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Article(id=1193523096893227407, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1193523095437799732, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2024-1013, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1729180800000, receivedDateStr=2024-10-18, revisedDate=1733760000000, revisedDateStr=2024-12-10, acceptedDate=null, acceptedDateStr=null, onlineDate=1762487680885, onlineDateStr=2025-11-07, pubDate=1739289600000, pubDateStr=2025-02-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1762487680885, onlineIssueDateStr=2025-11-07, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1762487680885, creator=13701087609, updateTime=1762487680885, updator=13701087609, issue=Issue{id=1193523095437799732, tenantId=1146029695717560320, journalId=1189982191388893191, year='2025', volume='60', issue='2', pageStart='245', pageEnd='532', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1762487680538, creator=13701087609, updateTime=1764224912893, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1200809576107987438, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1193523095437799732, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1200809576107987439, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1193523095437799732, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=442, endPage=448, ext={EN=ArticleExt(id=1193523097140691345, articleId=1193523096893227407, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Five new triterpenoid saponins from the kernels of Momordica cochinchinensis, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Five saponins were isolated from the kernels of Momordica cochinchinensis, by macroporous resin, silica gel, ODS column chromatography, and semi preparative HPLC. Based on MS and NMR analysis, combining with alkaline hydrolysis and acid hydrolysis, their structures were identified as: gypsogenin-3-O-{β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonosyl}-28-O-β-D-xylopyranosyl (1→3)-[β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl (1→2)-β-D-fucopyranoside (1), quillaic acid-3-O-{β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonosyl}-28-O-β-D-xylopyranosyl (1→3)-[β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl (1→2)-β-D-fucopyranoside (2), gypsogenin-3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonoside sodium (3), quillaic acid-3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonoside sodium (4), 18α-quillaic acid-3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonoside (5). Compounds 1-5 were new compounds, and named as mubezhisides A, B, C, D, E, respectively. They all could obviously inhibited the growth of Candida albicans, C. parapsilosis, and C. tropicalis.

, correspAuthors=Xiao-bo LI, Meng-yue WANG, 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=Ru DING, Jia-qi WANG, Yi-yang LUO, Yong-long HAN, Xiao-bo LI, Meng-yue WANG), CN=ArticleExt(id=1193523234869052202, articleId=1193523096893227407, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=木鳖子仁中5个新的三萜皂苷类成分, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用大孔树脂、硅胶、ODS柱层析、半制备HPLC等色谱技术, 从木鳖子种仁中分离了5个皂苷类成分; 利用HR-MS、NMR技术, 结合碱水解、酸水解方法, 鉴定为: 丝石竹皂苷元-3-O-{β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸基}-28-O-β-D-吡喃木糖基(1→3)-[β-D-吡喃木糖基(1→4)]-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃岩藻糖苷(1)、皂皮酸-3-O-{β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸基}-28-O-β-D-吡喃木糖基(1→3)-[β-D-吡喃木糖基(1→4)]-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃岩藻糖苷(2)、丝石竹皂苷元-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷钠(3)、皂皮酸-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷钠(4)、18α-皂皮酸-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷(5)。化合物1~5为新化合物, 分别命名为木鳖子苷A、B、C、D、E; 均能明显抑制白色念珠菌、近平滑念珠菌、热带念珠菌的生长。

, correspAuthors=李晓波, 王梦月, authorNote=null, correspAuthorsNote=
*李晓波, Tel: 86-21-34204806, E-mail:
王梦月, Tel: 86-21-34205222, E-mail:
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Chinese Pharmacopoeia (Vol Ⅰ) [M]. Beijing: China Medical Science and Technology Press, 2020: 66-67., articleTitle=null, refAbstract=null), Reference(id=1194709020545097963, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[2], rfOrder=1, authorNames=null, journalName=null, refType=null, unstructuredReference=Wang MY, Zhan ZB, Xiong Y, et al. New cytotoxic constituents in the water-soluble fraction from Momordicae Semen [J]. Nat Prod Res, 2020, 34: 823-829., articleTitle=null, refAbstract=null), Reference(id=1194709020620595438, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[3], rfOrder=2, authorNames=null, journalName=null, refType=null, unstructuredReference=Ai ZD, Ma C, Wan RM, et al. Anticancer activity and molecular mechanism of Momordica cochinchinensis seed extract in chronic myeloid leukemia cells [J]. Nutr Cancer, 2022, 74: 2644-2656., articleTitle=null, refAbstract=null), Reference(id=1194709020687704304, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[4], rfOrder=3, authorNames=null, journalName=null, refType=null, unstructuredReference=Fan R, Cheng RR, Zhu HT, et al. Two new oleanane-type triterpenoids from methanolyzed saponins of Momordica cochinchinensis [J]. Nat Prod Commun, 2016, 11: 725-728., articleTitle=null, refAbstract=null), Reference(id=1194709020788367602, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[5], rfOrder=4, authorNames=null, journalName=null, refType=null, unstructuredReference=Chan LY, Wang CKL, Major JM, et al. Isolation and characterization of peptides from Momordica cochinchinensis seeds [J]. J Nat Prod, 2009, 72: 1453-1458., articleTitle=null, refAbstract=null), Reference(id=1194709020897419508, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[6], rfOrder=5, authorNames=null, journalName=null, refType=null, unstructuredReference=Lan HY, Zhao B, Shen YL, et al. Phytochemistry, pharmacological activities, toxicity and clinical application of Momordica cochinchinensis [J]. Curr Pharm Des, 2019, 25: 715-728., articleTitle=null, refAbstract=null), Reference(id=1194709020972916982, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[7], rfOrder=6, authorNames=null, journalName=null, refType=null, unstructuredReference=Liu XY, Ma J, Li CJ, et al. New triterpenoid saponins from the leaves of Panax notoginseng [J]. Acta Pharm Sin (药学学报), 2017, 52: 1432-1436., articleTitle=null, refAbstract=null), Reference(id=1194709021035831544, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[8], rfOrder=7, authorNames=null, journalName=null, refType=null, unstructuredReference=Wang JQ, Wu ZW, Shi XY, et al. Study on NMR determination of momordica saponin Ⅰ [J]. Acad J Shanghai Univ Tradit Chin Med (上海中医药大学学报), 2023, 37: 42-47., articleTitle=null, refAbstract=null), Reference(id=1194709021144883450, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[9], rfOrder=8, authorNames=null, journalName=null, refType=null, unstructuredReference=Jung K, Chin YW, Yoon KD, et al. Anti-inflammatory properties of a triterpenoidal glycoside from Momordica cochinchinensis in LPS-stimulated macrophages [J]. Immunopharmacol Immunotoxicol, 2013, 35: 8-14., articleTitle=null, refAbstract=null), Reference(id=1194709021224575226, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[10], rfOrder=9, authorNames=null, journalName=null, refType=null, unstructuredReference=Liu J, Qin MJ. Chemical constituents from the roots of Arenaria juncea [J]. Chin J Nat Med, 2007, 5: 235-236., articleTitle=null, refAbstract=null), Reference(id=1194709021316849915, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[11], rfOrder=10, authorNames=null, journalName=null, refType=null, unstructuredReference=Liu W, Wang MM, Han YC, et al. Activities of 5-iodotubercidin against pathogenic fungi and its mode of actions [J]. 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No.12345
δCδHδCδHδCδHδCδHδCδH
138.01.54, m
0.95, m		38.11.54, m
1.01, m		37.91.56, m
0.97, m		38.01.54, m
1.01, m		38.11.54, m
0.95, m
224.71.95, m
1.60, m		24.61.99, m
1.58, m		24.81.96, m
1.57, m		24.81.99, m
1.58, m		24.81.98, m
1.59, m
382.03.73, m82.33.71, m83.33.74, m83.33.68, m83.83.61, m
454.554.654.554.554.3
547.31.25, m47.71.26, m47.81.26, m47.81.26, m48.11.27, m
620.21.32, m
0.78, m		20.31.35, m
0.79, m		20.31.35, m
0.79, m		20.31.35, m
0.79, m		20.41.35, m
0.80, m
731.91.40, m
1.18, m		32.51.41, m
1.18, m		32.41.41, m32.41.41, m
1.18, m		32.51.42, m
1.15, m
839.839.839.839.839.9
946.41.63, m46.41.60, m45.91.54, m46.41.60, m46.71.59, m
1035.935.936.036.036.0
1122.81.81, m23.31.81, m23.91.81, brs23.31.81, m23.31.81, m
