelactone C (4), pseudoguaianelactone B (5), elema-1,3,11(13)-trien-12-oic acid (6), α-costic acid (7), 3β-hydroxycostic acid (8) and rupestonic acid I (9), respectively. Compound 1 was a new guaiane-type sesquiterpenoid, and compounds 6 and 7 were first reported from the genus Lindera. The inhibitory activity of compounds 1-7 and 9 against both the proliferation of TNF-α-induced rheumatoid arthritis fibroblast-like synoviocytes cell line MH7A and the release of pro-inflammatory cytokines (IL-6 and IL-1β) were evaluated. The results showed that compound 1 had a significant inhibitory effect against TNF-α-induced MH7A cell proliferation and reduced the production of IL-6 and IL-1β effectively.

Lindera glauca  /  chemical constituent  /  sesquiterpenoid  /  structural identification  /  rheumatoid arthritis
陶玉佳, 任航洁, 李刚, 施琦, 秦路平, 李华强. 山胡椒根中一个新的愈创木烷型倍半萜. 药学学报, 2026 , 61 (5) : 1757 -1763 . DOI: 10.16438/j.0513-4870.2025-1447
Yu-jia TAO, Hang-jie REN, Gang LI, Qi SHI, Lu-ping QIN, Hua-qiang LI. A new guaiane-type sesquiterpenoid from the roots of Lindera glauca[J]. Acta Pharmaceutica Sinica, 2026 , 61 (5) : 1757 -1763 . DOI: 10.16438/j.0513-4870.2025-1447
正文
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山胡椒Lindera glauca (Sieb.et Zucc.) Bl.为樟科山胡椒属多年生落叶灌木或小乔木, 又名牛筋树、假死柴、野胡椒等[1], 其资源在我国十分丰富, 主要分布于长江流域以南[2]。山胡椒不仅有重要的经济与生态价值, 还具有极高的药用价值, 其根、叶及果实等部位在我国民间具有广泛的药用历史。根可用于风湿痹痛, 劳伤失力, 感冒, 扁桃体炎, 咽炎, 浮肿; 叶用于痈疮, 外伤出血; 果实可治疗胃痛, 气喘[3,4]。现代研究表明, 山胡椒中化学成分主要为萜类[5,6]、生物碱类[7]及黄酮类[8]等化合物, 具有抗炎、抗肿瘤、抗菌等多种活性[9]。
山胡椒根在我国南方被广泛用于治疗类风湿关节炎(rheumatoid arthritis, RA), 且具有显著效果。目前虽有成分分离及零星的抗炎活性报道[10-12], 但尚未见对其抗RA活性成分及药效的研究。因此, 为进一步挖掘山胡椒根中化学成分, 探究其抗RA的活性, 本研究对山胡椒根95%乙醇提取物进行分析, 从中分离得到了9个倍半萜类成分(图1), 其中1为新化合物, 6和7为首次从该属中发现。对化合物1~7和9进行活性研究, 发现化合物1对TNF-α诱导的MH7A细胞的增殖表现出了很好的抑制效果, 且能够有效降低IL-6和IL-1β的生成量。
结果与讨论
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1　新化合物1结构鉴定
