Trichilianones A-D,Novel Cyclopropane-Type Limonoids from Trichilia adolfi |
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| Authors: | Ivan Limachi Mariela Gonzalez-Ramirez Sophie Manner Juan C Ticona Efrain Salamanca Alberto Gimenez Olov Sterner |
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| Institution: | 1.Department of Chemistry, Centre for Analysis and Synthesis, Lund University, 22100 Lund, Sweden; (I.L.); (M.G.-R.); (S.M.);2.Instituto de Investigaciones Farmaco Bioquimicas, Universidad Mayor de San Andres, La Paz, Bolivia; (J.C.T.); (E.S.); (A.G.) |
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| Abstract: | The fractionation of an ethanol extract of the bark of Trichilia adolfi yielded four novel limonoids (trichilinones A-D, 1–4), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D (1 and 4), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo 5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent (2-oxo)-furan-(5H)-3-yl in trichilinone D (4)], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established based on extensive analysis of NMR spectroscopic data. As the crude extract possessed anti-leishmanial properties, the compounds were assayed for cytotoxic and anti-parasitic activities in vitro in murine macrophages cells (Raw 264.7) and leishmania promastigotes (L. amazoniensis and L. braziliensis), respectively. The compounds showed moderate cytotoxicity (approximately 70 μg/mL), but are not responsible for the leishmanicidal effect of the extract. |
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| Keywords: | Trichilia adolfi cyclopropane-limonoids cytotoxicity leishmanicidal activity |
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