Taeanamides A and B, Nonribosomal Lipo-Decapeptides Isolated from an Intertidal-Mudflat-Derived Streptomyces sp

• Published in: Marine drugs Vol. 20; no. 6; p. 400
• Main Authors: Cui, Jinsheng, Kim, Eunji, Moon, Dong Hyun, Kim, Tae Ho, Kang, Ilnam, Lim, Yeonjung, Shin, Daniel, Hwang, Sunghoon, Du, Young Eun, Song, Myoung Chong, Bae, Munhyung, Cho, Jang-Cheon, Jang, Jichan, Lee, Sang Kook, Yoon, Yeo Joon, Oh, Dong-Chan
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 16.06.2022; MDPI
• Subjects: Amino acids; Analytical methods; anti-tuberculosis; Bioinformatics; Biological activity; Cancer; Carbon; Connectivity; Constants; cytotoxicity; Genomes; Gram-positive bacteria; intertidal mudflat; Magnetic resonance spectroscopy; Mass spectrometry; Mass spectroscopy; Mud flats; NMR; NMR spectroscopy; nonribosomal peptide synthetase; Nuclear magnetic resonance; Nucleotide sequence; Peptides; Planar structures; Streptomyces; Streptomyces sp; Tuberculosis; Tumor cell lines
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md20060400

Two new lipo-decapeptides, namely taeanamides A and B (1 and 2), were discovered from the Gram-positive bacterium Streptomyces sp. AMD43, which was isolated from a mudflat sample from Anmyeondo, Korea. The exact molecular masses of 1 and 2 were revealed by high-resolution mass spectrometry, and the planar structures of 1 and 2 were elucidated using NMR spectroscopy. The absolute configurations of 1 and 2 were determined using a combined analysis of 1H-1H coupling constants and ROESY correlations, the advanced Marfey’s method, and bioinformatics. The putative nonribosomal peptide synthetase pathway for the taeanamides was identified by analyzing the full genome sequence data of Streptomyces sp. AMD43. We also found that taeanamide A exhibited mild anti-tuberculosis bioactivity, whereas taeanamide B showed significant bioactivity against several cancer cell lines.