化合物1为白色无定形粉末, 通过HR-ESI-MS的准分子离子峰为m/z 265.143 7 [M-H]- (计算值265.144 0), 确定其分子式为C15H22O4, 不饱和度为5。化合物1的 1H NMR数据(表1) 显示化合物中具有两个甲基信号[δH 1.87 (3H, m, 15-CH3), 0.84 (3H, d, J = 6.9 Hz, 14-CH3)] 以及低场区的两个末端烯质子信号[δH 6.14 (1H, d, J = 3.4 Hz, H-13a), 5.60 (1H, d, J = 3.4 Hz, H-13b)]。化合物1的13C NMR谱、DEPT谱和HSQC谱中显示了15个碳, 其中有两个甲基、4个亚甲基[包括一个烯烃亚甲基(δC 119.8)], 5个次甲基[包括两个氧化次甲基(δC 84.8, 79.2)] 和4个季碳[其中包含一个酯羰基碳(δC 172.3), 3个烯烃季碳(δC 143.2, 141.2, 134.4)]。
1H-1H COSY谱中能观察到H-3/H2-2/H-1/H-10/H2-9/H2-8/H-7/H-6和H-10/H3-14的两个自旋偶合系统(图2)。结合在HMBC谱中, H3-15与C-3/C-4/C-5相关, H3-14与C-1/C-9/C-10相关, H2-13与C-7/C-11/C-12相关以及H2-2与C-4/C-5相关, H-7与C-5相关(图2), 由此, 确定了化合物1的平面结构是一个典型的愈创木烷型倍半萜[13]。根据NOESY谱中相关信号, H-1 (δH 2.96) 与H-3 (δH 4.49)、H-9a (δH 1.73) 有相关, H-9a与H-7 (δH 2.87) 有相关, 确定H-1、H-3和H-7为同向并设定为β构型; H3-14 (δH 0.84) 与H-6 (δH 4.87) 有相关确定了H3-14与H-6同向(图2)。H-6与H-7之间的偶合常数(10.6 Hz) 确定两者为反向构型, 由此判定H-6与H3-14为α构型。因此, 确定了化合物1的相对结构为1R*,3R*,6R*,7R*,10R*。最后, 基于密度泛函理论的量子化学方法计算了1的两个对映异构体的ECD图谱(1R,3R,6R,7R,10R-1和1S,3S,6S,7S,10S-1), 其中1R,3R,6R,7R,10R-1的曲线趋势与实验ECD图谱基本一致(图3), 由此确定1的绝对构型为1R,3R,6R,7R,10R, 并命名为glaucatotone M。
2　化合物对TNF-α诱导的MH7A细胞增殖及炎症因子水平的影响作用
首先, 对化合物1~7和9进行MH7A细胞毒性测试, 结果发现所有化合物在10 μmol·L-1浓度下存活率均在90%以上, 表明在该浓度内均无明显毒性。因此, 进一步采用CCK-8法测定化合物对TNF-α诱导的MH7A细胞增殖的抑制作用, 在5和10 μmol·L-1浓度下进行活性评价, 结果显示, 化合物1对MH7A细胞的增殖显示出了最显著的抑制活性, 抑制率分别为33.42%和40.46% (表2)。最后, 对效果最佳的1在2.5、5和10 μmol·L-1浓度下测试其对TNF-α诱导的MH7A细胞中IL-6和IL-1β释放量的影响, 结果表明1对IL-6和IL-1β的生成均表现出了很好的抑制作用, 在一定浓度下效果与阳性药相当(图4)。
实验部分
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AB SCIEX TripleTOF 7600高分辨液相-质谱联用仪(美国AB SCIEX公司); Bruker AM-600核磁共振波谱仪(德国Bruker公司); Nicolet IS50型红外光谱仪(美国Thermo Fisher公司); UV-3600i Plus紫外可见近红外光谱仪(日本岛津公司); AUTOPOL IV-T全自动旋光仪(美国Rudolph Research Analytical公司); Chirascan V100圆二色光谱仪(英国Applied Photophysics Ltd.公司); LC-2010双泵半制备型高效液相色谱仪(武汉睿合色谱技术有限公司); RE-2000A旋转蒸发器(上海亚荣生化仪器厂); Tecan Infinite M200多功能酶标仪(瑞士Tecan公司); 3111型二氧化碳培养箱(美国Thermo公司); 柱色谱硅胶(200~300目, 青岛海洋化工有限公司); ODS (50 μm, 日本YMC公司); Sephadex LH-20葡聚糖凝胶(美国GE公司); Chirlpak IC色谱柱(250 mm × 4.6 mm, 5 μm, 上海大赛璐药物手性技术有限公司); 反相XB-C18半制备色谱柱(250 mm × 10 mm, 5 μm, 上海月旭有限公司); 高效薄层色谱硅胶板(GF254, 烟台化工研究所); 分析纯试剂(广东光华科技股份有限公司); 色谱乙腈、甲醇等(美国天地公司); 氘代试剂(北京金鸥翔科贸有限公司); DEME培养基、10%胎牛血清、胰酶(美国Gibco公司); TNF-α、甲氨蝶呤(武汉吉立德生物科技有限公司); PBS缓冲液、CCK-8试剂盒(白鲨生物科技有限公司); 人白介素6 (IL-6)、白介素1β (IL-1β) 酶联免疫分析(ELISA) 试剂盒(南京建成生物工程研究所); MH7A细胞株(中国科学院上海生命科学研究院细胞资源中心)。
