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Article(id=1210147951108813722, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147945840776034, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2021-1804, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1639584000000, receivedDateStr=2021-12-16, revisedDate=1641484800000, revisedDateStr=2022-01-07, acceptedDate=null, acceptedDateStr=null, onlineDate=1766451355005, onlineDateStr=2025-12-23, pubDate=1657555200000, pubDateStr=2022-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1766451355005, onlineIssueDateStr=2025-12-23, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1766451355005, creator=13701087609, updateTime=1766451355005, 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=2115, endPage=2119, ext={EN=ArticleExt(id=1210147952060920784, articleId=1210147951108813722, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Secondary metabolites from the dandelion-derived endophytic fungus Epicoccum sorghinum 1-2, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

The secondary metabolites from the dandelion-derived Epicoccum sorghinum 1-2 were isolated by silica gel and Sephadex gel column chromatography, and semi-preparative high performance liquid chromatography (HPLC). Their structures were identified by comprehensive NMR and MS methods. Their antibacterial activities were determined by filter paper method. Finally, seven compounds were isolated and identified from the fermentation product of E. sorghinum 1-2, including (4R*, 5R*, 6S*)-4, 5-dihydroxy-6-(6'-methylsalicyloxy)-2-methoxymethyl-2-cyclohexen-l-one (1), (4R*, 5R*, 6S*)-4, 5-dihydroxy-6-(6'-methylsalicyloxy)-2-methyl-2-cyclohexen-1-one (2), (4R, 5R, 6S)-4, 5-dihydroxy-6-(6'-methylsalicyloxy)-2-hydroxymethyl-2-cyclohexen-1-one (3), (-)-gabosine E (4), theobroxide (5), 3-chlorogentisyl alcohol (6), and 3-hydroxybenzyl alcohol (7), of which 1-5 are epoxydons, and 6 and 7 are phenolics. Compounds 1 and 2 are new structures reported for the first time. Compound 6 showed significant antibacterial activity against Staphylococcus aureus.

, correspAuthors=Min CHEN, 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=Bao-cong HAO, Yao-yao ZHENG, Xu CHEN, Qiu-xia CHEN, Ruo-nan JI, Min CHEN), CN=ArticleExt(id=1210147954304872509, articleId=1210147951108813722, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=一株蒲公英内生真菌Epicoccum sorghinum 1-2次级代谢产物研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

运用硅胶柱、凝胶柱和半制备高效液相色谱等方法对一株蒲公英内生真菌Epicoccum sorghinum 1-2发酵产物中的次级代谢产物进行分离纯化，通过核磁共振谱(NMR)及质谱(MS)等现代波谱分析方法进行化合物的结构解析，并采用滤纸片法测定化合物的抗菌活性。最终从E.sorghinum 1-2的发酵产物中分离鉴定了7个化合物，分别为(4R*，5R*，6S*)-4，5-二羟基-6-(6'-甲基水杨酸氧基)-2-甲氧基甲基-2-环己烯-1-酮(1)、(4R*，5R*，6S*)-4，5-二羟基-6-(6'-甲基水杨酸氧基)-2-甲基-2-环己烯-1-酮(2)、(4R，5R，6S)-4，5-二羟基-6-(6'-甲基水杨酸氧基)-2-羟基甲基-2-环己烯-1-酮(3)、(-)-gabosine E (4)、theobroxide (5)、3-氯代龙胆醇(6)和3-羟基苯甲醇(7)。其中化合物1~5是顶环氧菌素类化合物，化合物6和7是苯酚类化合物。化合物1和2为首次报道的新化合物，化合物6对金葡菌具有显著的抑菌作用。

