Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

Abstract

The phenolic composition of leaves from Phyllanthus acuminatus L., a plant commonly used in Costa Rica as traditional medicine, was studied using UPLC-ESI-MS on an enriched phenolic extract. A total of 20 phenolic compounds were identified, comprising eight flavonoids (two flavanones—pinocembrin isomers and six derivatives from apigenin, chrysin, quercetin, and kaempferol); seven ellagitannins, two flavan-3-ols (prodelphinidin B dimer and (epi)gallocatechin); and three phenolic acids (ellagic acid, trimethylellagic acid, and ferulic acid). All of these compounds are reported for the first time in P. acuminatus, while previously reported in the genus Phyllanthus. Antioxidant evaluation was performed for P. acuminatus phenolic extract obtaining DPPH results with a remarkably low IC50 value of 0.15 μg/mL. Also, cytotoxicity on gastric AGS and colon SW20 adenocarcinoma cell lines was evaluated, and highly promising results were obtained, with IC50 values of 11.3 μg/mL and 10.5 μg/mL, respectively. Furthermore, selectivity index values obtained when comparing cytotoxicity on normal Vero cells was SI > 20 for both cancer cell lines, indicating a particularly high selectivity. Additionally, Justicidin B, a metabolite extensively studied for its antitumoral activity, was isolated from a non-polar extract of P. acuminatus, and comparatively evaluated for both bioactivities. The DPPH value obtained for Justicidin B was moderate (IC50 = 14.28 μg/mL), while cytotoxicity values for both AGS (IC50 = 19.5 μg/mL) and SW620 (IC50 = 24.8 μg/mL) cell lines, as well as selectivity when compared with normal Vero cells (SI = 5.4 and 4.2 respectively), was good, but lower than P. acuminatus extract. These preliminary results suggest that P. acuminatus enriched phenolic extract containing flavonoids, ellagitannins, flavan-3-ols, and phenolic acids, reported for the first time in this plant, could be of interest for further cancer cytotoxicity studies to elucidate structure–bioactivity relationships, and the molecular mechanisms and pathways.

Polyphenol Profile and Pharmaceutical Potential of Quercus spp. Bark Extracts

“…For example, gallic acid has antibacterial, hypoglycemic, anticancer, and antimutagenic activities [20,21]. In agreement with the current study, ellagic acid is known for strong antioxidative, antiproliferative, and anticancer properties [22,23]. Protocatechuic acid has antifungal, antibacterial, antiviral, anti-inflammatory, antiatherosclerotic, antiulcer, and anticancer properties [20,24,25].…”

Chemical Components and Biological Activities of the Genus Phyllanthus: A Review of the Recent Literature

“…HPLC–MS is a powerful analytical tool, which could efficiently characterize the chemical composition of various Phyllanthus species. Detailed and pioneering explorations of the phenolic compounds in P. acuminatus L. and P. niruri L. were done, which unravelled the presence of nearly 40 different phenolic derivatives for the first time in these Phyllanthus species, including pinocembrin isomers, apigenin derivatives, chrysin, quercetin, kaempferol, ellagitannins, prodelphinidin B dimer, epi -gallocatechin, ellagic acid, trimethylellagic acid, and ferulic acid [ 39 , 40 ]. One recent extensive study confirmed the presence of various phenol, flavonoid, non-flavonoid, tannin, alkaloid, saponin, and phytosterol phytochemicals in dried P. emblica fruits through the use of various extraction solvents (diethyl ether, ethyl acetate, butanol, and water).…”

Cultivo Celular e Ingeniería de Tejidos: Aplicaciones en Biomedicina

“…En el LAINTEC también se cuenta con un pequeño banco de líneas celulares de distintos tipos de cáncer y algunas líneas de tejidos normales, y se han establecido modelos de cultivos tisulares tridimensionales de piel humana, los cuales se utilizan como modelos de estudio para realizar ensayos de citotoxicidad y de determinación de la actividad biológica (basado en marcadores moleculares de proliferación, viabilidad y muerte celular) de sustancias de origen natural. En estos modelos se ha evaluado -mayoritariamente-el potencial anticancerígeno de diversos extractos de plantas, incluyendo plantas medicinales (moringa, tempate, chilillo) y especies frutales (mora, mango, manzana, guayaba) [10]- [17]. En el caso de los modelos tisulares, al tratarse de reconstrucciones 3D, los constructos de piel recrean de forma más cercana el tejido in vivo, por lo que permiten generar información pre-clínica de alta calidad y de mayor potencial predictivo.…”

“…Esto permite proporcionar herramientas clave para facilitar la medicina personalizada, al tiempo que ahorra dinero y reduce la cantidad de animales utilizados para la investigación. A la fecha, estos estudios han permitido confirmar el potencial biomédico de sustancias bioactivas presentes en extractos de diversas plantas en Costa Rica, tales como la mora [10], manzana, anona y ciruelo [13]- [15], [30], guayaba [11] y varias plantas medicinales (Phyllanthus, Senna reticulata, Pettiveria alliaceae, Moringa) [12], [16], [17], [31], [32].…”