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Article(id=1308842044215357790, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2026-0221, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1772380800000, receivedDateStr=2026-03-02, revisedDate=1775318400000, revisedDateStr=2026-04-05, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981860450, onlineDateStr=2026-09-21, pubDate=1783785600000, pubDateStr=2026-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981860450, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981860450, creator=13701087609, updateTime=1789981860450, updator=13701087609, issue=Issue{id=1308841897058198067, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='7', pageStart='2377', pageEnd='2820', issueExtLink='null', onlineDate='null', pubDate='1783785600000', pubDateStr='2026-07-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981825365, creator='13701087609', updateTime=1789984154811, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851667525792021, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851667525792022, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=2618, endPage=2624, ext={EN=ArticleExt(id=1308842044441850207, articleId=1308842044215357790, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Three new furan type compounds from the mycelium of Cordyceps militaris, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

A total of seven furan natural products were isolated from the ethyl acetate extract of the fermentation product of the mycelium of Cordyceps militaris through a combination of chromatographic techniques, including silica gel column chromatography and semi-preparative HPLC. Based on their physicochemical properties and spectroscopic data, the structures of isolated compounds were identified as ethyl 5-[(3R)-hydroxybutyl]-2-furanacetate (1), 5-[(3R)-hydroxybutyl]-2-furancarboxylic acid (2), methyl 5-[(3R)-hydroxybutanoyl]-2-furanacetate (3), 5-[(3R)-hydroxybutyl]-2-furancarboxaldehyde (4), methyl 5-(2-hydroxyethyl)-2-furanacetate (5), 5-[(3R)-hydroxybutyl]-2-furanacetic acid (6), and methyl 5-[(3R)-hydroxybutyl]-2-furanacetate (7). Among them, compounds 1-3 were new compounds, compound 4 and 5 represents a new natural product, and compound 6 and 7 were isolated from Cordyceps militaris for the first time. Compounds 1 and 3-7 exhibited anti-inflammatory activity in varying degrees and significantly inhibited nitric oxide production in lipopolysaccharide-induced mouse mononuclear macrophage RAW264.7 cell line. Compound 2 showed some cytotoxic activity against Spodoptera frugiperda ovarian Sf9 cells with an IC50 value of 57.01 μmol·L-1.

, authors=Shuang-xia YING, Hong-ling YAN, Jia-xu QIN, Hai-yang LI, Qing-li HE, Qun-fei ZHAO*, authorsList=Shuang-xia YING, Hong-ling YAN, Jia-xu QIN, Hai-yang LI, Qing-li HE, Qun-fei ZHAO, authorCompany=null, correspAuthors=Qun-fei ZHAO, 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=1308842045419123048, articleId=1308842044215357790, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=蛹虫草菌丝体中三个新的呋喃类化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用硅胶柱层析、半制备液相色谱等多种色谱技术, 从蛹虫草(Cordyceps militaris) 菌丝体发酵产物的乙酸乙酯部位得到7个呋喃类化合物。结合所得成分的物化性质和波谱数据分析, 鉴定其结构为5-[(3R)-羟基丁基]-2-呋喃乙酸乙酯(1), 5-[(3R)-羟基丁基]-2-呋喃羧酸(2), 5-[(3R)-羟基丁酰基]-2-呋喃乙酸甲酯(3), 5-[(3R)-羟基丁基]-2-呋喃甲醛(4), 5-(2-羟基乙基)-2-呋喃乙酸甲酯(5), 5-[(3R)-羟基丁基]-2-呋喃乙酸(6), 5-[(3R)-羟基丁基]-2-呋喃乙酸甲酯(7)。其中, 化合物1~3为新化合物, 化合物4、5为新天然产物, 化合物6和7为首次从蛹虫草中分离得到。化合物1、3~7具有不同程度的抗炎活性, 对脂多糖诱导的小鼠单核巨噬细胞RAW264.7细胞系一氧化氮生成有明显的抑制作用。化合物2对草地贪夜蛾卵巢细胞Sf9有一定的细胞毒性, IC50值为57.01 μmol·L-1。

, authors=应双霞, 闫洪玲, 秦加旭, 李海阳, 贺庆利, 赵群飞*, authorsList=应双霞, 闫洪玲, 秦加旭, 李海阳, 贺庆利, 赵群飞, authorCompany=null, correspAuthors=赵群飞, authorNote=

#

共同第一作者.

作者贡献:

应双霞负责化合物分离、鉴定、活性测定、数据处理及文章撰写; 闫洪玲负责化合物结构鉴定、文章撰写和修改; 秦加旭参与化合物结构鉴定; 李海阳参与部分活性测定; 贺庆利负责实验设计和稿件修改; 赵群飞负责文章的选题、思路框架的提出, 全程指导了实验设计和论文撰写。

