Isoflavone C-glycosides

Shafiullah, M. et al., A new isoflavone C-glycoside from Cassia siamea, Fitoterapia, 66, 439, 1995. 

Lee DYW, Zhang W-Y, Kamati VVR (2003) Total synthesis of puerarin, an isoflavone C-glycoside. Tetrahedron Lett 44 6857-6859... 

Bhutan SP, Chibber SS, Seshadri TR 1969 Components of the roots of Pueraria tuberosa isolation of a new isoflavone C-glycoside (di-O-acetylpuerarin). Indian J Chem 7 210... 

Despite interest in the anti-microbial and anti-insect activities of flavonoid C-glycosides (e.g. from maize), and the potential therapeutic value of isoflavone C-glycosides such as genis-tein 8-C-glucoside (Fig. 6) or puerarin from Pueraria lobata, no plant gene encoding a C-glycosyltransferase has yet been cloned. 

Almost half of the isoflavonoids identified from the Leguminosae, in which prenylated isoflavones constitute >50% of the total (pterocarpanoids, rotenoids, isoflavanones, isoflavans, coumestans, 3-arylcoumarins, and coumaronochromones), exhibit a high degree of structural diversity and complexity of prenylation.8,86"148 More than half of the isoflavones are monoprenylated, whereas 40% are diprenylated, and very few are triprenyl derivatives, with prenylation at positions 6>8>3 5 >6,>2 and O-methylation at 4 >7=6=2 =3 >5 =5>8. A number of novel isoflavonoid structures with rare skeletons, as well as complex isoflavone O- and C-glycosides have recently been reported.8,148... 

DAY A, CANADA F J, DIAZ J C, KROON P A, MCLAUCHLAN R, FAULDS C B, PLUMB G W, MORGAN M R A and WILLIAMSON G (2000) Dietary flavonoid and isoflavone glycosides are hydrolyzed by the lactase site of lactase phlorizin hydrolase. FEES Lett 468, 166-70. 

Til. Coward, L., Barnes, N.C., Setchell, K.D.R., and Barnes, S., Genistein, daidzein, and their (3-glycoside conjugates antitumor isoflavones in soybean foods from American and Asian diets, J. Agric. Food Chem., 41, 1961, 1993. 

Veitch, N.C. et al.. Six new isoflavones and a 5-deoxyflavonol glycoside from the leaves oiAteleia herbert-smithii. Journal of Natural Products, 66, 210, 2003. 

Figure 4.3 Chemical structures of Isoflavone glycosides. In soy foods, Isoflavones form 7-0-P-glucosIde conjugates. A Is the simple glucoside commonly found In soy milk, B Is the 6"-0-malonyl-7-0-p-glucoslde from the soybean, and C Is the 6"-0-acetyl-7-O-p-glucoside, a product of toasting of soy flour. D is the 7-0-P-glucuronide that is the principal conjugate in the blood.

R.E. March, X.-S. Miao, C.D. Metcalfe, M. Stobiecki, L. Marczak, A fragmentation study of an isoflavone glycoside, genistein-7-O-glucoside, using ESI-Q-TOF-MS at high mass resolution, Int. J. Mass Spectrom., 232 (2004) 171. 

Eldridge, A.C. 1982b. High performance liquid chromatography separation of soybean isoflavones and their glycosides. J. Chromatogr. 234 494—496. 

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