Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor

Aspergoterpenins A–D (1–4), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (5–12), and their structures were elucidated by a comprehensive analysis of their NMR (Nucl...

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Main Authors: Zhi-Yong Guo, Ming-Hui Tan, Cheng-Xiong Liu, Meng-Meng Lv, Zhang-Shuang Deng, Fei Cao, Kun Zou, Peter Proksch
Format: Article
Language:English
Published: MDPI AG 2018-05-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/23/6/1291
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spelling doaj-111c845f926949ecbf186f6c14d0eba62020-11-24T23:16:16ZengMDPI AGMolecules1420-30492018-05-01236129110.3390/molecules23061291molecules23061291Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolorZhi-Yong Guo0Ming-Hui Tan1Cheng-Xiong Liu2Meng-Meng Lv3Zhang-Shuang Deng4Fei Cao5Kun Zou6Peter Proksch7Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaHubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaHubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaHubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaHubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaCollege of Pharmaceutical Sciences, Key Laboratory of Pharmaceutical Quality Control of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China, Hebei University, Baoding 071002, ChinaHubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, ChinaInstitute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, GermanyAspergoterpenins A–D (1–4), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (5–12), and their structures were elucidated by a comprehensive analysis of their NMR (Nuclear Magnetic Resonance), MS (Mass Spectrum) and CD (Circular Dichroism) spectra. Aspergoterpenin A (1) was the first example with a characteristic ketal bridged-ring part in the degraded natural bisabolane-type sesquiterpene structures. The compounds 1–12 displayed no significant activities against four cancer cell lines (A549, Caski, HepG2 and MCF-7). Further, the antimicrobial activities to Erwinia carotovora sub sp. Carotovora were evaluated, and the results showed that compounds 1–12 displayed antimicrobial activities with MIC values ranging from 15.2 to 85.2 μg/mL.http://www.mdpi.com/1420-3049/23/6/1291bisabolanese squiterpenoidendophytic fungusAspergillus versicolorstructural elucidationantimicrobial activities
collection DOAJ
language English
format Article
sources DOAJ
author Zhi-Yong Guo
Ming-Hui Tan
Cheng-Xiong Liu
Meng-Meng Lv
Zhang-Shuang Deng
Fei Cao
Kun Zou
Peter Proksch
spellingShingle Zhi-Yong Guo
Ming-Hui Tan
Cheng-Xiong Liu
Meng-Meng Lv
Zhang-Shuang Deng
Fei Cao
Kun Zou
Peter Proksch
Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
Molecules
bisabolanese squiterpenoid
endophytic fungus
Aspergillus versicolor
structural elucidation
antimicrobial activities
author_facet Zhi-Yong Guo
Ming-Hui Tan
Cheng-Xiong Liu
Meng-Meng Lv
Zhang-Shuang Deng
Fei Cao
Kun Zou
Peter Proksch
author_sort Zhi-Yong Guo
title Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
title_short Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
title_full Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
title_fullStr Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
title_full_unstemmed Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
title_sort aspergoterpenins a–d: four new antimicrobial bisabolane sesquiterpenoid derivatives from an endophytic fungus aspergillus versicolor
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2018-05-01
description Aspergoterpenins A–D (1–4), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (5–12), and their structures were elucidated by a comprehensive analysis of their NMR (Nuclear Magnetic Resonance), MS (Mass Spectrum) and CD (Circular Dichroism) spectra. Aspergoterpenin A (1) was the first example with a characteristic ketal bridged-ring part in the degraded natural bisabolane-type sesquiterpene structures. The compounds 1–12 displayed no significant activities against four cancer cell lines (A549, Caski, HepG2 and MCF-7). Further, the antimicrobial activities to Erwinia carotovora sub sp. Carotovora were evaluated, and the results showed that compounds 1–12 displayed antimicrobial activities with MIC values ranging from 15.2 to 85.2 μg/mL.
topic bisabolanese squiterpenoid
endophytic fungus
Aspergillus versicolor
structural elucidation
antimicrobial activities
url http://www.mdpi.com/1420-3049/23/6/1291
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