, correspAuthorsNote=
赵群飞, Tel: 86-21-51322768, E-mail:
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journalId=1189982191388893191, articleId=1308842044215357790, language=CN, orderNo=3, keyword=结构鉴定), Keyword(id=1308842049407906194, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=CN, orderNo=4, keyword=抗炎活性), Keyword(id=1308842049470820755, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=CN, orderNo=5, keyword=细胞毒性)], refs=[Reference(id=1308842050875912610, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=1, rfOrder=0, authorNames=null, journalName=null, refType=null, unstructuredReference=Wu N, Ge XD, Yin XM, et al. A review on polysaccharide biosynthesis in Cordyceps militaris [J]. Int J Biol Macromol, 2024, 260: 129336., articleTitle=null, refAbstract=null), Reference(id=1308842050959798691, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, 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=Hu Y, Wu YJ, Song JY, et al. Advancing Cordyceps militaris industry: Gene manipulation and sustainable biotechnological strategies [J]. 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J Food Sci Biotechnol (食品与生物技术学报), 2025, 44: 31-40., articleTitle=null, refAbstract=null), Reference(id=1308842052910150058, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, 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=Nxumalo W, Elateeq AA, Sun Y. Can Cordyceps cicadae be used as an alternative to Cordyceps militaris and Cordyceps sinensis? [J]. 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Mol Biotechnol, 2025, 67: 1382-1397., articleTitle=null, refAbstract=null), Reference(id=1308842053098893740, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, 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=Zhang JX, Wen CT, Duan YQ, et al. Advance in Cordyceps militaris (Linn) link polysaccharides: Isolation, structure, and bioactivities: A review [J]. 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Microbiol Chin (微生物学通报), 2023, 50: 3211-3231., articleTitle=null, refAbstract=null), Reference(id=1308842053304414639, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=12, rfOrder=11, authorNames=null, journalName=null, refType=null, unstructuredReference=Zhu LN, Gao XH, Liu YF, et al. Effect of culture method on the active components in Cordyceps militaris [J]. Acta Agric Shanghai (上海农业学报), 2019, 35: 57-62., articleTitle=null, refAbstract=null), Reference(id=1308842053379912112, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=13, rfOrder=12, authorNames=null, journalName=null, refType=null, unstructuredReference=Katsuta R, Fujikawa S, Yajima A, et al. Stereoselective synthesis of (-)-decarestrictine G [J]. Tetrahedron, 2015, 71: 3428-3432., articleTitle=null, refAbstract=null), Reference(id=1308842053455409585, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=14, rfOrder=13, authorNames=null, journalName=null, refType=null, unstructuredReference=Oller-López JL, Iranzo M, Mormeneo S, et al. Bassianolone: An antimicrobial precursor of cephalosporolides E and F from the entomoparasitic fungus Beauveria bassiana [J]. Org Biomol Chem, 2005, 3: 1172-1173., articleTitle=null, refAbstract=null), Reference(id=1308842053530907058, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=15, rfOrder=14, authorNames=null, journalName=null, refType=null, unstructuredReference=Zhang TH, Peng C, Zuo J, et al. A new patchoulane-type sequiterpenoid from patchouli oil and its anti-inflammatory activity [J]. Acta Pharm Sin (药学学报), 2022, 57: 3163-3167., articleTitle=null, refAbstract=null), Reference(id=1308842053598015923, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=16, rfOrder=15, authorNames=null, journalName=null, refType=null, unstructuredReference=Chen HY, Qin JX, Yan HL, et al. Isolation and biological activities of five alkaloids in Cephalotaxus fortune [J]. 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No.123
δH (J in Hz)δCδH (J in Hz)δCδH (J in Hz)δC
2147.5143.3
35.96 (1H, d, J = 2.8 Hz)109.57.15 (1H, d, J = 3.4 Hz)120.56.52 (1H, d, J = 3.5 Hz)112.3
46.09 (1H, d, J = 2.8 Hz)106.76.14 (1H, d, J = 3.4 Hz)108.27.34 (1H, d, J = 3.5 Hz)121.1
5156.7161.6153.7
1′3.64 (2H, s)34.8163.23.87 (2H, s)34.5
2′171.6170.7
3′4.16 (2H, q, J = 7.1 Hz)62.13.74 (3H, s)52.9
4′1.25 (3H, t, J = 7.1 Hz)14.4
1″2.67 (2H, m)25.32.80 (2H, m)24.8189.2
2″1.73 (2H, td, J = 7.7, 6.2 Hz)38.41.80 (2H, m)37.13.02 (1H, dd, J = 15.2, 7.7 Hz, Hb)
2.85 (1H, dd, J = 15.2, 7.7 Hz, Ha)		48.3
3″3.75 (1H, h, J = 6.2 Hz, H-3″)67.73.79 (1H, m)67.24.31 (1H, m)65.5
4″1.18 (3H, d, J = 6.2 Hz)23.41.22 (3H, d, J = 6.2 Hz)23.61.25 (3H, d, J = 6.3 Hz)23.6
), ArticleFig(id=1308842050464870813, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=CN, label=Tab.1, caption=

1H (600 MHz) and 13C (151 MHz) NMR data of compound 1 (in CD3OD) and 2 (in CDCl3), 1H (400 MHz) and 13C (101 MHz) NMR data of compound 3 (in CD3OD).

, figureFileSmall=null, figureFileBig=null, tableContent=
No.123
δH (J in Hz)δCδH (J in Hz)δCδH (J in Hz)δC
2147.5143.3
35.96 (1H, d, J = 2.8 Hz)109.57.15 (1H, d, J = 3.4 Hz)120.56.52 (1H, d, J = 3.5 Hz)112.3
46.09 (1H, d, J = 2.8 Hz)106.76.14 (1H, d, J = 3.4 Hz)108.27.34 (1H, d, J = 3.5 Hz)121.1
5156.7161.6153.7
1′3.64 (2H, s)34.8163.23.87 (2H, s)34.5
2′171.6170.7
3′4.16 (2H, q, J = 7.1 Hz)62.13.74 (3H, s)52.9
4′1.25 (3H, t, J = 7.1 Hz)14.4
1″2.67 (2H, m)25.32.80 (2H, m)24.8189.2
2″1.73 (2H, td, J = 7.7, 6.2 Hz)38.41.80 (2H, m)37.13.02 (1H, dd, J = 15.2, 7.7 Hz, Hb)
2.85 (1H, dd, J = 15.2, 7.7 Hz, Ha)		48.3
3″3.75 (1H, h, J = 6.2 Hz, H-3″)67.73.79 (1H, m)67.24.31 (1H, m)65.5
4″1.18 (3H, d, J = 6.2 Hz)23.41.22 (3H, d, J = 6.2 Hz)23.61.25 (3H, d, J = 6.3 Hz)23.6
), ArticleFig(id=1308842050544562590, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
No.45
δH (J in Hz)δCδH (J in Hz)δC
2153.4146.7
37.36 (1H, d, J = 3.5 Hz)126.06.14 (1H, d, J = 3.1 Hz)109.0
46.40 (1H, d, J = 3.5 Hz)110.16.06 (1H, d, J = 3.1 Hz)107.7
5165.4152.6
1′9.45 (1H, s)178.83.66 (2H, s)34.1
2′170.2
3′3.72 (3H, s)52.4
1″2.85 (2H, m)25.62.87 (2H, t, J = 6.2 Hz)31.8
2″1.81 (2H, m)37.73.86 (2H, t, J = 6.2 Hz)61.2
3″3.76 (1H, m)67.6
4″1.20 (3H, d, J = 6.3 Hz)23.5
), ArticleFig(id=1308842050624254367, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=CN, label=Tab.2, caption=

