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Article(id=1210147956049711393, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147945840776034, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2022-0133, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1643299200000, receivedDateStr=2022-01-28, revisedDate=1646668800000, revisedDateStr=2022-03-08, acceptedDate=null, acceptedDateStr=null, onlineDate=1766451356184, onlineDateStr=2025-12-23, pubDate=1657555200000, pubDateStr=2022-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1766451356184, onlineIssueDateStr=2025-12-23, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1766451356184, creator=13701087609, updateTime=1766451356184, updator=13701087609, issue=Issue{id=1210147945840776034, tenantId=1146029695717560320, journalId=1189982191388893191, year='2022', volume='57', issue='7', pageStart='1925', pageEnd='2244', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1766451353750, creator=13701087609, updateTime=1766451495727, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1210148541385798149, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147945840776034, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1210148541385798150, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147945840776034, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=2139, endPage=2145, ext={EN=ArticleExt(id=1210147956674662762, articleId=1210147956049711393, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new flavone glycoside from Eriocaulon buergerianum, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Ten compounds were isolated from the water extract of Eriocaulon buergerianum by HP20, ODS, Sephadex LH-20 and MCI Gel CHP-20 column chromatographic methods. Their structures were identified by spectroscopic and chemical approaches as 6-methoxyquercetin-3-O-(2'''-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1), syringaresinol-4'-O-β-D-glucopyranoside (2), rutin (3), 1-O-feruloylglycerol (4), 1, 2-benzenediol (5), vomifoliol (6), β-D-(6-O-trans-feruloyl) fructofuranosyl-α-D-O-glucopyranosied (7), dihydroferulic acid (8), guanosine (9) and quercetin-3-O-β-gentiobioside (10). The compound 1 is a new compound, the compounds 2 and 4-10 were obtained from Eriocaulon genus for the first time, and the compound 3 was isolated from this plant for the first time. Molecular docking study showed that 1 is a potential inhibitor of TNF-α. The compound 1 was evaluated for their anti-inflammatory activities in vitro, and 1 showed significant inhibitory activity against TNF-α production in lipopolysaccharide (LPS)-induced RAW264.7 macrophage cells at the concentrations of 1, 10 and 100 μmol·L-1.

, correspAuthors=Wei-liang ZHU, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2022 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=Yong ZHANG, Akber Aisa HAJI, Wei-liang ZHU), CN=ArticleExt(id=1210147959182856694, articleId=1210147956049711393, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=谷精草中1个新的黄酮苷类化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用大孔吸附树脂、反相硅胶、葡聚糖凝胶及微孔树脂等多种色谱技术，从谷精草水提取中分离得到10个化合物。通过NMR、ESI-MS、HR-ESI-MS、UV、IR等波谱技术并结合化学方法对其进行了结构鉴定，分别为6-methoxyquercetin-3-O-(2'''-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1)、丁香脂素-4'-O-β-D-葡萄糖苷(2)、芦丁(3)、1-O-feruloylglycerol (4)、邻苯二酚(5)、吐叶醇(6)、β-D-(6-O-trans-feruloyl) fructofuranosyl-α-D-O-glucopyranosied (7)、二氢阿魏酸(8)、鸟嘌呤核苷(9)和槲皮素-3-O-β-D-龙胆二糖苷(10)，化合物1为新化合物，化合物2、4~10为首次从谷精草属植物中分离得到，化合物3为首次从该植物中分离得到。分子对接结果显示化合物1具有潜在的肿瘤坏死因子-α(TNF-α)转换酶抑制活性。体外抗炎活性实验证实，化合物1在1、10和100 μmol·L-1能显著抑制脂多糖(LPS)诱导的RAW264.7细胞中TNF-α的升高，具有较好的体外抗炎活性。

, correspAuthors=朱维良, authorNote=null, correspAuthorsNote=
*朱维良, Tel: 86-21-50806600-1205, E-mail:
, copyrightStatement=版权所有©《药学学报》编辑部2022, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=YR5VkGZ/e5oGzAIWLaS/Jg==, magXml=6ZXqTfe2k3joKbMJ2eA1lw==, pdfUrl=null, pdf=/NLyUDnhOojiHQFeeBpPhg==, pdfFileSize=482840, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=6GRiVZZeugLTKrq86X1rkA==, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=cOQRE05AIh84X70umoBIfQ==, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=张勇, 阿吉艾克拜尔·艾萨, 朱维良)}, authors=[Author(id=1210147960067854938, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210147956049711393, orderNo=0, firstName=null, middleName=null, lastName=null, nameCn=null, orcid=null, stid=null, country=null, authorPic=null, dead=0, email=null, emailSecond=null, emailThird=null, correspondingAuthor=0, authorType=1, ext={EN=AuthorExt(id=1210147960248210030, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210147956049711393, authorId=1210147960067854938, language=EN, stringName=Yong ZHANG, firstName=Yong, middleName=null, lastName=ZHANG, prefix=null, suffix=null, authorComment=null, nameInitials=null, affiliation=null, department=null, xref=1, 2, 3, address=1. State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, CAS Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China
