Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B

Two previously undescribed lactones, phomolides A and B (1 and 2), and three new sesquiterpenoids, phomenes A–C (3–5), together with one known compound, colletotricholide A (6), were isolated from the endophytic fungus Phomopsis sp. SZSJ-7B. Their chemical structures, including the absolute configur...

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Main Authors: Yan Chen, Huan Wang, Xin Ke, Zihuan Sang, Min Kuang, Weiwei Peng, Jianbing Tan, Yuting Zheng, Zhenxing Zou, Haibo Tan
Format: Article
Language:English
Published: Frontiers Media S.A. 2022-11-01
Series:Frontiers in Plant Science
Subjects:
Online Access:https://www.frontiersin.org/articles/10.3389/fpls.2022.1049015/full
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author Yan Chen
Yan Chen
Yan Chen
Huan Wang
Xin Ke
Xin Ke
Xin Ke
Zihuan Sang
Zihuan Sang
Zihuan Sang
Min Kuang
Min Kuang
Weiwei Peng
Weiwei Peng
Weiwei Peng
Jianbing Tan
Jianbing Tan
Yuting Zheng
Yuting Zheng
Zhenxing Zou
Zhenxing Zou
Haibo Tan
Haibo Tan
Haibo Tan
author_facet Yan Chen
Yan Chen
Yan Chen
Huan Wang
Xin Ke
Xin Ke
Xin Ke
Zihuan Sang
Zihuan Sang
Zihuan Sang
Min Kuang
Min Kuang
Weiwei Peng
Weiwei Peng
Weiwei Peng
Jianbing Tan
Jianbing Tan
Yuting Zheng
Yuting Zheng
Zhenxing Zou
Zhenxing Zou
Haibo Tan
Haibo Tan
Haibo Tan
author_sort Yan Chen
collection DOAJ
description Two previously undescribed lactones, phomolides A and B (1 and 2), and three new sesquiterpenoids, phomenes A–C (3–5), together with one known compound, colletotricholide A (6), were isolated from the endophytic fungus Phomopsis sp. SZSJ-7B. Their chemical structures, including the absolute configurations, were comprehensively established by extensive analyses of NMR, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism powered by theoretical calculations, and X-ray diffractions. Moreover, the cytotoxic and antibacterial activities of compounds 1–6 were also evaluated, and the results demonstrated that compound 2 showed significant antibacterial effects towards methicillin-resistant Staphylococcus aureus and S. aureus strains with minimum inhibitory concentration as low as 6.25 μg/ml, which was comparable to that of the clinical drug vancomycin. Moreover, all compounds showed no cytotoxic activity.
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spelling doaj.art-da3d196769eb478cbc08f240bcbbca9c2022-12-22T04:35:30ZengFrontiers Media S.A.Frontiers in Plant Science1664-462X2022-11-011310.3389/fpls.2022.10490151049015Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7BYan Chen0Yan Chen1Yan Chen2Huan Wang3Xin Ke4Xin Ke5Xin Ke6Zihuan Sang7Zihuan Sang8Zihuan Sang9Min Kuang10Min Kuang11Weiwei Peng12Weiwei Peng13Weiwei Peng14Jianbing Tan15Jianbing Tan16Yuting Zheng17Yuting Zheng18Zhenxing Zou19Zhenxing Zou20Haibo Tan21Haibo Tan22Haibo Tan23Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaKey Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, ChinaKey Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaKey Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaKey Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaKey Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaXiangya School of Pharmaceutical Sciences, Central South University, Changsha, ChinaHunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, ChinaKey Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, ChinaTwo previously undescribed lactones, phomolides A and B (1 and 2), and three new sesquiterpenoids, phomenes A–C (3–5), together with one known compound, colletotricholide A (6), were isolated from the endophytic fungus Phomopsis sp. SZSJ-7B. Their chemical structures, including the absolute configurations, were comprehensively established by extensive analyses of NMR, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism powered by theoretical calculations, and X-ray diffractions. Moreover, the cytotoxic and antibacterial activities of compounds 1–6 were also evaluated, and the results demonstrated that compound 2 showed significant antibacterial effects towards methicillin-resistant Staphylococcus aureus and S. aureus strains with minimum inhibitory concentration as low as 6.25 μg/ml, which was comparable to that of the clinical drug vancomycin. Moreover, all compounds showed no cytotoxic activity.https://www.frontiersin.org/articles/10.3389/fpls.2022.1049015/fullendophytic fungusPhomopsissecondary metabolitesantibacterial activitycytotoxic activity
spellingShingle Yan Chen
Yan Chen
Yan Chen
Huan Wang
Xin Ke
Xin Ke
Xin Ke
Zihuan Sang
Zihuan Sang
Zihuan Sang
Min Kuang
Min Kuang
Weiwei Peng
Weiwei Peng
Weiwei Peng
Jianbing Tan
Jianbing Tan
Yuting Zheng
Yuting Zheng
Zhenxing Zou
Zhenxing Zou
Haibo Tan
Haibo Tan
Haibo Tan
Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B
Frontiers in Plant Science
endophytic fungus
Phomopsis
secondary metabolites
antibacterial activity
cytotoxic activity
title Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B
title_full Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B
title_fullStr Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B
title_full_unstemmed Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B
title_short Five new secondary metabolites from an endophytic fungus Phomopsis sp. SZSJ-7B
title_sort five new secondary metabolites from an endophytic fungus phomopsis sp szsj 7b
topic endophytic fungus
Phomopsis
secondary metabolites
antibacterial activity
cytotoxic activity
url https://www.frontiersin.org/articles/10.3389/fpls.2022.1049015/full
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