12122.05.18, brs121.95.16, brs121.05.11, brs121.45.20, brs120.45.20, brs
13143.6143.5145.4144.6145.6
1441.641.441.641.641.8
1527.61.53, m
1.08, m		35.31.90, m
1.11, m		27.71.53, m35.61.90, m
1.11, m		35.11.77, m
1.12, m
1623.31.50, m73.54.32, m23.41.50, m73.34.32, m74.04.20, m
1747.648.247.41.65, m47.948.5
1841.82.73, d (13.6)41.02.82, d (12.5)41.62.81, d (12.6)41.02.82, d (12.5)41.53.06, d (14.4)
1945.91.64, m
1.06, m		46.82.23, t (12.5)
0.99, m		46.21.65, m
1.04, m		46.92.23, t (12.5)
0.99, m		46.92.10, t (14.4)
0.90, m
2030.830.631.030.730.7
2133.51.17, m
1.34, m		35.11.33, m
1.18, m		33.41.18, m
1.33, m		35.01.33, m
1.18, m		35.91.76, m
1.01, m
2232.01.65, m
1.41, m		32.51.64, m
1.41, m		32.91.66, m32.41.64, m
1.41, m		32.51.61, m
23209.99.44, s210.19.44, s210.39.46, s210.29.47, s211.29.49, s
2410.51.06, s10.61.06, s10.71.05, s10.71.07, s10.91.09, s
2515.80.88, s15.90.91, s15.80.90, s15.80.90, s15.90.91, s
2617.10.67, s16.70.66, s17.30.74, s17.30.68, s17.60.73, s
2726.01.10, s26.81.32, s25.91.12, s26.91.33, s27.21.29, s
28175.9175.6178.9178.7178.4
2933.20.90, s33.30.84, s33.40.88, s33.30.83, s33.70.82, s
3024.00.87, s24.70.91, s23.40.86, s24.70.90, s24.70.91, s
), ArticleFig(id=1194709018213064915, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, language=CN, label=Table 1, caption=

NMR data of the aglycone moieties of compounds 1–5 in DMSO-d6 (700 MHz for 1H NMR, 176 MHz for 13C NMR, J in Hz)

, figureFileSmall=null, figureFileBig=null, tableContent=
No.12345
δCδHδCδHδCδHδCδHδCδH
138.01.54, m
0.95, m		38.11.54, m
1.01, m		37.91.56, m
0.97, m		38.01.54, m
1.01, m		38.11.54, m
0.95, m
224.71.95, m
1.60, m		24.61.99, m
1.58, m		24.81.96, m
1.57, m		24.81.99, m
1.58, m		24.81.98, m
1.59, m
382.03.73, m82.33.71, m83.33.74, m83.33.68, m83.83.61, m
454.554.654.554.554.3
547.31.25, m47.71.26, m47.81.26, m47.81.26, m48.11.27, m
620.21.32, m
0.78, m		20.31.35, m
0.79, m		20.31.35, m
0.79, m		20.31.35, m
0.79, m		20.41.35, m
0.80, m
731.91.40, m
1.18, m		32.51.41, m
1.18, m		32.41.41, m32.41.41, m
1.18, m		32.51.42, m
1.15, m
839.839.839.839.839.9
946.41.63, m46.41.60, m45.91.54, m46.41.60, m46.71.59, m
1035.935.936.036.036.0
1122.81.81, m23.31.81, m23.91.81, brs23.31.81, m23.31.81, m
12122.05.18, brs121.95.16, brs121.05.11, brs121.45.20, brs120.45.20, brs
13143.6143.5145.4144.6145.6
1441.641.441.641.641.8
1527.61.53, m
1.08, m		35.31.90, m
1.11, m		27.71.53, m35.61.90, m
1.11, m		35.11.77, m
1.12, m
1623.31.50, m73.54.32, m23.41.50, m73.34.32, m74.04.20, m
1747.648.247.41.65, m47.948.5
1841.82.73, d (13.6)41.02.82, d (12.5)41.62.81, d (12.6)41.02.82, d (12.5)41.53.06, d (14.4)
1945.91.64, m
1.06, m		46.82.23, t (12.5)
0.99, m		46.21.65, m
1.04, m		46.92.23, t (12.5)
0.99, m		46.92.10, t (14.4)
0.90, m
2030.830.631.030.730.7
2133.51.17, m
1.34, m		35.11.33, m
1.18, m		33.41.18, m
1.33, m		35.01.33, m
1.18, m		35.91.76, m
1.01, m
2232.01.65, m
1.41, m		32.51.64, m
1.41, m		32.91.66, m32.41.64, m
1.41, m		32.51.61, m
23209.99.44, s210.19.44, s210.39.46, s210.29.47, s211.29.49, s
2410.51.06, s10.61.06, s10.71.05, s10.71.07, s10.91.09, s
2515.80.88, s15.90.91, s15.80.90, s15.80.90, s15.90.91, s
2617.10.67, s16.70.66, s17.30.74, s17.30.68, s17.60.73, s
2726.01.10, s26.81.32, s25.91.12, s26.91.33, s27.21.29, s
28175.9175.6178.9178.7178.4
2933.20.90, s33.30.84, s33.40.88, s33.30.83, s33.70.82, s
3024.00.87, s24.70.91, s23.40.86, s24.70.90, s24.70.91, s
), ArticleFig(id=1194709018330505430, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compd.MIC/μmol·L-1Compd.MIC/μmol·L-1
CACPCTCACPCT
116.08.08.02bNANANA
1a32.016.016.0332.08.08.0
1bNANANA432.08.08.0
216.016.08.0564.016.016.0
2a64.016.016.0AMB16.08.08.0
), ArticleFig(id=1194709018401808600, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, language=CN, label=Table 3, caption=

The results of antifungal experiment. MIC: Minimal inhibit concentration; CA: Candida albicans; CP: C. parapsilosis; CT: C. tropicalis; NA: Not active; AMB: Amphotericin B

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Compd.MIC/μmol·L-1Compd.MIC/μmol·L-1
CACPCTCACPCT
116.08.08.02bNANANA
1a32.016.016.0332.08.08.0
1bNANANA432.08.08.0
216.016.08.0564.016.016.0
2a64.016.016.0AMB16.08.08.0
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No.12345No.12