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LPS: Lipopolysaccharide , figureFileSmall=DdGcJxLiHyZfd4zYzajuRQ==, figureFileBig=D1yWjsXOu9jFx9KMJFHSNA==, tableContent=null), ArticleFig(id=1210147965063271347, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210147956049711393, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
No.δH (J in Hz)δC
1
2158.5
3135.2
4179.4
4a105.8
5153.7
6133.0
7159.7
86.53 (1H, s)95.5
8a153.5
93.86 (3H, s)61.1
1′122.8
2′7.83 (1H, d, 1.9)117.5
3′146.1
4′150.3
5′6.91 (1H, d, 8.5)116.4
6′7.76 (1H, dd, 8.5, 1.9)123.6
Glc
1′′5.18 (1H, d, 7.8)104.2
2′′3.47 (1H, t-like, 8.7)75.5
3′′3.34 (1H, m)77.8
4′′3.15 (1H, t-like, 9.1)71.3
5′′3.22 (1H, m)79.7
6′′3.88 (1H, overlapped, 6′′-Ha)
3.73 (1H, dd, 12.9, 6.9, 6′′-Hb)		68.3
Glc
1′′′4.49 (1H, d, 8.1)101.7
2′′′4.68 (1H, t-like, 8.1)76.0
3′′′3.22 (1H, m)75.9
4′′′3.36 (1H, m)71.2
5′′′2.71 (1H, m)77.2
6′′′3.68 (1H, dd, 12.1, 1.9, 6′′′-Ha)62.0
3.63 (1H, dd, 12.1, 4.5, 6′′′-Hb)
Vanilloyl
1′′′′122.4
2′′′′7.46 (1H, d, 1.4)113.8
3′′′′148.7
4′′′′152.8
5′′′′6.67 (1H, d, 8.2)115.9
6′′′′7.22 (1H, d, 8.2, 1.4)124.6
7′′′′167.5
8′′′′3.85 (3H, s)56.4
), ArticleFig(id=1210147965168128957, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210147956049711393, language=CN, label=Table 1, caption=

1H and 13C NMR spectral data of compound 1 (CD3OD) (1H NMR 500 MHz; 13C NMR 125 MHz)

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No.δH (J in Hz)δC
1
2158.5
3135.2
4179.4
4a105.8
5153.7
6133.0
7159.7
86.53 (1H, s)95.5
8a153.5
93.86 (3H, s)61.1
1′122.8
2′7.83 (1H, d, 1.9)117.5
3′146.1
4′150.3
5′6.91 (1H, d, 8.5)116.4
6′7.76 (1H, dd, 8.5, 1.9)123.6
Glc
1′′5.18 (1H, d, 7.8)104.2
2′′3.47 (1H, t-like, 8.7)75.5
3′′3.34 (1H, m)77.8
4′′3.15 (1H, t-like, 9.1)71.3
5′′3.22 (1H, m)79.7
6′′3.88 (1H, overlapped, 6′′-Ha)
3.73 (1H, dd, 12.9, 6.9, 6′′-Hb)		68.3
Glc
1′′′4.49 (1H, d, 8.1)101.7
2′′′4.68 (1H, t-like, 8.1)76.0
3′′′3.22 (1H, m)75.9
4′′′3.36 (1H, m)71.2
5′′′2.71 (1H, m)77.2
6′′′3.68 (1H, dd, 12.1, 1.9, 6′′′-Ha)62.0
3.63 (1H, dd, 12.1, 4.5, 6′′′-Hb)
Vanilloyl
1′′′′122.4
2′′′′7.46 (1H, d, 1.4)113.8
3′′′′148.7
4′′′′152.8
5′′′′6.67 (1H, d, 8.2)115.9
6′′′′7.22 (1H, d, 8.2, 1.4)124.6
7′′′′167.5
8′′′′3.85 (3H, s)56.4
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谷精草中1个新的黄酮苷类化合物
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张勇 1, 2, 3 , 阿吉艾克拜尔·艾萨 1, 3 , 朱维良 1, 2, 3, *
药学学报 | 研究论文 2022,57(7): 2139-2145
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药学学报 | 研究论文 2022, 57(7): 2139-2145
谷精草中1个新的黄酮苷类化合物
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张勇1, 2, 3, 阿吉艾克拜尔·艾萨1, 3, 朱维良1, 2, 3, *
作者信息
  • 1.中国科学院新疆理化技术研究所, 省部共建新疆特有药用资源利用国家重点实验室培育基地, 中国科学院干旱区植物资源化学重点实验室, 新疆 乌鲁木齐 830011
  • 2.中国科学院上海药物研究所, 新药研究国家重点实验室, 中国科学院受体结构与功能重点实验室, 上海 201203
  • 3.中国科学院大学, 北京 100049

通讯作者:

*朱维良, Tel: 86-21-50806600-1205, E-mail:
A new flavone glycoside from Eriocaulon buergerianum
Yong ZHANG1, 2, 3, Akber Aisa HAJI1, 3, Wei-liang ZHU1, 2, 3, *
Affiliations
  • 1. State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, CAS Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China
  • 2. CAS Key Laboratory of Receptor Research, Stake Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
  • 3. University of Chinese Academy of Sciences, Beijing 100049, China
出版时间: 2022-07-12 doi: 10.16438/j.0513-4870.2022-0133
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摘要
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采用大孔吸附树脂、反相硅胶、葡聚糖凝胶及微孔树脂等多种色谱技术，从谷精草水提取中分离得到10个化合物。通过NMR、ESI-MS、HR-ESI-MS、UV、IR等波谱技术并结合化学方法对其进行了结构鉴定，分别为6-methoxyquercetin-3-O-(2'''-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1)、丁香脂素-4'-O-β-D-葡萄糖苷(2)、芦丁(3)、1-O-feruloylglycerol (4)、邻苯二酚(5)、吐叶醇(6)、β-D-(6-O-trans-feruloyl) fructofuranosyl-α-D-O-glucopyranosied (7)、二氢阿魏酸(8)、鸟嘌呤核苷(9)和槲皮素-3-O-β-D-龙胆二糖苷(10)，化合物1为新化合物，化合物2、4~10为首次从谷精草属植物中分离得到，化合物3为首次从该植物中分离得到。分子对接结果显示化合物1具有潜在的肿瘤坏死因子-α(TNF-α)转换酶抑制活性。体外抗炎活性实验证实，化合物1在1、10和100 μmol·L-1能显著抑制脂多糖(LPS)诱导的RAW264.7细胞中TNF-α的升高，具有较好的体外抗炎活性。

谷精草属  /  谷精草  /  黄酮苷  /  化学成分  /  抗炎

Ten compounds were isolated from the water extract of Eriocaulon buergerianum by HP20, ODS, Sephadex LH-20 and MCI Gel CHP-20 column chromatographic methods. Their structures were identified by spectroscopic and chemical approaches as 6-methoxyquercetin-3-O-(2'''-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1), syringaresinol-4'-O-β-D-glucopyranoside (2), rutin (3), 1-O-feruloylglycerol (4), 1, 2-benzenediol (5), vomifoliol (6), β-D-(6-O-trans-feruloyl) fructofuranosyl-α-D-O-glucopyranosied (7), dihydroferulic acid (8), guanosine (9) and quercetin-3-O-β-gentiobioside (10). The compound 1 is a new compound, the compounds 2 and 4-10 were obtained from Eriocaulon genus for the first time, and the compound 3 was isolated from this plant for the first time. Molecular docking study showed that 1 is a potential inhibitor of TNF-α. The compound 1 was evaluated for their anti-inflammatory activities in vitro, and 1 showed significant inhibitory activity against TNF-α production in lipopolysaccharide (LPS)-induced RAW264.7 macrophage cells at the concentrations of 1, 10 and 100 μmol·L-1.

