Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328

Five new diketopiperazine derivatives, (3Z,6E)-1-N-methyl-3-benzylidene-6-(2S-methyl-3-hydroxypropylidene)piperazine-2,5-dione (1), (3Z,6E)-1-N-methyl-3-benzylidene-6-(2R-methyl-3-hydroxypropylidene)piperazine-2,5-dione (2), (3Z,6Z)-3-(4-hydroxybenzylidene)-6-isobutylidenepiperazine-2,5-dione (3), (...

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Main Authors:	Wang, Pei, Xi, Lijun, Liu, Peipei, Wang, Yi, Wang, Wei, Huang, Ying, Zhu, Weiming
Format:	Online
Language:	English
Published:	MDPI 2013
Online Access:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3705386/

id	pubmed-3705386
recordtype	oai_dc
spelling	pubmed-37053862013-07-09 Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328 Wang, Pei Xi, Lijun Liu, Peipei Wang, Yi Wang, Wei Huang, Ying Zhu, Weiming Communication Five new diketopiperazine derivatives, (3Z,6E)-1-N-methyl-3-benzylidene-6-(2S-methyl-3-hydroxypropylidene)piperazine-2,5-dione (1), (3Z,6E)-1-N-methyl-3-benzylidene-6-(2R-methyl-3-hydroxypropylidene)piperazine-2,5-dione (2), (3Z,6Z)-3-(4-hydroxybenzylidene)-6-isobutylidenepiperazine-2,5-dione (3), (3Z,6Z)-3-((1H-imidazol-5-yl)-methylene)-6-isobutylidenepiperazine-2,5-dione (4), and (3Z,6S)-3-benzylidene-6-(2S-but-2-yl)piperazine-2,5-dione (5), were isolated from the marine-derived actinomycete Streptomyces sp. FXJ7.328. The structures of 1–5 were determined by spectroscopic analysis, CD exciton chirality, the modified Mosher’s, Marfey’s and the C3 Marfey’s methods. Compound 3 showed modest antivirus activity against influenza A (H1N1) virus with an IC50 value of 41.5 ± 4.5 μM. In addition, compound 6 and 7 displayed potent anti-H1N1 activity with IC50 value of 28.9 ± 2.2 and 6.8 ± 1.5 μM, respectively. Due to the lack of corresponding data in the literature, the 13C NMR data of (3Z,6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione (6) were also reported here for the first time. MDPI 2013-03-28 /pmc/articles/PMC3705386/ /pubmed/23538868 http://dx.doi.org/10.3390/md11041035 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ 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/).
repository_type	Open Access Journal
institution_category	Foreign Institution
institution	US National Center for Biotechnology Information
building	NCBI PubMed
collection	Online Access
language	English
format	Online
author	Wang, Pei Xi, Lijun Liu, Peipei Wang, Yi Wang, Wei Huang, Ying Zhu, Weiming
spellingShingle	Wang, Pei Xi, Lijun Liu, Peipei Wang, Yi Wang, Wei Huang, Ying Zhu, Weiming Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
author_facet	Wang, Pei Xi, Lijun Liu, Peipei Wang, Yi Wang, Wei Huang, Ying Zhu, Weiming
author_sort	Wang, Pei
title	Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
title_short	Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
title_full	Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
title_fullStr	Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
title_full_unstemmed	Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
title_sort	diketopiperazine derivatives from the marine-derived actinomycete streptomyces sp. fxj7.328
description	Five new diketopiperazine derivatives, (3Z,6E)-1-N-methyl-3-benzylidene-6-(2S-methyl-3-hydroxypropylidene)piperazine-2,5-dione (1), (3Z,6E)-1-N-methyl-3-benzylidene-6-(2R-methyl-3-hydroxypropylidene)piperazine-2,5-dione (2), (3Z,6Z)-3-(4-hydroxybenzylidene)-6-isobutylidenepiperazine-2,5-dione (3), (3Z,6Z)-3-((1H-imidazol-5-yl)-methylene)-6-isobutylidenepiperazine-2,5-dione (4), and (3Z,6S)-3-benzylidene-6-(2S-but-2-yl)piperazine-2,5-dione (5), were isolated from the marine-derived actinomycete Streptomyces sp. FXJ7.328. The structures of 1–5 were determined by spectroscopic analysis, CD exciton chirality, the modified Mosher’s, Marfey’s and the C3 Marfey’s methods. Compound 3 showed modest antivirus activity against influenza A (H1N1) virus with an IC50 value of 41.5 ± 4.5 μM. In addition, compound 6 and 7 displayed potent anti-H1N1 activity with IC50 value of 28.9 ± 2.2 and 6.8 ± 1.5 μM, respectively. Due to the lack of corresponding data in the literature, the 13C NMR data of (3Z,6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione (6) were also reported here for the first time.
publisher	MDPI
publishDate	2013
url	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3705386/
_version_	1611993117991370752

Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328

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