Bioactive Novel Polyphenols from the Fruit of Manilkara zapota (Sapodilla)

Abstract

Activity-guided fractionation of a methanol extract from the fruit of Manilkara zapota cv. Tikal resulted in the isolation of two new antioxidants, methyl 4-O-galloylchlorogenate (1) and 4-O-galloylchlorogenic acid (2), along with eight known polyphenolic antioxidants, namely, methyl chlorogenate (3), dihydromyricetin (4), quercitrin (5), myricitrin (6), (+)-catechin (7), (-)-epicatechin (8), (+)-gallocatechin (9), and gallic acid (10). Of the 10 polyphenols, 1 showed the highest antioxidant activity (IC(50) = 12.9 microM) in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free-radical assay and displayed cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 190 and 160 microM, respectively. Compound 2 showed high antioxidant activity (IC(50) = 23.5 microM) in the DPPH free-radical assay and displayed cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 154 and 134 microM, respectively.

Chemotaxonomic significance of flavonoids, coumarins and triterpenes of Augusta longifolia (Spreng.) Rehder, Rubiaceae-Ixoroideae, with new insights about its systematic position within the family

“…This glycosilated flavonol was also found in the fruits of Pouteria Aubl. (Sapotaceae; Ma et al, 2004) and of Manilkara zapota (L.) P. Royen (Sapotaceae; Ma et al, 2003). In addition, it was also isolated in the leaves Eugenia L. (Myrtaceae; Schmeda-Hirschmannet et al, 1987) and in the latex of Croton draco Schltdl.…”

Antioxidant, anti-collagenase and anti-elastase activities of Phyllanthus emblica, Manilkara zapota and silymarin: an in vitro comparative study for anti-aging applications

“…Ethanol pulp extract contains alkaloids, saponins, terpenoids, flavonoids, tannins, leucoanthocyanidins, anthroquinones, glucosides and catechol (Gomathy et al 2013). Ma et al (2003) found bioactive flavonoids from methanol extract of sapota fruit such as (À)-epicatechin, (+)-gallocatechin, gallic acid, quercetin, myricitrin and (+)-catechin, of which the latter three pure compounds were reported to inhibit enzyme collagenase and elastase activities (Sim et al 2007;Thring et al 2009). …”

Antitumor activity of Manilkara zapota (L.) fruits against Ehrlich ascites carcinoma in mice

“…In addition, flavonoids could also induce mechanisms that may kill cancer cells and inhibit tumor invasion (Lotito, Frei, 2006). On the other hand, it has been reported that the major constituents isolated from fruits of Manilkara zapota are polyphenols (methyl chlorogenate, dihydromyricetin, quercitrin, myricitrin, (+)-catechin, (-)-epicatechin, (+)-gallocatechin, and gallic acid (Ma et al, 2003). The inhibitory properties of EEFM against EAC may be due to the presence of these compounds.…”

“…Previous phytochemical investigations on the leaves of this plant have resulted in the isolation of lupeol acetate, oleanolic acid, apigenin-7-O-α-Lrhamnoside, myricetin-3-O-α-L-rhamnoside and caffeic acid (Fayek et al, 2012). Moreover, the major constituents isolated from fruits of Manilkara zapota are polyphenols (methyl chlorogenate, dihydromyricetin, quercitrin, myricitrin, (+)-catechin, (-)-epicatechin, (+)-gallocatechin, and gallic acid (Ma et al, 2003). But no studies to date have been conducted to demonstrate the antitumour activity of Manilkara zapota fruit.…”