Prenylated xanthonoids from Calophyllum apetalum

Three new xanthonoids, apetalinones A-C, were isolated from the roots of Calophyllum apetalum, as well as the known compounds, calozeyloxanthone and zeyloxanthonone. The stem bark of this species yielded a new xanthonoid, apetalinone D, and another known xanthonoid, tomentonone. Five known xanthones (3,8-dihydroxy-1,2-dimethoxy-, 1,3-dihydroxy-2,5-dimethoxy-, 1,5-dihydroxy-, 1,3,5-trihydroxy-2-methoxy- and 1,3,5-trihydroxyxanthone) and two flavonoids ((-)-epiafzelechin and (-)-epicatechin) were also characterized as constituents in the stem wood. Among them, apetalinone A was a novel xanthone with 1,1-dimethylallyl ether moiety, which indicated a new biosynthetic pathway including Claisen rearrangement and Diels-Alder reaction. (C) 1997 Elsevier Science Ltd.