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Iriflophenone-3-C-glucoside From Cyclopia Genistoides: Isolation and Quantitative Comparison of Antioxidant Capacity With Mangiferin and Isomangiferin Using On-Line HPLC Antioxidant Assays

Iriflophenone-3-C-glucoside From Cyclopia Genistoides: Isolation and Quantitative Comparison of Antioxidant Capacity With Mangiferin and Isomangiferin Using On-Line HPLC Antioxidant Assays

Christiaan J Malherbe, Elize Willenburg, Dalene de Beer, Susan L Bonnet, Jan H van der Westhuizen, Elizabeth Joubert

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

PMID: 24566268

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP104669025	Iriflophenone 3-C-β-D-glucopyranoside		104669-02-5	Price

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