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Article(id=1199782976188940341, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1199782966441378761, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2024-0648, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1720540800000, receivedDateStr=2024-07-10, revisedDate=1725206400000, revisedDateStr=2024-09-02, acceptedDate=null, acceptedDateStr=null, onlineDate=1763980152412, onlineDateStr=2025-11-24, pubDate=1733932800000, pubDateStr=2024-12-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763980152412, onlineIssueDateStr=2025-11-24, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1763980152412, creator=13701087609, updateTime=1763980152412, updator=13701087609, issue=Issue{id=1199782966441378761, tenantId=1146029695717560320, journalId=1189982191388893191, year='2024', volume='59', issue='12', pageStart='3179', pageEnd='3412', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1763980150088, creator=13701087609, updateTime=1764224975369, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1200809838151324146, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1199782966441378761, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1200809838151324147, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1199782966441378761, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=3335, endPage=3341, ext={EN=ArticleExt(id=1199782976604176451, articleId=1199782976188940341, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Two new diphenyl ethers from the whole plant of Canscora lucidissima, columnId=null, journalTitle=Acta Pharmaceutica Sinica, columnName=null, runingTitle=null, highlight=null, articleAbstract=

Twelve compounds were isolated and purified from 95% ethanol extract of the whole plant of C. lucidissima by silica gel column chromatography, MCI column chromatography and ODS column chromatography, polyamide column chromatography, Sephadex LH-20 column chromatography, combined with semi-preparative HPLC methods. Based on the physicochemical properties and spectral data (UV, IR, MS, NMR), the structures of the isolates were identified as canlucdiphenyl ether A (1), canlucdiphenyl ether B (2), canlucbenzophenone A (3), (-)-pinoresinol (4), 3-hydroxybenzoic acid (5), 1, 3, 8-trihydroxy-6-hydroxymethylanthraquinone (6), dihydrokaempferol (7), 6, 7-dihydroxycoumarin (8), 4-hydroxy-3, 5-dimethoxybenzoic acid (9), 4-hydroxy-3, 5-dimethoxycinnamic acid (10), 2-hydroxy-3-methoxybenzoic acid (11), (-)-syringaresinol (12). Among them, compounds 1 and 2 are two new diphenyl ether and 3 is a new natural product. Compound 8 exhibited some anti-inflammatory activity by inhibiting the lipopolysaccharide-induced NO production in RAW264.7 cells.

, correspAuthors=Tao ZHANG, Zhong-mei ZOU, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2024 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=Meng-yu ZHANG, Jiao LIU, Chang LIU, Tao ZHANG, Zhong-mei ZOU), CN=ArticleExt(id=1199782977489174642, articleId=1199782976188940341, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=穿心草全草中两个新的二苯醚类化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶柱色谱、MCI柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱及ODS柱色谱, 结合半制备高效液相色谱等技术手段, 从穿心草(Canscora lucidissima) 全草95%乙醇提取物中分离纯化得到12个化合物。依据其理化性质和波谱数据(UV、IR、MS、NMR) 等对所分离得到的化合物进行结构鉴定, 分别为穿心草二苯醚A (1)、穿心草二苯醚B (2)、穿心草二苯甲酮A (3)、(-)-松脂素(4)、间羟基苯甲酸(5)、ω-羟基大黄素(6)、二氢山柰酚(7)、6, 7-二羟基香豆素(8)、4-羟基-3, 5-二甲氧基苯甲酸(9)、4-羟基-3, 5-二甲氧基肉桂酸(10)、2-羟基-3-甲氧基苯甲酸(11)、(-)-丁香树脂酚(12)。其中, 化合物1和2为新化合物, 化合物3为新天然产物。化合物8通过抑制脂多糖诱导的RAW264.7细胞NO的生成, 表现出一定的抗炎活性。

, correspAuthors=张涛, 邹忠梅, authorNote=null, correspAuthorsNote=
*张涛, Tel: 86-10-57833281, E-mail: ;
邹忠梅, Tel: 86-10-57833290, E-mail:
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No. 1 2 3
δH (J in Hz) δC δH (J in Hz) δC δH (J in Hz) δC
1 - 147.7 - 138.9 7.11 dd (8.4, 2.4) 124.8
2 6.30 dd (8.4, 3.0) 110.4 6.44 d (9.0) 111.5 6.78 d (8.4) 114.6
3 6.71 d (8.4) 115.8 6.41 d (9.0) 102.4 - 151.2
