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6,8-Di-C-methyl-flavonoids with neuroprotective activities from Rhododendron fortunei
Yongji Lai1, Hong Zeng2, Meijun He3
1Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China; Department of Pharmacy, Central Hospital of Wuhan, Wuhan 430014, People's Republic of China.
Abstract:
Six 6,8-di-C-methyl-flavonoids, (2R,3R)-6,8-di-C-methyl-5,7,4'-trihydroxyflavanonol 7-O-β-d-gluco-pyranoside (1), (2R,3R)-6,8-di-C-methyl-5,7,4'-trihydroxyflavanonol 7-O-β-d-xylopyranosyl(1→6)-β-d-glucopyranoside (2), 6,8-di-C-methylkaempferol 7-O-β-d-glucopyranoside (3), (2R)-farrerol (4a), (2R/2S)-farrerol 7-O-β-d-glucopyranoside (5), and (2R/2S)-farrerol 7-O-β-d-xylopyranosyl(1→6)-β-d-glucopyranoside (6), and four known analogues, farrerol (4b), (2R,3R)-6,8-di-C-methyldihydrokae-mpferol (7), 6,8-di-C-methylkaempferol 7-O-β-d-glucopyranoside (8), and 6,8-di-C-methylkaempferol (9), were isolated from the twigs and leaves of Rhododendron fortunei. The structures of compounds 1-9 were determined by spectroscopic analyses (HRESIMS, 1D and 2D NMR, and CD) and chemical methods. Compounds 1-9 were evaluated for their neuroprotective effects on the human neuroblastoma SH-SY5Y cells apoptosis induced by hydrogen peroxide (H2O2) and amyloid β peptide (Aβ), respectively. Compounds 1-3 and 5-9 exhibited significant neuroprotective effects against H2O2-induced SH-SY5Y cell apoptosis, and compound 8 exhibited the strongest activity with a improvement of cell viability by about 30% at the concentration of 10μM. Compounds 1-9 showed significant neuroprotective effects against Aβ-induced SH-SY5Y cell apoptosis.
