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Cucurbitane glycosides derived from mogroside IIE: structure-taste relationships, antioxidant activity, and acute toxicity.

ABSTRACT: Mogroside IIE is a bitter triterpenoid saponin which is the main component of unripe Luo Han Guo fruit and a precursor of the commercially available sweetener mogroside V. In this study, we developed an enzymatic glycosyl transfer method, by which bitter mogroside IIE could be converted into a sweet triterpenoid saponin mixture. The reactant concentration, temperature, pH and buffer system were studied. New saponins with the ?-glucose group were isolated from the resulting mixtures, and the structures of three components of the extract were determined. The structure-taste relationships of these derivatives were also studied together with those of the natural mogrosides. The number and stereoconfiguration of glucose groups present in the mogroside molecules were found to be the main factor to determine the sweet or bitter taste of a compound. The antioxidant and food safety properties were initially evaluated by their radical scavenging ability and via 7 day mice survival tests, respectively. The results showed that the sweet triterpenoid saponin mixture has the same favorable physiological and safety characteristics as the natural mogrosides.

SUBMITTER: Wang L

PROVIDER: S-EPMC6271920 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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Project description:The traditional use of Onosma L. species as a remedy motivated scientists to discover great biological/pharmacological potentials in this plant. In the current study, in addition to the phytochemical composition of methanol (MeOH), water, and ethyl acetate extract of aerial parts of Onosma mutabilis Boiss., an endemic plant species in the flora of Kurdistan, Iraq, in vitro antioxidant, cytotoxicity, and oral toxicity activity were investigated. Results of total phenolic and total flavonoid tests show the MeOH extract superiority, and the results of Gas chromatography-mass spectrophotometer(GS/GS-MS) show 18 chemical compounds in the MeOH extract, and the majority of the detected compounds were alkaloids (78.77%) and steroids (11.48%), namely as 5,8-dihydroxy-2-(4-methylpent-3-enyl) naphthalene-1,4-dione (48.60%), 3-O-Methyl-d-glucose (27.49%), β-Sitosterol (6.81%), Phenol, 2,4-bis (1,1-dimethyl ethyl)-, phosphite (3.46%), and 24,25-Dihydroxycholecalciferol (3.14%). Results of the antioxidant tests show the MeOH extract superiority in the phosphomolybdenum assay, radical scavenging [on 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)] assays, and reducing power [cupric reducing antioxidant capacity (CUPRAC) and ferric reducing antioxidant power (FRAP)] assays (1.45, 3.54, 2.33, 1.12, 1.62, mg/ml, respectively). The cytotoxicity results of the plant extract are presented as IC50 (inhibitory concentration at 50%) on the prostate cancer cells (DU-145), mammary cancer cells (MCF-7), and human cervix carcinoma (Hep2c), at which values ranged from 28.79 to 41.83 μg/ml. Results of the acute toxicity in the dose-dependent trail (100, 200, 300, 600 mg/kg of MeOH) show the absence of the behavior and appearance changes of female Wister rats. Overall, O. mutabilis extract exhibited significant natural potentials probably because of its polar phytochemicals, which could be an alternative source for remedial, nutrient, and cosmetic manufacture.

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Cucurbitane glycosides derived from mogroside IIE: structure-taste relationships, antioxidant activity, and acute toxicity.

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