4 - 142.2 - 145.7 - 147.2
5 - 146.1 - 135.7 7.31d (2.4) 111.5
6 6.40 d (3.0) 108.0 - 137.1 - 130.7
7 - 168.1 - - - 194.2
1′ - 161.4 - 159.1 - 157.6
2′ 5.62 s 95.9 5.74 t (2.4) 95.4 - 106.8
3′ - 159.2 - 160.7 - 157.6
4′ - 101.0 5.88 t (2.4) 93.4 5.82 d (2.4) 94.2
5′ - 160.1 - 161.0 - 160.0
6′ 5.99 s 97.0 5.94 t (2.4) 94.6 5.82 d (2.4) 94.2
4-OCH3 - - 3.63 s 56.0 3.78 s 55.5
7-OCH3 3.72 s 52.0 - - - -
5′-OCH3 - - 3.76 s 55.0 - -
), ArticleFig(id=1200378741420577232, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1199782976188940341, language=CN, label=Table 1, caption=

1H NMR (600 MHz in DMSO-d6) and 13C NMR (150 MHz in DMSO-d6) data of 1-3

, figureFileSmall=null, figureFileBig=null, tableContent=
No. 1 2 3
δH (J in Hz) δC δH (J in Hz) δC δH (J in Hz) δC
1 - 147.7 - 138.9 7.11 dd (8.4, 2.4) 124.8
2 6.30 dd (8.4, 3.0) 110.4 6.44 d (9.0) 111.5 6.78 d (8.4) 114.6
3 6.71 d (8.4) 115.8 6.41 d (9.0) 102.4 - 151.2
4 - 142.2 - 145.7 - 147.2
5 - 146.1 - 135.7 7.31d (2.4) 111.5
6 6.40 d (3.0) 108.0 - 137.1 - 130.7
7 - 168.1 - - - 194.2
1′ - 161.4 - 159.1 - 157.6
2′ 5.62 s 95.9 5.74 t (2.4) 95.4 - 106.8
3′ - 159.2 - 160.7 - 157.6
4′ - 101.0 5.88 t (2.4) 93.4 5.82 d (2.4) 94.2
5′ - 160.1 - 161.0 - 160.0
6′ 5.99 s 97.0 5.94 t (2.4) 94.6 5.82 d (2.4) 94.2
4-OCH3 - - 3.63 s 56.0 3.78 s 55.5
7-OCH3 3.72 s 52.0 - - - -
5′-OCH3 - - 3.76 s 55.0 - -
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穿心草全草中两个新的二苯醚类化合物
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张梦雨 1, 2 , 刘娇 2, 3 , 刘畅 1, 2 , 张涛 2, * , 邹忠梅 1, 2, *
药学学报 | 研究论文 2024,59(12): 3335-3341
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药学学报 | 研究论文 2024, 59(12): 3335-3341
穿心草全草中两个新的二苯醚类化合物
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张梦雨1, 2, 刘娇2, 3, 刘畅1, 2, 张涛2, * , 邹忠梅1, 2, *
作者信息
  • 1.河南中医药大学药学院, 河南 郑州 450046
  • 2.中国医学科学院北京协和医学院, 药用植物研究所, 北京 100193
  • 3.沈阳药科大学中药学院, 辽宁 沈阳 110016

通讯作者:

*张涛, Tel: 86-10-57833281, E-mail: ;
邹忠梅, Tel: 86-10-57833290, E-mail:
Two new diphenyl ethers from the whole plant of Canscora lucidissima
Meng-yu ZHANG1, 2, Jiao LIU2, 3, Chang LIU1, 2, Tao ZHANG2, * , Zhong-mei ZOU1, 2, *
Affiliations
  • 1. School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China
  • 2. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China
  • 3. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
出版时间: 2024-12-12 doi: 10.16438/j.0513-4870.2024-0648
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摘要
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采用硅胶柱色谱、MCI柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱及ODS柱色谱, 结合半制备高效液相色谱等技术手段, 从穿心草(Canscora lucidissima) 全草95%乙醇提取物中分离纯化得到12个化合物。依据其理化性质和波谱数据(UV、IR、MS、NMR) 等对所分离得到的化合物进行结构鉴定, 分别为穿心草二苯醚A (1)、穿心草二苯醚B (2)、穿心草二苯甲酮A (3)、(-)-松脂素(4)、间羟基苯甲酸(5)、ω-羟基大黄素(6)、二氢山柰酚(7)、6, 7-二羟基香豆素(8)、4-羟基-3, 5-二甲氧基苯甲酸(9)、4-羟基-3, 5-二甲氧基肉桂酸(10)、2-羟基-3-甲氧基苯甲酸(11)、(-)-丁香树脂酚(12)。其中, 化合物1和2为新化合物, 化合物3为新天然产物。化合物8通过抑制脂多糖诱导的RAW264.7细胞NO的生成, 表现出一定的抗炎活性。

龙胆科  /  穿心草  /  化学成分  /  二苯醚  /  抗炎作用

Twelve compounds were isolated and purified from 95% ethanol extract of the whole plant of C. lucidissima by silica gel column chromatography, MCI column chromatography and ODS column chromatography, polyamide column chromatography, Sephadex LH-20 column chromatography, combined with semi-preparative HPLC methods. Based on the physicochemical properties and spectral data (UV, IR, MS, NMR), the structures of the isolates were identified as canlucdiphenyl ether A (1), canlucdiphenyl ether B (2), canlucbenzophenone A (3), (-)-pinoresinol (4), 3-hydroxybenzoic acid (5), 1, 3, 8-trihydroxy-6-hydroxymethylanthraquinone (6), dihydrokaempferol (7), 6, 7-dihydroxycoumarin (8), 4-hydroxy-3, 5-dimethoxybenzoic acid (9), 4-hydroxy-3, 5-dimethoxycinnamic acid (10), 2-hydroxy-3-methoxybenzoic acid (11), (-)-syringaresinol (12). Among them, compounds 1 and 2 are two new diphenyl ether and 3 is a new natural product. Compound 8 exhibited some anti-inflammatory activity by inhibiting the lipopolysaccharide-induced NO production in RAW264.7 cells.

