Isolation and Chemotaxonomic Implications of <i>Tenelloside</i>, a Novel Unusual C-Glycosyl Flavanone from <i>Phyllanthus tenellus</i> Roxb. in Tenerife Island
Antonio Francioso,
Ignacio Antonio Jiménez Díaz,
Carolina Pérez Reyes,
Cristina González Montelongo,
Marco Pierini,
Claudio Villani,
Isabel López Bazzocchi
Affiliations
Antonio Francioso
Department of Bioscience and Technology for Food Agriculture and Environment, University of Teramo, 64100 Teramo, Italy
Ignacio Antonio Jiménez Díaz
Instituto Universitario de Bio-Orgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez, 38206 La Laguna, Spain
Carolina Pérez Reyes
Instituto Universitario de Bio-Orgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez, 38206 La Laguna, Spain
Cristina González Montelongo
Departamento de Botánica, Ecología y Fisiología Vegetal, Facultad de Ciencias, Sección Biología, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez, 38206 La Laguna, Spain
Marco Pierini
Department of Chemistry and Technologies of Drugs, Sapienza University of Rome, 00185 Rome, Italy
Claudio Villani
Department of Chemistry and Technologies of Drugs, Sapienza University of Rome, 00185 Rome, Italy
Isabel López Bazzocchi
Instituto Universitario de Bio-Orgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez, 38206 La Laguna, Spain
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.
