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Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03

A novel indole alkaloid, misszrtine A (1), was isolated from marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. The planar structure of 1 was assigned by analysis of spectroscopic data, the absolute configuration of which was unambiguously determined by total synthesis. Compound 1 represen...

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Autores principales: Zhou, Rong, Liao, Xiaojian, Li, Hangbin, Li, Jing, Feng, Pengju, Zhao, BingXin, Xu, Shihai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6008316/
https://www.ncbi.nlm.nih.gov/pubmed/29951479
http://dx.doi.org/10.3389/fchem.2018.00212
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author Zhou, Rong
Liao, Xiaojian
Li, Hangbin
Li, Jing
Feng, Pengju
Zhao, BingXin
Xu, Shihai
author_facet Zhou, Rong
Liao, Xiaojian
Li, Hangbin
Li, Jing
Feng, Pengju
Zhao, BingXin
Xu, Shihai
author_sort Zhou, Rong
collection PubMed
description A novel indole alkaloid, misszrtine A (1), was isolated from marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. The planar structure of 1 was assigned by analysis of spectroscopic data, the absolute configuration of which was unambiguously determined by total synthesis. Compound 1 represents the first example of N-isopentenyl tryptophan methyl ester with a phenylpropanoic amide arm, which exhibited a potent antagonistic activity on HL60 (IC(50) = 3.1 μM) and LNCaP (IC(50) = 4.9 μM) cell lines. Bioactivity evaluation reveals that functional group on indole nitrogen of 1 has a great effect on its cytotoxity, which provides a mean to probe the structure-activity relationships of 1.
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spelling pubmed-60083162018-06-27 Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03 Zhou, Rong Liao, Xiaojian Li, Hangbin Li, Jing Feng, Pengju Zhao, BingXin Xu, Shihai Front Chem Chemistry A novel indole alkaloid, misszrtine A (1), was isolated from marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. The planar structure of 1 was assigned by analysis of spectroscopic data, the absolute configuration of which was unambiguously determined by total synthesis. Compound 1 represents the first example of N-isopentenyl tryptophan methyl ester with a phenylpropanoic amide arm, which exhibited a potent antagonistic activity on HL60 (IC(50) = 3.1 μM) and LNCaP (IC(50) = 4.9 μM) cell lines. Bioactivity evaluation reveals that functional group on indole nitrogen of 1 has a great effect on its cytotoxity, which provides a mean to probe the structure-activity relationships of 1. Frontiers Media S.A. 2018-06-13 /pmc/articles/PMC6008316/ /pubmed/29951479 http://dx.doi.org/10.3389/fchem.2018.00212 Text en Copyright © 2018 Zhou, Liao, Li, Li, Feng, Zhao and Xu. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Zhou, Rong
Liao, Xiaojian
Li, Hangbin
Li, Jing
Feng, Pengju
Zhao, BingXin
Xu, Shihai
Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03
title Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03
title_full Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03
title_fullStr Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03
title_full_unstemmed Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03
title_short Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03
title_sort isolation and synthesis of misszrtine a: a novel indole alkaloid from marine sponge-associated aspergillus sp. scsio xws03f03
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6008316/
https://www.ncbi.nlm.nih.gov/pubmed/29951479
http://dx.doi.org/10.3389/fchem.2018.00212
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