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

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

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Received: 13 December 2012; in revised form: 29 January 2013 / Accepted: 6 February 2013 / Published: 26 February 2013
(This article belongs to the Special Issue Marine Secondary Metabolites)
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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.
Keywords: unicellular bacteria; marine bacteria; Thalassospira; thalassospiramide; γ-amino acid; iNOS assay unicellular bacteria; marine bacteria; Thalassospira; thalassospiramide; γ-amino acid; iNOS assay
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

Um S, Pyee Y, Kim E-H, Lee SK, Shin J, Oh D-C. Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.. Marine Drugs. 2013; 11(3):611-622.

Chicago/Turabian Style

Um, Soohyun; Pyee, Yuna; Kim, Eun-Hee; Lee, Sang K.; Shin, Jongheon; Oh, Dong-Chan. 2013. "Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.." Mar. Drugs 11, no. 3: 611-622.



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