LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 2, 2000, Pages 354-365

  Lin, Long Ze ^a   He, Xian Guo ^a   Lindenmaier, Michael ^a   Yang, Jie ^a   Cleary, Michael ^a   Qiu, Sheng Xiang ^b   Cordell, Geoffrey A ^b  

^a Res Lab of Nat Products Chemistry   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Clovamides; Flavonoid glycoside malonates; Flavonoids; LC ESI MS analysis; Leguminosae; Red clover; Trifolium pratense

Indexed keywords

APIGENIN; BIOCHANIN A; BIOFLAVONOID; DAIDZEIN; FLAVONOID; FLAVONOID GLYCOSIDE; FORMONONETIN; GENISTEIN; GENISTIN; GLYCITEIN; GLYCOSIDE; HYPERIN; ISOQUERCITRIN; ISORHAMNETIN; KAEMPFEROL; LUTEOLIN; MALONIC ACID DERIVATIVE; MEDICARPIN; ONONIN; PRUNETIN;

ARTICLE; CHEMISTRY; DRUG ISOLATION; DRUG STRUCTURE; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LEGUME; MASS SPECTROMETRY; MODEL; PLANT;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FABACEAE; FLAVONOIDS; GLYCOSIDES; MALONATES; MASS SPECTROMETRY; MODELS, CHEMICAL; PLANTS, MEDICINAL;

FABACEAE; TRIFOLIUM PRATENSE;

EID: 0033996534     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf991002+     Document Type: Article

References (33)

