Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.

In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2–3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy-penta-2-e...

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Main Authors:	Sang Kook Lee, Dong-Chan Oh, Jongheon Shin, Eun-Hee Kim, Yuna Pyee, Soohyun Um
Format:	Article
Language:	English
Published:	MDPI AG 2013-02-01
Series:	Marine Drugs
Subjects:	unicellular bacteria marine bacteria Thalassospira thalassospiramide γ-amino acid iNOS assay
Online Access:	http://www.mdpi.com/1660-3397/11/3/611

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spelling	doaj-88126e7337e74b66bd733f937be524762020-11-25T00:11:53ZengMDPI AGMarine Drugs1660-33972013-02-0111361162210.3390/md11030611Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.Sang Kook LeeDong-Chan OhJongheon ShinEun-Hee KimYuna PyeeSoohyun UmIn the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2–3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy-penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H–1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2–3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.http://www.mdpi.com/1660-3397/11/3/611unicellular bacteriamarine bacteriaThalassospirathalassospiramideγ-amino acidiNOS assay
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Sang Kook Lee Dong-Chan Oh Jongheon Shin Eun-Hee Kim Yuna Pyee Soohyun Um
spellingShingle	Sang Kook Lee Dong-Chan Oh Jongheon Shin Eun-Hee Kim Yuna Pyee Soohyun Um Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp. Marine Drugs unicellular bacteria marine bacteria Thalassospira thalassospiramide γ-amino acid iNOS assay
author_facet	Sang Kook Lee Dong-Chan Oh Jongheon Shin Eun-Hee Kim Yuna Pyee Soohyun Um
author_sort	Sang Kook Lee
title	Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.
title_short	Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.
title_full	Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.
title_fullStr	Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.
title_full_unstemmed	Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.
title_sort	thalassospiramide g, a new γ-amino-acid-bearing peptide from the marine bacterium thalassospira sp.
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2013-02-01
description	In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2–3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy-penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H–1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2–3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.
topic	unicellular bacteria marine bacteria Thalassospira thalassospiramide γ-amino acid iNOS assay
url	http://www.mdpi.com/1660-3397/11/3/611
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Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.

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