| Inhibition of chitin synthases and antifungal activities by 2'-benzoyloxycinnamaldehyde from Pleuropterus ciliinervis and its derivatives. | |
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MedLine Citation:
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PMID: 17329866 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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In the course of search for potent chitin synthase inhibitors from natural resources, a novel chitin synthases inhibitor, 2'-benzoyloxycinnamaldehyde (2'-BCA) (I), was isolated from the aerial parts of Pleuropterus ciliinervis NAKAI. 2'-BCA inhibited chitin synthase 1 and 2 of Saccharomyces cerevisiae with the IC50s of 54.9 and 70.8 microg/ml, respectively, whereas it exhibited no inhibitory activity for chitin synthase 3 up to 280 microg/ml. Its derivatives, 2'-chloro- (V) and 2(-bromo-cinnamaldehyde (VI), each showed 1.9 and 2.7-fold stronger inhibitory activities than 2'-BCA, with the IC50s of 37.2 and 26.6 microg/ml, respectively. Especially, the IC50 of compound VI against chitin synthase 2 represented 1.7-fold more potent inhibitory activity than polyoxin D, a well-known chitin synthase inhibitor. Furthermore, compounds V and VI showed potent antifungal activities against various fungi including human pathogenic fungi, with a particularly strong inhibitory activity against Cryptococcus neoformans (MIC = 16 microg/ml). Although the chemical synthesis of this compound has been reported, the present study is the first report to describe the isolation of 2'-BCA from natural resources and chitin synthases inhibitory activities of its derivatives. These results suggested that 2'-BCA and its derivatives can potentially serve as useful lead compounds for development of antifungal agents. |
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Authors:
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Tae Hoon Kang; Eui Il Hwang; Bong Sik Yun; Ki Duk Park; Byoung Mog Kwon; Chul Soo Shin; Sung Uk Kim |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Biological & pharmaceutical bulletin Volume: 30 ISSN: 0918-6158 ISO Abbreviation: Biol. Pharm. Bull. Publication Date: 2007 Mar |
Date Detail:
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Created Date: 2007-03-01 Completed Date: 2007-08-20 Revised Date: 2009-11-19 |
Medline Journal Info:
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Nlm Unique ID: 9311984 Medline TA: Biol Pharm Bull Country: Japan |
Other Details:
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Languages: eng Pagination: 598-602 Citation Subset: IM |
Affiliation:
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Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Korea. |
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| MeSH Terms | |
Descriptor/Qualifier:
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Acrolein
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analogs & derivatives*,
chemistry,
isolation & purification,
pharmacology Aminoglycosides / pharmacology Antifungal Agents / chemistry, isolation & purification, pharmacology* Benzoates / chemistry, isolation & purification, pharmacology* Candida / drug effects, growth & development Chitin Synthase / antagonists & inhibitors*, metabolism Cryptococcus neoformans / drug effects, growth & development Dose-Response Relationship, Drug Enzyme Inhibitors / chemistry, isolation & purification, pharmacology* Humans Microbial Sensitivity Tests / methods Molecular Structure Plant Components, Aerial / chemistry Plant Extracts / chemistry, isolation & purification, pharmacology Polygonaceae / chemistry* Pyrimidine Nucleosides / pharmacology |
| Chemical | |
Reg. No./Substance:
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0/2'-benzoyloxycinnamaldehyde; 0/2'-chlorocinnamaldehyde; 0/2-bromocinnamaldehyde; 0/Aminoglycosides; 0/Antifungal Agents; 0/Benzoates; 0/Enzyme Inhibitors; 0/Plant Extracts; 0/Pyrimidine Nucleosides; 107-02-8/Acrolein; 22976-86-9/polyoxorim; 59456-70-1/nikkomycin; EC 2.4.1.16/Chitin Synthase; EC 2.4.1.16/chitin synthase 2 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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