Antioxidant Activity of 2,3,6-Tribromo-4,5-dihydroxy benzyl methyl ether from Symphyocladia latiuscula

Antioxidant activity of a methanol extract of Symphyocladia latiuscula was evaluated by the thiocyanate method in the linoleic acid system. The methanol extract inhibited the peroxidation of linoleic acid in a dose-dependent manner. The MeOH extract was then sequentially partitioned with n-hexane, $CH_2Cl_2$, EtOAc, n-BuOH and H20. The antioxidant activity of the fractions increased in order of $CH_2Cl_2$, n-hexane, EtOAc, and n-BuOH. There was no activity found in $H_2O$ partitoned fraction by the thiocyanate method. Especially, the activities of the fractions of n-hexane and $CH_2Cl_2$ were comparable to that of 2,6-di-tert­butylhydroxytoluene (BHT). Column chromatography of the $CH_2Cl_2$ fraction over silica gel yielded cholesterol (1) and 2,3,6-tribromo 4,5-dihydroxybenzyl methyl ether (2) which were identified by instrumental analysis of MS and $^1H-$ and $^{13}C-NMR$. The latter (2) demonstrated significant antioxidant activity.