Planta Med 2014; 80 - P1L118
DOI: 10.1055/s-0034-1394775

Anti-Dengue virus limonoids from the actual seeds of Swietenia macrophylla

YB Cheng 1, YT Chien 1, JC Lee 2, YC Wu 3, 4, 5, FR Chang 1
  • 1Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 2Department of Biotechnology, College of Life Science, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 3School of Pharmacy, College of Pharmacy, China Medical University, Taichung, Taiwan
  • 4Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung, Taiwan
  • 5Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan

Fractionation of ethanol extract from the actual seeds of Swietenia macrophylla afforded seven new limonoids, swielimonoids A-G (1-7), together with twenty known compounds. Compounds 1 and 2, mexicanolide-type limonoids, have a a,b-unsaturated d-lactone moiety (ring D) and a C = C bond between C-8 and C-30. Compounds 4-7 were categorized as a highly oxygenated phragmalin-type limonoid. The structures of these compounds were elucidated through the interpretation of spectroscopic methods, especially 2D NMR technologies (COSY, HMQC, HMBC, and NOESY). The anti-Dengue virus activities of isolated components from S. macrophylla were revealed for the first time. A dozen of compounds were subjected to the bioassay, and compounds 3 and 8-11 were active in the range of 3.5 – 12.5 mM. Among them, the new limonoid 3 exhibited significant activity (EC50= 7.2 ± 1.33 mM) with maximum selection index CC50/EC50 value > 27.7.

Keywords: Swietenia macrophylla, limonoid, anti-Dengue virus