, correspAuthors=陈敏, authorNote=null, correspAuthorsNote=
*陈敏, Tel: 18852703390, E-mail:
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Position12
δC, typeδH, mult. (J in Hz)δC, typeδH, mult. (J in Hz)
1194.0, C193.0, C
2143.4, C143.1, C
3136.5, CH7.08, dt, (6.0, 1.2)137.1, CH6.95, dd, (6.0, 1.8)
467.1, CH4.66, dd, (6.0, 4.2)66.8, CH4.57, dd, (6.0, 4.2)
570.8, CH4.26, dd, (10.8, 4.2)70.8, CH4.22, dd, (10.8, 4.2)
677.6, CH5.99, d, (10.8)77.5, CH5.97, d, (10.8)
768.8, CH24.10, m15.4, CH31.84, s
1′123.5, C123.5, C
2′161.7, C161.8, C
3′115.1, CH6.80, d, (7.8)114.9, CH6.80, d, (7.8)
4′134.6, CH7.34, t, (7.8)134.7, CH7.34, t, (7.8)
5′116.0, CH6.82, d, (7.8)116.0, CH6.82, d, (7.8)
6′141.8, C141.8, C
7′23.0, CH32.54, s23.0, CH32.54, s
8′170.4, C170.4, C
7-OCH358.8, CH33.37, s
), ArticleFig(id=1210147960378225220, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210147951108813722, language=CN, label=Table 1, caption=

1H and 13C NMR spectroscopic data (600/150 MHz, acetone-d6) for 1 and 2

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Position12
δC, typeδH, mult. (J in Hz)δC, typeδH, mult. (J in Hz)
1194.0, C193.0, C
2143.4, C143.1, C
3136.5, CH7.08, dt, (6.0, 1.2)137.1, CH6.95, dd, (6.0, 1.8)
467.1, CH4.66, dd, (6.0, 4.2)66.8, CH4.57, dd, (6.0, 4.2)
570.8, CH4.26, dd, (10.8, 4.2)70.8, CH4.22, dd, (10.8, 4.2)
677.6, CH5.99, d, (10.8)77.5, CH5.97, d, (10.8)
768.8, CH24.10, m15.4, CH31.84, s
1′123.5, C123.5, C
2′161.7, C161.8, C
3′115.1, CH6.80, d, (7.8)114.9, CH6.80, d, (7.8)
4′134.6, CH7.34, t, (7.8)134.7, CH7.34, t, (7.8)
5′116.0, CH6.82, d, (7.8)116.0, CH6.82, d, (7.8)
6′141.8, C141.8, C
7′23.0, CH32.54, s23.0, CH32.54, s
8′170.4, C170.4, C
7-OCH358.8, CH33.37, s
), ArticleFig(id=1210147960499860042, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210147951108813722, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Indicator bacteriaCompound 6Vancomycin
1025502
S. aureus ATCC 4330003.23 ± 0.5110.95 ± 0.315.47 ± 0.57
S. aureus ATCC 3359110.57 ± 0.4911.65 ± 0.8514.43 ± 0.458.29 ± 0.60
S. aureus ATCC 259238.36 ± 0.5510.42 ± 0.1913.72 ± 0.245.37 ± 0.75
S. aureus ATCC 292134.48 ± 0.818.97 ± 0.489.15 ± 0.535.15 ± 0.48
E. faecalis ATCC 512993.12 ± 0.585.34 ± 0.486.34 ± 0.280
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Antibacterial activity results of compound 6 (mm, $ \overline{x} $ ± s, n = 3)

