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C-glycosides

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Synthesis and Characterization of Glycosides

Abstract

C-glycosides have attracted much attention, considering that many of them have demonstrated their effectiveness as therapeutic agents. The increasing significance of C-glycosides is that the conformational differences compared to O- or N-glycosides are minimal, and that they are resistant to enzymatic or acidic hydrolysis since the anomeric center has been transformed from acetal to ether [1]. A glycoside is defined as C-glycoside when what is supposed to be the anomeric carbon of a sugar is interconnected to the aglycon, generating a new C–C bond. According to Levy and Tang [2] the term C-glycoside describes those structures in which a common structural motifs the presence of carbon functionality at what would otherwise be the anomeric position of a sugar or derivative. Structurally C-glycosides can be constituted by aliphatic, or aromatic aglycon, and the sugar can be pyranose or furanose. A variety of natural product C-glycosides have been described. Examples of C-glycosides isolated from different plant genera or insects and characterized spectroscopically are: Carminic acid (cochineal), Aloin (Aloe vera), Scoparin (Cytisus scoparius), Saponarin (Saponaria officinalis), flavonoid phytoalexins such as Cucumerins (Cucumis sativus) and Naringenin (grapefruit), [3] C-glucosyl xanthones [4], and complex benzoquinone Altromycin B [5] (actinomycetes), among others (Scheme 5.1).

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  1. Unidad Profesional Interdisciplinaria de Biotecnología Instituto Politécnico Nacional (UPIBI-IPN) Avenida Acueducto s/n Colonia La Laguna Ticomán, Ciudad de México, cp 07340, México

    Marco Brito-Arias

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Brito-Arias, M. (2016). C-glycosides. In: Synthesis and Characterization of Glycosides. Springer, Cham. https://doi.org/10.1007/978-3-319-32310-7_5

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