C-Ribosylating Enzymes in the (Bio)Synthesis of C-Nucleosides and C-Glycosylated Natural Products

Pfeiffer, Martin; Nidetzky, Bernd

doi:10.1021/acscatal.3c04436

Cited by 4 publications

(1 citation statement)

References 255 publications

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“…Our recent work on the Cuban endemic Phyllanthus orbicularis Kunth elucidated the natural product responsible for the plant's anti-inflammatory activity and identified this compound as a new C-glycoside flavonoid [14]. The scientific literature on this class of natural products still lacking, also because these compounds are very rare and their occurrence in nature is less represented with respect to their O-glycosyl-linked analogs [15][16][17][18]. The extreme interest in these compounds arises from the bioactivity profiles that C-glycosides can confer to poorly bioavailable active aglycones.…”

Section: Introductionmentioning

confidence: 99%

Isolation and Chemotaxonomic Implications of Tenelloside, a Novel Unusual C-Glycosyl Flavanone from Phyllanthus tenellus Roxb. in Tenerife Island

Francioso,

Jiménez Díaz,

Reyes

et al. 2023

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Phyllanthus is a large genus of the Euphorbiaceae family, which has been widely used in traditional medicine. The current study reports the isolation of an unusual C-glycosyl flavonoid, named tenelloside, from Phyllanthus tenellus Roxb., a non-endemic plant present in Canary Islands. The chemical structure of this secondary metabolite was established employing combined spectrometric and spectroscopic techniques, including 1D and 2D NMR experiments and mass spectrometry. The absolute stereochemical configuration was determined via the comparison of experimental and calculated electronic circular dichroism spectra. In our previous work, another C-glycosylated bioactive product was isolated from another Phyllanthus species, suggesting that this class of compounds can be produced in a genus-specific manner in different geographic regions. This work represents another important report for direct future studies on the biological and chemotaxonomic potential of C-glycosylated products of the Phyllanthus genus.

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