Bioassay-guided fractionation of different extracts of both stem and stem bark of Stereospermum personatum led to the isolation of free-radical-scavenging and xanthine oxidase inhibitory molecules along with three new anthraquinones, sterequinones F-H (1-3), a new naphthoquinone, sterequinone I (4), two new phenethyl esters, 2(4'-hydroxyphenyl)ethyl undecanoate (14) and 2(4'-hydroxyphenyl)ethyl nonacosanoate (15), and a new 3,4,5-trimethoxycinnamyl ether, 2-methoxy-4-[3'-(3'',4'',5''trimethoxyphenyl)allyloxymethyl]phenol (16), together with known compounds. The antioxidant and xanthine oxidase inhibitory potentials of the isolated compounds are reported.