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Phytochemical investigation of the stem bark of  Diospyros longiflora  yielded longiflorol ( 1 ), a new bergenin  α - d -apioside, together with bergenin ( 2 ) and five known compounds: lupeol ( S1 ), betulin ( S2 ), betulinic acid ( S3 ), stigmasterol ( S4 ) and stigmasterol glucoside ( S5 ). Their structures were determined by one-dimensional (1D) and 2D nuclear magnetic resonance experiments along with electrospray ionization high-resolution mass spectrometry and extended density-functional theory calculations of chiroptical properties. Longiflorol ( 1 ) and bergenin ( 2 ) were evaluated for their DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidant activity, with the crude extract for comparison and ascorbic acid as standard. The results showed that the extract and  2  had good antioxidant activity, whereas  1  showed only moderate activity at high concentration (&gt;2 mg mL −1 ).

Longiflorol, a bergenin α - d -apioside from the stem bark of Diospyros longiflora , and its antioxidant activity