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Molecules 2014, 19(8), 11760-11790; doi:10.3390/molecules190811760

Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents

1
Department of Food Science, Stellenbosch University, Private Bag X1, Matieland (Stellenbosch) 7602, South Africa
2
Post-Harvest and Wine Technology Division, Agricultural Research Council (ARC), Infruitec-Nietvoorbij, Private Bag X5026, Stellenbosch 7599, South Africa
3
Central Analytical Facility, Mass Spectrometry Unit, Room 255, JC Smuts Building, Private Bag X1, Matieland (Stellenbosch) 7602, South Africa
*
Author to whom correspondence should be addressed.
Received: 1 July 2014 / Revised: 30 July 2014 / Accepted: 1 August 2014 / Published: 7 August 2014
(This article belongs to the Section Natural Products)
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Abstract

A high-performance liquid chromatographic (HPLC) method coupled with diode-array detection (DAD) was optimized for the qualitative analysis of aqueous extracts of Cyclopia genistoides. Comprehensive insight into the phenolic profile of unfermented and fermented sample extracts was achieved with the identification of ten compounds based on comparison with authentic reference standards and the tentative identification of 30 additional compounds by means of electrospray ionization mass spectrometry (ESI-MS) and tandem MS detection. Three iriflophenone-di-O,C-hexoside isomers, three xanthone-dihydrochalcone derivatives and one dihydrochalcone are herein tentatively identified for the first time in C. genistoides. Of special interest is one iriflophenone-di-O,C-hexoside present in large amounts. New compounds (tentatively) identified for the first time in this species, and also in the genus Cyclopia, include two aromatic amino acids, one flavone, an iriflophenone-di-C-hexoside, a maclurin-di-O,C-hexoside, two tetrahydroxyxanthone-C-hexoside isomers, a tetrahydroxyxanthone-di-O,C-hexoside, two symmetric tetrahydroxyxanthone-C-hexoside dimers, nine glycosylated flavanone derivatives and five glycosylated phenolic acid derivatives. The presence of new compound subclasses in Cyclopia, namely aromatic amino acids and glycosylated phenolic acids, was demonstrated. The HPLC-DAD method was successfully validated and applied to the quantitative analysis of the paired sample extracts. In-depth analysis of the chemical composition of C. genistoides hot water extracts gave a better understanding of the chemistry of this species that will guide further research into its medicinal properties and potential uses. View Full-Text
Keywords: Cyclopia genistoides; iriflophenone-di-O,C-hexoside; phenolic compounds; amino acids; high-performance liquid chromatography (HPLC); electrospray ionization mass spectrometry (ESI-MS); method validation; quantification Cyclopia genistoides; iriflophenone-di-O,C-hexoside; phenolic compounds; amino acids; high-performance liquid chromatography (HPLC); electrospray ionization mass spectrometry (ESI-MS); method validation; quantification
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MDPI and ACS Style

Beelders, T.; de Beer, D.; Stander, M.A.; Joubert, E. Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents. Molecules 2014, 19, 11760-11790.

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