Comprehensive phenolic profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS reveals novel xanthone and benzophenone constituents

Molecules

Volumn 19, Issue 8, 2014, Pages 11760-11790

  Beelders, Theresa ^a,b   De Beer, Dalene ^b   Stander, Maria A ^c   Joubert, Elizabeth ^a,b  

^a STELLENBOSCH UNIVERSITY   (South Africa)

^b AGRICULTURAL RESEARCH COUNCIL   (South Africa)

^c Central Analytical Facility Mass Spectrometry Unit JC Smuts Building   (South Africa)

Author keywords

Amino acids; Cyclopia genistoides; Electrospray ionization mass spectrometry (ESI MS); High performance liquid chromatography (HPLC); Iriflophenone di O,C hexoside; Method validation; Phenolic compounds; Quantification

Indexed keywords

BENZOPHENONE; BENZOPHENONE DERIVATIVE; FLAVONOID; GLUCOSIDE; HYDROXYBENZOIC ACID DERIVATIVE; IRIFLOPHENONE 2-O-GLUCOPYRANOSIDE; PHENOL DERIVATIVE; PHENOLIC ACID; PLANT EXTRACT; XANTHONE; XANTHONE DERIVATIVE;

CHEMISTRY; CLASSIFICATION; ELECTROSPRAY MASS SPECTROMETRY; FABACEAE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; TANDEM MASS SPECTROMETRY;

BENZOPHENONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FABACEAE; FLAVONOIDS; GLUCOSIDES; HYDROXYBENZOATES; PHENOLS; PLANT EXTRACTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; XANTHONES;

EID: 84906672896     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190811760     Document Type: Article

References (51)