1. Anhut, S.; Zinsmeister, H. D.; Mues, R.; Barz, W.; Mackenbrock, K.; Köster, J.; Markham, K. R. The first identification of isoflavones from a bryophyte. Phytochemistry 1984, 23, 1073-1075.
2. Asen, S. High-pressure liquid chromatographic analysis of flavonoid chemical markers in petals from Gerbera flowers as an adjunct for cultivar and germplasm identification. Phytochemistry 1984, 23, 2523-2526.
3. Balogh, M. P. Advancing phytochemical development: characterization of plant extract isoflavonoids using LC-MS. LC-GC 1997, 15, 456, 458, 460, 462, and 466.
4. Barnes, S.; Kirk, M.; Coward, L. Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J. Agric. Food Chem. 1994, 42, 2466-2474.
5. Beck, A. B.; Knox, J. R. The acylated isoflavone glycosides from subterranean clover and red clover. Aust. J. Chem. 1971, 24, 1509-1518.
6. Biggs, D. R.; Lane, G. A. Identification of isoflavones calycosin and pseudobaptigenin in Trifolium pratense. Phytochemistry 1978, 17, 1683-1684.
7. Chadha, J. S. 3,5,8,4′-Tetrahymethoxyflavone and the constitution of pratoletin. Can. J. Chem. 1965, 43, 306-307.
8. Cook, R.; Tiller, S. A.; Mizen, K. A.; Edwards, R. Isoflavonoid metabolism in resistant and susceptible cultivars of white clover infected with the stem nematode Ditylenchus dipsaci. J. Plant Physiol. 1995, 146, 384-354.
9. Coronado, C.; Zuanazzi, J. A. S.; Sallaud, C.; Quirion, J.-C.; Esnault, R.; Husson, H.-P.; Kondorosi, A.; Ratet, P. Alfalfa root flavonoid production is nitrogen regulated. Plant Physiol. 1995, 108, 533-542.
10. Dewick, P. M. Biosynthesis of pterocarpan phytoalexins in Trifolium pratense. Phytochemistry 1977, 16, 93-97.
11. Dewick, P. M. Isoflavonoids. In The Flavonoids - Advances in Research since 1980; Harborne, J. B., Ed.; Chapman and Hall: New York, 1988; Chapter 5.
12. Edwards, R.; Tiller, S. A.; Parry, A. D. The effect of plant age and nodulation on the isoflavonoid content of red clover (Trifolium pratense). J. Plant Physiol. 1997, 150, 603-610.
13. Frainshtat, P. D.; Popravko, S. A.; Vul'fson, N. S. Clover secondary metabolites. II. Isolation of 5,4′-dihydroxy-6,7-methylenedioxyisoflavone and its 4′-β-D-glucoside from the roots of red clover (Trifolium pratense). Bioorg. Khim. 1979, 5, 228-233.
14. Frainshtat, P. D.; Popravko, S. A.; Vul'fson, N. S. Clover secondary metabolites. VII. Isoflavones from the roots of red clover (Trifolium pratense). Bioorg. Khim. 1980, 6, 1722-1732.
15. Gluchoff-Fiasson, K.; Fiasson, J. L.; Waton, H. Quercetin glycosides from European aquatic Ranunculus species of subgenus batrachlum. Phytochemistry 1997, 45, 1063-1067.
16. Harborne, J. B. For the content of "Flavonoids". In Dictionary of Natural Products; Buckingham, J., Ed.; Chapman and Hall: New York, 1994.
17. He, X.-G.; Lin, L.-Z.; Lian, L.-Z. Analysis of flavonoids from red clover by liquid chromatography-electrospray mass spectrometry. J. Chromatogr. A 1996, 755, 127-132.
18. Horowitz, R. M.; Asen, S. Decarboxylation and exchange reactions in flavonoid glycoside malonates. Phytochemistry 1989, 28, 2531-2532.
19. Jain, A. K.; Saxena, V. K. Isolation and characterization of 3-methoxyquercetin-7-O-β-D-glucopyranoside from Trifolium pratense. Natl. Acad. Sci. Lett. (India) 1986, 9, 379-380.
20. Kattaev, N. S.; Kharlamov, I. A.; Akhmedkhodzhaeva, N. M.; Nikonov, G. K.; Khalmatov, K. K. Trifoside, an isoflavone from Trifolium pratense. Khim. Prir. Soedin 1972, No. 6, 806-807.
21. Kudou, S.; Fleury, Y.; Welti, D.; Magnolato, D.; Uchida, T.; Kitamura, K.; Okubo, K. Malonyl isoflavone glycosides in soybean seeds (Glycine max Merrill). Agric. Biol. Chem. 1991, 55, 2227-2233.
22. Leung, A. Y.; Foster, S. Clover Tops, Red. In Encyclopedia of Common Natural Ingredients used in Food, Drugs and Cosmetics, 2nd ed.; Leung, A. Y., Foster, S., Eds.; Wiley: New York, 1996; pp 177-178.
23. Lin, L.-Z.; He, X.-G.; Lian, L.-Z.; King, W.; Elliott, J. Liquid chromatographic-electrospray mass spectrometric study of the phthalides of Angelica sinensis and chemical changes of Z-ligustilide. J. Chromatogr. A 1998, 810, 71-79.
24. Lin, L-Z.; He, X.-G.; Lindenmaier, M.; Nolan, G.; Yang, J.; Cleary, M.; Qiu, S.-X.; Cordell, G. A. LC-ESI-MS Study of the Flavonoids of the Roots of Astragalus mongholicus and A. membranaceus. J. Chromatogr. A 2000, submitted for publication.
25. Mabry, T. J.; Markham, K. R.; Thomas, M. B. The ultraviolet spectra of flavones and flavonols; The ultraviolet spectra of isoflavones, flavanones, and dihydroflavones. In The Systematic Identification of Flavonoids; Mabry, A. Y., Markham, K. R., Thomas, M. B., Eds.; Springer-Verlag: New York, 1970; Chapters V and VI.
26. Mackenbrock, U.; Vogelsang, R.; Barz, W. Isoflavone and pterocarpan malonylglucosides and β-1,3-glucan- and chitinhydrolases are vacuolar constituents in chickpea (Cicer arietinum L.). Z. Naturforsch. C: Biosci. 1992, 47, 815-822.
27. Park, H.-H.; Hakamatsuka, T.; Sankawa, U.; Ebizuka, Y. Rapid metabolism of isoflavonods in elicitor-treated cell suspension cultures of Pueraria lobata. Phytochemistry 1995, 38, 373-380.
28. Sachse, J. Quantitative high-pressure liquid chromatography of isoflavones in red clover (Trifolium pratense). J. Chromotogr. 1984, 298, 175-182.
29. Saxena, V. K.; Jain, A. K. A new isoflavone glycoside from Trifoliun pratense. Fitoterapia 1987, 58, 262-263.
30. Stein, W.; Anhut, S.; Zinsmeister, H. D.; Mues, R.; Barz, W.; Köster, J. New flavone glucoside malonyl-esters from Bryum capillare. Z. Naturforsch. C: Biosci. 1985, 40, 469-473.
31. Stobiecki, M.; Malosse, C.; Kerhoas, L.; Wojlaszek, P.; Einhorn, J. Detection of isoflavonoids and their glycosides by liquid chromatography/electrospray ionization mass spectrometry in root extracts of lupin (Lupinus albus). Phytochem. Anal. 1999, 10, 198-207.
32. Sumner, L. W.; Paiva, N. L.; Dixon, R. A.; Geno, P. W. High-performance liquid chromatography/continuous-flow liquid secondary ion mass spectrometry of flavonoid glycosides in leguminous plant extracts. J. Mass Spectrom. 1996, 31, 472-485.
33. Yoshihara, T.; Yoshikawa, H.; Kunimatsu, S.; Sakamura S.; Sakuma, T. New amino acid derivatives conjugated with caffeic acid and DOPA from red clover (Trifolium pratense). Agric. Biol. Chem. 1977, 41, 1679-1684.