Gageostatins A-C, Antimicrobial Linear Lipopeptides from a Marine Bacillus subtilis SCIE SCOPUS

Cited 33 time in WEB OF SCIENCE Cited 34 time in Scopus
Title
Gageostatins A-C, Antimicrobial Linear Lipopeptides from a Marine Bacillus subtilis
Author(s)
Tareq, Fakir Shahidullah; Lee, Min Ah; Lee, Hyi-Seung; Lee, Jong-Seok; Lee, Yeon-Ju; Shin, Hee Jae
KIOST Author(s)
Lee, Min Ah(이민아)Lee, Hyi Seung(이희승)Lee, Jong Seok(이종석)Lee, Yeon Ju(이연주)Shin, Hee Jae(신희재)
Alternative Author(s)
TAREQ; 이민아; 이희승; 이종석; 이연주; 신희재
Publication Year
2014-02
Abstract
Concerning the requirements of effective drug candidates to combat against high rising multidrug resistant pathogens, we isolated three new linear lipopeptides, gageostatins A-C (1-3), consisting of hepta-peptides and new 3--hydroxy fatty acids from the fermentation broth of a marine-derived bacterium Bacillus subtilis. Their structures were elucidated by analyzing a combination of extensive 1D, 2D NMR spectroscopic data and high resolution ESIMS data. Fatty acids, namely 3--hydroxy-11-methyltridecanoic and 3--hydroxy-9,11-dimethyltridecanoic acids were characterized in lipopeptides 1 and 2, respectively, whereas an unsaturated fatty acid (E)-7,9-dimethylundec-2-enoic acid was assigned in 3. The 3R configuration of the stereocenter of 3--hydroxy fatty acids in 1 and 2 was established by Mosher's MTPA method. The absolute stereochemistry of amino acid residues in 1-3 was ascertained by acid hydrolysis followed by Marfey's derivatization studies. Gageostatins 1-3 exhibited good antifungal activities with MICs values of 4-32 mu g/mL when tested against pathogenic fungi (R. solani, B. cinerea and C. acutatum) and moderate antibacterial activity against bacteria (B. subtilis, S. aeureus, S. typhi and P. aeruginosa) with MICs values of 8-64 mu g/mL. Futhermore, gageostatins 1-3 displayed cytotoxicity against six human cancer cell lines with GI(50) values of 4.6-19.6 mu g/mL. It is also noteworthy that mixed compounds 1+2 displayed better antifungal and cytotoxic activities than individuals.
ISSN
1660-3397
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/2906
DOI
10.3390/md12020871
Bibliographic Citation
MARINE DRUGS, v.12, no.2, pp.871 - 885, 2014
Publisher
MDPI AG
Subject
COMPLETE GENOME SEQUENCE; BACTERIUM; PEPTIDES; ANTIBACTERIAL; PURIFICATION; METABOLITES; INHIBITOR; INDUCTION; APOPTOSIS; SURFACTIN
Keywords
Bacillus subtilis; lipopeptides; antimicrobial activity; cytotoxicity
Type
Article
Language
English
Document Type
Article
Publisher
MDPI AG
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