1H (600 MHz) and 13C (151 MHz) NMR data of compound 4 (in CD3OD) and 5 (in CDCl3)

, figureFileSmall=null, figureFileBig=null, tableContent=
No.45
δH (J in Hz)δCδH (J in Hz)δC
2153.4146.7
37.36 (1H, d, J = 3.5 Hz)126.06.14 (1H, d, J = 3.1 Hz)109.0
46.40 (1H, d, J = 3.5 Hz)110.16.06 (1H, d, J = 3.1 Hz)107.7
5165.4152.6
1′9.45 (1H, s)178.83.66 (2H, s)34.1
2′170.2
3′3.72 (3H, s)52.4
1″2.85 (2H, m)25.62.87 (2H, t, J = 6.2 Hz)31.8
2″1.81 (2H, m)37.73.86 (2H, t, J = 6.2 Hz)61.2
3″3.76 (1H, m)67.6
4″1.20 (3H, d, J = 6.3 Hz)23.5
), ArticleFig(id=1308842050691363232, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
CompoundIC50/μmol·L-1CompoundIC50/μmol·L-1
1> 1005> 100
257.016> 100
3> 1007> 100
4> 100
), ArticleFig(id=1308842050775249313, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842044215357790, language=CN, label=Tab.3, caption=

Cytotoxic activity of compounds 1-7 against Sf9 cells

, figureFileSmall=null, figureFileBig=null, tableContent=
CompoundIC50/μmol·L-1CompoundIC50/μmol·L-1
1> 1005> 100
257.016> 100
3> 1007> 100
4> 100
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蛹虫草菌丝体中三个新的呋喃类化合物
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应双霞 , 闫洪玲 , 秦加旭 , 李海阳 , 贺庆利 , 赵群飞 *
药学学报 | 研究论文 2026,61(7): 2618-2624
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药学学报 |研究论文 2026 , 61 (7) : 2618 -2624
蛹虫草菌丝体中三个新的呋喃类化合物
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应双霞, 闫洪玲, 秦加旭, 李海阳, 贺庆利, 赵群飞*
作者信息
  • 上海中医药大学创新中药研究院, 中药功效成分发掘与利用全国重点实验室, 上海 201203
通讯作者:
赵群飞, Tel: 86-21-51322768, E-mail:
作者简介:

#

共同第一作者.

作者贡献:

应双霞负责化合物分离、鉴定、活性测定、数据处理及文章撰写; 闫洪玲负责化合物结构鉴定、文章撰写和修改; 秦加旭参与化合物结构鉴定; 李海阳参与部分活性测定; 贺庆利负责实验设计和稿件修改; 赵群飞负责文章的选题、思路框架的提出, 全程指导了实验设计和论文撰写。

Three new furan type compounds from the mycelium of Cordyceps militaris
Shuang-xia YING, Hong-ling YAN, Jia-xu QIN, Hai-yang LI, Qing-li HE, Qun-fei ZHAO*
Affiliations
  • State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
出版时间: 2026-07-12 doi: 10.16438/j.0513-4870.2026-0221
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摘要
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利用硅胶柱层析、半制备液相色谱等多种色谱技术, 从蛹虫草(Cordyceps militaris) 菌丝体发酵产物的乙酸乙酯部位得到7个呋喃类化合物。结合所得成分的物化性质和波谱数据分析, 鉴定其结构为5-[(3R)-羟基丁基]-2-呋喃乙酸乙酯(1), 5-[(3R)-羟基丁基]-2-呋喃羧酸(2), 5-[(3R)-羟基丁酰基]-2-呋喃乙酸甲酯(3), 5-[(3R)-羟基丁基]-2-呋喃甲醛(4), 5-(2-羟基乙基)-2-呋喃乙酸甲酯(5), 5-[(3R)-羟基丁基]-2-呋喃乙酸(6), 5-[(3R)-羟基丁基]-2-呋喃乙酸甲酯(7)。其中, 化合物1~3为新化合物, 化合物4、5为新天然产物, 化合物6和7为首次从蛹虫草中分离得到。化合物1、3~7具有不同程度的抗炎活性, 对脂多糖诱导的小鼠单核巨噬细胞RAW264.7细胞系一氧化氮生成有明显的抑制作用。化合物2对草地贪夜蛾卵巢细胞Sf9有一定的细胞毒性, IC50值为57.01 μmol·L-1。

蛹虫草  /  呋喃类衍生物  /  结构鉴定  /  抗炎活性  /  细胞毒性

A total of seven furan natural products were isolated from the ethyl acetate extract of the fermentation product of the mycelium of Cordyceps militaris through a combination of chromatographic techniques, including silica gel column chromatography and semi-preparative HPLC. Based on their physicochemical properties and spectroscopic data, the structures of isolated compounds were identified as ethyl 5-[(3R)-hydroxybutyl]-2-furanacetate (1), 5-[(3R)-hydroxybutyl]-2-furancarboxylic acid (2), methyl 5-[(3R)-hydroxybutanoyl]-2-furanacetate (3), 5-[(3R)-hydroxybutyl]-2-furancarboxaldehyde (4), methyl 5-(2-hydroxyethyl)-2-furanacetate (5), 5-[(3R)-hydroxybutyl]-2-furanacetic acid (6), and methyl 5-[(3R)-hydroxybutyl]-2-furanacetate (7). Among them, compounds 1-3 were new compounds, compound 4 and 5 represents a new natural product, and compound 6 and 7 were isolated from Cordyceps militaris for the first time. Compounds 1 and 3-7 exhibited anti-inflammatory activity in varying degrees and significantly inhibited nitric oxide production in lipopolysaccharide-induced mouse mononuclear macrophage RAW264.7 cell line. Compound 2 showed some cytotoxic activity against Spodoptera frugiperda ovarian Sf9 cells with an IC50 value of 57.01 μmol·L-1.