Eriocaulon Linn.  /  Eriocaulon buergerianum Koern.  /  flavone glycoside  /  chemical constituent  /  anti-inflammatory
张勇, 阿吉艾克拜尔·艾萨, 朱维良. 谷精草中1个新的黄酮苷类化合物. 药学学报, 2022 , 57 (7) : 2139 -2145 . DOI: 10.16438/j.0513-4870.2022-0133
Yong ZHANG, Akber Aisa HAJI, Wei-liang ZHU. A new flavone glycoside from Eriocaulon buergerianum[J]. Acta Pharmaceutica Sinica, 2022 , 57 (7) : 2139 -2145 . DOI: 10.16438/j.0513-4870.2022-0133
正文
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谷精草Eriocaulon buergerianum Koern.为谷精草科谷精草属一年或多年生草本植物, 该属植物全球约有400种, 我国约34种, 主产南部和西南地区。其中, 谷精草(E. buergerianum Koern.)、华南谷精草(E. sexangulare Linn.) 和毛谷精草(E. austral R. Br.) 可供药用, 具有清热祛风、清肝明目功效[1]。谷精草首载于《本草拾遗》 (唐), 距今已有近1 300年的历史, 此后在《开宝本草》 (宋)、《本草纲目》 (明) 和《植物名实图考》 (清) 中均有详细记载, 是治疗眼疾的常用中药[2]。《中国药典》记载, 仅谷精草E. buergerianum的干燥带花茎的头状花序可作为中药谷精草入药; 辛、甘, 性平, 归肝、肺经; 具有疏散风热, 明目退翳功效, 主治风热目赤、肿痛羞明、眼生翳膜、风热头痛[3]。现代研究表明, 谷精草主要含有黄酮、萘并吡喃酮和呫吨酮类化合物, 以及少量的酚类化合物[4-9]。谷精草提取物及单体化合物报道具有抗菌[4]、减肥[6]、降糖[9]、抗氧化[10]和神经保护[11]等生物活性。总体上, 国内外有关谷精草化学成分的研究较少, 现已报道的单体化合物主要来源于乙醇提取物, 为进一步明确谷精草的药效物质基础, 丰富其化合物组成, 本文对谷精草水提物中化学成分进行了系统研究, 从中分离得到10个化合物, 并通过多种波谱技术成功地对其结构进行了鉴定, 分别是6-methoxyquercetin-3-O-(2′′′-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1)、丁香脂素-4′-O-β-D-葡萄糖苷(2)、芦丁(3)、1-O-feruloylglycerol (4)、邻苯二酚(5)、吐叶醇(6)、β-D-(6-O-trans-feruloyl) fructofuranosyl-α-D-O-glucopyranosied (7)、二氢阿魏酸(8)、鸟嘌呤核苷(9) 和槲皮素-3-O-β-D-龙胆二糖苷(10)。化合物1为新化合物(图 1), 化合物2、4~10为首次从谷精草属植物中分离得到, 化合物3为首次从该植物中分离得到。同时, 采用自主开发的多靶标分子对接平台, 预测到化合物1具有抑制肿瘤坏死因子-α (TNF-α) 转换酶活性, 并通过细胞实验证实化合物1在1、10和100 μmol·L-1可显著抑制LPS诱导的RAW264.7细胞中TNF-α的升高, 具有较好的体外抗炎活性。
结果与讨论
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1 结构鉴定
化合物1: 淡黄色无定形粉末, 易溶于甲醇, [α]$ {}_{\mathrm{D}}^{20} $ 59.6 (c 0.5, MeOH); IR显示结构中含有羟基(3 362 cm-1)、苯环(1 558 cm-1); UV (MeOH) λmax: 255、290、345 nm; HR-ESI-MS [M+H]+ m/z: 807.198 3 (计算值807.197 8), 推断其分子式为C36H38O21, 不饱和度Ω = 18。
化合物1的1H NMR数据显示, 低场区存在7个芳香氢质子信号: δH 7.83 (1H, d, J = 1.9 Hz, H-2′)、7.76 (1H, dd, J = 8.5, 1.9 Hz, H-6′)、7.46 (1H, d, J = 1.4 Hz, H-2′′′′)、7.22 (1H, dd, J = 8.2, 1.4 Hz, H-6′′′′)、6.91 (1H, d, J = 8.5 Hz, H-5′)、6.67 (1H, d, J = 8.2 Hz, H-5′′′′)、6.53 (1H, s, H-8), 根据化学位移及耦合常数判断结构中含有2个ABX耦合系统的苯环; 2个糖的端基氢质子信号δH 5.18 (1H, d, J = 7.8 Hz, H-1′′) 和4.49 (1H, d, J = 8.1 Hz, H-1′′), 其耦合常数提示2个单糖的端基碳构型均为β-构型; 2个六碳糖6位亚甲基信号δH 3.88 (1H, overlapped)、3.73 (1H, dd, J = 12.9, 6.9 Hz)、3.68 (1H, dd, J = 12.1, 1.9 Hz)、3.63 (1H, dd, J = 12.1, 4.5 Hz), 该信号结合2个糖的端基氢质子信号提示六碳糖单糖可能为葡萄糖; 2个甲氧基信号δH 3.86 (3H, s) 和3.85 (3H, s)。化合物1的13C NMR、DEPT-135谱结合HSQC显示含有36个碳原子, 包括2个甲基碳信号δC 56.4和61.1; 2个亚甲基碳信号δC 62.0和68.3; 7个芳香环上次甲基信号δC 124.6、123.6、117.5、116.4、115.9、113.8、95.5; 10个糖上次甲基信号δC 104.2、101.7、79.7、77.8、77.2、76.0、75.9、75.5、71.3、71.2; 2个羰基信号δC 179.4和167.5; 13个芳香季碳信号δC 159.7、158.5、153.7、153.5、152.8、150.3、148.7、146.1、135.2、133.0、122.8、122.4、105.8。