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...

Full description

Saved in:
Bibliographic Details
Published in:Marine drugs 2013-02, Vol.11 (3), p.611-622
Main Authors: Um, Soohyun, Pyee, Yuna, Kim, Eun-Hee, Lee, Sang Kook, Shin, Jongheon, Oh, Dong-Chan
Format: Article
Language:English
Subjects:
Animals
Cell Line
Inhibitory Concentration 50
iNOS assay
Lipopolysaccharides - pharmacology
Macrophages - drug effects
Macrophages - metabolism
marine bacteria
Mice
Nitric Oxide - biosynthesis
Peptides - chemistry
Peptides - isolation & purification
Peptides - pharmacology
Peptides, Cyclic - administration & dosage
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - pharmacology
Rhodospirillaceae - chemistry
Spectrum Analysis
Thalassospira
thalassospiramide
unicellular bacteria
γ-amino acid
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 IC(50) values of 16.4 and 4.8 μM, respectively.
ISSN:1660-3397
1660-3397
DOI:10.3390/md11030611