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New Flavonol Glucuronides from the Flower Buds of Syzygium aromaticum (Clove)

Ryu, Byeol, Kim, Hye Mi, Lee, Jin Su, Lee, Chan Kyu, Sezirahiga, Jurdas, Woo, Jeong-Hwa, Choi, Jung-Hye, Jang, Dae Sik
Journal of agricultural and food chemistry 2016 v.64 no.15 pp. 3048-3053
Syzygium aromaticum, animal ovaries, buds, chemical structure, chromatography, cytotoxicity, ethanol, flavonols, humans, inhibitory concentration 50, neoplasm cells, nuclear magnetic resonance spectroscopy, ovarian neoplasms, spectral analysis
Repeated chromatography of the EtOAc-soluble fraction from the 70% EtOH extract of the flower buds of Syzygium aromaticum (clove) led to the isolation and characterization of four new flavonol glucuronides, rhamnetin-3-O-β-d-glucuronide (1), rhamnazin-3-O-β-d-glucuronide (2), rhamnazin-3-O-β-d-glucuronide-6″-methyl ester (3), and rhamnocitrin-3-O-β-d-glucuronide-6″-methyl ester (4), together with 15 flavonoids (5–19) having previously known chemical structures. The structures of the new compounds 1–4 were determined by interpretation of spectroscopic data, particularly by 1D- and 2D-NMR studies. Six flavonoids (6, 7, 9, 14, 18, and 19) were isolated from the flower buds of S. aromaticum for the first time in this study. The flavonoids were examined for their cytotoxicity against human ovarian cancer cells (A2780) using MTT assays. Among the isolates, pachypodol (19) showed the most potent cytotoxicity on A2780 cells with an IC50 value of 8.02 μM.