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Epicoccalone, a Coumarin‐Type Chymotrypsin Inhibitor, and Isobenzofuran Congeners from an Epicoccum sp. Associated with a Tree Fungus
Author(s) -
Kemami Wangun Hilaire V.,
Ishida Keishi,
Hertweck Christian
Publication year - 2008
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.200800447
Subject(s) - chemistry , coumarin , isobenzofuran , stereochemistry , polyketide , fungus , biochemistry , enzyme , botany , organic chemistry , biosynthesis , biology
The bioactivity‐guided fractionation of metabolites from an Epicoccum sp. isolated from the fruiting body of the tree fungus Pholiota squarrosa led to the discovery of a new inhibitor of the serine protease α‐chymotrypsin. The structure of the active compound, epicoccalone ( 1 ), was fully elucidated by spectrometric and spectroscopic methods, revealing a coumarin ring system with an unprecedented substitution pattern. Two isobenzofuran‐derived co‐metabolites were identified that are remarkably similar to the epicoccalone coumarin core, strongly suggesting that these metabolites share the same orsellinic acid like polyketide pathway.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)