Journal
MARINE DRUGS
Volume 11, Issue 3, Pages 611-622Publisher
MDPI AG
DOI: 10.3390/md11030611
Keywords
unicellular bacteria; marine bacteria; Thalassospira; thalassospiramide; gamma-amino acid; iNOS assay
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Funding
- National Research Foundation of Korea
- Korean Government (MEST) [NRF-M1A5A1-2010-0020429]
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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.-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 H-1-H-1 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 mu M, respectively.
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