Cordyceps militaris  /  furan derivatives  /  structure elucidation  /  anti-inflammatory activity  /  cytotoxic activity
应双霞, 闫洪玲, 秦加旭, 李海阳, 贺庆利, 赵群飞. 蛹虫草菌丝体中三个新的呋喃类化合物. 药学学报, 2026 , 61 (7) : 2618 -2624 . DOI: 10.16438/j.0513-4870.2026-0221
Shuang-xia YING, Hong-ling YAN, Jia-xu QIN, Hai-yang LI, Qing-li HE, Qun-fei ZHAO. Three new furan type compounds from the mycelium of Cordyceps militaris[J]. Acta Pharmaceutica Sinica, 2026 , 61 (7) : 2618 -2624 . DOI: 10.16438/j.0513-4870.2026-0221
正文
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蛹虫草(Cordyceps militaris) 又称北冬虫夏草, 是一种具有重要药用价值的可食用寄生真菌[1]。研究表明, 蛹虫草中富含多糖、腺苷、虫草素等多种活性成分, 具有抗氧化、抗炎、抗肿瘤等生物活性[2-6]。随着人工培养技术的成熟, 蛹虫草因其稳定的产量和可控的品质, 被广泛应用于药品、保健食品的研发[7, 8]。现有研究对蛹虫草次级代谢产物的挖掘, 仍主要集中在子实体来源, 而对其液体发酵培养体系中代谢产物的结构多样性及潜在生物活性关注较少[9, 10]。液体发酵培养具有生长周期短、条件可控、产物易于放大生产等优势, 是发现和制备新型天然产物的重要途径[11]。相较于子实体, 液体培养基中蛹虫草的代谢调控网络更为灵活, 能够诱导产生大量在子实体中低表达或不表达的特异性次级代谢产物, 为挖掘新颖结构和独特生物活性的化合物提供了丰富来源[12]。本实验以蛹虫草菌丝体的液体发酵产物作为研究对象, 从其乙酸乙酯萃取部位分离得到7个呋喃类化合物(图1), 其中化合物1~3为新化合物, 化合物4、5为新天然产物, 化合物6、7为首次从蛹虫草中分离得到。对分离得到的化合物进行抗炎活性和杀虫活性评价, 发现化合物1、3~7能抑制脂多糖诱导的小鼠单核巨噬细胞RAW264.7细胞系一氧化氮释放, 具有良好的抗炎活性。化合物2对草地贪夜蛾卵巢细胞Sf9有一定的细胞毒性, IC50值为57.01 μmol·L-1。
结果与讨论
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1　结构鉴定
化合物1为黄色油状物, 易溶于甲醇。[α]$ {}_{\mathrm{D}}^{25} $ -9.45 (c 0.31, MeOH)。根据其高分辨质谱(HR-ESI-MS) 的准分子离子峰m/z 227.128 5 [M+H]+ (C12H19O4, 计算值m/z 227.127 8), 推断其分子式为C12H18O4, 不饱和度为4。1H NMR (600 MHz, CD3OD) 谱(表1) 显示2个烯烃质子[δH 6.09 (1H, d, J = 2.8 Hz, H-4), 5.96 (1H, d, J = 2.8 Hz, H-3)], 1个与氧相连的亚甲基氢信号[δH 4.16 (2H, q, J = 7.1 Hz, H-3′)], 1个与氧相连的次甲基氢信号[δH 3.75 (1H, h, J = 6.2 Hz, H-3″)], 3个亚甲基氢信号[δH 3.64 (2H, s, H-1′), 2.67 (2H, m, H-1″), 1.73 (2H, td, J = 7.7, 6.2 Hz, H-2″)], 和2个甲基氢信号[δH 1.25 (3H, t, J = 7.1 Hz, H-4′), 1.18 (3H, d, J = 6.2 Hz, H-4″)]。13C NMR显示12个碳信号(表1), 结合DEPT-135提示有3个季碳, 包括1个酯羰基[δC 171.6 (C-2′)] 和2个烯碳[δC 156.7 (C-5), 147.5 (C-2)]; 3个次甲基, 包括2个烯碳[δC 109.5 (C-3), 106.7 (C-4)] 和1个与氧相连的叔碳[δC 67.7 (C-3″)]; 4个亚甲基, 包括1个与氧相连的仲碳[δC 62.1 (C-3′)] 和3个脂肪族的仲碳[δC 38.4 (C-2″), 34.8 (C-1′), 25.3 (C-1″)]; 和2个甲基[δC 23.4 (C-4″), 14.4 (C-4′)]。这些核磁数据与5-((3R)-羟基丁基)-2-呋喃乙酸甲酯(化合物7) 中的核磁数据非常相似[13, 14], 主要区别在于化合物1中与羰基C-2′直接相连的是乙氧基而不是甲氧基。进一步通过1H-1H COSY和HMBC进行验证(图2)。1H-1H COSY谱显示C-3′-C4′, C-3-C-4和C-1″-C-2″-C-3″-C-4″的碳链连接顺序。HMBC谱显示H-3与C-2、C-5相关, H-4与C-5相关, 提示2, 5-二取代呋喃环结构; H-3′与C-2′相关, 证明乙氧基与C-2′酯羰基的连接; H-1′与C-2′、C-2和C-3相关, 表明乙酸酯侧链与呋喃环的C-2相连; H-1″与C-4、C-5相关, 提示3-羟基丁基侧链与呋喃环中的C-5相连接。因此, 化合物1的平面结构被阐明, 经SciFinder数据库检索确认为新化合物。进一步采用旋光值比较的方法确定化合物的绝对构型, 其比旋光值与类似化合物7 [[α]$ {}_{\mathrm{D}}^{25} $ -14.44 (c 0.19, MeOH)] 接近, 手性应与其一致, 确定C-3″为R构型[13]。最终, 化合物被命名为5-[(3R)-羟基丁基]-2-呋喃乙酸乙酯。
