Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species

Liangxiong Xu; Ping Wu; Jinghua Xue; Istvan Molnar; Xiaoyi Wei

doi:10.1021/acs.jnatprod.7b00066

Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species

Liangxiong Xu, Ping Wu, Jinghua Xue, Istvan Molnar, Xiaoyi Wei

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

Abstract

Eight new β-resorcylic acid lactones (RALs), including the hypothemycin-type compounds paecilomycins N-P (1-3) and the radicicol-type metabolites dechloropochonin I (4), monocillins VI (5) and VII (6), 4′-hydroxymonocillin IV (7), and 4′-methoxymonocillin IV (8), along with nine known RALs (9-17), were isolated from the cultures of Paecilomyces sp. SC0924. Compounds 1 and 2 feature a novel 6/11/5 ring system, and 3 is the first 5′-keto RAL. The structures of 1-8 were elucidated on the basis of extensive spectroscopic analysis, X-ray diffraction analysis, and theoretical calculations of ECD spectra. Compounds 3, 5, and 6 exhibit cytotoxicity against MCF-7, A549, and HeLa cells, and compounds 5 and 7 display antifungal activity against Peronophythora litchii.

Original language	English (US)
Pages (from-to)	2215-2253
Number of pages	39
Journal	Journal Of Natural Products
Volume	80
Issue number	8
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00066
State	Published - Aug 25 2017

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.7b00066

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@article{4366047192c6491c8a4de27ab215ba27,

title = "Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species",

abstract = "Eight new β-resorcylic acid lactones (RALs), including the hypothemycin-type compounds paecilomycins N-P (1-3) and the radicicol-type metabolites dechloropochonin I (4), monocillins VI (5) and VII (6), 4′-hydroxymonocillin IV (7), and 4′-methoxymonocillin IV (8), along with nine known RALs (9-17), were isolated from the cultures of Paecilomyces sp. SC0924. Compounds 1 and 2 feature a novel 6/11/5 ring system, and 3 is the first 5′-keto RAL. The structures of 1-8 were elucidated on the basis of extensive spectroscopic analysis, X-ray diffraction analysis, and theoretical calculations of ECD spectra. Compounds 3, 5, and 6 exhibit cytotoxicity against MCF-7, A549, and HeLa cells, and compounds 5 and 7 display antifungal activity against Peronophythora litchii.",

author = "Liangxiong Xu and Ping Wu and Jinghua Xue and Istvan Molnar and Xiaoyi Wei",

note = "Funding Information: We thank Prof. T.-H. Li, Guangdong Institute of Microbiology, for morphological authentication of the producing fungus, Ms. A. Sun, South China Sea Institute of Oceanology, Chinese Academy of Sciences, for HRESIMS measurements, Ms. Y.-Y. Chen, School of Pharmaceutical Science, Sun Yat-Sen University, for X-ray diffraction analysis, Prof. L. Du from Chemistry Department, Nebraska University−Lincoln, NE, USA, and Prof. R.-Q. Pan from South China Agricultural University for the test fungi. This work was supported by grants from the National Science Foundation of China (Nos. 81172942 to X.W., 30901856 to L.X.), the U.S. National Institutes of Health (NIGMS R01GM114418-01A1 to I.M.), and the Guangzhou Science Technology and Innovation Commission (No. 201604020048 to L.X.). Publisher Copyright: {\textcopyright} 2017 The American Chemical Society and American Society of Pharmacognosy.",

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language = "English (US)",

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AU - Wu, Ping

AU - Xue, Jinghua

AU - Molnar, Istvan

AU - Wei, Xiaoyi

N1 - Funding Information: We thank Prof. T.-H. Li, Guangdong Institute of Microbiology, for morphological authentication of the producing fungus, Ms. A. Sun, South China Sea Institute of Oceanology, Chinese Academy of Sciences, for HRESIMS measurements, Ms. Y.-Y. Chen, School of Pharmaceutical Science, Sun Yat-Sen University, for X-ray diffraction analysis, Prof. L. Du from Chemistry Department, Nebraska University−Lincoln, NE, USA, and Prof. R.-Q. Pan from South China Agricultural University for the test fungi. This work was supported by grants from the National Science Foundation of China (Nos. 81172942 to X.W., 30901856 to L.X.), the U.S. National Institutes of Health (NIGMS R01GM114418-01A1 to I.M.), and the Guangzhou Science Technology and Innovation Commission (No. 201604020048 to L.X.). Publisher Copyright: © 2017 The American Chemical Society and American Society of Pharmacognosy.

PY - 2017/8/25

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N2 - Eight new β-resorcylic acid lactones (RALs), including the hypothemycin-type compounds paecilomycins N-P (1-3) and the radicicol-type metabolites dechloropochonin I (4), monocillins VI (5) and VII (6), 4′-hydroxymonocillin IV (7), and 4′-methoxymonocillin IV (8), along with nine known RALs (9-17), were isolated from the cultures of Paecilomyces sp. SC0924. Compounds 1 and 2 feature a novel 6/11/5 ring system, and 3 is the first 5′-keto RAL. The structures of 1-8 were elucidated on the basis of extensive spectroscopic analysis, X-ray diffraction analysis, and theoretical calculations of ECD spectra. Compounds 3, 5, and 6 exhibit cytotoxicity against MCF-7, A549, and HeLa cells, and compounds 5 and 7 display antifungal activity against Peronophythora litchii.

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Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species

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CCDC 1486556: Experimental Crystal Structure Determination

CCDC 1062538: Experimental Crystal Structure Determination

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Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species

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CCDC 1486556: Experimental Crystal Structure Determination

CCDC 1062538: Experimental Crystal Structure Determination

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