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Indicator bacteriaCompound 6Vancomycin
1025502
S. aureus ATCC 4330003.23 ± 0.5110.95 ± 0.315.47 ± 0.57
S. aureus ATCC 3359110.57 ± 0.4911.65 ± 0.8514.43 ± 0.458.29 ± 0.60
S. aureus ATCC 259238.36 ± 0.5510.42 ± 0.1913.72 ± 0.245.37 ± 0.75
S. aureus ATCC 292134.48 ± 0.818.97 ± 0.489.15 ± 0.535.15 ± 0.48
E. faecalis ATCC 512993.12 ± 0.585.34 ± 0.486.34 ± 0.280
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一株蒲公英内生真菌Epicoccum sorghinum 1-2次级代谢产物研究
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郝宝聪 1 , 郑瑶瑶 1, 2 , 陈旭 1 , 陈秋霞 1 , 季若男 1 , 陈敏 1, *
药学学报 | 研究论文 2022,57(7): 2115-2119
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药学学报 | 研究论文 2022, 57(7): 2115-2119
一株蒲公英内生真菌Epicoccum sorghinum 1-2次级代谢产物研究
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郝宝聪1, 郑瑶瑶1, 2, 陈旭1, 陈秋霞1, 季若男1, 陈敏1, *
作者信息
  • 1.扬州大学环境科学与工程学院, 海洋科学与技术研究所, 江苏 扬州 225127
  • 2.中国海洋大学医药学院, 海洋药物教育部重点实验室, 山东 青岛 266003

通讯作者:

*陈敏, Tel: 18852703390, E-mail:
Secondary metabolites from the dandelion-derived endophytic fungus Epicoccum sorghinum 1-2
Bao-cong HAO1, Yao-yao ZHENG1, 2, Xu CHEN1, Qiu-xia CHEN1, Ruo-nan JI1, Min CHEN1, *
Affiliations
  • 1. Marine Science & Technology Institute, College of Environmental Science & Engineering, Yangzhou University, Yangzhou 225127, China
  • 2. Key Laboratory of Marine Drugs, the Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
出版时间: 2022-07-12 doi: 10.16438/j.0513-4870.2021-1804
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摘要
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运用硅胶柱、凝胶柱和半制备高效液相色谱等方法对一株蒲公英内生真菌Epicoccum sorghinum 1-2发酵产物中的次级代谢产物进行分离纯化，通过核磁共振谱(NMR)及质谱(MS)等现代波谱分析方法进行化合物的结构解析，并采用滤纸片法测定化合物的抗菌活性。最终从E.sorghinum 1-2的发酵产物中分离鉴定了7个化合物，分别为(4R*，5R*，6S*)-4，5-二羟基-6-(6'-甲基水杨酸氧基)-2-甲氧基甲基-2-环己烯-1-酮(1)、(4R*，5R*，6S*)-4，5-二羟基-6-(6'-甲基水杨酸氧基)-2-甲基-2-环己烯-1-酮(2)、(4R，5R，6S)-4，5-二羟基-6-(6'-甲基水杨酸氧基)-2-羟基甲基-2-环己烯-1-酮(3)、(-)-gabosine E (4)、theobroxide (5)、3-氯代龙胆醇(6)和3-羟基苯甲醇(7)。其中化合物1~5是顶环氧菌素类化合物，化合物6和7是苯酚类化合物。化合物1和2为首次报道的新化合物，化合物6对金葡菌具有显著的抑菌作用。

蒲公英内生真菌  /  Epicoccum sorghinum  /  次级代谢产物  /  顶环氧菌素  /  抗菌活性

The secondary metabolites from the dandelion-derived Epicoccum sorghinum 1-2 were isolated by silica gel and Sephadex gel column chromatography, and semi-preparative high performance liquid chromatography (HPLC). Their structures were identified by comprehensive NMR and MS methods. Their antibacterial activities were determined by filter paper method. Finally, seven compounds were isolated and identified from the fermentation product of E. sorghinum 1-2, including (4R*, 5R*, 6S*)-4, 5-dihydroxy-6-(6'-methylsalicyloxy)-2-methoxymethyl-2-cyclohexen-l-one (1), (4R*, 5R*, 6S*)-4, 5-dihydroxy-6-(6'-methylsalicyloxy)-2-methyl-2-cyclohexen-1-one (2), (4R, 5R, 6S)-4, 5-dihydroxy-6-(6'-methylsalicyloxy)-2-hydroxymethyl-2-cyclohexen-1-one (3), (-)-gabosine E (4), theobroxide (5), 3-chlorogentisyl alcohol (6), and 3-hydroxybenzyl alcohol (7), of which 1-5 are epoxydons, and 6 and 7 are phenolics. Compounds 1 and 2 are new structures reported for the first time. Compound 6 showed significant antibacterial activity against Staphylococcus aureus.

