Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)

Phenylpropanoid glycosides, 1′-O-benzyl-α-l-rhamnopyranosyl-(1″ → 6′)-β-d-glucopyranoside (1) and α-l-xylopyranosyl-(4″ → 2′)-(3-O-β-d-glucopyranosyl)-1′-O-E-caffeoyl-β-d-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-β-d-glucopyranoside (3), 1-O-(E)-caffeoyl-β-d-glucopyranoside (4) and 1-O-(E)-feruloyl-β-d-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 μM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.