上述1H、13C NMR数据提示化合物1可能为含有两个六碳糖基的黄酮苷类化合物, 该结构中同时存在一个ABX耦合系统的苯环取代基, 具体数据见表 1。在HMBC谱(图 2) 中, δH 5.18 (1H, d, J = 7.8 Hz, H-1′′) 与δC 135.2 (C-3) 相关, δH 4.49 (1H, d, J = 8.1 Hz, H-1′′′) 与δC 68.3相关, 提示结构中1个六碳糖通过1′′位与黄酮苷元的3位形成β-糖苷键, 两个六碳糖则通过1′′′位与6′′位连接形成二糖结构; δH 3.86 (3H, s, 9-OCH3) 与δC 133.0 (C-6) 相关, δH 3.85 (3H, s, 8′′′′-OCH3) 与δC 148.7 (C-3′′′′) 相关, 提示两个甲氧基分别连接在黄酮苷元的6位和香草酰基(vanilloyl) 的3′′′′位; δH 4.68 (1H, t-like, J = 8.1 Hz, 2′′′-H) 与δC 167.5 (C-7′′′′) 相关, 提示香草酰基通过C-7′′′′与2′′′-H连接。两个六碳糖除端基氢质子以外的氢质子信号, 可由1H-1H COSY (图 2) 和HMBC进行确认。通过进一步的分析2D-NMR (1H-1H COSY、HSQC、HMBC) 结果, 同时结合1D-NMR数据, 化合物1的平面结构与文献报道的化合物6-methoxyquercetin-7-O-(6′′′-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside[12]类似, 主要差异体现在1的二糖结构与黄酮苷元的C-3位相连, 已报道化合物的二糖结构与黄酮苷元的C-7位相连; 1的C-6′′′信号向高场移动, H-2′′′信号则往低场移动, 上述结果提示1与已报道化合物相比, 香草酰基取代位置发生了变化; HMBC结果进一步证实1中香草酰基为C-2′′′位取代, 以及二糖结构与黄酮苷元的C-3位相连。通过以上波谱数据, 确定1为6-methoxyquercetin-3-O-(2′′′-vanilloyl)-β-glucopyranosyl-(1→6)-β-glucopyranoside。
化合物1糖的类型以及绝对构型通过酸水解的化学方法做了进一步确认。1经酸水解、中和后的水液部分, 经薄层色谱分析(TLC) 与D-葡萄糖标准品比较, 确定含有葡萄糖。为进一步确认水解液中葡萄糖绝对构型, 将获得的中和后水解液采用ODS填料进行纯化, TLC进行目标化合物检识, 富集葡萄糖纯品, 减压浓缩后冷冻干燥, 干燥样品测定旋光值, 与D-葡萄糖标准品旋光值比较, 确定化合物1中糖的绝对构型为D-葡萄糖。综上, 化合物1的结构进一步确定为6-methoxyquercetin-3-O-(2′′′-vanilloyl)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside, 为新化合物。
2 化合物1与TNF-α的分子对接结果
采用自主开发的多靶标分子对接平台, 以TNF-α的晶体结构(PDB ID: 2az5) 为基础开展分子对接, 预测化合物1与TNF-α转换酶的结合能力。结果显示, 化合物1与TNF-α转换酶的结合能为-10.33 kcal·mol-1, 而TNF-α结构中ATP结合位点配体6, 7-dimethyl-3-[(methyl{2-[methyl({1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl}methyl)amino]ethyl}amino)methyl]-4H-chromen-4-one (Kd = 5.36 μmol·L-1) 打分结果为-9.44 kcal·mol-1。化合物1与TNF-α的结合模式图显示, 化合物1与59位的酪氨酸形成了face-to-face的π-π相互作用, 与151位的酪氨酸、120位的亮氨酸形成氢键作用, 化合物1可能具有抑制TNF-α的活性(图 3)。
3 化合物1的抗炎活性检测
采用ELISA试剂盒检测了化合物1对LPS诱导的RAW264.7细胞中TNF-α的释放, 结果显示化合物1在1、10和100 μmol·L-1能显著抑制LPS诱导的RAW264.7细胞中TNF-α的升高, 且呈浓度依赖关系, 证实化合物1具有较强的体外抗炎活性(图 4)。
4 小结
本实验从谷精草水提物中分离并鉴定了10个化合物, 包括3个黄酮苷类化合物(1、3、10)、1个木脂素糖苷类化合物(2)、3个阿魏酸衍生物(4、7、8) 和3个其他类化合物(5、6、9)。其中, 化合物1为新化合物, 2、4~10为首次从谷精草属植物中分离得到, 3为首次从Eriocaulon buergerianum Koern.植物中分离得到。这些化合物进一步丰富了谷精草属植物的化合物类型, 可为后续进一步开展该植物的药效物质研究提供有益参考。
此外, 采用自主开发的多靶标分子对接平台, 预测到化合物1具有抑制TNF-α转换酶活性, 并在细胞层面证实化合物1可呈浓度依赖性的抑制LPS诱导的RAW264.7细胞中TNF-α的释放, 具有较强的体外抗炎活性。
实验部分
