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.

中文翻译：

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异黄酮、它们的糖苷和糖缀合物。合成与生物活性

天然或合成来源的小生物活性分子的糖基化对其溶解性、稳定性和生物活性具有深远的影响，使糖缀合物成为有吸引力的化合物作为治疗剂或营养品。大部分次生代谢物，包括类黄酮，以糖苷的形式存在于植物中，这增加了在药物化学研究中非常有价值的分子多样性。随后对糖苷天然产品不断增长的市场需求推动了糖苷制备的各种化学和生物技术方法的发展。该评论对异黄酮的合成过程进行了广泛的概述，并讨论了最近开发的异黄酮糖形成过程的主要途径。特别关注染料木黄酮的衍生物，主要异黄酮被认为是多种治疗类别中的有用先导物，特别关注抗癌药物设计。在一些理论和实践方面讨论了化学糖基化以及糖缀合物制备的效用。由于化学糖基化和糖缀合的新方法很多，并且其中许多被证明适用于多酚的衍生化，出现了新的证据，表明糖部分可以发挥更重要的作用，当连接到药效团时“增溶剂”。在许多情况下，已经证明半合成糖缀合物是比参考异黄酮更有效的细胞生长抑制剂和细胞毒性剂。而且，