title: New Flavonol Glucuronides from the Flower Buds of Syzygium aromaticum (Clove).
abstract: 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.
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Byeol
authors.initials: B
authors.lastname: Ryu
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Hye Mi
authors.initials: HM
authors.lastname: Kim
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Jin Su
authors.initials: JS
authors.lastname: Lee
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Chan Kyu
authors.initials: CK
authors.lastname: Lee
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Jurdas
authors.initials: J
authors.lastname: Sezirahiga
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Jeong-Hwa
authors.initials: JH
authors.lastname: Woo
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Jung-Hye
authors.initials: JH
authors.lastname: Choi
authors.affiliation: Department of Life and Nanopharmaceutical Sciences and ‡College of Pharmacy, Kyung Hee University , Seoul 02447, Republic of Korea.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D044948:Flavonols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D035264:Flowers / Q000737:chemistry*; D020719:Glucuronides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010051:Ovarian Neoplasms / Q000188:drug therapy; D056910:Republic of Korea; D027842:Syzygium / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D044948:Flavonols; D020719:Glucuronides
keywords: Syzygium aromaticum; clove; cytotoxicity; flavonol glucuronides; ovarian cancer