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质谱仪(Agilent G6520 Q-TOF LC-MS, 美国Agilent公司); 旋光仪(Autopol Ⅵ, 美国Rudolph公司); 红外光谱仪(IRAffinity-1S Fourier transform infrared spectrophotometer, 日本SHIMADZU公司); 核磁共振仪(Bruker Avance Ⅲ 500, 瑞士Bruker公司, 以TMS为内标)。Synergy2型多功能酶标仪(美国BioTek公司); 5804R型冷冻离心机(德国Eppendorf公司); FORMA STERI-CYCLE i160细胞培养箱(赛默飞公司)。TLC板(硅胶GF 254预制薄层色谱板, 烟台化学工业研究所); 大孔树脂(DIAION HP20)、微孔树脂(MCI GEL CHP20P) (日本三菱化学株式会社); 反相硅胶(ODS-A-HG 12 nm S-50 μm\ODS-AQ-HG 12 nm S-50 μm, 日本YMC公司); 葡聚糖凝胶(Sephadex LH-20, 瑞典GE Healthcare Bio-Sciences AB公司); 显色剂(硫酸-香兰素显色剂)、D-葡萄糖标准品(纯度≥ 98%)、乙酸乙酯、正丁醇、甲醇、盐酸、氢氧化钠等试剂(国药集团化学试剂有限公司)。RAW264.7细胞购自南京科佰生物科技有限公司, FBS购自Gibco公司, DMEM购自HyClone公司, 青霉素-链霉素溶液(双抗) 购自Gibco公司, ELISA小鼠TNF-α试剂盒购自深圳欣博盛生物科技有限公司(批号M210825-102a)。
谷精草药材2019年购于安徽省亳州药材市场, 经上海中医药大学石燕红副研究员鉴定为谷精草科谷精草属植物谷精草Eriocaulon buergerianum Koern.的干燥带花茎的头状花序。样品(No. GJC-20190614) 保存于中国科学院上海药物研究所药物发现与设计中心实验室。
1 提取与分离
干燥的谷精草中药材(带花茎的头状花序) 8 kg, 加入蒸馏水80 L, 浸泡30 min后, 100 ℃加热回流提取, 每次回流提取1 h, 提取结束后过滤收集滤液, 药渣重复上述工艺再提取一次, 合并两次滤液, 减压浓缩得到10 L水提浓缩液。水提浓缩液依次采用乙酸乙酯、正丁醇做溶剂进行萃取处理, 分别收集萃取液减压浓缩后得到乙酸乙酯、正丁醇层以及萃取后水层3个部位。正丁醇萃取部位(153 g) 采用HP 20型大孔吸附树脂柱色谱进行纯化, 乙醇-水作为流动相梯度洗脱, 依次得到水部位、20%乙醇部位、40%乙醇部位、60%乙醇部位、95%乙醇部位。
20%乙醇部位(36.2 g) 采用ODS填料, 甲醇-水(0∶100、10∶90、20∶80、40∶60、100∶0) 梯度洗脱得到Fr.1~Fr.10。Fr.1 (1.7 g) 采用Sephadex LH20纯化, 甲醇-水等度(30∶70) 洗脱得到Fr.1.1~Fr.1.4。Fr.1.1 (274 mg), 采用MCI填料, 甲醇-水(0∶100、10∶90、20∶80) 梯度洗脱, 得到化合物9 (21.2 mg)。Fr.4 (476.1 mg) 采用ODS填料, 甲醇-水(10∶90、20∶80、30∶70、50∶50) 梯度洗脱得到Fr.4.1~Fr.4.6。Fr.4.2 (52.6 mg) 采用Sephadex LH20纯化, 甲醇-水等度(30∶70) 洗脱, 得到化合物10 (23.1 mg)。
40%乙醇部位(2.4 g) 采用ODS填料, 甲醇-水(20∶80、40∶60、60∶40、100∶0) 梯度洗脱得到Fr.1~Fr.3。其中Fr.1 (78.1 mg) 经Sephadex LH20纯化, 甲醇-水(40%) 等度洗脱, 得到化合物5 (16.8 mg)。Fr.2 (964.2 mg) 经Sephadex LH20色谱, 甲醇-水(60∶40) 等度洗脱得到Fr.2.1~Fr.2.3。Fr.2.2 (346.1 mg) 经ODS甲醇-水(30∶70、40∶60、50∶50) 梯度洗脱得到Fr.2.2.1和Fr.2.2.2。Fr.2.2.2 (118.6 mg) 经Sephadex LH20、ODS色谱, 甲醇-水反复纯化, 得到化合物1 (4.6 mg)。Fr.2.2.1 (29.1 mg) 经ODS色谱, 甲醇-水(10∶90、20∶80、30∶70) 梯度洗脱, 得到化合物2 (2.4 mg)。Fr.2.1 (268.3 mg) 经Sephadex LH20纯化, 甲醇-水(40%) 等度洗脱, 得到化合物3 (30.5 mg)。Fr.2.3 (128.7 mg) 经Sephadex LH20、ODS反复纯化, 得到化合物4 (3.6 mg)。Fr.3 (188.7 mg) 经Sephadex LH20纯化, 甲醇-水(50%) 等度洗脱得到Fr.2.3.1~Fr.2.3.3。Fr.2.3.1 (38.7 mg) 经ODS色谱, 甲醇-水梯度洗脱(30∶70、40∶60、60∶40), 得到化合物6 (8.8 mg)。Fr.2.3.2 (71.4 mg) 经ODS、Sephadex LH20色谱, 甲醇-水反复纯化, 得到化合物7 (8.8 mg)。Fr.2.3.3 (58.9 mg) 经ODS色谱, 甲醇-水梯度洗脱(40∶60、50∶50、70∶30), 得到化合物8 (7.2 mg)。
2 化合物的酸水解
称取2 mg化合物1, 加入5%盐酸5 mL, 100 ℃水浴加热1 h, 加热结束放冷至室温后用5% NaOH调pH至7后, 采用乙酸乙酯萃取3次, 每次5 mL。萃取后水层减压浓缩得水溶性样品, 取样品适量, 水溶解后采用TLC (正丁醇∶吡啶∶水= 6∶4∶3) 检识, 与D-葡萄糖标准品比对, 两者Rf值(0.5) 基本一致。随后, 取萃取后的水溶性样品, 采用ODS填料(ODS-AQ-HG 12 nm S-50 μm) 进行纯化, 水洗脱, TLC检测并富集含葡萄糖的样品, 减压浓缩后冷冻干燥得葡萄糖干燥样品, 随后称取样品测定旋光值([α]$ {}_{\mathrm{D}}^{20} $ +62.0, c 0.5, H2O), 经与D-葡萄糖标准品([α]$ {}_{\mathrm{D}}^{20} $ +74.4, c 0.5, H2O) 和L-葡萄糖标准品([α]$ {}_{\mathrm{D}}^{20} $ -88.0, c 0.5, H2O) 旋光值比较, 最终确定化合物1中单糖为D-葡萄糖。
3 结构鉴定
