Identification of isoflavone glycosides in pueraria lobata cultures by tandem mass spectrometry

Phytochemical Analysis

Volumn 18, Issue 1, 2007, Pages 50-59

  Prasain, Jeevan K ^a,b   Reppert, Adam ^c   Jones, Kenneth ^a   Moore II, D Ray ^b   Barnes, Stephen ^a,b   Lila, Mary Ann ^c  

^a University of Alabama at Birmingham   (United States)

^b UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

HPLC UV MS; In vitro cultures; Isoflavone profiling; Metabolic profiling; Pueraria lobata; Puerarin

Indexed keywords

FLAVONOIDS; GLYCOSIDES; MASS SPECTROMETRY; SUGARS;

HPLC-UV/MS; IN VITRO CULTURE; IN-VITRO; ISOFLAVONE PROFILING; ISOFLAVONES; METABOLIC PROFILING; PUERARIA LOBATA; PUERARIN; ROOT CULTURES; VITRO CULTURE;

METABOLITES;

DAIDZEIN; DAIDZIN; FORMONONETIN; GENISTEIN; GENISTIN; GLYCOSIDE; ISOFLAVONE; METHANOL; PUERARIA EXTRACT; PUERARIA LOBATA EXTRACT; PUERARIN; UNCLASSIFIED DRUG;

ARTICLE; CALLUS CULTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MOLECULAR WEIGHT; PLANT LEAF; PLANT ROOT; PUERARIA; PUERARIA LOBATA; QUANTITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

PUERARIA MONTANA VAR. LOBATA;

EID: 33846422731     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.951     Document Type: Article

References (34)