δCδHδCδHδCδHδCδHδCδHδCδHδCδH
1′101.54.19, d (6.6)101.74.17, d (7.0)102.24.23, d (6.9)102.24.26, d (7.0)102.24.15, d (7.1)1⁗93.85.26, d (7.3)93.75.25, d (7.3)
2′78.33.37a78.33.39a78.13.39, m78.03.39, m78.23.35, m2⁗73.43.27a73.63.27a
3′83.23.37a82.63.39a82.03.49, m82.03.49, m81.93.42, m3⁗75.53.29, m75.53.29, m
4′71.83.23, m71.83.23, m71.93.23, m71.83.23, m71.83.21a4⁗72.43.16a72.63.16a
5′69.93.31a69.33.32a68.73.89, m68.73.89, m68.43.96, m5⁗70.33.31a70.33.31a
6′172.6172.4174.3173.9172.56⁗16.71.05, brs16.71.05, brs
1″102.84.28, d (7.8)102.84.28, d (7.8)102.94.28, d (7.3)102.94.28, d (7.8)103.04.25, d (7.1)1‴″99.95.22, brs100.25.11, brs
2″72.53.14, m73.33.14, m72.53.18, m72.53.18, m72.53.18, m2‴″71.73.41a71.73.41a
3″74.93.59, m74.53.43, m74.53.43, m74.63.43, m73.63.23a3‴″85.93.36, m85.93.37, m
4″71.13.71, m71.13.71, m71.13.71, m71.13.71, m71.13.70, m4‴″81.83.45, m81.73.42, m
5″75.53.29a75.53.29a75.63.29, m75.63.29, m75.73.23a5‴″68.43.65, m68.63.61, m
6″60.33.64, m
3.47, m		60.33.64, m
3.47, m		60.33.58, m
3.46, m		60.33.58, m
3.46, m		60.03.60, m
3.41, m		6‴″18.31.15, d (6.0)18.51.16, d (6.0)
1‴100.74.99, brs100.65.00, brs100.34.98, brs100.94.98, brs100.95.02, brs1‴‴105.44.43, d (7.8)105.14.43, d (7.7)
2‴71.23.60, m71.13.60, m70.93.60, m71.03.60, m71.13.42, m2‴‴74.33.06, m74.13.06, m
3‴74.03.25, m74.03.25, m74.03.26, m74.13.26, m73.93.23a3‴‴71.23.19, m76.43.19, d (9.9)
4‴74.13.10a74.13.09a74.03.09, m74.13.09, m73.93.23a4‴‴71.13.42a71.13.41a
5‴68.53.93, m68.53.93, m68.33.93, m68.33.93, m67.83.66, m5‴‴66.23.67, m
3.14, m		66.23.67, m
3.14, m
6‴18.21.05, d (6.0)18.31.06, d (6.0)18.31.07, d (6.2)18.31.07, d (6.2)18.21.05, d (6.1)1⁗‴104.64.41, d (7.8)104.74.41, d (7.7)
2⁗‴74.03.10a74.23.09a
3⁗‴71.23. 42, m71.13.41a
4⁗‴71.13.30, m69.93.31a
5⁗‴66.03.68, m
3.16a		66.03.68, m
3.15a
), ArticleFig(id=1194709018586357980, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1193523096893227407, language=CN, label=Table 2, caption=

NMR data of the sugar chain moieties of compounds 1–5 in DMSO-d6 (700 MHz for 1H NMR, 176 MHz for 13C NMR, J in Hz). aOverlapped

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No.12345No.12
δCδHδCδHδCδHδCδHδCδHδCδHδCδH
1′101.54.19, d (6.6)101.74.17, d (7.0)102.24.23, d (6.9)102.24.26, d (7.0)102.24.15, d (7.1)1⁗93.85.26, d (7.3)93.75.25, d (7.3)
2′78.33.37a78.33.39a78.13.39, m78.03.39, m78.23.35, m2⁗73.43.27a73.63.27a
3′83.23.37a82.63.39a82.03.49, m82.03.49, m81.93.42, m3⁗75.53.29, m75.53.29, m
4′71.83.23, m71.83.23, m71.93.23, m71.83.23, m71.83.21a4⁗72.43.16a72.63.16a
5′69.93.31a69.33.32a68.73.89, m68.73.89, m68.43.96, m5⁗70.33.31a70.33.31a
6′172.6172.4174.3173.9172.56⁗16.71.05, brs16.71.05, brs
1″102.84.28, d (7.8)102.84.28, d (7.8)102.94.28, d (7.3)102.94.28, d (7.8)103.04.25, d (7.1)1‴″99.95.22, brs100.25.11, brs
2″72.53.14, m73.33.14, m72.53.18, m72.53.18, m72.53.18, m2‴″71.73.41a71.73.41a
3″74.93.59, m74.53.43, m74.53.43, m74.63.43, m73.63.23a3‴″85.93.36, m85.93.37, m
4″71.13.71, m71.13.71, m71.13.71, m71.13.71, m71.13.70, m4‴″81.83.45, m81.73.42, m
5″75.53.29a75.53.29a75.63.29, m75.63.29, m75.73.23a5‴″68.43.65, m68.63.61, m
6″60.33.64, m
3.47, m		60.33.64, m
3.47, m		60.33.58, m
3.46, m		60.33.58, m
3.46, m		60.03.60, m
3.41, m		6‴″18.31.15, d (6.0)18.51.16, d (6.0)
1‴100.74.99, brs100.65.00, brs100.34.98, brs100.94.98, brs100.95.02, brs1‴‴105.44.43, d (7.8)105.14.43, d (7.7)
2‴71.23.60, m71.13.60, m70.93.60, m71.03.60, m71.13.42, m2‴‴74.33.06, m74.13.06, m
3‴74.03.25, m74.03.25, m74.03.26, m74.13.26, m73.93.23a3‴‴71.23.19, m76.43.19, d (9.9)
4‴74.13.10a74.13.09a74.03.09, m74.13.09, m73.93.23a4‴‴71.13.42a71.13.41a
5‴68.53.93, m68.53.93, m68.33.93, m68.33.93, m67.83.66, m5‴‴66.23.67, m
3.14, m		66.23.67, m
3.14, m
6‴18.21.05, d (6.0)18.31.06, d (6.0)18.31.07, d (6.2)18.31.07, d (6.2)18.21.05, d (6.1)1⁗‴104.64.41, d (7.8)104.74.41, d (7.7)
2⁗‴74.03.10a74.23.09a
3⁗‴71.23. 42, m71.13.41a
4⁗‴71.13.30, m69.93.31a
5⁗‴66.03.68, m
3.16a		66.03.68, m
3.15a
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木鳖子仁中5个新的三萜皂苷类成分
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丁如 1 , 王嘉祺 1 , 罗翌玚 1 , 韩永龙 2 , 李晓波 1, * , 王梦月 1, *
药学学报 | 研究论文 2025,60(2): 442-448
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药学学报 | 研究论文 2025, 60(2): 442-448
木鳖子仁中5个新的三萜皂苷类成分