山胡椒根于2022年11月采集于浙江省天目山地区, 并经浙江中医药大学张巧艳教授鉴定为樟科山胡椒属植物山胡椒Lindera glauca (Sieb.et Zucc.) Bl.的根。植物凭证标本(LHQ-LG-2022-11) 存放于浙江中医药大学药学院本草标本室(4A402)。
1　提取与分离
山胡椒根(45.0 kg) 切片后干燥, 用95%乙醇加热回流提取3次, 合并药材提取液并减压浓缩, 得乙醇粗提物浸膏3.4 kg。将总浸膏与水分散均匀形成混悬液, 并依次用石油醚和二氯甲烷分别进行萃取, 回收溶剂并减压浓缩得到石油醚萃取部位及二氯甲烷萃取部位。二氯甲烷部位(460.0 g) 经正相硅胶柱色谱层析, 以二氯甲烷-甲醇(1∶0→0∶1) 梯度洗脱, 根据TLC结果合并收集为10个组分(Fr.1~Fr.10)。
组分Fr.2 (17.7 g) 经反相ODS柱色谱(甲醇-水, 梯度40%、60%、80%、100%洗脱) 分离得到11个亚组分(Fr.2.1~Fr.2.11)。其中亚组分Fr.2.3经C18柱(35%乙腈-水, 2 mL·min-1) 分离, 得到Fr.2.3.1~Fr.2.3.7, 对Fr.2.3.6用IC柱(30%乙腈-水, 1 mL·min-1) 进一步纯化, 得到化合物4 (21.1 mg, tR = 12.2 min) 和化合物5 (23.8 mg, tR = 16.3 min)。Fr.2.3.7经IC柱(30%乙腈-水, 1 mL·min-1) 纯化, 得到化合物1 (6.0 mg, tR = 32.1 min)。亚组分Fr.2.4经C18柱(35%乙腈-水, 2 mL·min-1) 分离, 得到Fr.2.4.1~Fr.2.4.8, 对其中的Fr.2.4.5经IC柱(60%乙腈-水, 水相含0.1%甲酸, 1 mL·min-1) 分离, 得到化合物8 (2.0 mg, tR = 21.8 min), Fr.2.4.6经C18柱(70%乙腈-水, 2 mL·min-1) 分离, 得到化合物3 (6.4 mg, tR = 24.2 min), Fr.2.4.8经C18柱(58%甲醇-水, 2 mL·min-1) 分离, 得到化合物2 (3.4 mg, tR = 28.9 min)。亚组分Fr.2.5经C18柱(55%乙腈-水, 2 mL·min-1) 分离, 得到Fr.2.5.1~Fr.2.5.7, 对其中的Fr.2.5.7经IC柱(35%乙腈-水, 水相含0.1%甲酸, 1 mL·min-1) 分离, 得到化合物9 (6.7 mg, tR = 15.3 min)。最后亚组分Fr.2.8经凝胶柱(纯甲醇) 分离, 合并得到Fr.2.8.1~Fr.2.8.5, 对Fr.2.8.4用C18柱(75%甲醇-水, 水相含0.1%甲酸, 2 mL·min-1) 进一步分离得到5段组分Fr.2.8.4.1~Fr.2.8.4.5, Fr.2.8.4.2经IC柱(40%乙腈-水, 水相含0.1%甲酸, 1 mL·min-1) 进一步纯化, 得到化合物6 (3.2 mg, tR = 19.2 min), Fr.2.8.4.3经IC柱(45%乙腈-水, 水相含0.1%甲酸, 1 mL·min-1) 进一步纯化, 得到化合物7 (8.1 mg, tR = 14.6 min)。
2　结构鉴定
化合物1  白色无定形粉末, [α]$ {}_{\mathrm{D}}^{25} $ +145.4 (c 0.22, MeOH); UV (MeOH) λmax (log ε) = 207 (3.88) nm; IR (KBr) νmax = 3 423, 2 922, 2 361, 1 766, 1 627, 1 449, 1 254, 1 149 cm-1; ECD (MeOH) λmax (Δε) = 217 (+1.37) nm; HR-ESI-MS [M-H]- m/z 265.143 7 (calcd. for C15H21O4-, 265.144 0); 1H NMR (600 MHz, CD3OD) and 13C NMR (150 MHz, CD3OD) 见表1。
