N-Desmethylmajusculamide B, a lipopeptide isolated from the Okinawan cyanobacterium Okeania hirsuta

被引:0
|
作者
Zhang, Bo-Tao [1 ]
Nishino, Haruka [1 ]
Kawabe, Ryoya [1 ]
Kamio, Michiya [1 ]
Watanabe, Ryuichi [2 ]
Uchida, Hajime [2 ]
Satake, Masayuki
Nagai, Hiroshi [1 ]
机构
[1] Tokyo Univ Marine Sci & Technol, Dept Ocean Sci, Tokyo, Japan
[2] Japan Fisheries Res & Educ Agcy, Fisheries Technol Inst, Yokohama, Japan
关键词
lipopeptide; cyanobacteria; Okeania hirsuta; Marfey's method; semisynthesis; DERIVATIVES;
D O I
10.1093/bbb/zbae015
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new lipopeptide, N-desmethylmajusculamide B (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta along with 2 known compounds majusculamide A (2) and majusculamide B (3). The planar structure of (1) was elucidated by a detailed analysis of mass spectrometry and nuclear magnetic resonance spectra. The absolute configurations of the amino acid residues were determined using Marfey's analysis. The configuration of C-16 in the alpha-methyl-beta-keto-decanoyl moiety was determined unambiguously to be S by conducting a semisynthesis of N-desmethylmajusculamide B from 3. The cytotoxicity against mouse L1210 leukemia cells was evaluated for majusculamides (1-3). Graphical Abstract N-Desmethylmajusculamide B, a novel lipopeptide was isolated from the marine cyanobacterium Okeania hirsuta.
引用
收藏
页码:517 / 521
页数:5
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