化合物1    黄色无定形粉末, 易溶于甲醇; HR-ESI-MS m/z: 807.198 3 (计算值807.197 8), 分子式为C36H38O21, 不饱和度18; UV (MeOH) λmax: 255、290、345 nm; IR (KBr) νmax/cm-1: 3 362、1 717、1 699、1 684、1 653、1 600、1 558、1 506、1 472、1 456、1 364、1 283、1 200、1 074、1 028、1 001; 1H (500 MHz, CD3OD) 和13C NMR (125 MHz, CD3OD) 数据见表 1。
化合物2   淡黄色无定形粉末, ESI-MS m/z: 579.2 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 6.72 (2H, s, H-2′, 6′), 6.66 (2H, s, H-2, 6), 4.86 (1H, overlapped, glc-1′′), 4.77 (1H, d, J = 4.0 Hz, H-7), 4.73 (1H, d, J = 4.3 Hz, H-7′), 4.29 (2H, m, 9, 9′-H(a)), 3.91 (2H, m, 9, 9′-H(b)), 3.86 (6H, m, 3, 5-OCH3), 3.85 (6H, m, 3′, 5′-OCH3), 3.77 (1H, dd, J = 2.3, 12.0 Hz, glc-H-6′′a), 3.66 (1H, dd, J = 5.2, 12.0 Hz, glc-H-6′′b), 3.47 (1H, m, glc-2′′), 3.42 (2H, m, glc-4′′, 5′′), 3.20 (1H, m, glc-3′′), 3.14 (2H, m, H-8, 8′); 13C NMR (125 MHz, CD3OD) δC: 154.4 (C-3′, 5′), 149.4 (C-3, 5), 139.5 (C-1′), 136.3 (C-4), 135.6 (C-4′), 133.1 (C-1), 105.3 (C-1′′), 104.9 (C-2, 6), 104.6 (C-2′, 6′), 87.6 (C-7′), 87.2 (C-7), 78.3 (C-3′′), 77.8 (C-5′′), 75.7 (C-2′′), 72.9 (C-9, 9′), 71.4 (C-4′′), 62.6 (C-6′′), 57.1 (C-3′, 5′), 56.8 (C-3, 5), 55.7 (C-8), 55.5 (C-8′)。以上数据与文献[13]报道的丁香脂素-4′-O-β-D-葡萄糖苷基本一致。
化合物3    黄色无定形粉末, ESI-MS m/z: 609.5 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 7.67 (1H, d, J = 2.0 Hz, H-2′), 7.63 (1H, dd, J = 2.0, 8.4 Hz, H-6′), 6.88 (1H, d, J = 8.4 Hz, H-5′), 6.40 (1H, d, J = 1.9 Hz, H-8), 6.21 (1H, d, J = 1.9 Hz, H-6), 5.11 (1H, d, J = 7.7 Hz, glc-1′′), 4.52 (1H, s, rha-1′′′), 3.25~3.90 (glc-2′′, 3′′, 4′′, 5′′, 6′′; rha-2′′, 3′′, 4′′, 5′′), 1.13 (3H, d, J = 6.2 Hz, rha-6′′′); 13C NMR (125 MHz, CD3OD) δC: 179.4 (C-4), 166.0 (C-7), 163.0 (C-5), 159.3 (C-9), 158.5 (C-2), 149.8 (C-4′), 145.8 (C-3′), 135.6 (C-3), 123.6 (C-1′), 123.1 (C-6′), 117.7 (C-5′), 116.0 (C-2′), 105.6 (C-10), 104.7 (glc-1′′), 102.4 (rha-1′′′), 99.9 (C-6), 94.9 (C-8), 78.2 (C-3′′), 77.2 (C-5′′), 75.7 (C-2′′), 73.9 (C-4′′′), 72.2 (C-3′′′), 72.1 (C-2′′′), 71.4 (C-4′′), 69.7 (C-5′′′), 68.6 (C-6′′), 17.9 (C-6′′′)。以上数据与文献[14]报道的芦丁基本一致。
化合物4    淡黄色无定形粉末, ESI-MS m/z: 267.3 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 7.66 (1H, d, J = 15.9 Hz, H-7), 7.20 (1H, d, J = 1.8 Hz, H-2), 7.09 (1H, dd, J = 1.8, 8.2 Hz, H-6), 6.82 (1H, d, J = 8.2 Hz, H-5), 6.40 (1H, d, J = 15.9 Hz, H-8), 4.27 (1H, dd, J = 5.3, 11.4 Hz, glycerol H-1′(a)), 4.18 (1H, dd, J = 5.3, 11.4 Hz, glycerol H-1′(b)), 3.90 (3H, s, -OCH3), 3.89 (1H, m, glycerol H-2′), 3.61 (2H, dd, J = 5.5, 5.5 Hz, glycerol H-3′); 13C NMR (125 MHz, CD3OD) δC: 167.8 (C-9), 149.3 (C-4), 148.0 (C-3), 145.6 (C-7), 126.3 (C-1), 122.7 (C-6), 115.1 (C-5), 113.9 (C-8), 110.4 (C-2), 69.9 (C-2′), 65.2 (C-1′), 62.7 (C-3′), 55.1 (-OCH3)。以上数据与文献[15]报道的1-O-阿魏酸甘油酯基本一致。