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丁如1, 王嘉祺1, 罗翌玚1, 韩永龙2, 李晓波1, * , 王梦月1, *
作者信息
  • 1.上海交通大学药学院, 上海 200240
  • 2.上海市第六人民医院药剂科, 上海 200233

通讯作者:

*李晓波, Tel: 86-21-34204806, E-mail:
王梦月, Tel: 86-21-34205222, E-mail:
Five new triterpenoid saponins from the kernels of Momordica cochinchinensis
Ru DING1, Jia-qi WANG1, Yi-yang LUO1, Yong-long HAN2, Xiao-bo LI1, * , Meng-yue WANG1, *
Affiliations
  • 1. School of Pharmaceutical Science, Shanghai Jiao Tong University, Shanghai 200240, China
  • 2. Department of Pharmacy, Shanghai Sixth People's Hospital, Shanghai 200233, China
出版时间: 2025-02-12 doi: 10.16438/j.0513-4870.2024-1013
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摘要
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采用大孔树脂、硅胶、ODS柱层析、半制备HPLC等色谱技术, 从木鳖子种仁中分离了5个皂苷类成分; 利用HR-MS、NMR技术, 结合碱水解、酸水解方法, 鉴定为: 丝石竹皂苷元-3-O-{β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸基}-28-O-β-D-吡喃木糖基(1→3)-[β-D-吡喃木糖基(1→4)]-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃岩藻糖苷(1)、皂皮酸-3-O-{β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸基}-28-O-β-D-吡喃木糖基(1→3)-[β-D-吡喃木糖基(1→4)]-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃岩藻糖苷(2)、丝石竹皂苷元-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷钠(3)、皂皮酸-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷钠(4)、18α-皂皮酸-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷(5)。化合物1~5为新化合物, 分别命名为木鳖子苷A、B、C、D、E; 均能明显抑制白色念珠菌、近平滑念珠菌、热带念珠菌的生长。

木鳖子  /  种仁  /  三萜皂苷  /  木鳖子苷  /  抗真菌  /  念珠菌

Five saponins were isolated from the kernels of Momordica cochinchinensis, by macroporous resin, silica gel, ODS column chromatography, and semi preparative HPLC. Based on MS and NMR analysis, combining with alkaline hydrolysis and acid hydrolysis, their structures were identified as: gypsogenin-3-O-{β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonosyl}-28-O-β-D-xylopyranosyl (1→3)-[β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl (1→2)-β-D-fucopyranoside (1), quillaic acid-3-O-{β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonosyl}-28-O-β-D-xylopyranosyl (1→3)-[β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl (1→2)-β-D-fucopyranoside (2), gypsogenin-3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonoside sodium (3), quillaic acid-3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonoside sodium (4), 18α-quillaic acid-3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuropyranonoside (5). Compounds 1-5 were new compounds, and named as mubezhisides A, B, C, D, E, respectively. They all could obviously inhibited the growth of Candida albicans, C. parapsilosis, and C. tropicalis.

Momordica cochinchinensis  /  kernel  /  triterpenoid saponin  /  mubezhiside  /  antifungal activity  /  Candida
丁如, 王嘉祺, 罗翌玚, 韩永龙, 李晓波, 王梦月. 木鳖子仁中5个新的三萜皂苷类成分. 药学学报, 2025 , 60 (2) : 442 -448 . DOI: 10.16438/j.0513-4870.2024-1013
Ru DING, Jia-qi WANG, Yi-yang LUO, Yong-long HAN, Xiao-bo LI, Meng-yue WANG. Five new triterpenoid saponins from the kernels of Momordica cochinchinensis[J]. Acta Pharmaceutica Sinica, 2025 , 60 (2) : 442 -448 . DOI: 10.16438/j.0513-4870.2024-1013
正文
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木鳖子Momordicae Semen为葫芦科材植物木鳖Momordica cochinchinensis (Lour.) Spreng.的干燥成熟种子, 属常用中药, 载入历版中国药典中。以种仁药用, 具有散结消肿、攻毒疗疮之功效, 常用于疮疡肿毒、乳痈、瘰疬、痔瘘、干癣、秃疮等症[1]。现代研究发现木鳖子具有良好抗肿瘤作用, 对多种肿瘤细胞均有抑制作用[2-5]; 近年来, 药理作用研究亦发现木鳖子具有良好的抗菌作用, 能显著抑制白色念珠菌、金黄色葡萄球菌等致病菌的生长, 但其抗菌活性成分尚未见报道[6]。本研究基于传统用法, 对木鳖子种仁的水溶性成分进行了研究, 从中分离、鉴定了5个新的齐墩果烷型皂苷, 均具有良好的抗念珠菌活性(图 1、2)。
结果与讨论
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1 新化合物结构鉴定
化合物1  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -1.3 (c 0.18, H2O); HR-ESI-MS给出准分子离峰1 509.672 1 ([M-H]-, C70H109O35, 计算值1 509.674 9), 提示其分子式为C70H110O35。1H NMR (700 MHz, DMSO-d6) 高场区出现6个角甲基信号(δH 1.06、0.88、0.67、1.10、0.90、0.87); 13C NMR (176 MHz, DMSO-d6) 出现7个糖的端基碳信号(δC 101.5、100.7、102.8、93.8、99.9、105.4、104.6), 提示化合物1为含7个糖基的三萜皂苷(表 1)。氨水水解得丝石竹皂苷元-3-O-β-D-半乳糖基(1→2)-[α-L-鼠李糖基(1→3)]-β-D-葡萄糖醛酸苷(1a), 酸水解得石竹皂苷元(1b), 确定化合物1为石竹皂苷元7糖苷, C-3位糖链有3个糖基(1个半乳糖基、1个鼠李糖基、1个葡萄糖醛酸基)。酸水解确定化合物1含有1个D-葡萄糖醛酸基、1个D-半乳糖基、2个D-木糖基、1个D-岩藻糖基、2个L-鼠李糖基; 结合偶合常数, 确定D-葡萄糖醛酸、D-半乳糖、D-木糖、D-岩藻糖基均为β构型, L-鼠李糖基为α构型。HMBC谱中, δH 4.28 (Gal, H-1″) 与δC 78.3 (GluA, C-2′)、δH 4.99 (Rha, H-1‴) 与δC 83.2 (GluA, C-3′) 分别相关, 提示上述3糖基连接顺序为β-半乳糖基(1→2)-[α-鼠李糖基(1→3)]-β-葡萄糖醛酸基; δH 4.19 (GluA, H-1′)与δC 82.0 (C-3) 明显相关, 确定丝石竹皂苷元C-3位与葡萄糖醛酸基相连。与化合物1a、1b比较, 化合物1的C-28明显向高场位移(δC 175.9), 提示28位与糖基相连。结合酸水解结果, 确定28位糖链含有2个木糖基、1个岩藻糖基、1个鼠李糖基。HMBC谱中, δH 4.43 (Xyl, H-1′′′′′′) 与δC 85.9 (Rha′, C-3′′′′′)、δH 4.41 (Xyl′, H-1′′′′′′′) 与δC 81.8 (Rha′, C-4′′′′′)、δH 5.22 (Rha′, H-1′′′′′) 与δC 73.4 (Fuc, C-2⁗) 分别存在相关性, 提示上述4个糖基的连接顺序为β-木糖基(1→3)-[β-木糖基(1→4)-α-鼠李糖基]-(1→2)-β-岩藻糖基; δH 5.26 (Fuc, H-1⁗) 与δC 175.9 (C-28) 明显相关(图 2), 确定28位与岩藻糖基相连。最终确定化合物1结构为丝石竹皂苷元-3-O-{β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸基}-28-O-β-D-吡喃木糖基(1→3)-[β-D-吡喃木糖基(1→4)-α-L-吡喃鼠李糖基]-(1→2)-β-D-吡喃岩藻糖苷, 根据其来源命名为木鳖子苷A。