dandelion-derived endophytic fungus  /  Epicoccum sorghinum  /  secondary metabolite  /  epoxydon  /  antibacterial activity
郝宝聪, 郑瑶瑶, 陈旭, 陈秋霞, 季若男, 陈敏. 一株蒲公英内生真菌Epicoccum sorghinum 1-2次级代谢产物研究. 药学学报, 2022 , 57 (7) : 2115 -2119 . DOI: 10.16438/j.0513-4870.2021-1804
Bao-cong HAO, Yao-yao ZHENG, Xu CHEN, Qiu-xia CHEN, Ruo-nan JI, Min CHEN. Secondary metabolites from the dandelion-derived endophytic fungus Epicoccum sorghinum 1-2[J]. Acta Pharmaceutica Sinica, 2022 , 57 (7) : 2115 -2119 . DOI: 10.16438/j.0513-4870.2021-1804
正文
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蒲公英(Taraxacum mongolicum Hand.-Mazz.) 为菊科多年生草本植物, 含有多种化学成分, 包括萜[1]、黄酮[2]、香豆素、酚酸、甾醇和色素等[3, 4], 具有抗菌[5]、消炎[6]、利胆保肝[7]、抗肿瘤[8]和抗氧化[9, 10]等生物活性, 这些活性成分目前在临床上被广泛应用[11]。研究表明, 植物内生真菌可以产生与其宿主植物相同或相似的活性成分, 对大规模生产蒲公英药用产品具有重要的意义[12]。近年来, 关于蒲公英内生真菌的分离及筛选研究屡见报道, 其发酵粗产物显示了抗菌、抗肿瘤等生物活性[13, 14], 但蒲公英内生真菌的活性次级代谢产物分离与鉴定的研究报道仅有几例。例如, 2011年, 袁元[15]从蒲公英内生真菌PG23中分离得到间甲基苯酚、邻甲基水杨酸甲酯和2-氢-3-甲基-3-甲酸甲酯苯并噻吩3种抑菌活性物质。2012年, 张慧茹等[16]从蒲公英内生真菌PG2中分离出含有羰基、羟基等官能团的多糖类高抑菌活性物质SP1。2017年, 高原等[14]采用LC-MS/MS方法从蒲公英内生真菌PGY5中发现了木犀草苷, 其具有抗菌、消炎、清除自由基等活性。
本文对一株蒲公英内生真菌Epicoccum sorghinum 1-2的次级代谢产物及其抗菌活性进行研究, 从中分离获得了5个顶环氧菌素类化合物(1~5) 及2个苯酚类化合物(6、7) (图 1), 其中化合物1和2为首次报道的新化合物, 化合物6具有强抑菌作用。
结果与讨论
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1 结构鉴定
化合物1为淡黄色粉末。在其1H NMR谱(表 1) 中显示了1个烯氢信号(δH 7.08)、3个苯环氢信号(δH 7.34、6.82、6.80)、3个含氧次甲基信号(δH 5.99、4.66、4.26)、1个含氧亚甲基信号(δH 4.10)、1个甲氧基信号(δH 3.37) 和1个与苯环相连的甲基信号(δH 2.54)。其13C NMR谱给出了1个α, β不饱和酮羰基碳信号(δC 194.0)、1个酯羰基碳信号(δC 170.4)、8个苯环或双键碳信号(δC 161.7、143.4、141.8、136.5、134.6、123.5、116.0、115.1)、3个含氧次甲基信号(δC 77.6、70.8、67.1)、1个含氧亚甲基信号(δC 68.8)、1个甲氧基碳信号(δC 58.8) 和1个甲基信号(δC 23.0)。