Publication: Synthesis and Biological Activity of Triterpene-Coumarin Conjugates.
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Date
2021-05-06
Authors
Vega-Granados, Karina
Medina-O'Donnell, Marta
Rivas, Francisco
Reyes-Zurita, Fernando J
Martinez, Antonio
Alvarez de Cienfuegos, Luis
Lupiañez, Jose A
Parra, Andres
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Abstract
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.
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MeSH Terms
Animals
Antineoplastic Agents
Cell Cycle Checkpoints
Coumarins
HT29 Cells
Hep G2 Cells
Humans
Melanoma, Experimental
Membrane Potential, Mitochondrial
Mice
Molecular Structure
Olive Oil
Triterpenes
Antineoplastic Agents
Cell Cycle Checkpoints
Coumarins
HT29 Cells
Hep G2 Cells
Humans
Melanoma, Experimental
Membrane Potential, Mitochondrial
Mice
Molecular Structure
Olive Oil
Triterpenes