Cargando…

Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348

A new cyclic dipeptide, petrocidin A (1), along with three known compounds—2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4)—were isolated from the solid culture of Streptomyces sp. SBT348. The strain Streptomyces sp. SBT348 had been prioritized in a strain collection of 64 s...

Descripción completa

Detalles Bibliográficos
Autores principales: Cheng, Cheng, Othman, Eman M., Stopper, Helga, Edrada-Ebel, RuAngelie, Hentschel, Ute, Abdelmohsen, Usama Ramadan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742843/
https://www.ncbi.nlm.nih.gov/pubmed/29211005
http://dx.doi.org/10.3390/md15120383
_version_ 1783288465278894080
author Cheng, Cheng
Othman, Eman M.
Stopper, Helga
Edrada-Ebel, RuAngelie
Hentschel, Ute
Abdelmohsen, Usama Ramadan
author_facet Cheng, Cheng
Othman, Eman M.
Stopper, Helga
Edrada-Ebel, RuAngelie
Hentschel, Ute
Abdelmohsen, Usama Ramadan
author_sort Cheng, Cheng
collection PubMed
description A new cyclic dipeptide, petrocidin A (1), along with three known compounds—2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4)—were isolated from the solid culture of Streptomyces sp. SBT348. The strain Streptomyces sp. SBT348 had been prioritized in a strain collection of 64 sponge-associated actinomycetes based on its distinct metabolomic profile using liquid chromatography/high-resolution mass spectrometry (LC-HRMS) and nuclear magnetic resonance (NMR). The absolute configuration of all α-amino acids was determined by HPLC analysis after derivatization with Marfey’s reagent and comparison with commercially available reference amino acids. Structure elucidation was pursued in the presented study by mass spectrometry and NMR spectral data. Petrocidin A (1) and 2,3-dihydroxybenzamide (3) exhibited significant cytotoxicity towards the human promyelocytic HL-60 and the human colon adenocarcinoma HT-29 cell lines. These results demonstrated the potential of sponge-associated actinomycetes for the discovery of novel and pharmacologically active natural products.
format Online
Article
Text
id pubmed-5742843
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-57428432017-12-29 Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348 Cheng, Cheng Othman, Eman M. Stopper, Helga Edrada-Ebel, RuAngelie Hentschel, Ute Abdelmohsen, Usama Ramadan Mar Drugs Article A new cyclic dipeptide, petrocidin A (1), along with three known compounds—2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4)—were isolated from the solid culture of Streptomyces sp. SBT348. The strain Streptomyces sp. SBT348 had been prioritized in a strain collection of 64 sponge-associated actinomycetes based on its distinct metabolomic profile using liquid chromatography/high-resolution mass spectrometry (LC-HRMS) and nuclear magnetic resonance (NMR). The absolute configuration of all α-amino acids was determined by HPLC analysis after derivatization with Marfey’s reagent and comparison with commercially available reference amino acids. Structure elucidation was pursued in the presented study by mass spectrometry and NMR spectral data. Petrocidin A (1) and 2,3-dihydroxybenzamide (3) exhibited significant cytotoxicity towards the human promyelocytic HL-60 and the human colon adenocarcinoma HT-29 cell lines. These results demonstrated the potential of sponge-associated actinomycetes for the discovery of novel and pharmacologically active natural products. MDPI 2017-12-06 /pmc/articles/PMC5742843/ /pubmed/29211005 http://dx.doi.org/10.3390/md15120383 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
Cheng, Cheng
Othman, Eman M.
Stopper, Helga
Edrada-Ebel, RuAngelie
Hentschel, Ute
Abdelmohsen, Usama Ramadan
Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348
title Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348
title_full Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348
title_fullStr Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348
title_full_unstemmed Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348
title_short Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348
title_sort isolation of petrocidin a, a new cytotoxic cyclic dipeptide from the marine sponge-derived bacterium streptomyces sp. sbt348
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742843/
https://www.ncbi.nlm.nih.gov/pubmed/29211005
http://dx.doi.org/10.3390/md15120383
work_keys_str_mv AT chengcheng isolationofpetrocidinaanewcytotoxiccyclicdipeptidefromthemarinespongederivedbacteriumstreptomycesspsbt348
AT othmanemanm isolationofpetrocidinaanewcytotoxiccyclicdipeptidefromthemarinespongederivedbacteriumstreptomycesspsbt348
AT stopperhelga isolationofpetrocidinaanewcytotoxiccyclicdipeptidefromthemarinespongederivedbacteriumstreptomycesspsbt348
AT edradaebelruangelie isolationofpetrocidinaanewcytotoxiccyclicdipeptidefromthemarinespongederivedbacteriumstreptomycesspsbt348
AT hentschelute isolationofpetrocidinaanewcytotoxiccyclicdipeptidefromthemarinespongederivedbacteriumstreptomycesspsbt348
AT abdelmohsenusamaramadan isolationofpetrocidinaanewcytotoxiccyclicdipeptidefromthemarinespongederivedbacteriumstreptomycesspsbt348