以上数据表明化合物1含有1个顶环氧菌素片段和1个6-甲基水杨酸片段, 两个片段通过酯键相连接。该结构与已知化合物(4R, 5R, 6S)-4, 5-二羟基-6-(6′-甲基水杨酸氧基)-2-羟基甲基-2-环己烯-1-酮(3)[17, 18]的结构非常相似。仔细比较化合物1和3的氢谱和碳谱, 发现二者差别仅在于化合物1比3多出了1个甲氧基信号。化合物1的C-7的化学位移为δC 68.8, 与化合物3的C-7的化学位移(δC 57.3) 相比明显移向低场, 表明多出的甲氧基与化合物1的C-7位相连接。因此, 化合物1的平面结构得以确定, 是化合物3的C-7位羟基被甲基化的衍生物。
化合物1的相对构型通过耦合常数确定。化合物1的H-4与H-5之间的耦合常数为4.2 Hz, 而H-5与H-6之间的耦合常数为10.8 Hz, 表明H-4与H-5在环己烯酮环平面的相同侧, 而H-5与H-6在环己烯酮环平面的异侧, 这与已知化合物3的相对构型一致。因此, 新化合物1命名为(4R*, 5R*, 6S*)-4, 5-二羟基-6-(6'-甲基水杨酸氧基)-2-甲氧基甲基-2-环己烯-1-酮。
化合物2为淡黄色粉末, 与化合物1作为混合物(化合物2和1的摩尔比约为1∶2) 共同分离得到。虽尝试了多种分离方法, 仍无法将化合物1和2成功分离。因化合物1和2的摩尔比为2∶1, 在氢谱中可以很清楚地区分两个化合物的信号。化合物2与化合物1的氢谱非常相似, 明显不同之处在于, 在氢谱中化合物2比化合物1少了1个甲氧基信号和1个含氧亚甲基信号, 取而代之的是1个与双键相连的甲基信号(δH 1.84), 表明化合物2的C-7为CH3。两者的碳谱差异也验证了该结构差异之处。化合物2与已报道的化合物(4R, 5R, 6R)-4, 5-二羟基-6-(6′-甲基水杨酸氧基)-2-甲基-2-环己烯-1-酮[19]的平面结构相同, 然而仔细比较分析两个化合物的H-4、H-5和H-6的耦合常数发现两者相对构型存在差异。化合物2的H-4与H-5之间的耦合常数为4.2 Hz, 而H-5与H-6之间的耦合常数为10.8 Hz, 已知化合物(4R, 5R, 6R)-4, 5-二羟基-6-(6′-甲基水杨酸氧基)-2-甲基-2-环己烯-1-酮[19]的H-4与H-5之间的耦合常数为8.0 Hz, 而H-5与H-6之间的耦合常数为11.2 Hz, 表明化合物2构型与化合物1一致。因此新化合物2被鉴定为(4R*, 5R*, 6S*)-4, 5-二羟基-6-(6′-甲基水杨酸氧基)-2-甲基-2-环己烯-1-酮。
化合物3~7的氢谱、碳谱及质谱数据与文献报道基本一致, 均为已知化合物, 分别鉴定为(4R, 5R, 6S)-4, 5-二羟基-6-(6′-甲基水杨酸氧基)-2-羟基甲基-2-环己烯-1-酮[17, 18]、(-)-gabosine E[20]、theobroxide[21]、3-氯代龙胆醇[22]、3-羟基苯甲醇[23]。
2 化合物抗菌活性评价
化合物6对5种致病菌具有抑菌活性, 尤其是对4种金葡菌显示了较强的抗菌活性(表 2、图 2), 其中包括2株耐甲氧西林的金葡菌ATCC 43300和ATCC 33591。推测其活性可能与其分子中的氯原子和酚羟基有关。化合物6的抗菌活性值得深入研究。其他化合物均未显示抗菌活性。
3 小结
