Taste and structure in phenolic glycosides

Abstract

Certain intensely bitter flavanone glycosides occur in citrus fruits together with isomeric glycosides that are tasteless. The bitter compounds all contain the disaccharide -neohesperidose (2-O-q-lrhamnosyl-/3-D-glucose). The tasteless compounds contain an isomeric disaccharide, j3-rutinose (6-0a-L-rhamnosvi-3-D-glucose). When alterations are made at selected sites in the flavanone neohesperido-sides the product may be bitter, bittersweet, sweet, or tasteless. Corresponding changes made in the flavanone rutinosides usually result in tasteless compounds unless the rhamnose is removed from the 6position of glucose. Of particular interest in this series are the neohesperidosyl dihydrochalcones, several of which are intensely sweet. This paper reviews recent findings in this field.

Flavanone Glycoside Biosynthesis in Citrus

“…(Rutaceae) contain bitter tasting flavanone-disaccharides (18). They are used as food additives for their flavor or can be converted by hydrogenation into the extremely sweet dihydrochalcone derivatives (18).…”

Les composés phénoliques et la qualité des produits d'origine végétale consommés par l'homme

“…Chez les Citrus ce sont des glycosides de flavanones et I' oleuropeine (ester heterosidique de l'acide elenolique et du dihydroxyphenylethanol) chez I' olive . Les relations entre degre d' amertume des gl ycosides de flavanones et leurs structures ont ete bien etudiees (Horowitz et Gentili, 1969 ;Maier, 1983 ). Tous les composes contenant le disaccharide neohesperidose (2-0-a-L-rhamnosyl-B-D-glucose) sont amers (naringine, neohesperidine) alors que les memes aglycones lies au rutinose (6-0-a-L-rhamnosyl-B-D-glucose) sont sans gout (narirutine, hesperidine) ainsi que les aglycones euxmemes.…”

“…'heterocycle des flavanones conduit a Ia formation de dihydrochalcones ayant des saveurs sucrees (Horowitz et Gentili, 1969). La neohesperidine-dihydrochalcone a une valeur sucrante 500 fois superieure a celle du saccharose.…”

Biochemical studies of taste sensation: binding to taste tissue of 3H-labeled monellin, a sweet-tasting protein.

“…Furthermore, sugars and other sweet-tasting molecules appeared to compete to some extent with this sweet-tasting protein for its binding sites. These binding measurements of the intensely sweet-tasting protein monellin to taste receptor preparations help to establish the binding interaction as an initial step in taste sensation.Relatively little is understood about the biochemical basis of sweet taste despite considerable knowledge of a wide variety of sweet-tasting chemical compounds (1)(2)(3)(4)(5)(6). Most of the behavioral, physiological, and biochemical research on sweet taste has used sucrose or other sugars.…”

“…Relatively little is understood about the biochemical basis of sweet taste despite considerable knowledge of a wide variety of sweet-tasting chemical compounds (1)(2)(3)(4)(5)(6). Most of the behavioral, physiological, and biochemical research on sweet taste has used sucrose or other sugars.…”