Gageostatins A-C, Antimicrobial Linear Lipopeptides from a Marine Bacillus subtilis
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Title
- Gageostatins A-C, Antimicrobial Linear Lipopeptides from a Marine Bacillus subtilis
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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)
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Alternative Author(s)
- TAREQ; 이민아; 이희승; 이종석; 이연주; 신희재
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Publication Year
- 2014-02
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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.
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ISSN
- 1660-3397
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/2906
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DOI
- 10.3390/md12020871
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Bibliographic Citation
- MARINE DRUGS, v.12, no.2, pp.871 - 885, 2014
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Publisher
- MDPI AG
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Subject
- COMPLETE GENOME SEQUENCE; BACTERIUM; PEPTIDES; ANTIBACTERIAL; PURIFICATION; METABOLITES; INHIBITOR; INDUCTION; APOPTOSIS; SURFACTIN
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Keywords
- Bacillus subtilis; lipopeptides; antimicrobial activity; cytotoxicity
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Type
- Article
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Language
- English
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Document Type
- Article
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