Cytotoxic, anti-inflammatory, and alpha-glucosidase inhibitory effects of flavonoids from Lippia graveolens (Mexican oregano)
Por:
Amador, Sonia, Nieto-Camacho, Antonio, Teresa Ramirez-Apan, Ma, Martinez, Mahinda, MALDONADO, EMMA
Publicada:
1 ago 2020
Resumen:
Lippia graveolens is a plant used for a variety of medicinal purposes
and as a seasoning. Chemical investigation of a methanol extract
obtained by percolation of its leaves and flowers led to the isolation
of two monoterpenes (1-2) and twelve flavonoids, including two flavonols
(3-4), two flavones (5-6), four flavanones (7-10), two dihydroflavonols
(11-12), and two dihydrochalcone glucosides (13-14). beta-Sitosteryl
glucopyranoside (15) was also isolated. The structures of all the
isolates were elucidated by analysis of the NMR and MS spectra. The
configuration of chiral flavonoids was determined by optical rotation
and comparison with literature data. Based on the medicinal uses of the
plant, the flavonoids 3-14 were tested for their ability to inhibit the
activity of alpha-glucosidase, while the anti-inflammatory activity of 4
and 7-14 was evaluated in the 12-O-tetradecanoylphorbol-13-acetate
(TPA)-induced ear edema model. As a result, only the flavone 6 was a
significative inhibitor of alpha-glucosidase (IC50 = 37.19 mu M), while
the flavanones 9-10 and the dihydrochalcone 14 showed the best
anti-inflammatory properties with IC50 values ranging from 0.72 to 1.31
mu mol/ear. The cytotoxic activity of eleven of these flavonoids (3-5
and 7-14) against five cancer human cell lines was also evaluated. The
flavonol 4 inhibited moderately the proliferation of the U251
(glioblastoma) and SK-LU-1 (lung adenocarcinoma) cell lines.
Filiaciones:
Amador, Sonia:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Coyoacan 04510, Cd Mx, Mexico
Nieto-Camacho, Antonio:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Coyoacan 04510, Cd Mx, Mexico
Teresa Ramirez-Apan, Ma:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Coyoacan 04510, Cd Mx, Mexico
Martinez, Mahinda:
Univ Autonoma Queretaro, Fac Ciencias Nat, Ave Ciencias S-N, Santa Rosa Jauregui 76230, Queretaro, Mexico
MALDONADO, EMMA:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Coyoacan 04510, Cd Mx, Mexico
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