化合物2  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -1.8 (c 0.22, H2O); HR-ESI-MS给出准分子离峰HR-ESI-MS m/z 1 525.668 2 ([M-H]-, C70H109O36, 计算值1 525.669 9), 提示其分子式为C70H110O36。1H、13C NMR与化合物高度相似, 提示化合物2亦为含7个糖基的三萜皂苷。氨水水解得化合物皂皮酸-3-O-β-D-半乳糖基(1→2)-[α-L-鼠李糖基(1→3)]-β-D-葡萄糖醛酸苷(2a), 酸水解得皂皮酸(2b), 确定化合物2为皂皮酸7糖苷, C-3位糖链含3个糖基。酸水解确定糖基为D-葡萄糖醛酸、D-半乳糖、D-木糖、D-岩藻糖、L-鼠李糖基; 结合偶合常数, 确定D-葡萄糖醛酸、D-半乳糖、D-木糖、D-岩藻糖基均为β构型, L-鼠李糖基为α构型。HMBC谱中, δH 4.28 (Gal, H-1″) 与δC 78.3 (GluA, C-2′)、δH 5.00 (Rha, H-1‴) 与δC 82.6 (GluA, C-3′) 分别相关, 确定上述三糖基连接顺序为β-半乳糖基(1→2)-[α-鼠李糖基(1→3)]-β-葡萄糖醛酸基; δH 4.17 (GluA, H-1′) 与δc 82.3 (C-3) 明显相关, 确定皂皮酸C-3位与葡萄糖醛酸基相连。与化合物2a、2b比较, C-28明显向高场位移(δC 175.6), 提示28位糖基化。HMBC谱中, δH 4.43 (Xyl, H-1‴‴) 与85.9 (Rha′, C-3‴″)、δH 4.41 (Xyl′, H-1⁗‴) 与δC 81.7 (Rha′, C-4‴″)、δH 5.11 (Rha′, H-1‴″) 与δC 73.6 (Fuc, C-2⁗) 分别存在相关性, 确定上述4个糖基的连接顺序为β-木糖基(1→3)-[β-木糖基(1→4)-α-鼠李糖基]-(1→2)-β-岩藻糖基; δH 5.25 (Fuc H-1⁗) 与δC 175.6 (C-28) 明显相关, 确定28位与岩藻糖基相连。最终确定化合物2结构为皂皮酸-3-O-{β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸基}-28-O-β-D-吡喃木糖基(1→3)-[β-D-吡喃木糖基(1→4)-α-L-吡喃鼠李糖基]-(1→2)-β-D-吡喃岩藻糖苷钠, 命名为木鳖子苷B。
化合物3  白色粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -2.4 (c 0.22, MeOH); HR-ESI-MS给出准分子离子峰975.454 2 ([M-H]-, C48H72NaO19, 计算值975.456 5), 提示分子式为C48H73NaO19。1H、13C NMR与化合物1a非常相似, 但葡萄糖酸C-6信号(δC 174.3) 明显向低场位移, 提示葡萄糖酸C-6成盐。HMBC谱中, δH 4.28 (H-1″) 与δC 78.1 (C-2′)、δH 4.98 (H-1‴) 与δC 82.0 (C-3′) 分别相关, 确定糖基连接顺序为β-半乳糖基(1→2)-[α-鼠李糖基-(1→3)]-β-葡萄糖醛酸钠; δH 4.23 (H-1′) 与δC 83.3 (C-3) 明显相关, 确定丝石竹皂苷元C-3位与葡萄糖醛酸基相连。最终确定化合物3结构为丝石竹皂苷元-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷钠, 命名为木鳖子苷C。
化合物4  白色粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -3.8 (c 0.37, MeOH); HR-ESI-MS给出准分子离子峰为991.450 5 ([M-H]-, C48H72NaO20, 计算值991.451 5), 提示分子式为C48H73NaO20。1H、13C NMR与化合物2a非常相似, 但葡萄糖酸C-6信号(δC 173.9) 明显向低场位移, 提示C-6成盐。HMBC谱中, δH 4.28 (H-1″) 与δC 78.0 (C-2′)、δH 4.98 (H-1‴) 与δC 82.0 (C-3′) 分别相关, 确定糖基连接顺序为β-半乳糖基(1→2)-[α-鼠李糖基(1→3)]-β-葡萄糖醛酸钠; δH 4.26 (H-1′) 与δc 83.3 (C-3) 明显相关, 确定皂皮酸C-3位与葡萄糖醛酸基相连。最终确定化合物4结构为皂皮酸-3-O-β-D-吡喃半乳糖基(1→2)-[α-L-吡喃鼠李糖基(1→3)]-β-D-吡喃葡萄糖醛酸苷钠, 命名为木鳖子苷D。
化合物5  白色粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -3.1 (c 0.24, MeOH); HR-ESI-MS给出准分子离子峰为969.469 7 ([M-H]-, C48H73O20, 计算值969.469 5), 提示分子式为C48H74O20。1H NMR、13C NMR与化合物2a高度相似, 但H-18化学位移(δH 3.06) 明显不同, 提示H-18为α构型; NOESY谱中, δH 3.06 (H-18) 与δH 1.29 (H-27) 明显相关, 进一步确认H-18位为α构型。HMBC谱中, δH 4.25 (H-1″) 与δC 78.2 (C-2′)、δH 5.02 (H-1‴) 与δC 81.9 (C-3′) 分别相关, 确定糖基连接顺序为β-半乳糖基-(1→2)-[α-鼠李糖基-(1→3)]-β-葡萄糖醛酸基; δH 4.15 (H-1′) 与δc 83.8 (C-3) 明显相关, 确定皂皮酸C-3位与葡萄糖醛酸基相连。最终确定化合物5结构为18α-皂皮酸-3-O-β-D-吡喃半乳糖基-(1→2)-[α-L-吡喃鼠李糖基-(1→3)]-β-D-吡喃葡萄糖醛酸苷, 命名为木鳖子苷E。
2 抗真菌活性
白色念珠菌Candida albicans、近平滑念珠菌C. Parapsilosis、热带念珠菌C. tropicalis为常见致病菌, 往往导致化脓性炎症、皮肤炎症、阴道炎、口腔炎症、甲沟炎等。近年来, 随着抗生素的广泛应用, 大量耐药菌株出现, 从常用中药中寻找抗菌药物具有重要意义。木鳖子为传统中药, 具有抗真菌作用[6]。因此, 本实验通过微量液基稀释法, 对所得皂苷及其次级苷、苷元进行抗真菌活性评价。
结果发现, 5个三萜皂苷类化合物(1~5) 及其次级苷(1a、2a) 具有抗菌活性(表 3); 其中, 化合物1、2与阳性药物两性霉素B效果相当。非常有意思的是, 化合物1、3、1a、1b苷元相同, 化合物1活性最强, 3、1a活性次之, 而苷元(1b) 无抗真菌活性; 同样, 化合物2、4、2a、2b苷元相同, 但化合物2活性最强, 而苷元(2b) 无抗真菌活性。上述结果提示三萜皂苷去糖苷化会降低其抗真菌活性。
实验部分
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P-2000型全自动数字旋光仪(日本JASCO公司); Agilent 1290 UPLC-Q-TOF质谱联用仪(美国Agilent公司); Bruker Avance 700 MHz核磁共振仪(德国布鲁克公司); Agilent 1260 Infinity Ⅱ制备型高效液相色谱仪(PHPLC, 美国安捷伦科技有限公司), 配有自动进样器、UV检测器、G7159B馏分收集器、YMC色谱柱(20 mm × 250 mm, 5 μm); 7890A气相色谱-质谱联用仪(美国安捷伦公司), 配有HP-5色谱柱(30 m × 0.25 mm × 0.25 μm); EYELA N-101型旋转蒸发仪、KCL2000恒温恒湿培养箱(日本东京理化器械株式会社); DZF-6050型真空干燥箱(上海一恒科学仪器有限公司); SK6200H超声清洗器(上海科导超声仪器有限公司); LDZM立式压力蒸汽灭菌锅(上海申安医疗器械厂); Captair Bio 321超净工作台(法国Captair公司)。
二氯甲烷、乙酸乙酯、正丁醇、乙醇、甲醇(分析纯, 上海泰坦科技公司); 乙腈(色谱纯, 上海百灵威公司); D101大孔树脂(天津德力特公司); 柱层析(CC) 用硅胶(200~300目, 青岛海洋化工公司); ODS反相硅胶(40~63 μm, 德国Merck公司); HSGF254硅胶板(烟台江友硅胶开发公司); D-葡萄糖醛酸、D-半乳糖、D-木糖、D-岩藻糖、L-鼠李糖基、L-半胱氨酸甲酯、三甲基硅咪唑(麦克林生化公司); 盐酸两性霉素B (上海华联药业); RMPI1640培养基(德国Sigma-aldrich公司); 白色念珠菌(ATCC10231)、近平滑念珠菌(ATCC22019)、热带念珠菌(ATCC201380) 由中国医药工业研究总院提供。
