Excelsanone, a new isoflavonoid from Erythrina excelsa (Fabaceae), with in vitro antioxidant and in vitro cytotoxic effects on prostate cancer cells lines

Abstract

A new isoflavonoid, excelsanone (2), was isolated from the ethyl acetate extract of Erythrina excelsa Backer stem bark, together with three known compounds namely 6,8diprenylgenistein (3), β-sitosterol (1) and sitosteryl-β-D-glucopyranoside (4). Their structures were elucidated using spectroscopic methods (HR-ESI-MS, NMR and IR) and by comparison with some data reported in literature. The antioxidant activity of crude extracts and two isolated compounds was evaluated using free radical scavenging (DPPH) and Ferric Reducing Ability Power (FRAP) methods with catechin as standard. The results of this radical scavenging activity showed that excelsanone (2) has a moderate potential with an IC 50 of 1.31 mg/ml. The cytotoxicity of compounds 2 and 3 as well as the ethyl acetate extract was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in two prostate cancer cell lines (DU145 and PC3). Excelsanone (2) induced a greater cytotoxicity in all tested cell lines, with a significant inhibition of DU145 cells growth in a concentration-dependent manner.

Phytochemistry and pharmacology of natural prenylated flavonoids

“…Two derivatives, 1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2 H-1-benzopyran-5-yl]-1-propanone ( 672 ) and 2-geranyl-2′,3,4,4′-tetrahydroxydihydrochalcone ( 673 ), from Artocarpus altilis showed DPPH scavenging activities with IC 50 values of 82.2 and 82.4 µ M, respectively (Huong et al 2012 ). Excelsanone ( 694 ) and 6,8-diprenylgenistein ( 805 ) from Erythrina excelsa possessed actives for DPPH radical scavenging with IC 50 values of 1.31 and 0.07 mg/mL, respectively (Gbaweng et al 2020 ). Thonningiisoflavone ( 781 ) is from Ficus thonningii and showed strong DPPH radical scavenging activity with an IC 50 value of 65.5 µ M (Fongang et al 2015 ).…”

An overview of techniques and strategies for isolation of flavonoids from the genus Erythrina

“…Based on the chemical structure of the isolated flavonoids, they can be grouped into 17 groups as shown in Table 2 [3, 5]. The isolated Erythrina flavonoid compounds along with the extraction solvents and isolation and purification techniques are arranged alphabetically according to the names of the compounds in Table S1 [49–192]. The diversity of this flavonoid framework consists of 25 flavones (1–25), four flavanols (26–29), 103 flavanones (30–132), 16 chalcones (133–148), 12 isoflavans (149–160), eight isoflav‐3‐enes (161–168), 55 isoflavanones (169–223), 1011 isoflavones (224–324), 72 pterocarpans, 6α‐hydroxypterocarpans, and pterocarpenes (325–396), five coumestans (397–401), four 3‐arylcoumarins (402‐405), one coumaronochromones (406), 20 2‐arylbenzofurans and 3‐aryl‐2,3‐dihydrobenzofurans (407–426), and one bioflavonoids (427) (Table 2).…”

MicroRNAs and Natural Compounds Mediated Regulation of TGF Signaling in Prostate Cancer

“…Neferine obtained from Nelumbo nucifera triggered apoptosis in DU-145 cell through enhancement of apoptosis via modulation of TRAIL and phosphorylation of JNK (Nazim et al, 2020). Excelsanone, an isoflavonoid found in the bark of Erythrina excelsa, has been tested for its anticancer properties in PCa cell lines DU-145 and PC-3 cells, and enhanced cytotoxicity (Gbaweng et al, 2020). Phytoalexin resveratrol, abundantly present in grapes and berries, halts EMT in PCa.…”