Synthesis and Biological Activity of Triterpene-Coumarin Conjugates
Metadatos
Mostrar el registro completo del ítemAutor
Vega Granados, Dulce Karina; Medina O'Donnell, Marta; Rivas Sánchez, Francisco De Asís; Reyes Zurita, Fernando Jesús; Martínez Rodríguez, Antonio; Álvarez Cienfuegos Rodríguez, Luis; Lupiáñez Cara, José Antonio; Parra Sánchez, AndrésEditorial
American Chemical Society
Fecha
2021-05-06Referencia bibliográfica
J. Nat. Prod. 2021, 84, 1587−1597. [https://doi.org/10.1021/acs.jnatprod.1c00128]
Patrocinador
Junta de Andalucia B1-FQM-217-UGR18 B1-BIO-281-UGR18Resumen
A set of 12 maslinic acid−coumarin conjugates was
synthesized, with 9 being maslinic acid−diamine−coumarin
conjugates at the C-28 carboxylic acid group of triterpene acid
and the other three being maslinic acid−coumarin conjugates at C-
2/C-3 and/or C-28 of the triterpene skeleton. The cytotoxic effects
of these 12 triterpene conjugates were evaluated in three cancer
cell lines (B16-F10, HT29, and Hep G2) and compared,
respectively, with three nontumor cell lines from the same or
similar tissue (HPF, IEC-18, and WRL68). The most potent
cytotoxic results were achieved by a conjugate with two molecules
of coumarin-3-carboxylic acid coupled through the C-2 and C-3
hydroxy groups of maslinic acid. This conjugate showed
submicromolar IC50 values in two of the three cancer cell lines tested (0.6, 1.1, and 0.9 μM), being between 110- and 30-fold
more effective than its corresponding precursor. Furthermore, this conjugate (10) showed percentages of cell viability for the three
nontumor lines of 90%. Four maslinic acid−coumarin conjugates displayed apoptotic effects in the treated cells, with total apoptosis
rates of between 40 and 85%, relative to the control. Almost all the compounds assayed caused cell-cycle arrest in all cancer cell lines,
increasing the number of these cells in the G0/G1 phase.