化合物2为黄色油状物, 易溶于甲醇、二氯甲烷、氯仿。[α]$ {}_{\mathrm{D}}^{25} $ -11.18 (c 0.2, MeOH)。根据其高分辨质谱(HR-ESI-MS) 的准分子离子峰m/z 185.080 9 [M+H]+ (C9H13O4, 计算值185.080 8), 推断其分子式为C9H12O4, 不饱和度为4。1H NMR (600 MHz, CDCl3) 谱(表1) 中显示2个烯烃质子[δH 7.15 (1H, d, J = 3.4 Hz, H-3), 6.14 (1H, d, J = 3.4 Hz, H-4)], 1个与氧相连的次甲基氢[δH 3.79 (1H, m, H-3″)], 2个亚甲基氢[δH 2.80 (2H, m, H-1″), 1.80 (2H, m, H-2″)] 和1个甲基氢信号[δH 1.22 (3H, d, J = 6.2 Hz, H-4″)]。13C NMR显示9个碳信号(表1), 结合DEPT-135提示有3个季碳, 包括1个羧基碳信号[δC 163.2 (C-1′)] 和2个烯碳[δC 161.6 (C-5), 143.3 (C-2)]; 3个次甲基, 包括2个烯碳[δC 120.5 (C-3), 108.2 (C-4)] 和1个与氧相连的叔碳[δC 67.2 (C-3″)]; 2个亚甲基[δC 37.1 (C-2″), 24.8 (C-1″)] 和1个甲基[δC 23.6 (C-4″)]。这些数据与化合物1相似, 只是此化合物的C-2侧链直接与羧基[δC 163.2 (C-1′)] 相连。进一步通过1H-1H COSY和HMBC进行验证(图2)。1H-1H COSY显示C-3-C-4和C-1″-C-2″-C-3″-C-4″的碳链连接顺序。HMBC提示H-3与C-2、C-5相关, H-4与C-5相关, 提示2, 5-二取代呋喃环结构; H-1″与C-4、C-5相关, 提示3-羟基丁基侧链与呋喃环中的C-5相连接。因此, 化合物2的结构被阐明, 经SciFinder数据库检索确认为新化合物。进一步采用旋光值比较的方法确定化合物的绝对构型, 其比旋光值与类似化合物7接近, 手性应与其一致, 确定C-3″为R构型[13]。最终, 化合物被命名为5-[(3R)-羟基丁基]-2-呋喃羧酸。
化合物3为黄色油状物, 易溶于甲醇、二氯甲烷, [α]$ {}_{\mathrm{D}}^{25} $ -7.0 (c 0.2, MeOH)。根据其高分辨质谱(HR-ESI-MS) 的准分子离子峰m/z 227.091 7 [M+H]+ (C11H15O5, 计算值227.091 4), 推断其分子式为C11H14O5, 不饱和度为5。1H NMR (400 MHz, CD3OD) 谱(表1) 中显示2个烯烃质子[δH 7.34 (1H, d, J = 3.5 Hz, H-4), 6.52 (1H, d, J = 3.5 Hz, H-3)], 1个与氧相连的次甲基氢信号[δH 4.31 (1H, m, H-3″)], 2个亚甲基氢信号[δH 3.87 (2H, s, H-1′), 3.02 (1H, dd, J = 15.2, 7.7 Hz, H-2″, Hb), 2.85 (1H, dd, J = 15.2, 7.7 Hz, H-2″, Ha)], 和2个甲基氢信号[δH 3.74 (3H, s, H-3′), 1.25 (3H, d, J = 6.3 Hz, H-4″)]。13C NMR显示11个碳信号(表1), 结合DEPT-135提示有4个季碳, 包括1个酯羰基号[δC 170.7 (C-2′)]、1个酮羰基信号[δC 189.2 (C-1″)] 和2个烯碳[δC 155.3 (C-2), 153.7 (C-5)]; 3个次甲基, 包括2个烯碳[δC 112.3 (C-3), 121.1 (C-4)] 和1个与氧相连的叔碳[δC 65.5 (C-3″)]; 2个亚甲基[δC 48.3 (C-2″), 34.5 (C-1′)]; 和2个甲基[δC 52.9 (C-3′), 23.6 (C-4″)]。这些数据与5-((3R)-3-羟基丁基)-2-呋喃乙酸甲酯(化合物7) 中的数据非常相似[13, 14], 主要区别在C-1″位由酮羰基C-1″ (δC 189.2) 取代。此推测通过1H-1H COSY和HMBC可得到验证其连接位置(图2)。1H-1H COSY显示C-3-C-4和C-2″-C-3″-C-4″的碳链连接顺序。HMBC提示H-3与C-5相关, H-4与C-2、C-5相关, 提示2, 5-二取代呋喃环结构; H-3′与C-2′相关, 确认甲酯基的结构归属; H-1′与C-2′、C-2、C-3相关, 表明乙酸甲酯侧链与呋喃环的C-2相连; H2-2″与C-1″、C-3″、C-4″相关, 提示3-羟基丁酰基的侧链结构。因此, 化合物3的平面结构被阐明, 经SciFinder数据库检索确认为新化合物。进一步采用旋光值比较的方法确定化合物的绝对构型, 其比旋光值与类似化合物7接近, 手性应与其一致, 确定C-3″为R构型[13]。最终, 化合物被命名为5-[(3R)-羟基丁酰基]-2-呋喃乙酸甲酯。
化合物4为黄色油状物, 易溶于甲醇、二氯甲烷。[α]$ {}_{\mathrm{D}}^{25} $ -11.76 (c 0.17, MeOH)。根据其高分辨质谱(HR-ESI-MS) 的准分子离子峰m/z 169.086 3 [M+H]+ (C9H13O3, 计算值169.085 9), 推断其分子式为C9H12O3, 不饱和度为4。1H NMR (600 MHz, CD3OD) 谱(表2) 显示1个醛基质子[δH 9.45 (1H, s, H-1′)], 2个烯烃质子[δH 7.36 (1H, d, J = 3.5 Hz, H-3), 6.40 (1H, d, J = 3.5 Hz, H-4)], 1个和氧相连的次甲基氢信号[δH 3.76 (1H, m, H-3″)], 2个亚甲基氢信号[δH 2.85 (2H, m, H-1″), 1.81 (2H, m, H-2″)] 和1个甲基氢信号[δH 1.20 (3H, d, J = 6.3 Hz, H-4″)]。13C NMR显示9个碳信号(表2), 结合DEPT-135提示有2个季碳[δC 165.4 (C-5), 153.4 (C-2)]; 4个次甲基, 包括1个醛基[δC 178.8 (C-1′)], 2个烯碳[δC 126.0 (C-3), 110.1 (C-4)] 和1个与氧相连的叔碳[δC 67.6 (C-3″)]; 2个亚甲基[δC 25.6 (C-1″), 37.7 (C-2″)] 和1个甲基[δC 23.5 (C-4″)]。