Trichilianones A-D, novel cyclopropane-type limonoids from trichilia adolfi

Ivan Limachi, Mariela Gonzalez-Ramirez, Sophie Manner, Juan C. Ticona, Efrain Salamanca, Alberto Gimenez, Olov Sterner

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

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.

Original languageEnglish
Article number1019
JournalMolecules
Volume26
Issue number4
DOIs
StatePublished - 2 Feb 2021

Bibliographical note

Funding Information:
Funding: This research was funded by the Swedish International Development Comisión Nacional de Investigación Científica y Tecnológica (CONICYT) of Chile. Ph.D. scholarships for I.L (SIDA) and M.G.-R. (CONICYT) are gratefully acknowledge.

Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

  • Cyclopropane-limonoids
  • Cytotoxicity
  • Leishmanicidal activity
  • Trichilia adolfi

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