1. Akashi T, Aoki T, Ayabe S. 1999. Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol 121: 821-328.
2. Akashi T, Sawada Y, Aoki T, Ayabe S. 2000. New scheme of the biosynthesis of formononetin involving 2,7,4?′-trihydroxyisoflavanone but not daidzein as the methyl acceptor. Biosci Biotechnol Biochem 64: 2276-2279.
3. Barz W, Welle R. 1992. Biosynthesis and metabolism of isoflavones and pterocarpan phytoalexins in chickpea, soybean and phytopathogenic fungi. Rec Adv Phytochem 26: 139-164.
4. Barnes S, Peterson TG. 1995. Biochemical targets of the isoflavone genistein in tumor cell lines. Proc Soc Exp Biol Med 208: 103-108.
5. Barnes S, Kirk M, Coward L. 1994. Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J Agric Food Chem 42: 2466-2474.
6. Boue 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.
7. Coward L, Smith M, Kirk M, Barnes S. 1998. Chemical modification of isoflavones in soy foods during cooking and processing. Am J Clin Nutr 68: 1486S-1491S.
8. Edwards R, Dixon RA. 1991. Isoflavone O-methyltransferase activities in elicitor-treated cell suspension cultures of Medicago sativa. Phytochemistry 30: 2597-2606.
9. Fridman E, Pichersky E. 2005. Metabolomics, genomics, proteomics, and the identification of enzymes and their substrates and products. Curr Opin Plant Biol 8: 242-248.
10. Gamborg OL, Miller RA, Ojima K. 1968. Nutrient requirements of suspension cultures of soybean root cells. Exp Cell Res 50: 151-158.
11. Hakamatsuka T, Ebizuka Y, Sankawa U. 1994. Pueraria lobata (kudzu vine): in vitro culture and the production of isoflavonoids. In Biotechnology in Agriculture and Forestry, Vol. 28, Bajai, R.P.S. (ed.). Medicinal and Aromatic Plants Vil. Springer: Heidelberg.
12. He XZ, Dixon RA. 1996. Affinity chromatography, substrate/product specificity, and amino acid sequence analysis of an isoflavone O-methyltransferase from alfalfa (Medicago sativa L.). Arch Biochem Biophys 336: 121-129.
13. Hsu FL, Liu IM, Kuo DH, Chen WC, Su HC, Cheng JT. 2003. Antihyperglycemic effect of puerarin in streptozotocin-induced diabetic rats. J Nat Prod 66: 788-792.
14. Jiang RW, Lau KM, Lam HM, Yam WS, Leung LK, Choi KL, Waye MM, Mak TC, Woo KS, Fung KP. 2005. A comparative study on aqueous root extracts of Pueraria thomsonil and Pueraria lobata by antioxidant assay and HPLC fingerprint analysis. J Ethnopharmacol 96; 133-138.
15. Jung W, Yu O, Lau SM, O'Keefe DP, Odell J, Fader G, McGonigle B. 2000. Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nat Biotechnol 18: 208-2012.
16. Justesen U. 2001. Collision-induced fragmentation of deprotonated methoxylated flavonoids, obtained by electrospray ionization mass spectrometry. J Mass Spectrom 36: 169-178.
17. Keung WM, Vallee BL. 1998. Kudzu root: an ancient Chinese source of modern antidipsotropic agents. Phytochemistry 47: 499-506.
18. Keung WM, Vallee BL. 1993. Daidzin and daidzein suppress free-choice ethanol intake by Syrian golden hamsters. Proc Natl Acad Sci USA 90: 10008-10012.
19. Kochs G, Grisebach H. 1986. Enzymic synthesis of isoflavones. Eur J Biochem 1155: 311-318.
20. Lee JS. 2004. Supplementation of Pueraria radix water extract on changes of antioxidant enzymes and lipid profile in ethanol-treated rats. Clin Chim Acta 347: 121-128.
21. Liu CJ, Dixon RA. 2001. Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. Plant Cell 13: 2643-2658.
22. Liu H., Li L. 2002. Cell cultures of Pueraria lobata (Willd.): growth and production of isoflavones and puerarin. S Afr J Bot 68: 542-544.
23. Murashige T, Skoog F. 1962. A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15: 473-497.
24. Otani K, Takahashi T, Furuya T, Ayabe S. 1994. Licodione synthase, a cytochrome P450 monooxygenase catalyzing 2-hydroxylation of 5-deoxyflavanone, in cultured glycyrrhiza echinata L. cells. Plant Physiol 105: 1427-1432.
25. Prasain JK, Jones K, Kirk M, Wilson L, Smith-Johnson M, Weaver C, Barnes S. 2003. Profiling and quantification of isoflavonoids in kudzu dietary supplements by high-performance liquid chromatography and electrospray ionization tandem mass spectrometry, J Agric Food Chem 51: 4213-4218.
26. Prasain JK, Wang CC, Barnes S. 2004a. Mass spectrometric methods for the determination of flavonoids in biological samples. Free Radic Biol Med. 37: 1324-1350.
27. Prasain JK, Jones K, Brissie N, Moore R, Wyss JM, Barnes S. 2004b. Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry. J Agric Food Chem 52: 3708-3712.
28. Rauha JP, Vuorela H. Kostiainen R. 2001. Effect of eluent on the ionization efficiency of flavonoids by ion spray, atmospheric pressure chemical ionization, and atmospheric pressure photoionization mass spectrometry. J Mass Spectrom 36: 1269-1280.
29. Rogers RB, Smith MAL. 1992. Consequences of in vitro and ex vitro root initiation for miniature rose production. J Hort Sci 67: 535-540.
30. Steele CL, Gijzen M, Qutob D, Dixon RA. 1999. Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean. Arch Biochem Biophys 367: 146-150.
31. Waridel P, Wolfender JL, Ndjoko K, Hobby KR, Major HJ, Hostettmann K. 2001. Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. J Chromatogr A 926: 29-41.
32. Wu CT, Mulabagal V, Nalawade SM, Chen CL, Yang TF, Tsay HS. 2003. Isolation and quantitative analysis of cryptotanshinone, an active quinoid diterpene formed in callus of Salvia miltiorrhiza BUNGE. Biol Pharm Bull 26: 845-848.
33. Xu X, Hu Y, Ruan Q. 2004. Effects of puerarin on learning-memory and amino acid transmitters of brain in ovariectomized mice. Planta Med 70: 627- 631.
34. Zhu JH, Wang XX, Chen JZ, Shang YP, Zhu JH, Guo XG, Sun J. 2004. Effects of puerarin on number and activity of endothelial progenitor cells from peripheral blood. Acta Pharmac Sin 25: 1045-1051.