化合物5    白色无定形粉末, ESI-MS m/z: 109.1 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 6.75 (2H, m, H-3, 6), 6.65 (2H, m, H-2, 5); 13C NMR (125 MHz, CD3OD) δC: 146.3 (C-1, 2), 120.9 (C-4, 5), 116.4 (C-3, 6)。以上数据与文献[16]报道邻苯二酚基本一致。
化合物6    白色无定形粉末, ESI-MS m/z: 247.2 [M+Na]+。1H NMR (500 MHz, CD3OD) δH: 5.88 (1H, s, H-2), 5.80 (1H, m, H-8), 5.77 (1H, d, J = 15.7 Hz, H-7), 4.32 (1H, m, H-9), 2.48 (1H, d, J = 16.9 Hz, 6-Ha), 2.17 (1H, d, J = 16.9 Hz, 6-Hb), 1.92 (3H, s, 11-CH3), 1.25 (3H, d, J = 6.5 Hz, 10-CH3), 1.04 (3H, s, 12-CH3), 1.02 (3H, s, 13-CH3); 13C NMR (125 MHz, CD3OD) δC: 201.2 (C-3), 167.4 (C-5), 136.9 (C-8), 130.0 (C-7), 127.1 (C-4), 80.0 (C-6), 68.6 (C-9), 50.7 (C-2), 42.4 (C-1), 24.5 (C-12), 23.8 (C-10), 23.5 (C-11), 19.6 (C-13)。以上数据与文献[17]报道吐叶醇基本一致。
化合物7    淡黄色无定形粉末, ESI-MS m/z: 517.1 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 7.66 (1H, d, J = 15.9 Hz, H-7′′), 7.21 (1H, s, H-2′′), 7.10 (1H, d, J = 8.1 Hz, H-6′′), 6.83 (1H, d, J = 8.1 Hz, H-5′′), 6.41 (1H, d, J = 15.9 Hz, H-8′′), 5.42 (1H, d, J = 3.6 Hz, H-1′), 4.51 (1H, m, H-6), 4.46 (1H, dd, J = 3.6, 11.8 Hz, H-6′a), 4.17 (2H, m, H-3), 4.10 (1H, m, H-5), 4.02 (1H, m, H-5′), 3.91 (3H, s, -OCH3), 3.88 (1H, m, H-4), 3.86 (1H, m, H-6′b), 3.74 (1H, dd, J = 9.3, 9.3 Hz, H-3′), 3.66 (1H, brs, H-1), 3.44 (1H, dd, J = 3.5, 9.5 Hz, H-2′), 3.37 (1H, m, H-4′); 13C NMR (125 MHz, CD3OD) δC: 169.0 (C-9′′), 150.7 (C-4′′), 149.4 (C-3′′), 147.1 (C-7′′), 127.7 (C-1′′), 124.2 (C-6′′), 116.5 (C-5′′), 115.2 (C-8′′), 111.7 (C-2′′), 105.6 (C-2), 93.5 (C-1′), 80.8 (C-5), 79.0 (C-3), 76.8 (C-4), 74.8 (C-3′), 74.3 (C-2′), 73.3 (C-4′), 71.6 (C-5′), 66.7 (C-6), 63.9 (C-6′), 62.5 (C-1), 56.5 (-OCH3)。以上数据与文献[18]报道β-D-(6-O-trans-Feruloyl)fructofuranosyl-α-D-O-glucopyranosied基本一致。
化合物8   淡黄色无定形粉末, ESI-MS m/z: 195.2 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 6.79 (1H, s, H-2), 6.70 (1H, d, J = 7.9 Hz, H-5), 6.64 (1H, d, J = 7.9 Hz, H-6), 3.82 (3H, s, -OCH3), 2.82 (2H, t, J = 7.6 Hz, H-7), 2.55 (2H, t, J = 7.6 Hz, H-8); 13C NMR (125 MHz, CD3OD) δC: 177.2 (-COOH), 148.8 (C-4), 145.8 (C-5), 133.7 (C-3), 121.6 (C-6), 116.1 (C-2), 113.0 (C-1), 56.3 (-OCH3), 37.3 (C-8), 31.7 (C-7)。以上数据与文献[19]报道二氢阿魏酸基本一致。
化合物9    白色无定形粉末, ESI-MS m/z: 282.2 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 7.92 (1H, s, H-8), 5.68 (1H, d, J = 6.0 Hz, H-1′), 4.38 (1H, t, J = 3.4 Hz, H-2′), 4.07 (1H, t, J = 4.0 Hz, H-3′), 3.88 (1H, d, J = 3.3 Hz, H-4′), 3.59 (1H, dd, J = 3.6, 12.0 Hz, H-5′a), 3.51 (1H, dd, J = 3.6, 12.0 Hz, H-5′b); 13C NMR (125 MHz, CD3OD) δC: 156.7 (C-6), 153.3 (C-2), 151.2 (C-4), 135.8 (C-8), 116.4 (C-5), 86.2 (C-1′), 85.0 (C-4′), 73.4 (C-2′), 70.1 (C-3′), 61.1 (C-5′)。以上数据与文献[20]报道鸟嘌呤核苷基本一致。