Gentiaceae  /  Canscora lucidissima  /  chemical constituent  /  diphenyl ether  /  anti-inflammatory effect
张梦雨, 刘娇, 刘畅, 张涛, 邹忠梅. 穿心草全草中两个新的二苯醚类化合物. 药学学报, 2024 , 59 (12) : 3335 -3341 . DOI: 10.16438/j.0513-4870.2024-0648
Meng-yu ZHANG, Jiao LIU, Chang LIU, Tao ZHANG, Zhong-mei ZOU. Two new diphenyl ethers from the whole plant of Canscora lucidissima[J]. Acta Pharmaceutica Sinica, 2024 , 59 (12) : 3335 -3341 . DOI: 10.16438/j.0513-4870.2024-0648
正文
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龙胆科(Gentiannaceae) 穿心草属(Canscora Lam.) 植物在全球有30余种, 分布于非洲、亚洲及大洋洲的热带和亚热带地区[1]。而在我国仅有3种, 主要分布于华南地区[2], 均被作为民族用药。穿心草[Canscora lucidissima (H. Lév. & Vaniot) Hand.-Mazz.][3], 又称串钱草、穿钱草、顶心风, 为龙胆科穿心草属一年生直立分枝草本植物, 其性凉, 微甘微苦。根据《广西中草药》中记载: “穿心草理气, 止痛, 止咳。治肺热咳嗽, 心胃气痛, 毒蛇咬伤”[4]。现有研究表明, 穿心草中主要含有𠮿酮类、黄酮类、三萜类等化学成分。现代药理学研究表明, 穿心草具有抗炎、抗氧化、抗肿瘤、镇静、抗菌、保肝等多方面药理活性[5-9]。作为壮族、仫佬族等民族特色药材, 资源丰富, 疗效确切, 具有较大的开发潜力。课题组前期从穿心草中发现18个𠮿酮类成分[10], 为了进一步阐明穿心草的药效物质基础, 寻找具有生物活性的化合物, 本文对穿心草95%乙醇提取物的化学成分进行了深入研究, 从其乙酸乙酯萃取部位分离得到12个化合物, 并鉴定为: 穿心草二苯醚A (1)、穿心草二苯醚B (2)、穿心草二苯甲酮A (3)、(-)-松脂素(4)、间羟基苯甲酸(5)、ω-羟基大黄素(6)、二氢山柰酚(7)、6, 7-二羟基香豆素(8)、4-羟基-3, 5-二甲氧基苯甲酸(9)、4-羟基-3, 5-二甲氧基肉桂酸(10)、2-羟基-3-甲氧基苯甲酸(11), (-)-丁香树脂酚(12)。其中化合物1和2为新化合物, 化合物3为新天然产物, 结构如图 1所示, 本文主要介绍了新化合物的分离纯化、结构鉴定以及活性评价。
结果与讨论
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1 结构鉴定
化合物1   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃)。UV显示在207 nm处有最大吸收峰, IR图谱中显示有羟基(3 251 cm-1)、羰基(1 652 cm-1) 和苯环(1 620、1 519 cm-1) 存在。HR-ESI-MS m/z: 291.049 2 [M-H]- (计算值291.050 5, C14H11O7), 结合1H NMR和13C NMR数据推测分子式为C14H12O7。
该化合物1H NMR谱(表 1) 显示苯环上有一对间位取代的芳香族质子信号δH 5.99 (1H, d, J = 2.4 Hz, H-6′), 5.62 (1H, d, J = 2.4 Hz, H-2′); 同时提示结构中还存在一个ABX耦合系统, δH 6.71 (1H, d, J = 8.4 Hz, H-3), 6.40 (1H, d, J = 3.0 Hz, H-6), 6.30 (1H, dd, J = 8.4, 3.0 Hz, H-2)。分析其13C NMR谱(表 1) 共观察到14个碳信号, 包括一个酯羰基信号δC 168.1 (C-7), 一个甲氧基信号δC 52.0 (7-OCH3) 以及12个苯环碳原子信号, 其中包括四个连氧碳原子[δC 147.7 (C-1), 142.2 (C-4), 161.4 (C-1′), 160.1 (C-5′)]。结合化合物的分子式, 除去苯环上四个连氧碳原子及酯羰基上的两个氧原子, 推测另外一个氧原子可能通过形成醚键连接两个苯环, 且该化合物的NMR数据与文献[11, 12]报道的diphlorethol数据类似, 因此可推测该化合物为二苯醚类化合物。
为了确定母核与取代基之间的连接方式, 首先根据HSQC谱确定了与碳直接相关的质子的信号(表 1)。在HMBC谱(图 2) 中, H-2 (δH 6.30)/H-3 (δH 6.71)/H-6 (δH 6.40) 与C-1 (δC 147.7) 和C-4 (δC 142.2) 相关以及H-6 (δH 6.40) 与C-5 (δC 146.1) 相关, 可证实酚羟基取代在C-1位和C-4位; H-2′ (δH 5.62)/H-6′ (δH 5.99) 与C-4′ (δC 101.0)、C-1′ (δC 161.4) 和C-7 (δC 168.1) 相关, H-2′ (δH 5.62) 与C-3′ (δC 159.2) 相关, 以及H-6′ (δH 5.99) 与C-5′ (δC 160.1) 相关, 可证实酚羟基取代在C-1′位和C-5′位, 酯羰基取代在C-4′位; 7-OCH3与C-7 (δC 168.1) 和C-4′ (δC 101.0) 相关, 可证实甲氧基与酯羰基直接相连。根据以上数据, 结合1H-1H COSY谱(图 2) 中的相关信号, 化合物1鉴定为1, 4, 1′, 5′-四羟基-4′-乙酰氧基二苯醚, 命名为穿心草二苯醚A (canlucdiphenyl ether A)。
化合物2   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃)。UV显示在214 nm处有最大吸收峰, IR图谱中显示有羟基(3 271 cm-1) 和苯环(1 602 cm-1) 存在。HR-ESI-MS m/z: 277.071 7 [M-H]- (计算值277.071 2, C14H12O6), 结合1H NMR和13C NMR数据推测分子式为C14H13O6。
