Hopane-type triterpenes from Cnidoscolus spinosus and their bioactivities

  • Bioorg Chem. 2020 Jul;100:103919. doi: 10.1016/j.bioorg.2020.103919.
Fabiola A López-Huerta  1 ,  Antonio Nieto-Camacho  1 ,  Félix Morales-Flores  1 ,  Simón Hernández-Ortega  1 ,  María Isabel Chávez  1 ,  Carlos A Méndez Cuesta  2 ,  Ignacio Martínez  3 ,  Bertha Espinoza  3 ,  Francisco J Espinosa-García  4 ,  Guillermo Delgado  5
Affiliations
  • 1. Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán 04510, Ciudad de México, Mexico.
  • 2. Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana, Unidad Xochimilco, Calzada del Hueso 1100, Ciudad de México 04960, Mexico.
  • 3. Departamento de Inmunología, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Coyoacán 04510, Ciudad de México, Mexico.
  • 4. Instituto de Investigaciones en Ecosistemas y Sustentabilidad, Universidad Nacional Autónoma de México, Ex Hacienda de San José de la Huerta 58190, Morelia, Mexico.
  • 5. Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán 04510, Ciudad de México, Mexico. Electronic address: [email protected].
PMID: 32417524 DOI: 10.1016/j.bioorg.2020.103919
Abstract

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.

Keywords
3β-acetoxy-hop-22(29)-ene; Anti-inflammation; Cnidoscolus spinosus; Hopanes; Triterpenes.
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