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

Abstract

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.

Marine natural products

“…Seven siderophore-related compounds 124 – 130 were isolated from a sponge-associated S. diastaticus . 34 Other Streptomyces -sourced peptide NPs included the epoxy cinnamoyl-containing epoxinnamide 131 , 35 teanamides A 132 and B 133 , 36 xanthostatin B 134 , 37 cystargamides C 135 and D 136 (ref. 38) and levesquamide B 137 , 39 as well as four diketopiperazines 138 – 140 (ref.…”

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

“…Compound 45 showed antitubercular activity against Mycobacterium tuberculosis mc 2 6230, with a concentration at which 50% of the strains were inhibited (MIC 50 ) of 27 µM. Bedaquiline was used as the positive control with an MIC 50 = 0.4 µM [ 168 ].…”