Three new quinic acid derivatives, 4-O-caffeoyl-3-O-sinapoylquinic acid methyl ester (1), 5-O-caffeoyl-4-O-syringoylquinic acid methyl ester (2), and 4-O-caffeoyl-3-O-syringoylquinic acid methyl ester (3), as well as four new coumarin glycosides, 7-O-(3-O-sinapoyl-β-D-glucopyranosyl)-6-methoxycoumarin (12), 7-O-(6-O-sinapoyl-β-D-glucopyranosyl)-6-methoxycoumarin (13), 7-O-(2-O-sinapoyl-β-D-glucopyranosyl)-6-methoxycoumarin (14), and 7-O-(6-O-syringoyl-β-D-glucopyranosyl)-6-methoxycoumarin (15), together with eight known compounds (4–11) were isolated from the roots and stems of Erycibe obtusifolia. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the compounds were screened for their in vitro antiviral activity against respiratory syncytial virus with a cytopathic effect reduction assay. Among them, the di-O-caffeoyl quinates 8–11 displayed a potent in vitro anti-respiratory syncytial virus effect. * These authors contributed equally to this work.
Two novel dimeric diarylheptanoids, alpinidinoids A [(±)-1] and B (2), with two unusual coupling patterns, together with a new naturally occurring diarylheptanoid dimer possessing a rare pyridine ring linkage (alpinidinoid C, 3), were isolated from the rhizomes of Alpinia officinarum. Their structures including absolute configurations were determined by extensive spectroscopic methods and theoretical calculations. All isolates were examined for their neuroprotective activities against oxygen-glucose deprivation and reoxygenation (OGD/R) damage in primary cortical neurons. Remarkably, the dextrorotatory enantiomer of alpinidinoid A [(+)-1] significantly ameliorated OGD/R-induced neuronal apoptosis, which was dependent on the activation of the AKT/mTOR signaling pathway.