Studies on the Chemical Constituents and Anti-inflammatory Activities from the Fruit of Swietenia macrophylla

• Main Authors: Sheng-Shiou Huang, 黃聖秀
• Other Authors: none
• Format: Others
• Language: zh-TW
• Published: 2009
• Online Access: http://ndltd.ncl.edu.tw/handle/92318857304868692946

碩士 === 大仁科技大學 === 製藥科技研究所 === 97 === Swietenia macrophylla King (Meliaceae) is a tropical timber tree, natively distributed throughout tropical regions of the Americas, mainly in Honduras, Mexico, Bolivia, and Central America. In our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro inhibitory activity on neutrophil pro- inflammatory responses, and S. macrophylla has been found to be an active species. In our search for compounds with anti-inflammatory activities, a new phragmalin-type limonoid, 6-O-acetyl-3′-demethylswietephragmin E (1) and 16 known compounds (2–17) have been isolated and identified from the fruits of S. macrophylla. Sixteen known compounds include ten limonoids, swietenine (2), swietenine acetate (3), febrifugin (4), 3,6-O,O- diacetylswietenolide (5), 3-O-tigloylswietenolide (6), khayasin T (7), 3-O- tigloyl-6-O-acetylswietenolide (8), swietemahonin E (9), 6-O-acetylswie- temahonin G (10), and 2-hydroxyswietemahonolide (11), a coumarin, scopoletin (12), four steroids, β-sitostenone (13), 3β-hydroxystigmast- 5-en-7-one (14), and a mixture of β-sitosterol (15) and stigmasterol (16), and a fatty acid ester, stearic acid methyl ester (17). The structures of above isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures. Among the isolated compounds, 6-O-acetyl-3′-demethylswietephrag- min E (1), 3,6-O,O-diacetylswietenolide (5), 3-O-tigloylswietenolide (6), 3-O-tigloyl-6-O-acetylswietenolide (8), swietemahonin E (9), and 6-O- acetylswietemahonin G (10) exhibited inhibition (IC50 ≤ 35.71 μM) of superoxide anion generation by human neutrophils in response to formyl- L-methionyl-L-leucyl-L-phenylalanine (fMLP).