木鳖子药材, 2021年购自成都五块石药材市场, 经李晓波教授鉴定为葫芦科植物木鳖子Momordica cochinchinensis (Lour.) Spreng.的干燥成熟种子, 标本(MBZ202108) 保存于上海交大药学院标本馆。
1 提取分离
木鳖子仁7.5 kg, 60 L乙醇回流2次, 每次2 h, 滤过, 减压回收溶剂得醇浸膏(719 g)。醇浸膏悬浮于3 L水中, 依次用二氯甲烷、乙酸乙酯、正丁醇萃取3次, 每次2 L, 回收溶剂, 得石油醚部位(433 g)、二氯甲烷部位(28 g)、乙酸乙酯部位(44 g)、正丁醇部位(83 g); 萃余水层减压回收溶剂, 得水部位(113 g)。
水部位(106 g) 经大孔树脂柱色谱分离, 依次用水、30%、60%、90%乙醇洗脱, 减压回收溶剂得Fr. A~D。Fr. B (5.9 g) 经ODS柱色谱分离(MeOH-H2O 3∶7~4∶1) 后, 得Fr. B1~B3。Fr. B1 (589.2 mg) 经PHPLC分离(MeCN-H2O 1∶9~1∶1, 30 min; 10 mL·min-1; 210 nm), 得化合物1 (37.8 mg, tR = 14.6 min)。Fr. B2 (155.7 mg) 经PHPLC分离(MeCN-H2O 1∶4~2∶3, 30 min; 12 mL·min-1; 210 nm), 得化合物2 (27.0 mg, tR = 13.7 min); Fr. B3 (73.4 mg) 经PHPLC分离(MeCN-H2O 1∶4~3∶2, 35 min; 12 mL·min-1; 210 nm), 得化合物3 (8.4 mg, tR = 19.6 min)。Fr. C (4.1 g) 经ODS柱色谱分离(MeOH-H2O 3∶7~9∶1) 后, 得Fr. C1~C3。Fr.C1 (80.2 mg) 经PHPLC分离(MeCN-H2O 1∶4~3∶2, 30 min; 12 mL·min-1; 210 nm), 得化合物4 (7.2 mg, tR = 19.6 min)。Fr.C2 (37.4 mg) 经PHPLC分离(MeCN-H2O 9∶11, 12 mL·min-1; 210 nm), 得化合物5 (4.8 mg, tR = 14.6 min)。
2 水解
碱水解: 化合物1、2 (各6 mg) 加入5%氨水3 mL, 60 ℃水浴中加热4 h, 盐酸调至中性, 3 mL水饱和正丁醇萃取2次, 合并正丁醇层, 减压回收溶剂, 得萃取物。萃取物进一步经制备HPLC纯化(MeCN-H2O 2∶3; 15 mL·min-1; 210 nm), 得化合物1a (1.4 mg, tR = 20.6 min)、2a (1.6 mg, tR = 19.9 min)。
酸水解: 化合物2 mg加入5% HCl溶液5 mL, 95 ℃水浴中加热6 h。5 mL二氯甲烷萃取2次, 回收溶剂, 得二氯甲烷层, 经半制备液相纯化(MeCN-H2O 7∶3; 12 mL·min-1; 210 nm) 得1b (0.4 mg, tR = 18.5 min)、2b (0.6 mg, tR = 16.9 min)。将水层减压干燥后用水复溶, 再次干燥后得到残渣; 1 mg残渣用2 mL吡啶溶解, 加入2 mg L-半胱氨酸甲酯盐酸盐, 于60 ℃加热2 h。将溶剂用N2吹干后, 加入0.2 mL三甲基硅咪唑, 于60 ℃反应2 h, 将反应液转移至2 mL水中, 用等体积环己烷萃取3次, 合并萃取液浓缩, 制成糖噻唑三甲基硅醚衍生物, 取0.5 mL环己烷溶解后, 于14 000 r·min-1离心20 min, 取上清液, 进行GC分析(进样量: 1 μL; 进样器温度: 270 ℃; 载气: 氦气(99.999%); 流量: 1.0 mL·min-1; 柱温: 初始为160 ℃, 以4 ℃·min-1升至200 ℃, 保持5 min, 以10 ℃·min-1升至240 ℃, 保持10 min。对照品按相同方法衍生化后, GC进行分析。通过与单糖对照品衍生物的保留时间对比, 确定化合物中糖基的种类[7]。
3 结构鉴定
化合物1  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -1.3 (c 0.18, H2O); HR-ESI-MS m/z 1 509.672 1 ([M-H]-, C70H109O35, 计算值1 509.674 9); 1H、13C NMR见表 1、2。
化合物2  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -1.8 (c 0.22, H2O); HR-ESI-MS m/z 1 525.668 2 ([M-H]-, C70H109O36, 计算值1 525.669 9); 1H、13C NMR见表 1、2。
化合物3  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -2.4 (c 0.22, MeOH); HR-ESI-MS m/z 975.454 2 ([M-H]-, C48H72NaO19, 计算值975.456 5); 1H、13C NMR见表 1、2。
化合物4  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -3.8 (c 0.37, MeOH); HR-ESI-MS m/z: 991.450 5 ([M-H]-, C48H72NaO20, 计算值991.451 5); 1H、13C NMR见表 1、2。
化合物5  白色粉末; $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ = -3.1 (c 0.24, MeOH); HR-ESI-MS m/z: 969.469 7 ([M-H]-, C48H73O20, 计算值969.469 5); 1H、13C NMR见表 1、2。
化合物1a  白色粉末; 1H NMR (DMSO-d6, 700 MHz) δ: 9.43 (1H, s, H-23), 5.18 (1H, brs, H-12), 4.99 (1H, brs, H-1‴), 4.28 (1H, d, J = 7.3 Hz, H-1″), 4.24 (1H, d, J = 7.0 Hz, H-1′), 1.11 (3H, s, H-27), 1.08 (3H, d, J = 6.3 Hz, H-6‴), 0.88 (6H, s, H-25, 30), 0.86 (3H, s, H-29), 0.74 (3H, s, H-26); 13C NMR (DMSO-d6, 176 MHz) δ: 38.0 (C-1), 24.1 (C-2), 83.2 (C-3), 54.5 (C-4), 48.2 (C-5), 20.3 (C-6), 31.5 (C-7), 39.8 (C-8), 47.3 (C-9), 35.9 (C-10), 24.0 (C-11), 121.7 (C-12), 144.3 (C-13), 41.7 (C-14), 27.4 (C-15), 23.4 (C-16), 46.0 (C-17), 41.6 (C-18), 46.2 (C-19), 30.9 (C-20), 33.3 (C-21), 32.6 (C-22), 210.3 (C-23), 10.6 (C-24), 15.8 (C-25), 17.2 (C-26), 26.0 (C-27), 179.1 (C-28), 33.8 (C-29), 23.1 (C-30), 102.2 (C-1′), 78.2 (C-2′), 81.8 (C-3′), 71.8 (C-4′), 76.1 (C-5′), 172.4 (C-6′), 100.8 (C-1″), 71.1 (C-2″), 82.5 (C-3″), 76.5 (C-4″), 68.4 (C-5″), 18.3 (C-6″), 102.9 (C-1‴), 73.3 (C-2‴), 74.6 (C-3‴), 71.0 (C-4‴), 76.4 (C-5‴), 61.1 (C-6‴)。以上数据与文献[8]报道的丝石竹皂苷元-3-O-β-D-半乳糖基(1→2)-[α-L-鼠李糖基(1→3)]-β-D-葡萄糖醛酸苷一致。
化合物2a  白色粉末; 1H NMR (DMSO-d6, 700 MHz) δ: 9.47 (1H, s, H-23), 5.19 (1H, s, H-12), 4.98 (1H, brs, H-1‴), 4.28 (1H, d, J = 7.8 Hz, H-1″), 4.25 (1H, d, J = 7.0 Hz, H-1′), 1.33 (3H, s, H-27), 1.08 (3H, d, J = 6.3 Hz, H-6‴), 1.07 (3H, s, H-24), 0.90 (6H, s, H-25, 30), 0.83 (3H, s, H-29), 0.67 (3H, s, H-26); 13C NMR (DMSO-d6, 176 MHz) δ: 38.1 (C-1), 24.6 (C-2), 82.5 (C-3), 54.6 (C-4), 47.7 (C-5), 20.3 (C-6), 32.5 (C-7), 40.8 (C-8), 47.0 (C-9), 35.9 (C-10), 23.3 (C-11), 121.4 (C-12), 144.5 (C-13), 40.5 (C-14), 35.6 (C-15), 73.3 (C-16), 47.7 (C-17), 40.3 (C-18), 46.8 (C-19), 30.7 (C-20), 35.0 (C-21), 31.9 (C-22), 210.2 (C-23), 10.7 (C-24), 15.8 (C-25), 17.3 (C-26), 26.9 (C-27), 178.7 (C-28), 33.3 (C-29), 24.7 (C-30), 102.2 (C-1′), 78.2 (C-2′), 81.8 (C-3′), 71.8 (C-4′), 69.3 (C-5′), 172.3 (C-6′), 100.9 (C-1″), 71.1 (C-2″), 73.5 (C-3″), 74.0 (C-4″), 68.5 (C-5″), 18.3 (C-6″), 102.9 (C-1‴), 72.6 (C-2‴), 74.5 (C-3‴), 71.1 (C-4‴), 75.5 (C-5‴), 60.3 (C-6‴)。以上数据与文献[9]报道的皂皮酸-3-O-β-D-半乳糖基(1→2)-[α-L-鼠李糖基(1→3)]-β-D-葡萄糖醛酸苷一致。
