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Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp.
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 151-742, Korea
Division of Magnetic Resonance, Korea Basic Science Institute, Ochang, Chungbuk 363-883, Korea
* Author to whom correspondence should be addressed.
Received: 13 December 2012; in revised form: 29 January 2013 / Accepted: 6 February 2013 / Published: 26 February 2013
Abstract: 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.
Keywords: unicellular bacteria; marine bacteria; Thalassospira; thalassospiramide; γ-amino acid; iNOS assay
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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.
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.
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.