Isoflavone C-glycosides isolated from the root of kudzu (Pueraria lobata) and their estrogenic activities

Add time:08/27/2019    Source:sciencedirect.com

The chemical structures of six isoflavones (1–6) isolated from the kudzu root (Pueraria lobata) were elucidated on the basis of the NMR and MS analyses to be four isoflavone C-glycosides as 6″-O-α-d-glucopyranosylpuerarin (1), puerarin (2), 3′-methoxypuerarin (3), 6″-O-α-d-apiofranosylpuerarin (4), and two aglycons as biochanin A (5) and formononetin (6), respectively. The estrogenic activities of isolated compounds and related isoflavones were evaluated using a yeast two-hybrid assay. Genistein exhibited the highest activity among the evaluated compounds at 10−6 M followed by daidzein (10−5 M), baiochanin A (5) (10−5 M), daidzin (10−5 M), 3′,4′,7-trihydroxyisoflavone (10−3 M), and formononetin (6) (10−2 M). The isoflavone C-glycosides (1–4) and 4′,7-dimethoxyisoflavone showed no activities. In these results, it was found that the addition of 8-C-glucose or 3′-hydroxyl group to daidzein skeleton, or the substitution of hydroxyl functions to methoxyl groups, decreased the estrogenic activity of daidzein, on the other hand, the addition of 7-O-glucose moiety had no influence on the activity.

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