Iriflophenone 3-C-beta-D-glucopyranoside

Bio-assay guided isolation and identification of alpha-glucosidase inhibitors from the leaves of Aquilaria sinensis.[Pubmed:21215978]

Phytochemistry. 2011 Feb;72(2-3):242-7.

Eight alpha-glucosidase inhibitors including four new compounds were isolated from the 70% aqueous ethanolic extract of leaves of Aquilaria sinensis (Lour.) Gilg by activity-directed fractionation and purification processes. The ethanolic extract was first separated into petroleum ether, ethyl acetate, n-butanol and water soluble fractions and screened for inhibitory activity against alpha-glucosidase. Further activity-directed investigation lead to the isolation of four new compounds with moderate inhibitory activity, viz, aquilarisinin (1), aquilarisin (2), hypolaetin 5-O-beta-D-glucuronopyranoside (3) and aquilarixanthone (4) from the n-butanol fraction, and four known compounds showing potent activity including mangiferin (5), iriflophenone 2-O-alpha-L-rhamnopyranoside (6), iriflophenone 3-C-beta-D-glucoside (7) and iriflophenone 3,5-C-beta-D-diglucopyranoside (8) from the most potent ethyl acetate fraction. The structures of these compounds were determined by extensive spectroscopic analyses, including IR, UV, ESIMS, HRESIMS, 1D and 2D NMR.

Evaluation of Cholesterol-lowering Activity of Standardized Extract of Mangifera indica in Albino Wistar Rats.[Pubmed:28250649]

Pharmacognosy Res. 2017 Jan-Mar;9(1):21-26.

INTRODUCTION: Cholesterol lowering activity of Mangifera indica L. has been determined by earlier researchers and kernel, leaf and bark have shown significant activity. However, the specific cholesterol lowering activity of leaf methanol extract has not been determined. MATERIALS AND METHODS: The present study involved evaluation of cholesterol lowering potential of methanol extract of M. indica leaves using high cholesterol diet model in albino Wistar rats. The acute oral toxicity at a dose of 5000 mg/ kg body weight was also determined in female albino Wistar rats. Phytoconstituents Iriflophenone 3-C-beta-D-glucoside and mangiferin were quantified in methanol extracts of different varieties of mango leaves using high performance liquid chromatography. RESULTS AND DISCUSSION: Significant cholesterol lowering activity was observed with methanol extract of M. indica leaves, at dose of 90 mg/kg body weight in rats and it was also found to be safe at dose of 5000 mg/kg rat body. Iriflophenone 3-C-beta-D-glucoside and mangiferin were found to be in the range of 1.2 to 2.8% w/w and 3.9 to 4.6% w/w, respectively which along with 3 beta taraxerol and other sterols could be contributing to the cholesterol lowering activity of mango leaves extract. CONCLUSIONS: The phytosterols rich extract of Mangifera indica leaves is a good source of nutraceutical ingredient that have the potential to lower serum cholesterol levels. SUMMARY: The Mangifera indica leaves methanolic extract showed significant cholesterol lowering activity in high cholesterol diet induced hypercholesterolaemia model in rats when evaluated at a dose of 90 mg/kg rat body weight. The extract was found to contain Iriflophenone 3-C-beta-D-glucoside and mangiferin which along with 3 beta taraxerol and other sterols could be contributing to the cholesterol lowering activity.

Iriflophenone-3-C-glucoside from Cyclopia genistoides: isolation and quantitative comparison of antioxidant capacity with mangiferin and isomangiferin using on-line HPLC antioxidant assays.[Pubmed:24566268]

J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 1;951-952:164-71.

The benzophenone, iriflophenone-3-C-glucoside, was isolated from Cyclopia genistoides using a combination of fluid-fluid extraction, high performance counter-current chromatography (HPCCC) and semi-preparative high performance liquid chromatography (HPLC). The microplate oxygen radical absorbance capacity (ORAC) assay, with fluorescein as probe, was adapted for use in an on-line HPLC configuration. The method was validated using a mixture of authentic standards including iriflophenone-3-C-glucoside, and the xanthones, mangiferin and isomangiferin. Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) was included in the mixture for calculation of Trolox equivalent antioxidant capacity (TEAC) values. Using the on-line HPLC-ORAC assay, as well as 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(+)) on-line assays, the antioxidant activity of iriflophenone-3-C-glucoside and isomangiferin was demonstrated for the first time. Iriflophenone-3-C-glucoside presented no radical scavenging ability against DPPH, but scavenged ABTS(+) and peroxyl radicals (TEACABTS of 1.04 and TEACORAC of 3.61). Isomangiferin showed slightly lower antioxidant capacity than mangiferin against DPPH (TEACDPPH of 0.57 vs. 0.62), but higher capacity against ABTS(+) (TEACABTS of 1.82 vs. 1.67) and peroxyl radical (TEACORAC of 4.14 vs. 3.69) than mangiferin. The on-line HPLC-ORAC assay was shown to be more sensitive for radical scavengers, but at the same time less selective for rapid radical scavengers than the DPPH assay.