1. Joubert, E.; Joubert, M.E.; Bester, C.; de Beer, D.; de Lange, J.H. Honeybush (Cyclopia spp.): From local cottage industry to global markets - The catalytic and supporting role of research. S. Afr. J. Bot. 2011, 77, 887-907.
2. Greenish, H. Cape tea. Pharm. J. 1881, 11, 549-551.
3. Joubert, E.; Otto, F.; Grüner, S.; Weinreich, B. Reversed-phase HPLC determination of mangiferin, isomangiferin and hesperidin in Cyclopia and the effect of harvesting date on the phenolic composition of C. genistoides. Eur. Food Res. Technol. 2003, 216, 270-273.
4. Joubert, E.; Manley, M.; Botha, M. Evaluation of spectrophotometric methods for screening of green rooibos (Aspalathus linearis) and green honeybush (Cyclopia genistoides) extracts for high levels of bio-active compounds. Phytochem. Anal. 2008, 19, 169-178.
5. Joubert, E.; de Beer, D.; Hernández, I.; Munné-Bosch, S. Accummulation of mangiferin, isomangiferin, iriflophenone-3-c-β-glucoside and hesperidin in honeybush leaves (Cyclopia genistoides Vent.) in response to harvest time, harvest interval and seed source. Ind. Crops Prod. 2014, 56, 74-82.
6. Vyas, A.; Syeda, K.; Ahmad, A.; Padhye, S.; Sarkar, F.H. Perspectives on medicinal properties of mangiferin. Mini-Rev. Med. Chem. 2012, 12, 412-425.
7. Kokotkiewicz, A.; Luczkiewicz, M.; Pawlowska, J.; Luczkiewicz, P.; Sowinski, P.; Witkowski, J.; Bryl, E.; Bucinski, A. Isolation of xanthone and benzophenone derivatives from Cyclopia genistoides (L.) Vent. (honeybush) and their pro-apoptotic activity on synoviocytes from patients with rheumatoid arthritis. Fitoterapia 2013, 90, 199-208.
8. Zhang, Y.; Han, L.; Ge, D.; Liu, X.; Liu, E.; Wu, C.; Gao, X.; Wang, T. Isolation, structural elucidation, MS profiling, and evaluation of triglyceride accumulation inhibitory effects of benzophenone c-glucosides from leaves of Mangifera indica L. J. Agric. Food Chem. 2013, 61, 1884-1895.
9. Verhoog, N.; Joubert, E.; Louw, A. Screening of four Cyclopia (honeybush) species for putative phyto-oestrogenic activity by oestrogen receptor binding assays. S. Afr. J. Sci. 2007, 103, 13-21.
10. Joubert, E.; Richards, E.S.; van der Merwe, J.D.; de Beer, D.; Manley, M.; Gelderblom, W.C.A. Effect of species variation and processing on phenolic composition and in vitro antioxidant activity of aqueous extracts of Cyclopia spp. (honeybush tea). J. Agric. Food Chem. 2008, 56, 954-963.
11. De Beer, D.; Joubert, E. Development of HPLC method for Cyclopia subternata phenolic compound analysis and application to other Cyclopia spp. J. Food Comp. Anal. 2010, 23, 289-297.
12. De Beer, D.; Schulze, A.E.; Joubert, E.; de Villiers, A.; Malherbe, C.J.; Stander, M.A. Food ingredient extracts of Cyclopia subternata (honeybush): Variation in phenolic composition and antioxidant capacity. Molecules 2012, 17, 14602-14624.
13. Schulze, A.E. HPLC Method Development for Characterisation of the Phenolic Composition of Cyclopia subternata and C. maculata Extracts and Chromatographic Fingerprint Analysis for Quality Control. Master's Thesis, Stellenbosch University, Stellenbosch, South Africa, December 2013.
14. De Villiers, A.; Lestremau, F.; Szucs, R.; Gélébart, S.; David, F.; Sandra, P. Evaluation of ultra performance liquid chromatography: Part I. Possibilities and limitations. J. Chromatogr. A 2006, 1127, 60-69.
15. Kalili, K.M.; Cabooter, D.; Desmet, G.; de Villiers, A. Kinetic optimisation of the reversed phase liquid chromatographic separation of proanthocyanidins on sub-2 μm and superficially porous phases. J. Chromatogr. A 2012, 1236, 63-76.
16. Dolan, J.W. Temperature selectivity in reversed-phase high performance liquid chromatography. J. Chromatogr. A 2002, 965, 195-205.
17. Abad-García, B.; Berrueta, L.A.; Garmón-Lobato, S.; Gallo, B.; Vicente, F. A general analytical strategy for the characterization of phenolic compounds in fruit juices by high-performance liquid chromatography with diode array detection coupled to electrospray ionization and triple quadrupole mass spectrometry. J. Chromatogr. A 2009, 1216, 5398-5415.
18. Cuyckens, F.; Claeys, M. Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom. 2004, 39, 461-461.
19. Ito, T.; Kakino, M.; Tazawa, S.; Oyama, M.; Maruyama, H.; Araki, Y.; Hara, H.; Iinuma, M. Identification of phenolic compounds in Aquilaria crassna leaves via liquid chromatography-electrospray ionization mass spectroscopy. Food Sci. Technol. Res. 2012, 18, 259-262.
20. Feng, J.; Yang, X.W.; Wang, R.F. Bio-assay guided isolation and identification of α-glucosidase inhibitors from the leaves of Aquilaria sinensis. Phytochemistry 2011, 72, 242-247.
21. Malherbe, C.J.; Willenburg, E.; de Beer, D.; Bonnet, S.L.; van der Westhuizen, J.H.; Joubert, E. Iriflophenone-3-c-glucoside from Cyclopia genistoides: Isolation and quantitative comparison of antioxidant capacity with mangiferin and isomangiferin using on-line HPLC antioxidant assays. J. Chromatogr. B 2014, 951-952C, 164-171.
22. Du, X.G.; Wang, W.; Zhang, Q.Y.; Cheng, J.; Avula, B.; Khan, I.A.; Guo, D.A. Identification of xanthones from Swertia punicea using high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2012, 26, 2913-2923.
23. Ichiki, H.; Miura, T.; Kubo, M.; Ishihara, E.; Komatsu, Y.; Tanigawa, K.; Okada, M. New antidiabetic compounds, mangiferin and its glucoside. Biol. Pharm. Bull. 1998, 21, 1389-1390.
