A labeling study on the formation of perillene by submerged cultured oyster mushroom, Pleurotus ostreatus.
The conversion of beta-myrcene to the furanoid flavour compound perillene by Pleurotus ostreatus was investigated using trideutero beta-myrcene, trideutero alpha-(Z)-acaridiol and non-labeled 1,2- and 3,10-epoxy-beta-myrcene, alpha,alpha-acarilactol, and perillene as substrates. Myrcene diols were formed from the cleavage of myrcene epoxides, but only alpha-(Z)-acaridiol, a 1,4-butanediol derivative most likely generated through a base-catalysed epoxide opening, was a suitable precursor of perillene. Once formed, this key intermediate was rapidly oxidised and the resulting cyclic lactol was dehydrated to yield perillene. Bioconversion of the supplemented perillene to alpha,alpha-acariolide indicated that perillene was another intermediate of the pathway and prone to further oxidative degradation. The data suggest that the fungus converted the cytotoxic beta-myrcene in its environment into a metabolically useable carbon source along this route.
Krings
Ulrich
U
Zentrum für Angewandte Chemie der Leibniz Universität Hannover, Institut für Lebensmittelchemie, Wunstorfer Str. 14, D-30453, Hannover, Germany. krings@lci.uni-hannover.de
Hapetta
Darius
D
Berger
Ralf G
RG
D000080462:Acyclic Monoterpenes; D000475:Alkenes / Q000378:metabolism; D003903:Deuterium / Q000378:metabolism*; D005663:Furans / Q000138:chemical synthesis / Q000378:metabolism*; D039821:Monoterpenes / Q000138:chemical synthesis / Q000378:metabolism*; D020076:Pleurotus / Q000378:metabolism*
D000080462:Acyclic Monoterpenes; D000475:Alkenes; D005663:Furans; D039821:Monoterpenes; C008574:beta-myrcene; C509595:myrcene; C090823:perillene; D003903:Deuterium