Tonantzitlolone A and other cytotoxic constituents of Sapium macrocarpum (Euphorbiaceae)

Authors

  • Fernando Novillo 1. Universidad Nacional Autónoma de México 2. Universidad Central del Ecuador
  • Verónica Rosero 1. Universidad Nacional Autónoma de México 2. Universidad Central del Ecuador
  • María Isabel Chávez Universidad Nacional Autónoma de México
  • Simón Hernández-Ortega Universidad Nacional Autónoma de México
  • Esteban M. Martínez Universidad Nacional Autónoma de México
  • Guillermo Delgado Universidad Nacional Autónoma de México

DOI:

https://doi.org/10.29356/jmcs.v61i1.130

Keywords:

sitostenone, diterpenes, flexibilane, Euphorbiaceae, NMR reassignments, cytotoxicity

Abstract

Sapium macrocarpum (Euphorbiaceae) is a tropical tree located mainly in the southern part of Mexico and in Central America, and it is used in the Mayan traditional medicine for the treatment of several skin diseases. The dichloromethane-MeOH extract of the aerial parts displayed cytotoxic activity against certain cancer cell lines. Lupeol (1), lupenone (2), sitostenone (3), β-sitosterol (4), stigmasterol (5), sitosteryl β-D-glucopyranoside (6) and the rare diterpene tonantzitlolone A (7) were characterized from this extract. The structural analysis allowed the 1H NMR reassignments for H-12α and H-12β, and for H-13α and H-13β of tonantzitlolone A (7). The cytotoxic activity of compounds 1-3, 6 and 7 was evaluated against selected cancer cell lines. Compounds 3, 6 and 7 displayed clear activity against K562 (leukemia). This is the first report on the chemical constituents of S. macrocarpum, and points out that this species is an additional source of tonantzitlolone A. Compound 7 has only been reported previously from species of the Stillingia, Sebastiania and Sapium genera, which belong to the Hippomaninae subtribe of the family Euphorbiaceae.

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Author Biographies

Fernando Novillo, 1. Universidad Nacional Autónoma de México 2. Universidad Central del Ecuador

  1. Instituto de Química
  2. Facultad de Ciencias Químicas

Verónica Rosero, 1. Universidad Nacional Autónoma de México 2. Universidad Central del Ecuador

  1. Instituto de Química
  2. Facultad de Ciencias Químicas

María Isabel Chávez, Universidad Nacional Autónoma de México

Instituto de Química

Simón Hernández-Ortega, Universidad Nacional Autónoma de México

Instituto de Química

Esteban M. Martínez, Universidad Nacional Autónoma de México

Instituto de Biología

Guillermo Delgado, Universidad Nacional Autónoma de México

Instituto de Química

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Published

2017-10-12

Issue

Section

Regular Articles

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