该化合物1H NMR谱(表 1) 显示苯环上有一对邻位取代的芳香族质子信号δH 6.44 (1H, d, J = 9.0 Hz, H-2), 6.41 (1H, d, J = 9.0 Hz, H-3); 同时显示三个芳香质子信号δH 5.94 (1H, t, J = 2.4 Hz, H-6′), 5.88 (1H, t, J = 2.4 Hz, H-4′), 5.74 (1H, t, J = 2.4 Hz, H-2′), 提示结构中存在一个1, 3, 5-三取代苯环。分析其13C NMR谱(表 1) 共观察到14个碳信号, 包括2个甲氧基信号δC 56.0 (4-OCH3) 和δC 55.0 (5′-OCH3) 以及12个苯环碳原子信号, 其中包括五个连氧碳原子[δC 138.9 (C-1), 145.7 (C-4), 137.1 (C-6), 159.1 (C-1′), 161.0 (C-5′)]。
为了确定母核与取代基之间的连接方式, 首先根据HSQC谱确定了与碳直接相关的质子的信号(表 1)。将以上数据与化合物1的NMR数据对比时发现化合物2与化合物1结构类似, 区别在于苯环上的4位和5′位羟基变为甲氧基。在HMBC谱(图 2) 中, H3-4 (δH 3.63) 与C-4 (δC 145.7) 的相关以及H3-5′ (δH 3.76) 与C-5′ (δC 161.0) 的相关也证实了这点; 同时结合H-2 (δH 6.44)/H-3 (δH 6.41) 与C-1 (δC 138.9)、C-4 (δC 145.7)、C-5 (δC 135.7) 和C-6 (δC 137.1) 的相关, H3-4 (δH 3.63) 与C-3 (δC 102.4) 的相关, H-2′ (δH 5.74)/H-4′ (δH 5.88)与C-3′ (δC 160.7) 的相关, H-4′ (δH 5.88)/H-6′ (δH 5.94) 与C-5′ (δC 161.0) 的相关以及H-2′ (δH 5.74)/H-6′ (δH 5.94) 与C-1′ (δC 159.1) 的相关, 化合物2鉴定为1, 6, 1′-三羟基-4, 5′-二甲氧基二苯醚, 命名为穿心草二苯醚B (canlucdiphenyl ether B)。
化合物3   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃)。HR-ESI-MS m/z: 275.056 3 [M-H]- (计算值275.055 6, C14H11O6), 结合1H NMR和13C NMR数据推测分子式为C14H12O6。
该化合物1H NMR谱(表 1) 显示苯环上存在一个ABX耦合系统, δH 7.31 (1H, d, J = 2.4 Hz, H-5), 6.78 (1H, d, J = 8.4 Hz, H-2), 7.11 (1H, dd, J = 8.4, 2.4 Hz, H-1); 同时存在一对间位取代的芳香族质子信号δH 5.82 (2H, d, J = 2.4 Hz, H-4′, H-6′)。分析其13C NMR谱(表 1) 共观察到14个碳信号, 包括一个酮羰基信号δC 194.2 (C-7), 一个甲氧基信号δC 55.5 (4-OCH3) 以及12个苯环碳原子信号, 其中包括五个连氧碳原子[δC 151.2 (C-3), 147.2 (C-4), 157.6 (C-1′), 157.6 (C-3′), 160.0 (C-5′)]。在1H NMR和13C NMR谱中羟基信号、芳香氢信号和芳香碳信号有重叠现象, 推测该化合物中有对称结构的苯环片段。
为了确定母核与取代基之间的连接方式, 首先根据HSQC谱确定了与碳直接相关的质子的信号(表 1)。将化合物3的NMR数据与文献[13]报道的mangostanone II对比时发现数据类似, 因此推测该化合物为二苯甲酮类化合物, 区别在于苯环上的4位羟基变为甲氧基, 5′位甲氧基变为羟基。在HMBC谱(图 2) 中H3-4 (δH 3.78)与C-4 (δC 147.2) 和C-5 (δC 111.5) 的相关信号以及1H-1H COSY谱(图 2) 中H3-4 (δH 3.78) 与C-5 (δC 111.5) 的相关信号也证实了这点; 结合H-1 (δH 7.11)/H-2 (δH 6.78)/H-5 (δH 7.31) 与C-3 (δC 151.2)、C-4 (δC 147.2) 和C-7 (δC 194.2) 的相关以及H-4′ (δH 5.82)/H-6′ (δH 5.82) 与C-1′ (δC 157.6)、C-2′ (δC 106.8)、C-3′ (δC 157.6) 和C-5′ (δC 160.0) 的相关, 化合物3鉴定为3, 1′, 3′, 5′-四羟基-4-甲氧基二苯甲酮, 命名为穿心草二苯甲酮A (canlucbenzophenone A)。经SciFinder数据库检索发现该化合物目前仅通过合成[14]获得, 因此该化合物为新天然产物, 本文首次报道了该化合物核磁和质谱数据。
2 化合物的活性测试
采用MTT法检测化合物1~12对RAW264.7细胞活力的影响, 结果显示所有化合物在浓度为50 μmol·L-1时对RAW264.7细胞活力无明显影响。以地塞米松为阳性对照, 进一步对化合物1~12进行抗炎活性筛选发现, 地塞米松在10 μmol·L-1浓度下对NO生成的抑制率为87.32%; 化合物8通过抑制脂多糖诱导的RAW264.7细胞NO的生成, 表现出一定的抗炎活性(IC50为38.05 ± 3.45 μmol·L-1)。其余化合物在50 μmol·L-1浓度下未表现明显抗炎活性。
此外, 采用MTT法检测化合物1~12对人胃SGC7901细胞的细胞毒活性。结果显示, 化合物1~12对人胃SGC7901细胞在50 μmol·L-1浓度下均未表现出明显的抑制作用。
实验部分
收起