这些数据与化合物2中的数据非常相似, 只是多了一组醛基质子信号[δH 9.45 (1H, s, H-1′)], 由此推测化合物4中C-1′位是醛基而非羧基。1H-1H COSY谱(图3) 显示C-3-C4和C-1″-C-2″- C-3″-C-4″的碳链连接顺序。HMBC谱(图3) 提示H-3与C-2、C-5相关, H-4与C-5相关, 提示2, 5-二取代呋喃环结构; H-1′与C-2相关, 表明醛基C-1′与呋喃环的C-2位连接; H-1″与C-4、C-5、C-3″相关, H-2″与C-5、C-4″相关, 表明3-羟基丁基侧链与呋喃环C-5位连接。因此, 化合物4的结构被阐明, 经SciFinder数据库检索为新天然产物。进一步采用旋光值比较的方法确定化合物的绝对构型, 其比旋光值与类似化合物7接近, 手性应与其一致, 确定C-3″为R构型[13]。最终, 化合物被命名为5-[(3R)-3-羟基丁基]-2-呋喃甲醛。
化合物5为黄色油状物, 易溶于甲醇、二氯甲烷、氯仿。根据其高分辨质谱(HR-ESI-MS) 的准分子离子峰m/z 185.081 2 [M+H]+ (C9H13O4, 计算值185.080 8), 推断其分子式为C9H12O4, 不饱和度为4。1H NMR (600 MHz, CDCl3) 谱(表2) 中显示2个烯烃质子[δH 6.14 (1H, d, J = 3.1 Hz, H-3), 6.06 (1H, d, J = 3.1 Hz, H-4)], 3个亚甲基氢信号[δH 3.86 (2H, t, J = 6.2 Hz, H-2″), 3.66 (2H, s, H-1′), 2.87 (2H, t, J = 6.2 Hz, H-1″)] 和1个与氧相连的甲基氢信号[δH 3.72 (3H, s, H-3′)]。13C NMR显示9个碳信号(表2), 结合DEPT-135提示有3个季碳, 包括1个酯羰基信号[δC 170.2 (C-2′)] 和2个烯碳[δC 152.6 (C-5), 146.7 (C-2)]; 3个次甲基, 包括2个烯碳[δC 109.0 (C-3), 107.7 (C-4)] 和1个与氧相连的叔碳[δC 61.4 (C-2″)]; 2个亚甲基[δC 34.1 (C-1′), 31.8 (C-1″)] 和1个与氧相连的甲基[δC 52.4 (C-3′)]。以上数据与已知化合物7相似[13, 14], 但缺少了一个末端甲基信号, 多了一个与氧相连的亚甲基氢信号[δH 3.86 (2H, t, J = 6.2 Hz, H-2″)], 由此推测化合物5中呋喃环的C-5侧链为2-羟基乙基。进一步1H-1H COSY谱(图3) 显示C-3-C4和C-1″-C-2″的碳链连接顺序。HMBC谱(图3) 提示H-3与C-2、C-5相关, H-4与C-5相关, 提示2, 5-二取代呋喃环结构; H-3′与C-2′相关, H-1′与C-2′、C-2、C-3相关, 表明乙酸甲酯侧链与呋喃环的C-2位连接; H-1″与C-4、C-5相关, 提示2-羟基乙基与呋喃环中的C-5位连接。因此, 化合物5的平面结构被阐明, 经SciFinder数据库检索确认为新天然产物, 被命名5-(2-羟基乙基)-2-呋喃乙酸甲酯。
2　化合物活性检测
2.1　抗炎活性测试
为了评估化合物的抗炎作用, 采用了脂多糖(LPS) 诱导的小鼠单核巨噬细胞RAW 264.7细胞系NO生成模型, 实验结果(图4) 显示化合物1、3~7能浓度依赖性地抑制NO的释放, 表现出良好的抗炎效果。为了排除细胞毒性作为潜在的干扰因素, 使用Alamar Blue测定法评估了用受试化合物处理的RAW 264.7细胞的存活率。化合物1、3~7在浓度高达100 μmol·L-1时细胞存活率均大于90%, 表明化合物1、3~7对NO生成的抑制作用并非由于细胞活力受损所致。而化合物2在10 μmol·L-1仍对RAW264.7细胞系具有明显的细胞毒性, 排除在抗炎活性的考察范围之外。
2.2　杀虫活性测试
为了评估化合物的杀虫活性, 采用Alamar Blue法测定7个呋喃类化合物对草地贪夜蛾卵巢来源Sf9细胞的细胞毒作用。实验结果(表3) 显示化合物1、3~7对Sf9细胞存活率的IC50值均大于100 μmol·L-1, 表明该6个化合物对Sf9细胞无明显的细胞毒作用。化合物2对Sf9细胞具一定的细胞毒性, IC50值为57.01 μmol·L-1。
3　讨论
本研究从蛹虫草菌丝体发酵产物乙酸乙酯部位分离得到7个呋喃类化合物。相较于已有研究多集中在核苷、多糖、甾醇等常见成分, 本研究进一步丰富了蛹虫草的化学多样性, 体现了发酵菌丝体在挖掘新颖小分子代谢产物方面的潜力。结构分析表明, 该类化合物均以2, 5-二取代呋喃为母核, 多含有(3R)-羟基丁基手性侧链, 结构差异主要集中于呋喃环C-2位取代基的变化。活性评价结果表明, 化合物1、3~7对脂多糖诱导的RAW264.7细胞一氧化氮生成具有不同程度的抑制作用, 而仅化合物2表现出对草地贪夜蛾卵巢细胞Sf9的细胞毒性, 提示C-2位为游离羧基时更有利于昆虫细胞毒活性, 酯基、醛基等取代则更倾向于展现抗炎活性, 初步揭示了该类呋喃化合物结构与生物活性之间的关联。本研究的创新之处在于系统发现蛹虫草中结构新颖的呋喃类成分, 并同时阐明其抗炎与细胞毒活性, 为蛹虫草的药用开发及农用生物活性物质研究提供了新的物质基础; 但本研究仍存在一定局限性, 如活性机制尚未阐明。综上, 该类呋喃化合物在抗炎药物研发及生物源杀虫剂先导化合物发现方面具有潜在应用价值, 可为后续结构修饰、作用机制阐释及资源综合利用提供研究方向。
实验部分
收起