化合物2  白色无定形粉末, [α]$ {}_{\mathrm{D}}^{25} $ -63.8 (c 0.26, MeOH), HR-ESI-MS m/z: 273.146 2 [M+Na]+, 分子式为C15H22O3。1H NMR (600 MHz, CDCl3) δH: 5.21 (1H, d, J = 2.0 Hz, H-15a), 5.13 (1H, d, J = 2.0 Hz, H-15b), 2.66 (1H, m, H-3a), 2.54 (1H, m, H-11), 2.47 (1H, m, H-3b), 2.43 (1H, m, H-2a), 2.27 (1H, m, H-6a), 2.15 (1H, m, H-6b), 2.06 (1H, m, H-7), 2.04 (1H, m, H-10), 1.98 (1H, m, H-8a), 1.92 (1H, m, H-9a), 1.62 (1H, m, H-8b), 1.53 (1H, m, H-2b), 1.44 (1H, m, H-9b), 1.34 (3H, d, J = 7.5 Hz, 13-CH3), 1.05 (3H, d, J = 7.5 Hz, 14-CH3); 13C NMR (150 MHz, CDCl3) δC: 84.8 (C-1), 33.2 (C-2), 27.4 (C-3), 152.0 (C-4), 93.6 (C-5), 21.0 (C-6), 33.9 (C-7), 30.5 (C-8), 28.3 (C-9), 41.9 (C-10), 41.2 (C-11), 174.1 (C-12), 17.9 (C-13), 17.8 (C-14), 110.2 (C-15)。以上数据与文献[14]报道一致, 故鉴定化合物2为glaucatotone K。
化合物3  无色针状晶体, [α]$ {}_{\mathrm{D}}^{25} $ -13.8 (c 0.30, MeOH), HR-ESI-MS m/z: 273.146 4 [M+Na]+, 分子式为C15H22O3。1H NMR (600 MHz, CDCl3) δH: 6.21 (1H, d, J = 1.7 Hz, H-13a), 5.43 (1H, d, J = 1.7 Hz, H-13b), 2.89 (1H, m, H-7), 2.47 (1H, m, H-6a), 2.43 (1H, m, H-2a), 2.25 (1H, m, H-4), 2.00 (2H, m, H-8a, H-10), 1.98 (1H, m, H-3a), 1.92 (1H, m, H-9a), 1.75 (1H, dd, J = 14.5, 4.1 Hz, H-6b), 1.69 (1H, m, H-8b), 1.51 (1H, m, H-3b), 1.44 (2H, m, H-2b, H-9b), 1.03 (3H, d, J = 7.4 Hz, 14-CH3), 0.89 (3H, d, J = 6.9 Hz, 15-CH3); 13C NMR (150 MHz, CDCl3) δC: 85.8 (C-1), 34.4 (C-2), 27.8 (C-3), 41.6 (C-4), 97.7 (C-5), 27.1 (C-6), 35.5 (C-7), 30.9 (C-8), 28.0 (C-9), 42.9 (C-10), 141.2 (C-11), 166.6 (C-12), 124.4 (C-13), 17.8 (C-14), 12.5 (C-15)。以上数据与文献[15]报道一致, 故鉴定化合物3为glaucatotone G。
化合物4  白色晶体, [α]$ {}_{\mathrm{D}}^{25} $ -88.4 (c 0.61, MeOH), HR-ESI-MS m/z: 273.146 1 [M+Na]+, 分子式为C15H22O3。