Nicolet IS5 FT-IR红外光谱仪和Thermo Genesys-10S UV-vis紫外分光光度仪(美国赛默飞世尔科技有限公司); Bruker AM 600型核磁共振仪(瑞士布鲁克科技有限公司); Q-TOF SYNAPT HDMS质谱仪和Waters 2535型semi-PHPLC (配置2489型UV检测器) (美国沃特世科技有限公司); YMC-Pack ODS-A色谱柱(250 mm × 10 mm, 5 μm)、YMC-Pack ODS-A色谱柱(250 mm × 20 mm, 5 μm) 和YMC-Pack ODS-A色谱柱(250 mm × 30 mm, 5 μm), 日本YMC株式会社; Buchi Heating Both Ⅱ 490型旋转蒸发仪(瑞士步琦有限公司); SephadexLH-20柱色谱材料(美国Parmacia Biotech公司); 柱色谱用硅胶和薄层色谱用硅胶GF254 (60~100、100~200、200~300和300~400目, 青岛海洋化工有限公司); 真空隔膜泵(德国伊尔姆真空泵制造有限公司); SHB-B型循环水式真空泵(郑州长城科工贸有限公司); JY02S型紫外分析仪(北京君意设备有限公司); 色谱甲醇、色谱乙腈(天津市永大化学试剂有限公司); 常规用试剂均为分析级(北京化工厂); CKX41显微镜(日本奥林巴斯株式会社); 洁净工作台(北京东联哈尔仪器制造有限公司); MCO-15AC细胞孵育箱(日本三洋贸易株式会社); 细胞级DMSO、DMEM培养基、胎牛血清(FBS), 美国Gibco生物技术有限公司; 细胞增殖及毒性检测试剂(MTT, 大连美仑生物技术有限公司)。
穿心草于2019年8月购自广西省玉林市玉州区偏冷中药材购销部, 经广西中医药研究院中药资源研究所黄云峰研究员鉴定为龙胆科穿心草属植物穿心草Canscora lucidissima干燥全草。标本(SCI-NCL006382) 现存于中国医学科学院药用植物研究所国家中药化合物库。
1 提取分离
将穿心草全草30 kg粉碎, 用95%乙醇加热回流提取2次, 每次2 h, 合并提取液, 减压浓缩得到95%乙醇总浸膏5 kg。取95%乙醇浸膏4.3 kg, 用9 L蒸馏水分散后, 分别用石油醚、乙酸乙酯、正丁醇进行萃取, 得到石油醚部位Fr.A (583 g)、乙酸乙酯部位Fr.B (1 147 g)、正丁醇部位Fr.C (923 g)、水部位Fr.D (1 298 g)。
取乙酸乙酯部位Fr.B (1 000 g) 经硅胶柱色谱分离, 以石油醚-丙酮系统(10∶1~0∶100) 梯度洗脱, 通过TLC检测合并, 得到Fr.B1~Fr.B5共5个流分。Fr.B4 (240 g) 经硅胶柱色谱, 以石油醚-丙酮系统(4∶1~0∶100) 洗脱, 通过TLC合并得到Fr.B4.1~Fr.B4.5共5个亚组分。Fr.B4.2 (1.5 g) 经MCI柱色谱(MeOH-H2O, 80∶20~0∶100) 洗脱除去色素得到Fr.B4.2.1 (1 g)。Fr.B4.2.1 (1 g) 经半制备高效液相(57%甲醇-0.1%甲酸水) 得到Fr.B4.2.1.1~Fr.B4.2.1.10共10个亚组分。Fr.B4.2.1.2 (160 mg) 经半制备高效液相(40%乙腈-0.1%甲酸水) 纯化, 得到化合物4 (tR = 21.6 min; 35.5 mg); Fr.B4.2.1.10 (16 mg) 经半制备高效液相(52%乙腈-0.1%甲酸水) 纯化, 得到化合物6 (tR = 8.7 min; 1.7 mg)。
将Fr.B4.3 (73 g) 分离沉淀与母液, 母液(50 g) 经MCI柱色谱(MeOH-H2O, 70∶30~0∶100) 洗脱除去色素得到Fr.B4.3.1~Fr.B4.3.6共6个亚组分; Fr.B4.4 (32.1 g) 经MCI柱色谱(MeOH-H2O, 50∶50~0∶100) 洗脱除去色素得到Fr.B4.4.1 (29 g)。将Fr.B4.3.1、Fr.B4.3.2以及Fr.B4.4.1合并(46 g) 经硅胶柱色谱, 以二氯甲烷-甲醇系统(100∶0~0∶100) 洗脱, 通过TLC合并得到Fr.B4.4.1.1~Fr.B4.4.1.5共5个亚组分。Fr.B4.4.1.3 (4.9 g) 经聚酰胺柱色谱, 以二氯甲烷-甲醇系统(100∶0~0∶100) 洗脱, 得到Fr.B4.4.1.3.1~Fr.B4.4.1.3.5共5个亚组分。Fr.B4.4.1.3.5 (210 mg) 经半制备高效液相(50%甲醇-0.1%甲酸水) 纯化, 得到化合物11 (tR = 27.1 min; 3.7 mg)。Fr.B4.4.1.3.1 (2.8 g) 经硅胶柱色谱, 以二氯甲烷-甲醇系统(100∶0~0∶100) 洗脱, 通过TLC合并得到Fr.B4.4.1.3.1.1~Fr.B4.4.1.3.1.4共4个亚组分。Fr.B4.4.1.3.1.2 (73 mg) 经半制备高效液相(35%甲醇-0.1%甲酸水) 纯化, 得到化合物9 (tR = 23.1 min; 5.0 mg) 和化合物10 (tR = 42.9 min; 3.1 mg)。Fr.B4.4.1.3.3 (1.7 g) 经Sephadex LH-20凝胶柱色谱分离, 甲醇洗脱, 通过TLC合并得到Fr.B4.4.1.3.3.1~Fr.B4.4.1.3.3.15共15个流分。Fr.B4.4.1.3.3.3 (160 mg) 经半制备高效液相(30%甲醇-0.1%甲酸水) 纯化, 得到化合物8 (tR = 19.2 min; 66.6 mg); Fr.B4.4.1.3.3.4 (47 mg) 经半制备高效液相(30%乙腈-0.1%甲酸水) 纯化, 得到化合物3 (tR = 28.1 min; 4.0 mg)。Fr.B4.4.1.3.4 (460 mg) 经半制备高效液相(30%乙腈-0.1%甲酸水) 得到Fr.B4.4.1.3.4.1~Fr.B4.4.1.3.4.5共5个亚组分; Fr.B4.4.1.3.4.1 (29 mg) 经半制备高效液相(12%乙腈-0.1%甲酸水) 纯化, 得到化合物5 (tR = 10.4 min; 3.5 mg) 和化合物1 (tR = 13.9 min; 2.5 mg); Fr.B4.4.1.3.4.2 (32 mg) 经半制备高效液相(40%乙腈-0.1%甲酸水) 纯化, 得到化合物7 (tR = 21.9 min; 8.6 mg); Fr.B4.4.1.3.4.4 (29 mg) 经半制备高效液相(30%乙腈-0.1%甲酸水) 纯化, 得到化合物2 (tR = 32.4 min; 3.5 mg)。Fr.B4.4.1.2 (3.1 g) 经Sephadex LH-20凝胶柱色谱分离, 甲醇洗脱, 通过TLC合并得到Fr.B4.4.1.2.1~Fr.B4.4.1.2.5共5个流分; Fr.B4.4.1.2.1 (2.2 g) 经ODS柱色谱, 以甲醇-水系统(0∶100~100∶0) 洗脱, 通过TLC合并得到Fr.B4.4.1.2.1.1~Fr.B4.4.1.2.1.5共5个亚组分; Fr.B4.4.1.2.1.3 (640 mg) 经半制备高效液相(50%乙腈-0.1%甲酸水) 纯化, 得到化合物12 (tR = 24.2 min; 207 mg)。
