Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi

Summary, in English

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.

• Author: Ivan Limachi; Mariela Gonzalez-Ramirez; Sophie Manner; Juan C. Ticona; Efrain Salamanca; Alberto Gimenez; Olov Sterner
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2021
• Language: English
• Publication/Series: Molecules (Basel, Switzerland)
• Volume: 26
• Issue: 4
• Links: http://dx.doi.org/10.3390/molecules26041019
• Document type: Journal article
• Publisher: MDPI AG
• Topic: Organic Chemistry
• Keywords: cyclopropane-limonoids; cytotoxicity; leishmanicidal activity; Trichilia adolfi
• Status: Published
• ISBN/ISSN/Other: ISSN: 1420-3049