4-O-Caffeoyl-3-O-syringoylquinic acid

Planta Med . 2013 Nov;79(16):1558-1564.

Chemical constituents from the roots and stems of Erycibe obtusifolia and their in vitro antiviral activity[Pubmed: 24081686]

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.

Fitoterapia . 2014 Dec;99:109-116.

Acyl quinic acid derivatives from the stems of Erycibe obtusifolia[Pubmed: 25256062]

Eleven new acyl quinic acid derivatives, 4-O-Caffeoyl-3-O-syringoylquinic acid methyl ester (1), 4-O-caffeoyl-3-O-vanilloylquinic acid (2), 4-O-caffeoyl-3-O-vanilloylquinic acid methyl ester (3), 5-O-caffeoyl-3-O-vanilloylquinic acid (4), 5-O-caffeoyl-3-O-vanilloylquinic acid methyl ester (5), 5-O-caffeoyl-3-O-sinapoylquinic acid (6), 5-O-caffeoyl-4-O-vanilloylquinic acid (7), 4-O-(7‴S, 8‴R)-glycosmisoyl-5-O-caffeoylquinic acid methyl ester (8), 4-O-(7‴S, 8‴R)-glycosmisoyl-5-O-caffeoylquinic acid (9), 3-O-(7‴S, 8‴R)-glycosmisoyl-4-O-caffeoylquinic acid (10), and 3-O-(7‴S, 8‴R)-glycosmisoyl-4-O-caffeoylquinic acid methyl ester (11), have been isolated from the stems of Erycibe obtusifolia together with eight known compounds (12-19). Their structures were elucidated on the basis of spectroscopic data analysis (UV, IR, HRESIMS, CD, and 1D and 2D NMR) and chemical evidence. In in vitro assay, compounds 7 and 16-18 exhibited significant neuroprotective effects against rotenone induced PC12 cell damage at 10 μM.