1H NMR (600 MHz, CDCl3) δH: 6.29 (1H, d, J = 1.5 Hz, H-13a), 5.46 (1H, d, J = 1.5 Hz, H-13b), 3.04 (1H, m, H-7), 2.55 (1H, td, J = 9.4, 7.3 Hz, H-1), 2.14 (1H, m, H-10), 2.12 (1H, m, H-3a), 2.08 (1H, m, H-6a), 1.98 (1H, m, H-6b), 1.96 (1H, m, H-8a), 1.88 (1H, m, H-2a), 1.76 (1H, m, H-8b), 1.75 (1H, m, H-9a), 1.71 (1H, m, H-2b), 1.68 (1H, m, H-3b), 1.50 (1H, m, H-9b), 1.21 (3H, s, 15-CH3), 0.95 (3H, d, J = 7.3 Hz, 14-CH3); 13C NMR (150 MHz, CDCl3) δC: 49.2 (C-1), 23.4 (C-2), 37.8 (C-3), 83.8 (C-4), 96.6 (C-5), 29.9 (C-6), 35.2 (C-7), 31.1 (C-8), 30.6 (C-9), 31.5 (C-10), 140.2 (C-11), 165.5 (C-12), 125.5 (C-13), 16.4 (C-14), 21.4 (C-15)。以上数据与文献[11]报道一致, 故鉴定化合物4为pseudoguaianelactone C。
化合物5  无色晶体, [α]$ {}_{\mathrm{D}}^{25} $ -130.6 (c 0.53, MeOH), HR-ESI-MS m/z: 273.146 1 [M+Na]+, 分子式为C15H22O3。1H NMR (600 MHz, CDCl3) δH: 5.69 (1H, d, J = 1.5 Hz, H-13a), 5.36 (1H, d, J = 1.5 Hz, H-13b), 2.81 (1H, m, H-7), 2.51 (1H, dd, J = 14.2, 3.5 Hz, H-6a), 2.23 (1H, td, J = 9.2, 5.2 Hz, H-1), 2.06 (1H, m, H-10), 1.99 (1H, m, H-6b), 1.94 (2H, m, H-3a, H-3b), 1.75 (2H, m, H-8a, H-8b), 1.71 (2H, m, H-9a, H-9b), 1.69 (1H, m, H-2a), 1.61 (1H, m, H-2b), 1.46 (3H, s, 15-CH3), 0.88 (3H, d, J = 7.0 Hz, 14-CH3); 13C NMR (150 MHz, CDCl3) δC: 56.3 (C-1), 22.3 (C-2), 38.1 (C-3), 82.8 (C-4), 93.5 (C-5), 40.3 (C-6), 40.5 (C-7), 34.4 (C-8), 27.9 (C-9), 35.0 (C-10), 147.8 (C-11), 172.4 (C-12), 123.0 (C-13), 21.5 (C-14), 18.1 (C-15)。以上数据与文献[11]报道一致, 故鉴定化合物5为pseudoguaianelactone B。
化合物6  浅黄色油状物, [α]$ {}_{\mathrm{D}}^{25} $ +34.5 (c 0.12, MeOH), HR-ESI-MS m/z: 233.154 0 [M-H]-, 分子式为C15H22O2。1H NMR (600 MHz, CDCl3) δH: 6.28 (1H, s, H-12a), 5.82 (1H, dd, J = 17.4, 10.9 Hz, H-1), 5.64 (1H, s, H-12b), 4.92 (1H, d, J = 6.5 Hz, H-2a), 4.90 (1H, s, H-3a), 4.82 (1H, t, J = 1.8 Hz, H-2b), 4.58 (1H, s, H-3b), 2.49 (1H, m, H-7), 2.07 (1H, dd, J = 12.6, 3.1 Hz, H-5), 1.70 (3H, s, 14-CH3), 1.65 (2H, m, H-8a, H-8b), 1.54 (2H, m, H-6a, H-6b), 1.45 (2H, m, H-9a, H-9b), 1.01 (3H, s, 15-CH3); 13C NMR (150 MHz, CDCl3) δC: 150.2 (C-1), 110.2 (C-2), 112.4 (C-3), 147.5 (C-4), 52.7 (C-5), 33.4 (C-6), 39.9 (C-7), 27.4 (C-8), 39.8 (C-9), 39.5 (C-10), 145.1 (C-11), 124.9 (C-12), 172.7 (C-13), 25.0 (C-14), 16.7 (C-15)。以上数据与文献[16]报道一致, 故鉴定化合物6为elema-1,3,11(13)-trien-12-oic acid。
