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Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291

A new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative, varioloid A (1), was isolated from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291. Its structure was elucidated on the basis of extensive analysis of 1D and 2D NMR data and the absolute configuration was de...

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Autores principales: Zhang, Peng, Li, Xiao-Ming, Mao, Xin-Xin, Mándi, Attila, Kurtán, Tibor, Wang, Bin-Gui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082447/
https://www.ncbi.nlm.nih.gov/pubmed/27829905
http://dx.doi.org/10.3762/bjoc.12.188
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author Zhang, Peng
Li, Xiao-Ming
Mao, Xin-Xin
Mándi, Attila
Kurtán, Tibor
Wang, Bin-Gui
author_facet Zhang, Peng
Li, Xiao-Ming
Mao, Xin-Xin
Mándi, Attila
Kurtán, Tibor
Wang, Bin-Gui
author_sort Zhang, Peng
collection PubMed
description A new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative, varioloid A (1), was isolated from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291. Its structure was elucidated on the basis of extensive analysis of 1D and 2D NMR data and the absolute configuration was determined by time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculations. A similar compound, whose planar structure was previously described but the relative and absolute configurations and (13)C NMR data were not reported, was also identified and was tentatively named as varioloid B (2). Both compounds 1 and 2 exhibited cytotoxicity against A549, HCT116, and HepG2 cell lines, with IC(50) values ranging from 2.6 to 8.2 µg/mL.
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spelling pubmed-50824472016-11-09 Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291 Zhang, Peng Li, Xiao-Ming Mao, Xin-Xin Mándi, Attila Kurtán, Tibor Wang, Bin-Gui Beilstein J Org Chem Full Research Paper A new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative, varioloid A (1), was isolated from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291. Its structure was elucidated on the basis of extensive analysis of 1D and 2D NMR data and the absolute configuration was determined by time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculations. A similar compound, whose planar structure was previously described but the relative and absolute configurations and (13)C NMR data were not reported, was also identified and was tentatively named as varioloid B (2). Both compounds 1 and 2 exhibited cytotoxicity against A549, HCT116, and HepG2 cell lines, with IC(50) values ranging from 2.6 to 8.2 µg/mL. Beilstein-Institut 2016-09-09 /pmc/articles/PMC5082447/ /pubmed/27829905 http://dx.doi.org/10.3762/bjoc.12.188 Text en Copyright © 2016, Zhang et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Zhang, Peng
Li, Xiao-Ming
Mao, Xin-Xin
Mándi, Attila
Kurtán, Tibor
Wang, Bin-Gui
Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291
title Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291
title_full Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291
title_fullStr Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291
title_full_unstemmed Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291
title_short Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291
title_sort varioloid a, a new indolyl-6,10b-dihydro-5ah-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus paecilomyces variotii en-291
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082447/
https://www.ncbi.nlm.nih.gov/pubmed/27829905
http://dx.doi.org/10.3762/bjoc.12.188
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