2 结构鉴定
化合物1   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), UV显示在207 nm处有最大吸收峰, IR图谱中显示有羟基(3 251 cm-1)、羰基(1 652 cm-1) 和苯环(1 620、1 519 cm-1) 存在。HR-ESI-MS m/z: 291.049 2 [M-H]- (计算值291.050 5, C14H11O7), 推测分子式为C14H12O7。1H NMR (600 MHz, DMSO-d6) 和13C NMR (150 MHz, DMSO-d6) 数据见表 1。
化合物2   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), UV显示在214 nm处有最大吸收峰, IR图谱中显示有羟基(3 271 cm-1) 和苯环(1 602 cm-1) 存在。HR-ESI-MS m/z: 277.071 7 [M-H]- (计算值277.071 2, C14H12O6), 推测分子式为C14H13O6。1H NMR (600 MHz, DMSO-d6) 和13C NMR (150 MHz, DMSO-d6) 数据见表 1。
化合物3   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), HR-ESI-MS m/z: 275.056 3 [M-H]- (计算值275.055 6, C14H11O6), 推测分子式为C14H12O6。1H NMR (600 MHz, DMSO-d6) 和13C NMR (150 MHz, DMSO-d6) 数据见表 1。
化合物4   无色油状物, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显浅黄色(120 ℃), HR-ESI-MS m/z: 359.147 4 [M+H]+ (计算值359.144 4, C20H23O6), 推测分子式为C20H22O6。1H NMR (600 MHz, DMSO-d6) δH 8.94 (2H, s, 4-OH, 4′-OH), 6.89 (2H, d, J = 1.8 Hz, H-2, H-2′), 6.75 (2H, dd, J = 8.4, 1.8 Hz, H-6, H-6′), 6.72 (2H, d, J = 8.4 Hz, H-5, H-5′), 4.60 (2H, d, J = 4.2 Hz, H-7, H-7′), 4.11 (2H, dd, J = 9.0, 6.6 Hz, H-9a, H-9′a), 3.76 (6H, s, 3-OCH3, 3′-OCH3), 3.71 (2H, dd, J = 9.0, 3.6 Hz, H-9b, H-9′b), 3.03 (2H, m, H-8, H-8′); 13C NMR (150 MHz, DMSO-d6) δC 132.2 (C-1, C-1′), 110.4 (C-2, C-2′), 147.5 (C-3, C-3′), 145.9 (C-4, C-4′), 115.1 (C-5, C-5′), 118.7 (C-6, C-6′), 85.2 (C-7, C-7′), 53.6 (C-8, C-8′), 70.9 (C-9, C-9′), 55.6 (3-OCH3, 3′-OCH3); 以上数据与文献[15]报道基本一致, 故鉴定化合物4为(-)-松脂素。
化合物5   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), HR-ESI-MS m/z: 137.024 2 [M-H]- (计算值137.023 9, C7H5O3), 推测分子式为C7H6O3。1H NMR (600 MHz, DMSO-d6) δH 7.36 (1H, dd, J = 8.4, 2.4 Hz, H-3), 7.33 (1H, d, J = 2.4 Hz, H-1), 7.26 (1H, t, J = 8.4 Hz, H-4), 6.96 (2H, dd, J = 8.4, 2.4 Hz, H-5); 13C NMR (150 MHz, DMSO-d6) δC 115.9 (C-1), 133.0 (C-2), 120.0 (C-3), 119.5 (C-4), 133.0 (C-5), 157.4 (C-6), 167.7 (C-7); 以上数据与文献[16]报道基本一致, 故鉴定化合物5为间羟基苯甲酸。
化合物6   红棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显黄色(120 ℃), HR-ESI-MS m/z: 285.036 8 [M-H]- (计算值285.039 9, C15H9O6), 推测分子式为C15H10O6。1H NMR (600 MHz, CD3OD) δH 7.73 (1H, d, J = 2.4 Hz, H-5), 7.27 (1H, d, J = 8.4, 2.4 Hz, H-7), 7.19 (1H, d, J = 2.4 Hz, H-4), 6.55 (1H, d, J = 2.4 Hz, H-2), 4.69 (1H, s, H-1′), 4.63 (1H, s, H-2′); 13C NMR (150 MHz, CD3OD) δC 161.4 (C-1), 122.2 (C-2), 153.1 (C-3), 118.4 (C-4), 134.9 (C-4a), 110.6 (C-5), 136.9 (C-5a), 163.7 (C-6), 110.3 (C-7), 166.7 (C-8), 191.8 (C-9), 183.2 (C-10), 64.1 (CH2OH); 以上数据与文献[17]报道基本一致, 故鉴定化合物6为ω-羟基大黄素。
