Hopane-type triterpenes from Cnidoscolus spinosus and their bioactivities.

Bioorganic chemistry 2020 Jul

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Chemical investigation of the aerial parts of Cnidoscolus spinosus resulted in the isolation of relatively infrequent hopane-type triterpenes, 3β-acetoxy-hop-22(29)-ene (1), first reported here as natural product, together with 3-oxo-hop-22(29)-ene (2), and 3β-hydroxy-hop-22(29)-ene (3). β-Amyrin palmitate and three phytosterols were also characterized. The structures of the compounds were established using spectroscopic methods, and those of 1 and 2 were confirmed by crystallographic analysis. Selected biological activities for the isolated hopane-type triterpenes were tested through a series of assays for determining the cytotoxic, anti-inflammatory, α-glucosidase inhibition and antiparasitic activities. Compounds 1-3 did not show cytotoxic activity, compound 1 displayed an important inhibitory effect in the mouse ear induced inflammation assay, and significantly inhibited the yeast α-glucosidase activity in vitro and in silico. Additionally, compounds 2 and 3 showed marginal activities against Trypanosoma cruzi and Leishmania mexicana. Therefore, the bioactivities of hopane-type triterpenes deserve further investigation, particularly their anti-inflammatory properties. Copyright © 2020 Elsevier Inc. All rights reserved.

Citation

Fabiola A López-Huerta, Antonio Nieto-Camacho, Félix Morales-Flores, Simón Hernández-Ortega, María Isabel Chávez, Carlos A Méndez Cuesta, Ignacio Martínez, Bertha Espinoza, Francisco J Espinosa-García, Guillermo Delgado. Hopane-type triterpenes from Cnidoscolus spinosus and their bioactivities. Bioorganic chemistry. 2020 Jul;100:103919