Identification of centrolobol as the platyphylloside metabolite responsible for the observed effect on in vitro digestibility of hay.
Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4'-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers of 1,7-bis(4'-hydroxyphenyl)-3-heptanol (centrolobol) and 1,7-bis(4-hydroxyphenyl)heptane (platyphyllane) were synthesized and tested regarding digestibility inhibition in vitro in cow rumen fluid. All compounds tested induced a decreased digestion. Centrolobol was found to be the metabolite causing the observed effect, and (R)-centrolobol was found to be the enantiomer formed in the rumen liquor in vitro.
Sunnerheim
Kerstin
K
Department of Chemistry, Uppsala University, Box 599, SE-751 24 Uppsala, Sweden. kerstin.sunnerheim@kei.uu.se
Bratt
Katharina
K
D000818:Animals; D001826:Body Fluids / Q000737:chemistry; D002417:Cattle; D004063:Digestion / Q000187:drug effects*; D010636:Phenols / Q000032:analysis / Q000138:chemical synthesis / Q000494:pharmacology*; D012417:Rumen / Q000378:metabolism
C492804:1,7-bis(4'-hydroxyphenyl)-3-heptanol; D010636:Phenols