title: Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum.
abstract: The methanolic extract from the flowers of Punica granatum L. (Punicaceae) was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 1 ng/ml)-induced cytotoxicity in L929 cells. By bioassay-guided separation, a new taraxastane-type triterpene, punicanolic acid (1), was isolated from the active fraction (ethyl acetate-soluble fraction) together with four triterpenes (2--5), two galloyl glucoses (6, 7), two flavones (8, 9), and beta-sitosterol. Among the constituents, 1, oleanolic acid (2), maslinic acid (4), 1,2,6-tri-O-galloyl beta-D-glucopyranoside (6), 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl beta-D-glucopyranoside (7), and luteolin (8) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.
authors.affiliation: Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan.
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Xie
authors.forename: Toshio
authors.initials: T
authors.lastname: Morikawa
authors.forename: Kiyofumi
authors.initials: K
authors.lastname: Ninomiya
authors.forename: Katsuya
authors.initials: K
authors.lastname: Imura
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Dan
authors.initials: D
authors.lastname: Yuan
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D035264:Flowers / Q000737:chemistry; D006801:Humans; D029561:Lythraceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet; D013778:Tetrazolium Salts; D013844:Thiazoles; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors*
chemical_list: D010936:Plant Extracts; D013778:Tetrazolium Salts; D013844:Thiazoles; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha; C534659:punicanolic acid; C022616:thiazolyl blue