Cargando…

Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx

Three indole derivatives, a novel benzoxazine-indole hybrid (1) and two known indole trimers (2, 3), were isolated from the metagenomic library of the marine sponge Discodermia calyx based on functional screening. Their structures were elucidated by extensive spectroscopic analysis and comparison of...

Descripción completa

Detalles Bibliográficos
Autores principales: Liu, Feng-Lou, Yang, Xiao-Long
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154727/
https://www.ncbi.nlm.nih.gov/pubmed/28441364
http://dx.doi.org/10.3390/molecules22050681
_version_ 1783357751111450624
author Liu, Feng-Lou
Yang, Xiao-Long
author_facet Liu, Feng-Lou
Yang, Xiao-Long
author_sort Liu, Feng-Lou
collection PubMed
description Three indole derivatives, a novel benzoxazine-indole hybrid (1) and two known indole trimers (2, 3), were isolated from the metagenomic library of the marine sponge Discodermia calyx based on functional screening. Their structures were elucidated by extensive spectroscopic analysis and comparison of their NMR data to that of known compounds. The antibacterial assay indicated that only compound 2 displayed significant antibacterial activity against Bacillus cereus, with approximately 20 mm diameter growth inhibition at 10 µg/paper. HPLC analyses revealed that compound 2 is a newly induced metabolite, and the concentration of 3 was obviously enhanced in contrast to negative control, while 1 was not detected, allowing us to predict that the formation of 2 might be induced by exogenous genes derived from the sponge metagenome, whereas compound 1 could be formed through a non-enzymatic process during the isolation procedure.
format Online
Article
Text
id pubmed-6154727
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61547272018-11-13 Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx Liu, Feng-Lou Yang, Xiao-Long Molecules Article Three indole derivatives, a novel benzoxazine-indole hybrid (1) and two known indole trimers (2, 3), were isolated from the metagenomic library of the marine sponge Discodermia calyx based on functional screening. Their structures were elucidated by extensive spectroscopic analysis and comparison of their NMR data to that of known compounds. The antibacterial assay indicated that only compound 2 displayed significant antibacterial activity against Bacillus cereus, with approximately 20 mm diameter growth inhibition at 10 µg/paper. HPLC analyses revealed that compound 2 is a newly induced metabolite, and the concentration of 3 was obviously enhanced in contrast to negative control, while 1 was not detected, allowing us to predict that the formation of 2 might be induced by exogenous genes derived from the sponge metagenome, whereas compound 1 could be formed through a non-enzymatic process during the isolation procedure. MDPI 2017-04-25 /pmc/articles/PMC6154727/ /pubmed/28441364 http://dx.doi.org/10.3390/molecules22050681 Text en © 2017 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
Liu, Feng-Lou
Yang, Xiao-Long
Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx
title Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx
title_full Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx
title_fullStr Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx
title_full_unstemmed Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx
title_short Indole Derivatives Produced by the Metagenome Genes of the Escherichia coli-Harboring Marine Sponge Discodermia calyx
title_sort indole derivatives produced by the metagenome genes of the escherichia coli-harboring marine sponge discodermia calyx
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154727/
https://www.ncbi.nlm.nih.gov/pubmed/28441364
http://dx.doi.org/10.3390/molecules22050681
work_keys_str_mv AT liufenglou indolederivativesproducedbythemetagenomegenesoftheescherichiacoliharboringmarinespongediscodermiacalyx
AT yangxiaolong indolederivativesproducedbythemetagenomegenesoftheescherichiacoliharboringmarinespongediscodermiacalyx