An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10

A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic an...

Descripción completa

Detalles Bibliográficos
Autores principales: Pan, Chengqian, Shi, Yutong, Auckloo, Bibi Nazia, Chen, Xuegang, Chen, Chen-Tung Arthur, Tao, Xinyi, Wu, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4999917/
https://www.ncbi.nlm.nih.gov/pubmed/27548192
http://dx.doi.org/10.3390/md14080156
_version_ 1782450188637437952
author Pan, Chengqian
Shi, Yutong
Auckloo, Bibi Nazia
Chen, Xuegang
Chen, Chen-Tung Arthur
Tao, Xinyi
Wu, Bin
author_facet Pan, Chengqian
Shi, Yutong
Auckloo, Bibi Nazia
Chen, Xuegang
Chen, Chen-Tung Arthur
Tao, Xinyi
Wu, Bin
author_sort Pan, Chengqian
collection PubMed
description A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL.
format Online
Article
Text
id pubmed-4999917
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-49999172016-09-01 An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10 Pan, Chengqian Shi, Yutong Auckloo, Bibi Nazia Chen, Xuegang Chen, Chen-Tung Arthur Tao, Xinyi Wu, Bin Mar Drugs Article A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL. MDPI 2016-08-18 /pmc/articles/PMC4999917/ /pubmed/27548192 http://dx.doi.org/10.3390/md14080156 Text en © 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Pan, Chengqian
Shi, Yutong
Auckloo, Bibi Nazia
Chen, Xuegang
Chen, Chen-Tung Arthur
Tao, Xinyi
Wu, Bin
An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
title An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
title_full An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
title_fullStr An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
title_full_unstemmed An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
title_short An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
title_sort unusual conformational isomer of verrucosidin backbone from a hydrothermal vent fungus, penicillium sp. y-50-10
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4999917/
https://www.ncbi.nlm.nih.gov/pubmed/27548192
http://dx.doi.org/10.3390/md14080156
work_keys_str_mv AT panchengqian anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT shiyutong anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT auckloobibinazia anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT chenxuegang anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT chenchentungarthur anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT taoxinyi anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT wubin anunusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT panchengqian unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT shiyutong unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT auckloobibinazia unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT chenxuegang unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT chenchentungarthur unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT taoxinyi unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010
AT wubin unusualconformationalisomerofverrucosidinbackbonefromahydrothermalventfunguspenicilliumspy5010

Ejemplares similares