Next Article in Journal
Glycosylation of Conotoxins
Next Article in Special Issue
Recent Advances in the Discovery and Development of Marine Microbial Natural Products
Previous Article in Journal
Eleganolone, a Diterpene from the French Marine Alga Bifurcaria bifurcata Inhibits Growth of the Human Pathogens Trypanosoma brucei and Plasmodium falciparum
Previous Article in Special Issue
Probing a Coral Genome for Components of the Photoprotective Scytonemin Biosynthetic Pathway and the 2-Aminoethylphosphonate Pathway
Article Menu

Export Article

Open AccessArticle
Mar. Drugs 2013, 11(3), 611-622; doi:10.3390/md11030611

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

1
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea
2
Division of Magnetic Resonance, Korea Basic Science Institute, Ochang, Chungbuk 363-883, Korea
*
Author to whom correspondence should be addressed.
Received: 13 December 2012 / Revised: 29 January 2013 / Accepted: 6 February 2013 / Published: 26 February 2013
(This article belongs to the Special Issue Marine Secondary Metabolites)
View Full-Text   |   Download PDF [627 KB, uploaded 24 February 2015]   |  

Abstract

In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (23), 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 (23) 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. View Full-Text
Keywords: unicellular bacteria; marine bacteria; Thalassospira; thalassospiramide; γ-amino acid; iNOS assay unicellular bacteria; marine bacteria; Thalassospira; thalassospiramide; γ-amino acid; iNOS assay
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary materials

Share & Cite This Article

MDPI and ACS Style

Um, S.; Pyee, Y.; Kim, E.-H.; Lee, S.K.; Shin, J.; Oh, D.-C. Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.. Mar. Drugs 2013, 11, 611-622.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top