化合物1b  白色粉末; 1H NMR (DMSO-d6, 700 MHz) δ: 9.24 (1H, s, H-23), 5.17 (1H, brs, H-12), 2.73 (1H, d, J = 13.6 Hz, H-18), 1.12 (3H, s, H-27), 0.88 (6H, H-25, 30), 0.87 (3H, s, H-24), 0.83 (3H, s, H-29), 0.71 (3H, s, H-26); 13C NMR (DMSO-d6, 176 MHz) δ: 38.1 (C-1), 26.8 (C-2), 70.9 (C-3), 55.6 (C-4), 47.4 (C-5), 20.7 (C-6), 32.1 (C-7), 39.7 (C-8), 46.7 (C-9), 35.8 (C-10), 23.8 (C-11), 121.8 (C-12), 144.4 (C-13), 41.9 (C-14), 27.6 (C-15), 23.4 (C-16), 45.9 (C-17), 41.3 (C-18), 46.1 (C-19), 30.9 (C-20), 33.3 (C-21), 32.5 (C-22), 207.5 (C-23), 9.3 (C-24), 15.7 (C-25), 17.3 (C-26), 26.1 (C-27), 179.0 (C-28), 33.8 (C-29), 23.0 (C-30)。以上数据与文献[8]报道的丝石竹皂苷元一致。
化合物2b  白色粉末; 1H NMR (DMSO-d6, 700 MHz) δ: 9.24 (1H, s, H-23), 5.21 (1H, brs, H-11), 4.32 (1H, m, H-16), 2.82 (1H, d, J = 12.6 Hz, H-18), 1.34 (3H, s, H-27), 0.91 (3H, s, H-30), 0.89 (3H, s, H-25), 0.87 (3H, s, H-24), 0.83 (3H, s, H-29), 0.68 (3H, s, H-26); 13C NMR (DMSO-d6, 176 MHz) δ: 38.1 (C-1), 26.4 (C-2), 70.9 (C-3), 55.6 (C-4), 46.8 (C-5), 20.7 (C-6), 32.3 (C-7), 41.5 (C-8), 46.5 (C-9), 35.8 (C-10), 23.3 (C-10), 121.4 (C-12), 144.5 (C-13), 40.5 (C-14), 35.6 (C-15), 73.3 (C-16), 47.7 (C-17), 40.3 (C-18), 46.8 (C-19), 30.7 (C-20), 35.0 (C-21), 31.9 (C-22), 207.5 (C-23), 9.3 (C-24), 15.8 (C-25), 17.2 (C-26), 26.9 (C-27), 178.6 (C-28), 33.3 (C-29), 24.6 (C-30)。以上数据与文献[10]报道的皂皮酸一致。
4 活性评价
将念珠菌株培养过夜, RPMI1640培养基调整菌浓度至每毫升1×103~5×103个, 混匀。取无菌96孔板, 加入样品(用RPMI1640液体培养倍比稀释, 各孔的药物终浓度依次为128、64、32、16、8、4、2、1、0.5、0.25 μmol·L-1); 另加等量RPMI1640液体培养基作空白对照。35 ℃恒温培养, 于24 h后进行观察记录, 得对应最小抑菌浓度(minimal inhibit concentration, MIC)。上述实验均平行操作两次, 所得MIC值相同视为有效结果; 否则, 重新实验直到数据符合要求[11]。
作者贡献: 丁如、王嘉祺、罗翌玚负责化合物的分离纯化和结构鉴定; 丁如负责数据整理及文章撰写; 韩永龙负责活性测定实验; 共同通讯作者李晓波负责实验设计、实验指导; 共同通讯作者王梦月负责指导实验设计、结构解析和文章修改。
利益冲突: 所有作者均声明本文不存在任何利益冲突。
基金
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  • 国家自然科学基金(82274061)
  • 内蒙古自治区“科技兴蒙”计划(2022XYJG0001-02-01)
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Chinese Pharmacopoeia Commission. Chinese Pharmacopoeia (Vol Ⅰ) [M]. Beijing: China Medical Science and Technology Press, 2020: 66-67.
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Wang MY, Zhan ZB, Xiong Y, et al. New cytotoxic constituents in the water-soluble fraction from Momordicae Semen [J]. Nat Prod Res, 2020, 34: 823-829.
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Fan R, Cheng RR, Zhu HT, et al. Two new oleanane-type triterpenoids from methanolyzed saponins of Momordica cochinchinensis [J]. Nat Prod Commun, 2016, 11: 725-728.
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Chan LY, Wang CKL, Major JM, et al. Isolation and characterization of peptides from Momordica cochinchinensis seeds [J]. J Nat Prod, 2009, 72: 1453-1458.
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Liu XY, Ma J, Li CJ, et al. New triterpenoid saponins from the leaves of Panax notoginseng [J]. Acta Pharm Sin (药学学报), 2017, 52: 1432-1436.
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Wang JQ, Wu ZW, Shi XY, et al. Study on NMR determination of momordica saponin Ⅰ [J]. Acad J Shanghai Univ Tradit Chin Med (上海中医药大学学报), 2023, 37: 42-47.
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doi: 10.16438/j.0513-4870.2024-1013
  • 接收时间：2024-10-18
  • 首发时间：2025-11-07
  • 出版时间：2025-02-12
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  • 收稿日期：2024-10-18
  • 修回日期：2024-12-10
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国家自然科学基金(82274061)
内蒙古自治区“科技兴蒙”计划(2022XYJG0001-02-01)
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    1.上海交通大学药学院, 上海 200240
    2.上海市第六人民医院药剂科, 上海 200233

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*李晓波, Tel: 86-21-34204806, E-mail:
王梦月, Tel: 86-21-34205222, 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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