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Studies on the Biosynthesis of Bovilactone‐4,4 and Related Fungal Meroterpenoids
Author(s) -
Lang Martin,
Mühlbauer Andrea,
Jägers Erhard,
Steglich Wolfgang
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.200800232
Subject(s) - chemistry , biosynthesis , stereochemistry , catechol , side chain , terpene , biochemistry , organic chemistry , enzyme , polymer
The initial step in the biosynthesis of suillin ( 1 ), boviquinone‐4 ( 2 ) and bovilactone‐4,4 ( 3 ) in Suillus species is the geranylgeranylation of 3,4‐dihydroxybenzoic acid at the 2‐position. Feeding experiments with advanced precursors have identified boviquinone‐4 and deacetylsuillin ( 9 ) as building blocks for the dilactone and catechol moieties, respectively, of bovilactone‐4,4 ( 3 ). In order to explain the failure of boviquinone‐4 ( 2 ) to incorporate side‐chain‐labelled deacetylsuillin ( 9 # ), an alternative sequence for the formation of 2 is proposed. During these experiments an interesting change in metabolism was noticed: after administration of larger quantities of aromatic carboxylic acids, the boviquinone‐4 present in the fruit bodies disappeared and de novo synthesis of bovilactone‐4,4 occurred. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)