Bruker AVANCE Ⅲ 400型核磁共振仪和Bruker AVANCE NEO 600型核磁共振仪(德国Bruker公司); Anton Paar MCP5500旋光仪(奥地利Anton Paar公司); IRAffinity-1S型傅里叶红外光谱仪(日本岛津公司); Agilent 6545 Q-TOF高分辨质谱仪和1260 InfinityⅡ型半制备液相色谱仪(美国Agilent公司); Shimadzu Prominence高效液相色谱仪(日本岛津公司, 配备PDA光电二极管阵列检测器); Sepa Bean中压过柱机(常州三泰科技公司); Spark多功能酶标仪型号为(瑞士Tecan公司); Agilent SB-C18 (250 mm × 4.6 mm, 5 μm) 分析柱; Agilent SB-C18 PrePHT (250 mm × 21.2 mm, 7 μm) 半制备柱; YMC-Pack ODS-A column (250 mm × 10 mm, 5 μm) 半制备柱; 柱色谱硅胶(200~300目, 上海泰坦科技股份公司); 一氧化氮检测试剂盒、脂多糖(LPS, 来源于大肠杆菌055:B5, 上海碧云天生物科技股份有限公司); 刃天青钠(美国Sigma-Aldrich公司); 所有色谱纯试剂、分析纯试剂均购于安徽泽升科技有限公司。
蛹虫草菌株通过中国微生物菌种查询网购买, 菌种编号(bio-57563), 经ITS测序鉴定为Cordyceps militaris。
1　菌株的发酵与培养
将蛹虫草菌株接种于固体PDA培养基上(去皮土豆200 g, 葡萄糖20 g, MgSO4·7H2O 1.5 g, K2HPO4 3.0 g, 维生素B1 10 mg, 琼脂粉20 g, 加水定容至1 L), 在25 ℃的培养箱中培养7~10天进行活化。将活化好的真菌菌丝接种至液体PDA培养基(去皮土豆200 g, 葡萄糖20 g, MgSO4·7H2O 1.5 g, K2HPO4 3.0 g, 维生素B1 10 mg, 加水定容至1 L), 在25 ℃, 150 r·min-1的摇床中振荡培养14天, 获得蛹虫草种子培养液。将种子培养液转移至装有1 L液体PDA培养基的2 L三角瓶中, 发酵40瓶, 在25 ℃、150 r·min-1的摇床中振荡培养14天。
2　提取与分离
发酵结束后, 用纱布过滤分离发酵液与菌体。发酵液加入等体积乙酸乙酯萃取3次, 菌体用甲醇超声提取3次。合并发酵液萃取液与菌体提取液经减压浓缩得到总提取物。总提取物加800 mL水分散, 依次用等体积石油醚、乙酸乙酯各萃取5、6次, 减压浓缩得到石油醚层和乙酸乙酯层。乙酸乙酯层(6.5 g) 经正相硅胶柱色谱分离, 依次用二氯甲烷∶甲醇(100∶0~1∶1) 梯度洗脱, 得到14个组分Fr.1~Fr.14。Fr.6经半制备高效液相色谱(检测波长: 190和254 nm, 乙腈-水, 30∶70~100∶0, 15 mL·min-1) 下制备, 得到化合物1 (27.3 mg, tR = 15.8 min) 和化合物7 (140.0 mg, tR = 13.3 min), 以及3个亚组分Fr.6.1~Fr.6.3。Fr.6.1经半制备高效液相色谱(检测波长: 190和254 nm, 乙腈-水, 15∶85, 5 mL·min-1) 纯化, 得到化合物2 (4.6 mg, tR = 24.7 min); Fr.6.2经半制备高效液相色谱(检测波长: 190和254 nm, 乙腈-水, 20∶80, 3 mL·min-1) 分离, 得到化合物3 (2.1 mg, tR = 16.3 min)、4 (7.3 mg, tR = 15.2 min) 和6 (80.7 mg, tR = 19.8 min); Fr.6.3经半制备高效液相色谱(检测波长: 190和254 nm, 乙腈-水, 20∶80, 3 mL·min-1) 制备, 得到化合物5 (7.4 mg, tR = 15.3 min)。
3　结构鉴定
化合物1  黄色油状物; [α]$ {}_{\mathrm{D}}^{25} $ -9.45 (c 0.31, MeOH); UV (MeOH) λmax: 219 nm; IR (CH2Cl2) vmax 3 447, 2 928, 1 738, 1 369, 1 225, 1 028, 1 015 cm-1; HR-ESI-MS m/z 227.128 5 [M+H]+ (C12H19O4, 计算值227.127 8); 1H NMR和13C NMR数据见表1。
化合物2  黄色油状物; [α]$ {}_{\mathrm{D}}^{25} $ -11.18 (c 0.2, MeOH); UV (MeOH) λmax: 203, 265 nm; IR (CH2Cl2) vmax 3 418, 2 968, 2 930, 1 709, 1 524, 1 290, 1 205, 1 018 cm-1; HR-ESI-MS m/z 185.080 9 [M+H]+, (C9H13O4, 计算值185.080 8); 1H NMR和13C NMR数据见表1。
化合物3  黄色油状物; [α]$ {}_{\mathrm{D}}^{25} $ -7.0 (c 0.2, MeOH); UV (MeOH) λmax: 224, 284 nm; IR (CH2Cl2) vmax 3 395, 2 963, 2 924, 1 740, 1 665, 1 616, 1 516, 1 217 cm-1; HR-ESI-MS m/z 227.091 7 [M+H]+ (C11H15O5, 计算值227.091 4); 1H NMR和13C NMR数据见表1。
化合物4  黄色油状物; [α]$ {}_{\mathrm{D}}^{25} $ -11.76 (c 0.17, MeOH); UV (MeOH) λmax: 226, 292 nm; IR (CH2Cl2) vmax 3 443, 2 967, 2 926, 1 672, 1 518, 1 398, 1 126, 1 024 cm-1; HR-ESI-MS m/z 169.086 3 [M+H]+ (C9H13O3, 计算值169.085 9); 1H NMR和13C NMR数据见表2。
化合物5  黄色油状物; UV (MeOH) λmax: 217 nm; IR (CH2Cl2) vmax 3 393, 2 920, 2 851, 1 740, 1 520, 1 435, 1 223, 1 047 cm-1; HR-ESI-MS m/z 185.081 2 [M+H]+ (C9H13O4, 计算值185.080 8); 1H NMR和13C NMR数据见表2。