化合物7   淡黄色粉末, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显黄色(120 ℃), HR-ESI-MS m/z: 287.051 2 [M-H]- (计算值287.055 6, C15H11O6), 推测分子式为C15H12O6。1H NMR (600 MHz, DMSO-d6) δH 7.31 (2H, m, H-2′, 6′), 6.78 (2H, m, H-3′, 5′), 5.89 (1H, d, J = 1.8 Hz, H-4), 5.83 (1H, d, J = 2.4 Hz, H-2), 5.03 (1H, d, J = 11.4 Hz, H-7), 4.68 (1H, d, J = 11.4 Hz, H-6); 13C NMR (150 MHz, DMSO-d6) δC 163.3 (C-1), 96.2 (C-2), 167.4 (C-3), 95.2 (C-4), 162.6 (C-5), 82.9 (C-6), 71.5 (C-7), 197.8 (C-8), 100.3 (C-9), 129.5 (C-1′), 127.6 (C-2′), 114.7 (C-3′), 157.8 (C-4′), 114.9 (C-5′), 128.9 (C-6′); 以上数据与文献[18]报道基本一致, 故鉴定化合物7为二氢山柰酚。
化合物8   棕色固体, 溶于甲醇, 紫外254 nm下显示为蓝色荧光, 10%浓硫酸乙醇溶液加热显淡黄色(120 ℃), HR-ESI-MS m/z: 177.015 8 [M-H]- (计算值177.018 8, C9H5O4), 推测分子式为C9H6O4。1H NMR (600 MHz, DMSO-d6) δH 9.83 (2H, s, 2-OH, 3-OH), 7.86 (1H, d, J = 9.6 Hz, H-8), 6.97 (1H, s, H-1), 6.74 (1H, s, H-4), 6.16 (1H, d, J = 9.0 Hz, H-7); 13C NMR (150 MHz, DMSO-d6) δC 160.9 (C-2), 111.6 (C-3), 144.5 (C-4), 112.4 (C-5), 142.9 (C-6), 150.4 (C-7), 102, 7 (C-8), 148.6 (C-9), 110.8 (C-10); 以上数据与文献[19]报道基本一致, 故鉴定化合物8为6, 7-二羟基香豆素。
化合物9   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), HR-ESI-MS m/z: 197.040 7 [M-H]- (计算值197.045 0, C9H9O5), 推测分子式为C9H10O5。1H NMR (600 MHz, CD3OD) δH 7.33 (2H, s, H-2, H-6), 3.88 (6H, s, 3-OCH3, 5-OCH3); 13C NMR (150 MHz, CD3OD) δC 122.3 (C-1), 108.2 (C-2), 148.8 (C-3), 141.5 (C-4), 148.8 (C-5), 108.2 (C-6), 164.5 (C-7), 56.7 (3-OCH3), 56.7 (5-OCH3); 以上数据与文献[20]报道基本一致, 故鉴定化合物9为4-羟基-3, 5-二甲氧基苯甲酸。
化合物10   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), HR-ESI-MS m/z: 223.061 7 [M-H]- (计算值223.060 6, C11H11O5), 推测分子式为C11H12O5。1H NMR (600 MHz, CD3OD) δH 7.56 (1H, d, J = 16.2 Hz, H-7), 6.90 (2H, s, H-2, H-6), 6.35 (1H, d, J = 15.6 Hz, H-8), 3.88 (6H, s, 3-OCH3, 5-OCH3); 13C NMR (150 MHz, CD3OD) δC 126.9 (C-1), 108.9 (C-2), 148.6 (C-3), 139.2 (C-4), 149.4 (C-5), 106.6 (C-6), 146.5 (C-7), 117.2 (C-8), 171.5 (C-9), 56.7 (3-OCH3), 56.7 (5-OCH3); 以上数据与文献[21]报道基本一致, 故鉴定化合物10为4-羟基-3, 5-二甲氧基肉桂酸。
化合物11   棕色固体, 溶于甲醇, 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), HR-ESI-MS m/z: 167.034 8 [M-H]- (计算值167.034 4, C8H7O4), 推测分子式为C8H8O4。1H NMR (600 MHz, CD3OD) δH 7.31 (1H, dd, J = 7.8, 1.8 Hz, H-6), 7.00 (2H, dd, J = 7.8, 1.8 Hz, H-4), 6.65 (1H, t, J = 7.8 Hz, H-5), 3.74 (3H, s, 3-OCH3); 13C NMR (150 MHz, CD3OD) δC 115.4 (C-1), 152.8 (C-2), 148.1 (C-3), 116.4 (C-4), 121.6 (C-5), 118.2 (C-6), 172.1 (C-7), 55.7 (6-OCH3); 以上数据与文献[22]报道基本一致, 故鉴定化合物11为2-羟基-3-甲氧基苯甲酸。
