Cargando…

A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.

Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1–3 were determined to be a new benzofuran glycoside and new ind...

Descripción completa

Detalles Bibliográficos
Autores principales: Kwon, Yun, Kim, Seong-Hwan, Shin, Yoonho, Bae, Munhyung, Kim, Byung-Yong, Lee, Sang Kook, Oh, Ki-Bong, Shin, Jongheon, Oh, Dong-Chan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4012469/
https://www.ncbi.nlm.nih.gov/pubmed/24759001
http://dx.doi.org/10.3390/md12042326
_version_ 1782314937379454976
author Kwon, Yun
Kim, Seong-Hwan
Shin, Yoonho
Bae, Munhyung
Kim, Byung-Yong
Lee, Sang Kook
Oh, Ki-Bong
Shin, Jongheon
Oh, Dong-Chan
author_facet Kwon, Yun
Kim, Seong-Hwan
Shin, Yoonho
Bae, Munhyung
Kim, Byung-Yong
Lee, Sang Kook
Oh, Ki-Bong
Shin, Jongheon
Oh, Dong-Chan
author_sort Kwon, Yun
collection PubMed
description Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1–3 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116.
format Online
Article
Text
id pubmed-4012469
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-40124692014-05-07 A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp. Kwon, Yun Kim, Seong-Hwan Shin, Yoonho Bae, Munhyung Kim, Byung-Yong Lee, Sang Kook Oh, Ki-Bong Shin, Jongheon Oh, Dong-Chan Mar Drugs Article Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1–3 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116. MDPI 2014-04-22 /pmc/articles/PMC4012469/ /pubmed/24759001 http://dx.doi.org/10.3390/md12042326 Text en © 2014 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 license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Kwon, Yun
Kim, Seong-Hwan
Shin, Yoonho
Bae, Munhyung
Kim, Byung-Yong
Lee, Sang Kook
Oh, Ki-Bong
Shin, Jongheon
Oh, Dong-Chan
A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
title A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
title_full A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
title_fullStr A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
title_full_unstemmed A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
title_short A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
title_sort new benzofuran glycoside and indole alkaloids from a sponge-associated rare actinomycete, amycolatopsis sp.
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4012469/
https://www.ncbi.nlm.nih.gov/pubmed/24759001
http://dx.doi.org/10.3390/md12042326
work_keys_str_mv AT kwonyun anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT kimseonghwan anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT shinyoonho anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT baemunhyung anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT kimbyungyong anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT leesangkook anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT ohkibong anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT shinjongheon anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT ohdongchan anewbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT kwonyun newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT kimseonghwan newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT shinyoonho newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT baemunhyung newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT kimbyungyong newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT leesangkook newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT ohkibong newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT shinjongheon newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp
AT ohdongchan newbenzofuranglycosideandindolealkaloidsfromaspongeassociatedrareactinomyceteamycolatopsissp