DOI: 10.1093/bbb/zbae015 ISSN: 1347-6947
N-Desmethylmajusculamide B, a lipopeptide isolated from the Okinawan cyanobacterium Okeania hirsuta
Bo-Tao Zhang, Haruka Nishino, Ryoya Kawabe, Michiya Kamio, Ryuichi Watanabe, Hajime Uchida, Masayuki Satake, Hiroshi Nagai- Organic Chemistry
- Molecular Biology
- Applied Microbiology and Biotechnology
- General Medicine
- Biochemistry
- Analytical Chemistry
- Biotechnology
Abstract
A new lipopeptide, N-desmethylmajusculamide B (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta along with two known compounds majusculamide A (2) and majusculamide B (3). The planar structure of 1 was elucidated by a detailed analysis of MS and NMR spectra. The absolute configurations of the amino acid residues were determined using Marfey's analysis. The configuration of C-16 in the α-methyl-β-keto-decanoyl moiety was determined unambiguously to be S by conducting a semi-synthesis of N-desmethylmajusculamide B from 3. The cytotoxicity against mouse L1210 leukemia cells was evaluated for majusculamides (1-3).