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A previously unreported gallocatechin glycoside, (2  R ,3 S ) 4′- O -methyl-gallocatechin-3- O -α-ʟ-rhamnopyranoside ( 1 ) and an unseparable mixture of two previously undescribed dihydromyricetin glycosides, (2  R ,3 R ) 4′- O -methyl-dihydromyricetin-3- O -α-ʟ-rhamnopyranoside ( 2a ) and (2  R ,3 S ) 4′- O -methyl-dihydromyricetin-3- O -α-ʟ-rhamnopyranoside ( 2 b ) along with three known compounds were isolated from the  n -butanol soluble fraction of the stem bark of  Olax subscorpioidea  Oliv. Their structures were elucidated by detailed spectroscopic analyses, including  1 H NMR,  13 C NMR,  1 H- 1 H COSY, HSQC, HMBC, NOESY, HR-ESI-MS and chemical methods. The crude ethanol extract, the fractions, and some of the isolated compounds were screened for their antioxidant and antibacterial activities. They showed significant antioxidant activities with EC 50  ranging from 6.29 to 18.19 µg/mL in 2,2-diphenyl-1-picrylhydrazyl (DPPH) method and EC 50  ranging from 85.77 to 86.39 mmol FeSO 4 /g in ferric reducing antioxidant power (FRAP) methods compared with 2.29 µg/mL and 3.52 mmol FeSO 4 /g for the positive control (ʟ-ascorbic acid). Nevertheless, no inhibition was observed against the tested bacterial strains at a MIC less than 256 μg/mL.

New bioactive flavonoid glycosides with antioxidant activity from the stem bark of Olax subscorpioidea Oliv