化合物10    黄色无定形粉末, ESI-MS m/z: 625.1 [M-H]-。1H NMR (500 MHz, CD3OD) δH: 7.70 (1H, s, H-2′), 7.66 (1H, d, J = 8.4 Hz, H-6′), 6.87 (1H, d, J = 8.4 Hz, H-5′), 6.40 (1H, s, H-8), 6.20 (1H, s, H-6), 5.24 (1H, d, J = 7.4 Hz, H-1′′), 4.15 (1H, d, J = 7.7Hz, H-1′′′), 3.99 (1H, d, J = 11.6 Hz, H-6′′a), 3.87 (1H, d, J = 12.2 Hz, H-6′′′a), 3.76 (1H, dd, J = 2.4, 11.6 Hz, H-6′′b), 3.65 (1H, dd, J = 5.6, 12.2 Hz, H-6′′′b), 3.61 (1H, m, H-5′′), 3.50 (1H, t, J = 8.6 Hz, H-2′′), 3.44 (1H, m, H-3′′), 3.38 (1H, m, H-4′′), 3.23 (1H, t, J = 9.0 Hz, H-3′′′), 3.18 (1H, t, J = 8.9 Hz, H-4′′′), 3.07 (1H, t, J = 8.1 Hz, H-2′′′), 3.01 (1H, m, H-5′′′); 13C NMR (125 MHz, CD3OD) δC: 177.7 (C-4), 164.2 (C-7), 161.3 (C-5), 157.2 (C-9), 156.8 (C-2), 148.1 (C-4′), 144.2 (C-3′), 133.9 (C-3), 121.8 (C-6′), 121.4 (C-1′), 115.9 (C-2′), 114.4 (C-5′), 104.1 (C-10), 102.9 (C-1′′′), 102.3 (C-1′′), 98.2 (C-6), 93.1 (C-8), 76.3 (C-5′′′), 76.2 (C-5′′), 76.1 (C-3′′′), 75.9 (C-3′′), 74.0 (C-2′′), 73.4 (C-2′′′), 69.6 (C-4′′, 4′′′), 67.9 (C-6′′), 60.8 (C-6′′′)。以上数据与文献[21]报道槲皮素-3-O-β-D-龙胆二糖苷基本一致。
4 化合物1与TNF-α的分子对接结合模型
采用自主开发的多靶标分子对接平台, 以TNF-α的晶体结构(PDB ID: 2az5) 为基础开展分子对接, 通过比较化合物1和TNF-α结构中ATP结合位点配体6, 7-dimethyl-3-[(methyl{2-[methyl({1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl}methyl)amino]ethyl}amino)methyl]-4H-chromen-4-one (Kd = 5.36 μmol·L-1) 两者的打分结果, 从而预测化合物1是否具有TNF-α转换酶的抑制活性。
5 化合物1对LPS诱导的RAW264.7细胞的抗炎作用
将RAW264.7细胞培养于含10% FBS、1%青霉素-链霉素的DMEM培养基中, 置于37 ℃、5% CO2培养箱中培养, 收集对数增长期细胞备用。调整细胞数为每毫升4×104个, 然后在24孔细胞培养板中每孔加入2 mL的细胞悬液, 放入37 ℃、5% CO2培养箱中培养。实验分组为正常组、模型组(LPS, 100 ng·mL-1) 和给药组。给药组分别加入LPS (100 ng·mL-1) 和不同浓度的化合物1 (1、10、100 μmol·L-1) 共孵育48 h。48 h后取上清培养液, 按照ELISA试剂盒说明书操作, 检测化合物1对TNF-α释放的影响。
作者贡献: 张勇是本文的第一作者, 负责谷精草化学成分的分离鉴定、活性测试和文章撰写; 朱维良、阿吉艾克拜尔·艾萨负责设计研究; 朱维良是本文的通讯作者, 负责实验设计、分子对接打分预测、论文框架的构建及稿件修改, 并最终定稿。
利益冲突: 作者声明本文的研究内容无任何利益冲突。
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2022年第57卷第7期
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doi: 10.16438/j.0513-4870.2022-0133
  • 接收时间：2022-01-28
  • 首发时间：2025-12-23
  • 出版时间：2022-07-12
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  • 收稿日期：2022-01-28
  • 修回日期：2022-03-08
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国家自然科学基金资助项目(81603270)
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    1.中国科学院新疆理化技术研究所, 省部共建新疆特有药用资源利用国家重点实验室培育基地, 中国科学院干旱区植物资源化学重点实验室, 新疆 乌鲁木齐 830011
    2.中国科学院上海药物研究所, 新药研究国家重点实验室, 中国科学院受体结构与功能重点实验室, 上海 201203
    3.中国科学院大学, 北京 100049

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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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