化合物7  无色油状物, [α]$ {}_{\mathrm{D}}^{25} $ +23.5 (c 0.34, MeOH), HR-ESI-MS m/z: 233.154 1 [M-H]-, 分子式为C15H22O2。1H NMR (600 MHz, CDCl3) δH: 6.31 (1H, s, H-13a), 5.68 (1H, s, H-13b), 5.32 (1H, brs, H-3), 2.52 (1H, m, H-7), 2.10 (1H, m, H-2a), 2.00 (1H, m, H-5), 1.96 (1H, m, H-2b), 1.85 (1H, m, H-9a), 1.69 (1H, m, H-8a), 1.60 (1H, m, 15-CH3), 1.55 (1H, m, H-8b), 1.47 (1H, m, H-6a), 1.36 (2H, m, H-1a, H-1b), 1.28 (1H, m, H-9b), 1.26 (1H, m, H-6b), 0.82 (3H, s, 14-CH3); 13C NMR (150 MHz, CDCl3) δC: 37.8 (C-1), 23.4 (C-2), 121.0 (C-3), 134.8 (C-4), 46.8 (C-5), 40.1 (C-6), 40.0 (C-7), 29.3 (C-8), 27.4 (C-9), 32.3 (C-10), 145.3 (C-11), 172.3 (C-12), 124.9 (C-13), 15.6 (C-14), 21.1 (C-15)。以上数据与文献[17]报道一致, 故鉴定化合物7为α-costic acid。
化合物8  白色无定形粉末, [α]$ {}_{\mathrm{D}}^{25} $ +25.6 (c 0.16, MeOH), HR-ESI-MS m/z: 247.169 3 [M-H]-, 分子式为C16H24O2。1H NMR (600 MHz, CDCl3) δH: 6.26 (1H, d, J = 1.1 Hz, H-13a), 5.62 (1H, d, J = 1.1 Hz, H-13b), 5.04 (1H, s, H-15a), 4.58 (1H, s, H-15b), 4.01 (1H, m, H-3), 2.50 (1H, m, H-7), 1.98 (1H, m, H-2a), 1.81 (1H, m, H-5), 1.67 (1H, m, H-6a), 1.60 (2H, m, H-2b, H-8a), 1.56 (1H, m, H-1a), 1.48 (2H, m, H-9a, H-6b), 1.43 (1H, m, H-8b), 1.35 (1H, m, H-1b), 1.30 (1H, m, H-9b), 0.72 (3H, s, 14-CH3); 13C NMR (150 MHz, CDCl3) δC: 40.6 (C-1), 32.7 (C-2), 73.2 (C-3), 152.5 (C-4), 48.0 (C-5), 27.1 (C-6), 39.1 (C-7), 29.9 (C-8), 39.6 (C-9), 35.6 (C-10), 145.3 (C-11), 170.9 (C-12), 123.9 (C-13), 16.4 (C-14), 102.4 (C-15)。以上数据与文献[18]报道一致, 故鉴定化合物8为3β-hydroxycostic acid。
化合物9  白色无定形粉末, [α]$ {}_{\mathrm{D}}^{25} $ +58.4 (c 0.83, MeOH), HR-ESI-MS m/z: 247.133 0 [M-H]-, 分子式为C15H20O3。