On-line identification of phenolic compounds of trifolium species using HPLC-UV-MS and post-column UV-derivatisation

Phytochemical Analysis

Volumn 18, Issue 1, 2007, Pages 13-23

  Polasek, Johanne ^a   Queiroz, Emerson F ^a   Hostettmann, Kurt ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

HPLC MS; HPLC UV PAD; Isoflavonoids; Leguminosae; Post column derivatisation; Trifolium spp.

Indexed keywords

FLAVONOIDS; PHENOLS;

HPLC UV PADS; HPLC-MS; HPLC-UV/MS; ISOFLAVONOIDS; LEGUMINOSAE; ON-LINE IDENTIFICATION; PHENOLIC COMPOUNDS; POST-COLUMN; POST-COLUMN DERIVATIZATION; TRIFOLIUM SPP.;

DICHLOROMETHANE;

AGLYCONE; BIOCHANIN A; DICHLOROMETHANE; FLAVONOID; FORMONONETIN; GENISTEIN; GLUCOSIDE; GLYCOSIDE; HYPERIN; ISOFLAVONOID; ISOQUERCITRIN; MALONIC ACID DERIVATIVE; METHANOL; ONONIN; OROBOL; PHENOL DERIVATIVE; PHYTOESTROGEN; PLANT EXTRACT; PRUNETIN; QUERCETIN; QUERCETIN DERIVATIVE; RED CLOVER EXTRACT; TRIFOLIUM ALPINUM EXTRACT; TRIFOLIUM PALLESCENS EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CLOVER; CONTROLLED STUDY; DERIVATIZATION; DRUG IDENTIFICATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LEGUME; MASS SPECTROMETRY; ONLINE SYSTEM; RED CLOVER; SPECIES DIFFERENCE; SWITZERLAND; TIME OF FLIGHT MASS SPECTROMETRY; TRIFOLIUM ALPINUM; TRIFOLIUM PALLESCENS; ULTRAVIOLET SPECTROSCOPY;

FABACEAE; TRIFOLIUM; TRIFOLIUM ALPINUM; TRIFOLIUM PALLESCENS; TRIFOLIUM PRATENSE;

EID: 33846451418     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.946     Document Type: Article

References (30)

