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...
Main Authors: | , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2013-02-01
|
Series: | Marine Drugs |
Subjects: | |
Online Access: | http://www.mdpi.com/1660-3397/11/3/611 |
id |
doaj-88126e7337e74b66bd733f937be52476 |
---|---|
record_format |
Article |
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 |
work_keys_str_mv |
AT sangkooklee thalassospiramideganewgaminoacidbearingpeptidefromthemarinebacteriumthalassospirasp AT dongchanoh thalassospiramideganewgaminoacidbearingpeptidefromthemarinebacteriumthalassospirasp AT jongheonshin thalassospiramideganewgaminoacidbearingpeptidefromthemarinebacteriumthalassospirasp AT eunheekim thalassospiramideganewgaminoacidbearingpeptidefromthemarinebacteriumthalassospirasp AT yunapyee thalassospiramideganewgaminoacidbearingpeptidefromthemarinebacteriumthalassospirasp AT soohyunum thalassospiramideganewgaminoacidbearingpeptidefromthemarinebacteriumthalassospirasp |
_version_ |
1725402353213898752 |