1H NMR (600 MHz, acetone-d6) δH: 6.13 (1H, d, J = 1.5 Hz, H-13a), 5.20 (1H, d, J = 1.5 Hz, H-13b), 3.86 (1H, m, H-7), 2.69 (1H, m, H-2a), 2.34 (1H, m, H-10), 2.29 (1H, m, H-4), 2.22 (1H, m, H-2b), 2.07 (1H, m, H-3a), 1.73 (1H, m, H-3b), 1.68 (1H, m, H-9a), 1.65 (2H, m, H-8a, H-8b), 1.29 (1H, m, H-9b), 1.16 (3H, d, J = 7.1 Hz, 15-CH3), 1.05 (3H, d, J = 7.0 Hz, 14-CH3); 13C NMR (150 MHz, acetone-d6) δC: 161.8 (C-1), 26.8 (C-2), 30.1 (C-3), 41.3 (C-4), 199.9 (C-5), 132.8 (C-6), 34.3 (C-7), 26.7 (C-8), 27.6 (C-9), 35.7 (C-10), 144.9 (C-11), 168.1 (C-12), 124.3 (C-13), 15.6 (C-14), 19.4 (C-15)。以上数据与文献[19]报道一致, 故鉴定化合物9为rupestonic acid I。
3　计算ECD
化合物1的绝对构型是通过计算ECD图谱与实验ECD图谱的对比来确定的。首先, 在MMFF94分子力场下对化合物1进行构象分析并通过Spartan 14软件进行构象搜索。随后, 使用ORCA 5.0.3程序在气相条件下采用def2-mTZVPP/r2SCAN-3c级别的密度泛函理论对所得构象进行优化, 以确认重新优化的各构象能量处于极小值, 并在PWPB95/def2-TZVPP级别下重新计算各结构的单点能。选取吉布斯自由能的玻尔兹曼分布大于0.1%的优化构象, 利用含时密度泛函理论方法及PBE0/def2-SV(P) 基组进行电子圆二色谱计算。所有计算均引入了DFT-D4经验色散修正。
4　活性研究
4.1　化合物对MH7A细胞毒性测试
将MH7A细胞以5×103个/孔的细胞数接种于96孔板, 设空白组和给药组, 置于37 ℃、5% CO2培养箱中培养24 h。空白组加入空白培养基, 给药组分别加入用空白培养基配置的不同浓度化合物(终浓度为2.5、5和10 μmol·L-1), 每个浓度设3个复孔, 24 h后每孔加入10 μL CCK-8溶液, 在37 ℃条件下孵育1 h, 用酶标仪在450 nm处检测各孔的吸光度(A) 值, 计算细胞存活率。
4.2　化合物对TNF-α诱导的MH7A细胞增殖抑制活性评价
设空白组、模型组、阳性对照组及给药组, 空白组加入空白培养基, 阳性对照组加入5 μmol·L-1甲氨蝶呤(MTX) 阳性药, 给药组分别加入浓度为5和10 μmol·L-1的不同化合物, 每个浓度设3个复孔。MH7A细胞用TNF-α (10 ng·mL-1) 刺激12 h后分别加入上述阳性药和不同浓度的样品继续培养24 h, 24 h后每孔加入CCK-8溶液10 μL, 在37 ℃条件下孵育1 h, 用酶标仪在450 nm处检测各孔的吸光度值[20], 计算细胞增殖抑制率。
4.3　化合物1对TNF-α诱导的MH7A细胞炎症因子含量测定
检测化合物1对MH7A细胞中IL-6和IL-1β含量的影响[21], 设2.5、5和10 μmol·L-1三个浓度。设置空白组、模型组、阳性对照组(MTX: 5 μmol·L-1) 及给药组, MH7A细胞用TNF-α (10 ng·mL-1) 刺激12 h后分别加入上述阳性药和样品继续培养24 h, 然后收集细胞上清液, 用ELISA试剂盒测定上清液中IL-6和IL-1β的含量。具体操作方法参照说明书。
4.4　统计学分析实验数据以均数±标准差($ \overline{x} $ ± s) 表示, 采用GraphPad Prism 9软件进行统计学分析。

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doi: 10.16438/j.0513-4870.2025-1447
  • 接收时间：2025-12-03
  • 首发时间：2026-09-21
  • 出版时间：2026-05-12
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  • 收稿日期：2025-12-03
  • 修回日期：2026-01-08
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    浙江中医药大学药学院, 浙江 杭州 311403

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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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