Title:Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity
Volume: 21
Issue: 3
Author(s): Wieslaw Szeja, Grzegorz Grynkiewicz and Aleksandra Rusin
Affiliation:
Keywords:
Isoflavones, chemical glycosylations, isoflavone glycoconjugates.
Abstract: Glycosylation of small biologically active molecules, either of natural or synthetic origin, has a profound
impact on their solubility, stability, and bioactivity, making glycoconjugates attractive compounds as
therapeutic agents or nutraceuticals. A large proportion of secondary metabolites, including flavonoids, occur in
plants as glycosides, which adds to the molecular diversity that is much valued in medicinal chemistry studies.
The subsequent growing market demand for glycosidic natural products has fueled the development of various
chemical and biotechnological methods of glycosides preparation. The review gives an extensive overview of the
processes of the synthesis of isoflavones and discusses recently developed major routes towards isoflavone-sugar
formation processes. Special attention is given to the derivatives of genistein, the main isoflavone recognized as a
useful lead in several therapeutic categories, with particular focus on anticancer drug design. The utility of
chemical glycosylations as well as glycoconjugates preparation is discussed in some theoretical as well as practical
aspects. Since novel approaches to chemical glycosylations and glycoconjugations are abundant and many of
them proved suitable for derivatization of polyphenols a new body of evidence has emerged, indicating that sugar
moiety can play a much more significant role, when attached to a pharmacophore, then being a mere “solubilizer”.
In many cases, it has been demonstrated that semisynthetic glycoconjugates are much more potent cytostatic
and cytotoxic agents than reference isoflavones. Moreover, the newly designed glycosides or glycoside
mimics can act through different mechanisms than the parent active molecule.
