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

作者：Novillo Fernando; Rosero Veronica; Isabel Chavez Maria; Hernandez Ortega Simon; Martinez Esteban M; Delgado Guillermo^*

来源：Journal of the Mexican Chemical Society, 2017, 61(1): 67-73.

DOI：10.29356/jmcs.v61i1.130

• sitostenone
• diterpenes
• flexibilane
• Euphorbiaceae
• NMR reassignments
• cytotoxicity

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), beta-sitosterol (4), stigmasterol (5), sitosteryl beta-D-glucopyranoside (6) and the rare diterpene tonantzitlolone A (7) were characterized from this extract. The structural analysis allowed the H-1 NMR reassignments for H-12 alpha and H-12 beta, and for H-13 alpha and H-13 beta 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.

• 出版日期2017-3