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Orsellides A–E: An Example for 6‐Deoxyhexose Derivatives Produced by Fungi
Author(s) -
Schlörke Oliver,
Zeeck Axel
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500793
Subject(s) - chemistry , strain (injury) , biosynthesis , stereochemistry , chaetomium , organic chemistry , enzyme , medicine , food science , penicillium
The antibacterial orsellides A–E ( 1 – 5 ), novel esters consisting of orsellinic acid ( 6 ) and a 6‐deoxyhexose, were isolated from Chaetomium sp . (strain Gö 100/9) together with the known metabolites globosumones A ( 7 ) and B ( 8 ). The structures of the new compounds were elucidated by detailed spectroscopic analysis. The biosynthesis of these metabolites was studied by feeding 13 C‐labelled precursors to growing cultures of strain Gö 100/9. The sugar moieties of the orsellides A–E ( 1 – 5 ) as well as the side chains of globosumones A ( 7 ) and B ( 8 ) originate from carbohydrate intermediates. Thus, the orsellides are rare examples for fungal metabolites containing deoxyhexose building blocks that are normally characteristic for bacterial secondary metabolites. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)