1. Alonso-Salces RM, Ndjoko K, Queiroz EF, Ioset JR, Hostettmann K, Berrueta LA, Gallo B, Vicente F. 2004. On-line characterisation of apple polyphenols by liquid chromatography coupled with mass spectrometry and ultraviolet absorbance detection. J Chromatogr A 1046: 89-100.
2. Barnes S, Coward L, Kirk M, Sfakianos J. 1998. HPLC-Mass spectrometry analysis of isoflavones. Proc Soc Exp Biol Med 217: 254-262.
3. Beck V, Unterrieder E, Krenn L, Kubelka W, Jungbauer A. 2003. Comparison of hormonal activity (estrogen, androgen and progestin) of standardized plant extracts for large scale use in hormone replacement therapy. J Steroid Biochem Mol Biol 84: 259-268.
4. Boué SM, Wiese TE, Nehls S, Burow ME, Elliott S, Carter-Wientjes CH, Shih BY, McLachlan JA, Cleveland TE. 2003. Evaluation of the estrogenic effects of legume extracts containing phytoestrogens. J Agric Food Chem 51: 2193-2199.
5. De Rijke E, Zafra-Gomez A, Ariese F, Brinkman UAT, Gooijer C. 2001. Determination of isoflavone glucoside malonates in Trifolium pratense L. (red clover) extracts: quantification and stability studies. J Chromatogr A 932: 55-64.
6. De Rijke E, De Kanter F, Ariese F, Brinkman UAT, Gooijer C. 2004. Liquid chromatography coupled to nuclear magnetic resonance spectroscopy for the identification of isoflavone glucoside malonates in Trifolium pratense leaves. J Sep Sci 27: 1061-1070.
7. Dewick PM, Harborne JB. 1988. Isoflavonoids. The Flavonoids. Advances in Research since 1980. Chapman and Hall: New York.
8. Dornstauder E, Jisa E, Unterrieder I, Krenn L, Kubelka W, Jungbauer A. 2001. Estrogenic activity of two standardized red clover extracts (Menoflavon®) intended for large scale use in hormone replacement therapy. J Steroid Biochem Mol Biol 78: 67-75.
9. Ducrey B, Wolfender JL, Marston A, Hostettmann K. 1995. Analysis of flavonol glycosides of 13 Epilobium species (Onagaceae) by LC-UV and thermospray LC-MS. Phytochemistry 38: 129-137.
10. Escarpa A, Gonzalez MC. 1998. High-performance liquid chromatography with diode-array detection for the determination of phenolic compounds in peel and pulp from different apple varieties. J Chromatogr A 823: 331-337.
11. Hagers. 1998. Handbuch der Pharmazeutischen Praxis (5 Auflage). Springer: Heidelberg.
12. Harbone JB, Marbry TJ, Marbry H. 1975. The Flavonoids. Academic Press: London.
13. Hedin PA, Phillips VA. 1992. Electron impact mass spectral analysis of flavonoids. J Agric Food Chem 40: 607-611.
14. Hostettmann K, Domon B, Schaufelberger D, Hostettmann M. 1984. On-line high-performance liquid-chromatography-ultraviolet visible spectroscopy of phenolic-compounds in plant-extracts using post-column derivatization. J Chromatogr 283: 137-147.
15. Klejdus B, Vitamvasova-Sterbova D, Kuban V. 2001. Identification of isoflavone conjugates in red clover (Trifoltum pratense) by liquid chromatography-mass spectrometry after two-dimensional solid-phase extraction. Anal Chim Acta 450: 81-97.
16. Krenn L, Unterrieder I, Ruprechter R. 2002. Quantification of isoflavones in red clover by high-performance liquid chromatography. J Chromatogr B 777: 123-128.
17. Lin L, He X, Lindenmaier M, Yang J, Cleary M, Qiu S, Cordell GA. 2000. LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). J Agric Food Chem 48: 354-365.
18. Mabry TL, Markham KR, Thomas HB. 1970. The Systematic Identification of Flavonoids. Springer: Heidelberg.
19. Markham KR. 1982. Techniques of Flavonoid Identification. Academic Press: London.
20. Miksicek RJ. 1995. Estrogenic flavonoids: structural requirements for biological activity. Proc Soc Exp Biol Med 208: 44-50.
21. Oleszek W, Stochmal A. 2002. Triterpene saponins and flavonoids in the seeds of Trifolium species. Phytochemistry 61: 165-170.
22. Queiroz EF, Wolfender JL, Atindehou KK, Traore D, Hostettmann K. 2002. On-line identification of the antifungal constituents of Erythrina vogelii by liquid chromatography with tandem mass spectrometry, ultraviolet absorbance detection and nuclear magnetic resonance spectrometry combined with liquid chromatographic micro-fractionation. J Chromatogr A 974: 123-134.
23. Slimestad R, Hostettmann K. 1996. Characterization of phenolic constituents from juvenile and mature needles of Norway spruce by means of high performance liquid chromatography mass spectrometry. Phytochem Anal 7: 42-48.
24. Taylor NL. 1990. The true clovers. In Advances in New Crops, Janick J, Simon JE (eds). Timber Press: Portland, OR; 177-182.
25. Terreaux C, Polasek J, Hostettmann K. 2003. Plant constituents with hormonal effects. Curr Org Chem 7: 1151-1161.
26. Underwood EJ, Shier FL. 1951. The permanence of the oestrogenic effects of subterranean clover grazing on the ewe. Aust Vet J 27: 61-67.
27. Vaya J, Tamir S. 2004. The relation between the chemical structure of flavonoids and their estrogen-like activities. Curr Med Chem 11: 1333-1343.
28. Wolfender JL, Hostettmann K. 1993. Liquid-chromatographic UV detection and liquid chromatographic thermospray mass-spectrometric analysis of Chironia (Gentianaceae) species - a rapid method for the screening of polyphenols in crude plant extracts. J Chromatogr 647: 191-202.
29. Wolfender JL, Waridel P, Ndjoko K, Hobby KR, Major HJ, Hostettmann K. 2000. Evaluation of Q-TOF-MS/MS and multiple stage IT-MSn for the dereplication of flavonoids and related compounds in crude plant extracts. Analusis 28: 895-906.
30. Wu Q, Wang M, Simon JE. 2003. Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection. J Chromatogr A 1016: 19-209.