Isolation and Characterisation of Two Quercetin Glucosides with Potent Anti-Reactive Oxygen Species (ROS) Activity and an Olean-12-en Triterpene Glucoside from the Fruit of Abelmoschus esculentus (L.) Moench.

Abstract

Abelmoschus esculentus (Okra) is used in the traditional treatment of cancer, hyperlipidaemia and hyperglycaemia. We, therefore, investigated its composition and potential cytotoxic or antioxidant properties that might underlie its phytotherapeutic applications. Its methanolic fruit extract yielded compounds 1, 2 and 3, identified through NMR, UV and MS analyses as olean-12-en-3-O-β-d-glucopyranoside, isoquercitrin (quercetin glucoside) and 5,7,3',4'-tetrahydroxy-flavonol-3-O-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranoside (quercetin diglucoside), respectively. Following 48 h exposure, oleanene glucoside was mildly toxic to the HeLa and the MRC5-SV2 cancer cells, isoquercitrin was not toxic except at 100 μg/ml in HeLa, and quercetin diglucoside elicited no toxicity. In a 2',7'-dichlorofluorescein diacetate (DCFDA) assay of intracellular levels of reactive oxygen species (ROS), hydrogen peroxide increased ROS levels, an effect not affected by oleanene glucoside but protected against by isoquercitrin and quercetin diglucoside, with IC50 values, respectively, of 2.7±0.5 μg/ml and 1.9±0.2 μg/ml (3 h post-treatment) and 2.0±0.8 μg/ml and 1.5±0.4 μg/ml (24 h post-treatment.) This is the first report of this oleanene skeleton triterpenoid in the plant. The work provides some insight into why the plant is included in remedies for cancers, cardiovascular complications and diabetes, and reveals it as a potential source of novel therapeutics.