24. Miura, T.; Ichiki, H.; Iwamoto, N.; Kato, M.; Kubo, M.; Sasaki, H.; Okada, M.; Ishida, T.; Seino, Y.; Tanigawa, K. Antidiabetic activity of the rhizoma of Anemarrhena asphodeloides and active components, mangiferin and its glucoside. Biol. Pharm. Bull. 2001, 24, 1009-1011.
25. Muruganandan, S.; Srinivasan, K.; Gupta, S.; Gupta, P.K.; Lal, J. Effect of mangiferin on hyperglycemia and atherogenicity in streptozotocin diabetic rats. J. Ethnopharmacol. 2005, 97, 497-501.
26. Abdel-Mageed, W.M.; Bayoumi, S.A.H.; Chen, C.; Vavricka, C.J.; Li, L.; Malik, A.; Dai, H.; Song, F.; Wang, L.; Zhang, J.; et al. Benzophenone c-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. Bioorg. Med. Chem. 2014, 22, 2236-2243.
27. Huang, C.F.; Gan, X.W.; Bai, H.Y.; Ma, L.; Hu, L.H. Schoepfin A, B, C: Three new chalcone c-glycosides from Schoepfia chinensis. Nat. Prod. Res. 2008, 22, 623-627.
28. Wang, J.N.; Hou, C.Y.; Liu, Y.L.; Lin, L.Z.; Gil, R.R.; Cordell, G.A. Swertifrancheside, an HIV-Reverse transcriptase inhibitor and the first flavone-xanthone dimer, from Swertia franchetiana. J. Nat. Prod. 1994, 57, 211-217.
29. Andersen, Ø.M.; Markham, K.R. Flavonoids: Chemistry, Biochemistry and Applications; CRC Press: Boca Raton, FL, USA, 2005.
30. Djoukeng, J.D.; Arbona, V.; Argamasilla, R.; Gomez-Cadenas, A. Flavonoid profiling in leaves of citrus genotypes under different environmental situations. J. Agric. Food Chem. 2008, 56, 11087-11097.
31. Cuyckens, F.; Rozenberg, R.; de Hoffmann, E.; Claeys, M. Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry. J. Mass Spectrom. 2001, 36, 1203-1210.
32. Domon, B.; Costello, C.E. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J. 1988, 5, 397-409.
33. Louw, A.; Joubert, E.; Visser, K. Phytoestrogenic potential of Cyclopia extracts and polyphenols. Planta Med. 2013, 79, 580-590.
34. Natella, F.; Nardini, M.; di Felice, M.; Scaccini, C. Benzoic and cinnamic acid derivatives as antioxidants: Structure-activity relation. J. Agric. Food Chem. 1999, 47, 1453-1459.
35. Bartsch, M.; Bednarek, P.; Vivancos, P.D.; Schneider, B.; von Roepenack-Lahaye, E.; Foyer, C.H.; Kombrink, E.; Scheel, D.; Parker, J.E. Accumulation of isochorismate-derived 2,3-dihydroxybenzoic 3-O-beta-D-xyloside in arabidopsis resistance to pathogens and ageing of leaves. J. Biol. Chem. 2010, 285, 25654-25665.
36. Fayos, J.; Bellés, J.M.; López-Gresa, M.P.; Primo, J.; Conejero, V. Induction of gentisic acid 5-O-β-D-xylopyranoside in tomato and cucumber plants infected by different pathogens. Phytochemistry 2006, 67, 142-148.
37. Zhang, S.; Xuan, L. New phenolic constituents from the stems of Spatholobus suberectus. Helv. Chim. Acta 2006, 89, 1241-1245.
38. Tsopmo, A.; Muir, A.D. Chemical profiling of lentil (Lens culinaris Medik.) cultivars and isolation of compounds. J. Agric. Food Chem. 2010, 58, 8715-8721.
39. Sánchez-Rabaneda, F.; Jáuregui, O.; Lamuela- Raventós, R.M.; Bastida, J.; Viladomat, F.; Codina, C. Identification of phenolic compounds in artichoke waste by high-performance liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2003, 1008, 57-72.
40. Lu, Y.; Yeap Foo, L. Flavonoid and phenolic glycosides from Salvia officinalis. Phytochemistry 2000, 55, 263-267.
41. Meng, D.; Wu, J.; Zhao, W. Glycosides from Breynia fruticosa and Breynia rostrata. Phytochemistry 2010, 71, 325-331.
42. Ferreira, D.; Kamara, B.I.; Brandt, E.V.; Joubert, E. Phenolic compounds from Cyclopia intermedia (honeybush tea). 1. J. Agric. Food Chem. 1998, 46, 3406-3410.
43. Kamara, B.I.; Brandt, E.V.; Ferreira, D.; Joubert, E. Polyphenols from honeybush tea (Cyclopia intermedia). J. Agric. Food Chem. 2003, 51, 3874-3879.
44. Kamara, B.I.; Brand, D.J.; Brandt, E.V.; Joubert, E. Phenolic metabolites from honeybush tea (Cyclopia subternata). J. Agric. Food Chem. 2004, 52, 5391-5395.
45. Wang, M.; Shao, Y.; Li, J.; Zhu, N.; Rangarajan, M.; LaVoie, E.J.; Ho, C.T. Antioxidative phenolic glycosides from sage (Salvia officinalis). J. Nat. Prod. 1999, 62, 454-456.
46. Vitalini, S.; Braca, A.; Fico, G. Study on secondary metabolite content of Helleborus niger L. leaves. Fitoterapia 2011, 82, 152-154.
47. Beelders, T.; Sigge, G.O.; Joubert, E.; de Beer, D.; de Villiers, A. Kinetic optimisation of the reversed phase liquid chromatographic separation of rooibos tea (Aspalathus linearis) phenolics on conventional high performance liquid chromatographic instrumentation. J. Chromatogr. A 2012, 1219, 128-139.
48. Beelders, T.; Sigge, G.O.; Joubert, E.; de Beer, D.; de Villiers, A. Erratum to "Kinetic optimisation of the reversed phase liquid chromatographic separation of rooibos tea (Aspalathus linearis) phenolics on conventional high performance liquid chromatographic instrumentation" [J. Chromatogr. A 1219 (2012) 128-139]. J. Chromatogr. A 2012, 1241, 128.
49. Kokotkiewicz, A.; Luczkiewicz, M.; Sowinski, P.; Glod, D.; Gorynski, K.; Bucinski, A. Isolation and structure elucidation of phenolic compounds from Cyclopia subternata Vogel (honeybush) intact plant and in vitro cultures. Food Chem. 2012, 133, 1373-1382.
50. Roowi, S.; Crozier, A. Flavonoids in tropical citrus species. J. Agric. Food Chem. 2011, 59, 12217-12225.
51. Snyder, L.R.; Kirkland, J.J.; Glajch, J.L. Practical HPLC Method Development, 2nd ed.; John Wiley & Sons, Inc.: New York, NY, USA, 1997.