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Title: Biotransformation of natural compounds. Oxido-reduction of Sch-642305 by Aspergillus ochraceus ATCC 1009
Authors: Emilie Adelin
Claudine Servy
Sylvie Cortial
Hélne Lévaique
Jean Franois Gallard
Marie Thérse Martin
Pascal Retailleau
Boonsom Bussaban
Saisamorn Lumyong
Jamal Ouazzani
Keywords: Biochemistry, Genetics and Molecular Biology
Pharmacology, Toxicology and Pharmaceutics
Issue Date: 15-Apr-2011
Abstract: Sch-642305 is the major compound produced by the endophytic fungi Phomopsis sp. CMU-LMA. Incubation of Sch-642305 with Aspergillus ochraceus ATCC 1009 resting cells leads to three new derivatives through an oxido-reduction of the six-membered ring of the molecule. Reduction of the double bound leads to compound (1), which subsequently undergoes carbonyl reduction to (2) and ring hydroxylation to (3). According to the previously solved crystal structure of Sch-642305 coupled with1H NMR NOE correlation and the crystal structure of compound 1, the absolute configurations of the new derivatives were established. In contrast to the parent compound Sch-642305, compound (1) exhibits antimicrobial activity against Gram-negative bacteria. Furthermore, while all derivatives exhibit cytotoxic activity against various cancer cell lines, compound (2) achieved an IC50of 4 nM against human myelogenous leukemia K 562, compared to 20 nM for the parent Sch-642305. © 2011 Elsevier Ltd. All rights reserved.
ISSN: 0960894X
Appears in Collections:CMUL: Journal Articles

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