Document Detail


Inhibition of chitin synthases and antifungal activities by 2'-benzoyloxycinnamaldehyde from Pleuropterus ciliinervis and its derivatives.
MedLine Citation:
PMID:  17329866     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
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:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biological & pharmaceutical bulletin     Volume:  30     ISSN:  0918-6158     ISO Abbreviation:  Biol. Pharm. Bull.     Publication Date:  2007 Mar 
Date Detail:
Created Date:  2007-03-01     Completed Date:  2007-08-20     Revised Date:  2009-11-19    
Medline Journal Info:
Nlm Unique ID:  9311984     Medline TA:  Biol Pharm Bull     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  598-602     Citation Subset:  IM    
Affiliation:
Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Korea.
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MeSH Terms
Descriptor/Qualifier:
Acrolein / 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:
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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