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. 2021 Feb 15;26(4):1019.
doi: 10.3390/molecules26041019.

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

Ivan Limachi  1   2 , Mariela Gonzalez-Ramirez  1 , Sophie Manner  1 , Juan C Ticona  2 , Efrain Salamanca  2 , Alberto Gimenez  2 , Olov Sterner  1
Affiliations

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

Ivan Limachi et al. Molecules. .

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.

Keywords: Trichilia adolfi; cyclopropane-limonoids; cytotoxicity; leishmanicidal activity.

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Conflict of interest statement

The authors declare no conflict of interest. The sponsors had no role in the design, execution, interpretation, or writing of the study.

Figures

Figure 1
Figure 1
Related compounds isolated from other sources.
Figure 2
Figure 2
Trichilianones A (1), B (2), C (3) and D (4), isolated from Trichilia adolfi.
Figure 3
Figure 3
COSY correlations observed with compounds 1–4.
Figure 4
Figure 4
HMBC correlations observed with compounds 1–4.
Figure 5
Figure 5
NOESY correlations observed with compounds 1–4.
See this image and copyright information in PMC

References

    1. Ulloa C., Acevedo-Rodríguez P., Beck S., Belgrano M.J., Bernal R., Berry P.E., Brako L., Celis M., Davidse G., Forzza R.C., et al. Vascular Plants of the Americas (VPA) Website. Tropicos, Botanical Information System at the Missouri Botanical Garden, St. Louis, Missouri, USA. [(accessed on 19 January 2021)];2018 Available online: http://legacy.tropicos.org/Project/VPA.
    1. Queveno C., Bourdy G., Gimenez A. Tacana. Ed. UMSA-CIPTA-IRD-FONAMA-EIA; La Paz, Bolivia: 1999. O.L: 4-1-400-99.
    1. Bourdy G., DeWalt S.J., Chavez de Michel L.R., Roca A., Deharo E., Muñoz V., Balderrama L., Quenevo C., Gimenez A. Medicinal plants uses of the Tacana, an amazonian Bolivian ethnic group. J. Ethnopharmacol. 2000;70:87–109. doi: 10.1016/S0378-8741(99)00158-0. - DOI - PubMed
    1. Arévalo-Lopéz D., Nina N., Ticona J.C., Limachi I., Salamanca E., Udaeta E., Paredes C., Espinoza B., Serato A., Garnica D., et al. Leishmanicidal and cytotoxic activity of plants used in Tacana traditional medicine (Bolivia) J. Etnopharmacol. 2018;216:120–133. doi: 10.1016/j.jep.2018.01.023. - DOI - PubMed
    1. Tan Q.G., Luo X.D. Meliaceous limonoids: Chemistry and biological activities. Chem. Rev. 2011;111:7437–7522. doi: 10.1021/cr9004023. - DOI - PubMed

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