title: Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of Mammea siamensis.
abstract: A methanol extract of the flowers of Mammea siamensis (Calophyllaceae) was found to inhibit enzymatic activity against aromatase (IC50=16.5 µg/mL). From the extract, two new geranylated coumarins, mammeasins C (1) and D (2), were isolated together with seven coumarins: 8-hydroxy-5-methyl-7-(3,7-dimethyl-octa-2,6-dienyl)-9-(2-methyl-1-oxobutyl)-4,5-dihydropyrano[4,3,2-de]chromen-2-one (9), 8-hydroxy-5-methyl-7-(3,7-dimethyl-octa-2,6-dienyl)-9-(3-methyl-1-oxobutyl)-4,5-dihydropyrano[4,3,2-de]chromen-2-one (10), mammeas A/AA (14), A/AB (15), A/AA cyclo D (18), E/BA (23), and E/BC cyclo D (25). The structures of 1 and 2 were elucidated on the basis of spectroscopic evidence. Among the isolates including 17 previously reported coumarins, 1 (IC50=2.7 µM), 2 (3.6 µM), and mammea B/AB cyclo D (21, 3.1 µM) showed relatively strong inhibitory activities comparable to the activity of the synthetic nonsteroidal aromatase inhibitor aminoglutethimide (2.0 µM).
authors.affiliation: Pharmaceutical Research and Technology Institute, Kindai University.
authors.forename: Kiyofumi
authors.initials: K
authors.lastname: Ninomiya
authors.forename: Kanae
authors.initials: K
authors.lastname: Shibatani
authors.forename: Mayumi
authors.initials: M
authors.lastname: Sueyoshi
authors.forename: Saowanee
authors.initials: S
authors.lastname: Chaipech
authors.forename: Yutana
authors.initials: Y
authors.lastname: Pongpiriyadacha
authors.forename: Takao
authors.initials: T
authors.lastname: Hayakawa
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Toshio
authors.initials: T
authors.lastname: Morikawa
mesh_terms: D001141:Aromatase / Q000378:metabolism*; D047072:Aromatase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D035264:Flowers / Q000737:chemistry*; D006801:Humans; D031252:Mammea / Q000737:chemistry*; D015394:Molecular Structure; D011994:Recombinant Proteins / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D047072:Aromatase Inhibitors; D003374:Coumarins; D011994:Recombinant Proteins; C000613651:mammeasin C; C000613652:mammeasin D; D001141:Aromatase