Limonoids from the seeds of Swietenia macrophylla with inhibitory activity against dengue virus 2. 2014

Yuan-Bin Cheng, and Yi-Ting Chien, and Jin-Ching Lee, and Chin-Kai Tseng, and Hui-Chun Wang, and I-Wen Lo, and Yi-Hung Wu, and Sheng-Yang Wang, and Yang-Chang Wu, and Fang-Rong Chang
Graduate Institute of Natural Products, College of Pharmacy, and ‡Department of Biotechnology, College of Life Science, Kaohsiung Medical University , Kaohsiung, Taiwan.

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.

UI MeSH Term Description Entries
D003716 Dengue Virus A species of the genus FLAVIVIRUS which causes an acute febrile and sometimes hemorrhagic disease in man. Dengue is mosquito-borne and four serotypes are known. Breakbone Fever Virus,Breakbone Fever Viruses,Dengue Viruses,Fever Virus, Breakbone,Fever Viruses, Breakbone,Virus, Breakbone Fever,Virus, Dengue,Viruses, Breakbone Fever,Viruses, Dengue
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D012639 Seeds The encapsulated embryos of flowering plants. They are used as is or for animal feed because of the high content of concentrated nutrients like starches, proteins, and fats. Rapeseed, cottonseed, and sunflower seed are also produced for the oils (fats) they yield. Diaspores,Elaiosomes,Embryos, Plant,Plant Embryos,Plant Zygotes,Zygotes, Plant,Diaspore,Elaiosome,Embryo, Plant,Plant Embryo,Plant Zygote,Seed,Zygote, Plant
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D019906 Nuclear Magnetic Resonance, Biomolecular NMR spectroscopy on small- to medium-size biological macromolecules. This is often used for structural investigation of proteins and nucleic acids, and often involves more than one isotope. Biomolecular Nuclear Magnetic Resonance,Heteronuclear Nuclear Magnetic Resonance,NMR Spectroscopy, Protein,NMR, Biomolecular,NMR, Heteronuclear,NMR, Multinuclear,Nuclear Magnetic Resonance, Heteronuclear,Protein NMR Spectroscopy,Biomolecular NMR,Heteronuclear NMR,Multinuclear NMR,NMR Spectroscopies, Protein,Protein NMR Spectroscopies,Spectroscopies, Protein NMR,Spectroscopy, Protein NMR
D029582 Meliaceae The mahogany plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Dysoxylum,Guarea,Khaya,Sandoricum,Trichilia,Carapa,Swietenia,Turraea,Carapas,Dysoxylums,Guareas,Khayas,Sandoricums,Swietenias,Trichilias,Turraeas
D036701 Limonins A group of degraded TRITERPENES in which the four terminal carbons of the C17 side chain have been removed, and the remaining portion often forming C17 furans. Limonoid,Limonoid Tetranortriterpene,Limonoid Tetranortriterpenes,Limonoids,Tetranortriterpene,Tetranortriterpenes,Tetranortriterpenoid,Tetranortriterpenoids,Tetranortriterpene, Limonoid

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