Glycosides, flavanone

Of this class of naturally occurring, sweet compounds, the flavanone glycosides found in citrus fruits have achieved considerable interest, owing to the systematic studies of Horowitz and Gentili " (see Fig. 20). 

In terms of taste, the flavanone glycosides can be divided into two groups. The first group consists of compounds that are bitter. These are glycosides... 

The conversion of the bitter flavanone glycosides into those of the corresponding chalcones by alkali-catalyzed fission of the pyrone ring, and of the dihydrochalcone glycosides by hydrogenation thereof (see Scheme 1)... 

Citrus species are well-known for their accumulation of flavone- and flavanone-glycosides, and thus should contain all of the enzyme activities necessary for the synthesis of these compounds. Two tentative consensus sequences for FNS-II have been identified by in silico analysis of the CitEST database, apparently representing the first identification of putative FNS-II genes in this genus [29]. Biochemical determination of function and analysis of the proteins encoded by these genes will be an important step toward elucidating flavone synthesis in Citrus. 

Lewinsohn E, Britsch L, Mazur Y, Gressel J (1989) Flavanone glycoside biosynthesis in Citrus chalcone synthase, UDP-glucose flavanone-7-0-glucosy-transferase and -rhamnosyltransferase activities in cell-free extracts. Plant Physiol 91 1321-1328... 

Fang W, Ruan J, Wang Z, Zhao Z, Zou J, Zhou D, Cai Y. (2006) Acetylated flavanone glycosides from the rhizomes of Cyclosorus acuminatus. J Nat Prod 69 1641-1644. 

Matsuda H, Morikawa T, Toguchida 1, Harima S, Yoshikawa M. (2002) Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L. Their inhibitory activities for rat lens aldose reductase. Chem Pharm Bull 50 972-975. 

Takahashi, H. et al., Triterpene and flavanone glycoside from Rhododendron simsii. Phytochemistry, 56, 875, 2001. 

Singh, V.P., Yadav, B., and Pandey, V.B., Flavanone glycosides from Alhagi pseudalhagi. Phytochemistry, 51, 587, 1999. 

Miyake, Y. et al., New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit, Biosci. Biotechnol. Biochem., 67, 1443, 2003. 

Mouly, P.P. et ak, Differentiation of citrus juices by factorial discriminant analysis using liquid chromatography of flavanone glycosides, J. Agric. Food Chem., 42, 70, 1994. 

Marini, D. and Balestrieri, F., Multivariate analysis of flavanone glycosides in citrus juices, Ital. J. Food Sci., 1, 255, 1995. 

No. Flavanone Glycoside Formula Trivial Name Plant Source Family Organ" Ref. 

Xu, Y., Kubo, L, and Ma, Y., A cytotoxic flavanone glycoside from Onychium japonicum structure of onychin, Phytochemistry, 33, 510, 1993. 

Wang, B. et al., Two new flavanone glycosides from Glycyrrhiza inflata, Yaoxue Xuebao, 32, 199, 1997. 

Yin, S., A novel flavanone glycoside from Glycyrrhiza uralensis Fisch., Zhangguo Yaoke Daxue Xuebao, 50, 19, 1999. 

Yadava, R.N., Mathews, S.R., and Jain, N., Naringenin 4 -0-a-L-rhamnopyranoside, a novel flavanone glycoside from the stem of Crotalaria striata D.C., J. Indian Chem. Soc., 74, 426, 1997. 

Yuldashev, M.P. et al., Acylated flavanone glycosides from Ricinus communis, Khim. Prir. Soedin., 362, 1993. 

Ali, M.S. et al., A chlorinated monoterpene ketone, acylated (J-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae), Phytochemistry, 59, 889, 2002. 

Yadava, R.N. and Tripathi, P., A novel flavanone glycoside from Albizzia procera Benth., J. Inst. Chem. (India), 71, 202, 1999. 

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