从一株蒲公英内生真菌E. sorghinum 1-2的发酵产物中分离并鉴定了7个聚酮类化合物, 包括5个顶环氧菌素类化合物和2个苯酚类化合物, 其中化合物1和2为新化合物。化合物6对4种金葡菌有显著抗菌作用。近年来蒲公英内生真菌的报道多见于真菌的分离与粗提物的活性筛选研究, 而蒲公英内生真菌的次级代谢产物分离与生物活性研究报道较少。本文首次对一株蒲公英内生真菌的次级代谢产物及其抗菌活性进行研究, 从中发现了2个新化合物和1个抑菌活性化合物, 为蒲公英内生真菌的抗菌活性物质的开发和利用奠定了基础。蒲公英作为一种药食同源的中草药, 在药品、食品及保健品等方面有着广泛的开发应用, 其内生真菌作为药用微生物资源的潜力也不容忽视。本课题组将继续对蒲公英内生真菌的抗菌等活性次级代谢产物进行深入研究。
实验部分
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AVANCE 600核磁共振波谱仪、Maxis超高分辨飞行时间质谱仪(德国Bruker公司); Agilent DD2 400 MHz型核磁共振波谱仪(美国Agilent公司); L-2000半制备型高效液相色谱仪[HPLC, Kromasil C18 (5 μm, 250 mm × 10 mm), L-2455检测器, 日本日立公司]; TOMYSX-300SX-500高压灭菌锅(上海珂淮仪器有限公司); R-210旋转蒸发仪(BUCHI实验室设备贸易有限公司)。
葡聚糖凝胶(LH-20, 美国Amersham公司); 十八烷基硅胶(45~60 μm, Unicorn公司); 薄层色谱硅胶板(G60 F-254, 烟台江友硅胶开发有限公司); 琼脂、葡萄糖、提取和分离所用甲醇、乙酸乙酯、二氯甲烷、石油醚等均为分析纯产品(国药集团化学试剂有限公司); 氘代试剂(美国CIL公司); 甲醇(色谱级, 天津四友精细化学品有限公司)。
1 菌株来源与发酵
菌株Epicoccum sorghinum 1-2分离自扬州大学扬子津校园内的蒲公英样品的根部, 保藏于扬州大学环境科学与工程学院海洋科学与技术研究所。该菌经形态学观察及分子生物学鉴定(ITS-rDNA), 确定其种属为Epicoccum sorghinum, 其ITS序列已经提交到NCBI网站, 登录号为MZ148819.1。
将E. sorghinum 1-2菌种从冻存管中取出, 接种到PDA马铃薯琼脂培养基[蒸馏水1 L、土豆200 g (煮沸取汁)、葡萄糖20 g、琼脂20 g] 平板上复苏培养, 然后将生长良好的菌株接种到PDB马铃薯液体培养基[蒸馏水1 L、土豆200 g (煮沸取汁)、葡萄糖20 g] 中, 于28 ℃摇床(150 r·min-1) 培养3天制成种子液备用。将种子液分别接种到75瓶PDB培养基中(1 L锥形瓶, 每瓶加培养基400 mL), 室温静置培养30天后结束发酵。
2 提取与分离
利用纱布将菌体和发酵液分离, 发酵液用乙酸乙酯萃取3次, 经减压浓缩后得到粗浸膏16.5 g。首先用减压硅胶柱对粗浸膏进行梯度洗脱(乙酸乙酯/石油醚, 0~100%; 甲醇/二氯甲烷, 0~100%), 获得6个组分(Frs.1~6)。Fr.3经凝胶柱分离(二氯甲烷/甲醇, v/v = 1∶1)、半制备型HPLC (5%甲醇/水) 分离得到化合物7 (tR = 15.80 min, 3.7 mg)。Fr.4经过正相硅胶柱色谱梯度洗脱(乙酸乙酯/石油醚, 0~100%) 得到Frs.4.1~4.8, 其中Fr.4.1经过凝胶柱分离(二氯甲烷/甲醇, v/v = 1∶1), 再经过ODS柱色谱分离(80%~100%甲醇/水) 以及半制备型HPLC分离(80%甲醇/水) 得到化合物5 (tR = 6.54 min, 8.7 mg); Fr.4.2经过ODS柱色谱分离(70%~100%甲醇/水) 和半制备型HPLC分离(50%甲醇/水) 得到化合物1和2的混合物(tR = 42.67 min, 共22 mg, 化合物1和2的摩尔比约为2∶1); Fr.4.6经过ODS柱色谱分离(80%~100%甲醇/水) 和半制备型HPLC分离(90%甲醇/水) 得到化合物3 (tR = 6.94 min, 20 mg)。