title: Limonoids from the seeds of Swietenia macrophylla with inhibitory activity against dengue virus 2.
abstract: Fractionation of an ethanol-soluble extract of the seeds of Swietenia macrophylla yielded six new limonoids, swielimonoids A-F (1-6), along with 20 known compounds. Compounds 1 and 2, mexicanolide-type limonoids, were assigned with an α,β-unsaturated δ-lactone moiety (ring D) and a C═C bond between C-8 and C-30. Compounds 3-6 could be categorized as highly oxygenated phragmalin-type limonoids. The structures of these new compounds were elucidated through the interpretation of spectroscopic data. The antidengue virus 2 activities of the isolated components from S. macrophylla were investigated, and of 12 compounds subjected to bioassay, compounds 2 and 7-10 were found to show inhibitory activity in the range 3.5 to 12.5 μM. Among these, the new limonoid 2 exhibited significant antiviral activity (EC50 = 7.2 ± 1.33 μM) with a selectivity index (CC50/EC50) value of >27.7.
authors.affiliation: Graduate Institute of Natural Products, College of Pharmacy, and ‡Department of Biotechnology, College of Life Science, Kaohsiung Medical University , Kaohsiung, Taiwan.
authors.forename: Yuan-Bin
authors.initials: YB
authors.lastname: Cheng
authors.forename: Yi-Ting
authors.initials: YT
authors.lastname: Chien
authors.forename: Jin-Ching
authors.initials: JC
authors.lastname: Lee
authors.forename: Chin-Kai
authors.initials: CK
authors.lastname: Tseng
authors.forename: Hui-Chun
authors.initials: HC
authors.lastname: Wang
authors.forename: I-Wen
authors.initials: IW
authors.lastname: Lo
authors.forename: Yi-Hung
authors.initials: YH
authors.lastname: Wu
authors.forename: Sheng-Yang
authors.initials: SY
authors.lastname: Wang
authors.forename: Yang-Chang
authors.initials: YC
authors.lastname: Wu
authors.forename: Fang-Rong
authors.initials: FR
authors.lastname: Chang
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D003716:Dengue Virus / Q000187:drug effects*; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012639:Seeds / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D036701:Limonins; C554989:mexicanolide