化合物12   白色针晶(甲醇), 紫外254 nm下显示为暗斑, 10%浓硫酸乙醇溶液加热显棕色(120 ℃), HR-ESI-MS m/z: 419.167 3 [M+H]+ (计算值419.170 6, C22H27O8), 推测分子式为C22H26O8。1H NMR (600 MHz, DMSO-d6) δH 8.30 (2H, s, 4-OH, 4′-OH), 6.60 (4H, s, H-2, H-2′, H-6, H-6′), 4.60 (2H, d, J = 4.2 Hz, H-7, H-7′), 4.61 (2H, m, H-9a, H-9′a), 3.75 (12H, s, 3-OCH3, 3′-OCH3, 5-OCH3, 5′-OCH3), 3.77 (2H, m, H-9b, H-9′b), 3.05 (2H, m, H-8, H-8′); 13C NMR (150 MHz, DMSO-d6) δC 131.4 (C-1, C-1′), 103.6 (C-2, C-2′), 147.9 (C-3, C-3′), 134.8 (C-4, C-4′), 147.9 (C-5, C-5′), 103.6 (C-6, C-6′), 85.4 (C-7, C-7′), 53.7 (C-8, C-8′), 71.1 (C-9, C-9′), 56.0 (3-OCH3, 3-OCH3′, 5-OCH3, 5-OCH3′); 以上数据与文献[23]报道基本一致, 故鉴定化合物12为(-)-丁香树脂酚。
3 活性测试
3.1 化合物1~12对RAW264.7细胞活力影响
采用MTT法检测化合物1~12对RAW264.7的细胞毒活性。待RAW264.7细胞处于对数生长期时, 用一次性无菌刮刀将其轻轻刮下, 用完全培养基将其制成每毫升2×106个细胞的混悬液, 按每孔100 μL的体积接种于96孔板中, 待细胞贴壁后加入50 μmol·L-1浓度的单体化合物100 μL, 向空白组中加入100 μL含DMSO的空白培养基, 培养箱孵育24 h后, 向每孔加入MTT 10 μL, 细胞培养箱内孵育4 h后, 吸干上清, 每孔加入100 μL DMSO溶解, 振荡15 min后在波长490 nm下测定各孔吸光度值。实验重复三次, 每组设置三个平行复孔, 结果取平均值。
3.2 化合物1~12对LPS诱导的RAW 264.7细胞中NO水平的影响
采用脂多糖LPS刺激小鼠巨噬细胞RAW264.7模型, 检测对NO释放量的影响。实验设置为正常对照组、LPS (10 ng·mL-1) 模型组、化合物(50、25、12.5、6.25、3.125 μmol·L-1) 给药组, 以地塞米松(dexamethasone, 10 μmol·L-1) 为阳性对照。取对数生长期的RAW264.7细胞以每毫升2×106个接种于96孔板中, 每孔加100 μL细胞悬液, 随后加入DEX、不同浓度化合物和LPS, 在CO2细胞孵育箱中培养24 h之后, 吸取50 μL细胞培养上清液到新的96孔板中, 分别加入Griess Ⅰ和Griess Ⅱ各50 μL, 振荡15 min使其充分反应, 于540 nm波长处测定各孔吸光度值, 最后根据标准曲线计算出每孔NO含量[24]。实验重复三次, 每组设置三个平行复孔, 结果取平均值。
3.3 化合物1~12人胃癌SGC-7901细胞的细胞毒活性测试
采用MTT法检测化合物1~12对人胃癌细胞SGC-7901的细胞毒活性。取培养至第三代以上且长至90%的细胞, 以每孔6×103个细胞均匀接种于96孔板, 每孔100 μL, 置于37 ℃、5% CO2培养箱中培养24 h。待细胞贴壁后弃掉完全培养基, 实验组加入50 μmol·L-1浓度的单体化合物100 μL, 每个浓度设3个复孔, 空白对照组加入100 μL空白培养基(含千分之一DMSO), 阳性对照药选用伏立诺他(vorinostat, 10 μmol·L-1)。继续孵育48 h后, 吸掉上清, 每孔避光加入10 μL的MTT, 继续孵育4 h。孵育完成后, 吸掉上清, 加入DMSO 100 μL, 用酶标仪缓慢振板15 min后于490 nm处测其吸光度并计算细胞存活率。
3.4 统计学分析
采用GraphPad Prism (version 8) 统计学软件对实验结果进行统计学分析。实验重复3次, 每组设置3个平行复孔, 结果取平均值, 所有数据均以$ \overline{x} $ ± s表示。各组分别与对照组进行单因素方差分析, 以P < 0.01为差异有统计学意义。
作者贡献: 邹忠梅负责研究方案设计、写作建议、论文修改并最终定稿; 张涛负责实验和写作指导、论文修改; 张梦雨负责整体实验、数据分析处理及文章撰写; 刘娇、刘畅参与穿心草全草样品提取与萃取工作。
利益冲突: 所有作者均声明不存在利益冲突。
基金
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  • 中国医学科学院医学与健康科技创新工程项目(2022-I2M-1-017)
  • 国家“重大新药创制”科技重大专项(2019ZX09735002)
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doi: 10.16438/j.0513-4870.2024-0648
  • 接收时间：2024-07-10
  • 首发时间：2025-11-24
  • 出版时间：2024-12-12
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  • 收稿日期：2024-07-10
  • 修回日期：2024-09-02
基金
中国医学科学院医学与健康科技创新工程项目(2022-I2M-1-017)
国家“重大新药创制”科技重大专项(2019ZX09735002)
作者信息
    1.河南中医药大学药学院, 河南 郑州 450046
    2.中国医学科学院北京协和医学院, 药用植物研究所, 北京 100193
    3.沈阳药科大学中药学院, 辽宁 沈阳 110016

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*张涛, Tel: 86-10-57833281, E-mail: ;
邹忠梅, Tel: 86-10-57833290, 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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