化合物6  黄色油状物; [α]$ {}_{\mathrm{D}}^{25} $ -14.15 (c 0.21, MeOH); HR-ESI-MS m/z 199.096 9 [M+H]+, 分子式为C10H14O4; 1H NMR (600 MHz, CD3OD) δH: 6.08 (1H, d, J = 3.0 Hz, H-4), 5.94 (1H, d, J = 3.0 Hz, H-3), 3.74 (1H, h, J = 6.3 Hz, H-3″), 3.59 (2H, s, H-1′), 2.67 (2H, m, H-1″), 1.72 (2H, td, J = 7.9, 6.3 Hz, H-2″), 1.17 (3H, d, J = 6.3 Hz, H-4″); 13C NMR (151 MHz, CD3OD) δC: 173.5 (C-2′), 156.6 (C-5), 147.8 (C-2), 109.7 (C-3), 106.6 (C-4), 67.7 (C-3″), 38.3 (C-2″), 34.6 (C-1′), 25.3 (C-1″), 23.4 (C-4″)。以上数据与文献[14]报道基本一致, 比旋光值和已知化合物7接近[13], 确定C-3″为R构型, 故鉴定化合物6为5-[(3R)-羟基丁基]-2-呋喃乙酸。
化合物7  黄色油状物; [α]$ {}_{\mathrm{D}}^{25} $ -14.44 (c 0.19, MeOH); HR-ESI-MS m/z 213.113 7 [M+H]+; 1H NMR (600 MHz, CD3OD) δH: 6.05 (1H, d, J = 3.0 Hz, H-4), 5.91 (1H, d, J = 3.0 Hz, H-3), 3.71 (1H, h, J = 6.3 Hz, H-3″), 3.64 (3H, s, H-3′), 3.60 (2H, s, H-1′), 2.62 (2H, m, H-1″), 1.69 (2H, m, H-2″), 1.14 (3H, d, J = 6.3 Hz, H-4″); 13C NMR (151 MHz, CD3OD) δC: 171.9 (C-2′), 156.7 (C-5), 147.3 (C-2), 109.5 (C-3), 106.6 (C-4), 67.7 (C-3″), 52.6 (C-3′), 38.3 (C-2″), 34.4 (C-1′), 25.2 (C-1″), 23.5 (C-4″)。以上数据与文献[13, 14]报道基本一致, 故鉴定化合物7为5-[(3R)-羟基丁基]-2-呋喃乙酸甲酯。
4　抗炎活性测试
采用经典LPS诱导RAW264.7巨噬细胞NO生成模型来评价化合物的抗炎活性, 详细的实验流程和步骤见文献[15]报道。简而言之, 取对数生长期细胞以每孔5×104个接种于96孔板中, 孵育16 h后, 使细胞铺满板底80%, 弃去原培养基。除正常对照组不做任何药物处理外, LPS模型组细胞只加入LPS (1 μg·mL-1), 各给药组加入LPS (1 μg·mL-1) 以及不同浓度的待测样品。继续培养24 h后, 每孔取50 μL上清液于96孔板中, 加入50 μL Griess Reagent I和50 μL Griess Reagent II, 室温下反应15 min, 用酶标仪测定540 nm处测定吸光度OD值, 根据标准曲线计算NO的释放量。
5　细胞活力测定
采用Alamar Blue法进行RAW264.7和Sf9细胞活力测定[16]。RAW264.7细胞在含有10%胎牛血清、100 u·mL-1青霉素和100 μg·mL-1链霉素的DMEM培养基中, 在37 ℃、含有5% CO2的培养箱中培养。Sf9细胞采用含有10%胎牛血清、100 u·mL-1青霉素和100 μg·mL-1链霉素的Grace's Insect Medium (Supplemented) 培养基, 于28 ℃培养箱中培养。将对数生长期的RAW264.7 (每孔1×104个) 和Sf9细胞(每孔5×103个) 接种于96孔板中, 孵育16 h后, 弃去原培养基, 加入不同浓度的受试化合物。分别继续培养24和72 h后, 每孔加入10 μL刃天青钠水溶液(0.2 mg·L-1), 继续培养4~6 h, 置于570 nm的激发波长和590 nm的发射波长下检测荧光值。公式如下: 细胞存活率% = [(F给药组-F调零组) / (F对照组-F调零组)] × 100%。
6　统计学分析
采用GraphPad Prism 9.0软件对数据进行统计学分析。所有实验设置3个重复, 实验数据以$ \overline{x} $ ± s表示。抗炎活性测试以LPS组为对照, 组间比较采用单因素方差分析, P < 0.001为差异具有极显著统计学意义。对于具有细胞毒性的化合物, 通过非线性回归模型拟合浓度-抑制曲线, 计算IC50值。

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2026年第61卷第7期
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doi: 10.16438/j.0513-4870.2026-0221
  • 接收时间：2026-03-02
  • 首发时间：2026-09-21
  • 出版时间：2026-07-12
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  • 收稿日期：2026-03-02
  • 修回日期：2026-04-05
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    上海中医药大学创新中药研究院, 中药功效成分发掘与利用全国重点实验室, 上海 201203

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2种不同金属材料的力学参数
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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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