Fr.5通过正相硅胶柱色谱梯度洗脱(乙酸乙酯/石油醚, 0~100%) 得到组分Frs.5.1~5.10, 其中Fr.5.2经过凝胶柱分离(二氯甲烷/甲醇, v/v = 1∶1) 及半制备HPLC分离(5%甲醇/水) 得到化合物6 (tR = 31.87 min, 10.0 mg); Fr.5.8经过凝胶柱分离(二氯甲烷/甲醇, v/v = 1∶1) 及半制备HPLC分离(10%甲醇/水)得到化合物4 (tR = 8.28 min, 5.0 mg)。
3 抗菌活性评价
采用滤纸片法[24]测定化合物1~7的抗菌活性, 7种指示菌株包括金葡菌(Staphylococcus aureus ATCC 43300、33591、25923、29213)、粪肠球菌(Enterococcus faecalis ATCC 51299)、屎肠球菌(E. faecium ATCC 35667)、大肠杆菌(Escherichia coli ATCC 25922)。配制细菌用肉膏蛋白胨LB培养基(去离子水1 L、胰蛋白胨10 g、酵母提取物5 g、NaCl 10 g, pH 7.0), 待温度冷却到30~40 ℃时加入200 μL指示菌株混合均匀, 制作平板备用。将化合物配制成50 μg·μL-1的甲醇溶液, 分别用移液枪吸取0.2、0.5及1 μL溶液到滤纸片上(测试浓度分别为每片10、25、50 μg), 待甲醇充分挥干后, 贴在混有指示菌的LB平板上。采用万古霉素为阳性对照药, 测试浓度为每片2 μg。每组设置3组平行实验。放置于37 ℃细菌培养箱培养18~24 h后观察是否产生抑菌圈, 并测量抑菌圈直径(抑菌圈直径=空白圈直径- 滤纸片直径, 单位mm)。
作者贡献: 郝宝聪和陈秋霞完成了化合物的分离和论文初稿的撰写; 郑瑶瑶完成了化合物核磁数据的解析和结构的确定; 陈旭完成了菌种的纯化和发酵萃取; 季若男完成了化合物抑菌圈实验; 陈敏设计了实验方案并对论文进行修改和指导。
利益冲突: 所有作者均声明不存在利益冲突。
基金
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  • 国家自然科学基金资助项目(81703411)
  • 大学生创新创业训练计划项目资助(X20180476)
文献
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doi: 10.16438/j.0513-4870.2021-1804
  • 接收时间：2021-12-16
  • 首发时间：2025-12-23
  • 出版时间：2022-07-12
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  • 收稿日期：2021-12-16
  • 修回日期：2022-01-07
基金
国家自然科学基金资助项目(81703411)
大学生创新创业训练计划项目资助(X20180476)
作者信息
    1.扬州大学环境科学与工程学院, 海洋科学与技术研究所, 江苏 扬州 225127
    2.中国海洋大学医药学院, 海洋药物教育部重点实验室, 山东 青岛 266003

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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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