Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents
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...
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doaj-85bc7e00046c4964ae5d4164f75b64062020-11-25T00:13:31ZengMDPI AGMolecules1420-30492014-08-01198117601179010.3390/molecules190811760molecules190811760Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone ConstituentsTheresa Beelders0Dalene de Beer1Maria A. Stander2Elizabeth Joubert3Department of Food Science, Stellenbosch University, Private Bag X1, Matieland (Stellenbosch) 7602, South AfricaPost-Harvest and Wine Technology Division, Agricultural Research Council (ARC), Infruitec-Nietvoorbij, Private Bag X5026, Stellenbosch 7599, South AfricaCentral Analytical Facility, Mass Spectrometry Unit, Room 255, JC Smuts Building, Private Bag X1, Matieland (Stellenbosch) 7602, South AfricaDepartment of Food Science, Stellenbosch University, Private Bag X1, Matieland (Stellenbosch) 7602, South AfricaA 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.http://www.mdpi.com/1420-3049/19/8/11760Cyclopia genistoidesiriflophenone-di-O,C-hexosidephenolic compoundsamino acidshigh-performance liquid chromatography (HPLC)electrospray ionization mass spectrometry (ESI-MS)method validationquantification |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Theresa Beelders Dalene de Beer Maria A. Stander Elizabeth Joubert |
spellingShingle |
Theresa Beelders Dalene de Beer Maria A. Stander Elizabeth Joubert Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents Molecules 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 |
author_facet |
Theresa Beelders Dalene de Beer Maria A. Stander Elizabeth Joubert |
author_sort |
Theresa Beelders |
title |
Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents |
title_short |
Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents |
title_full |
Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents |
title_fullStr |
Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents |
title_full_unstemmed |
Comprehensive Phenolic Profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS Reveals Novel Xanthone and Benzophenone Constituents |
title_sort |
comprehensive phenolic profiling of cyclopia genistoides (l.) vent. by lc-dad-ms and -ms/ms reveals novel xanthone and benzophenone constituents |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2014-08-01 |
description |
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. |
topic |
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 |
url |
http://www.mdpi.com/1420-3049/19/8/11760 |
work_keys_str_mv |
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