Insights into the Phytochemistry of the Cuban Endemic Medicinal Plant <i>Phyllanthus orbicularis</i>: Fideloside, a Novel Bioactive 8-<i>C</i>-glycosyl 2,3-Dihydroflavonol

Abstract

Phyllanthus orbicularis (Phyllanthaceae) is an endemic evergreen tropical plant of Cuba that grows in the western part of the island and is used in traditional medicine as an infusion. The aqueous extract of this plant presents a wide range of pharmacological activitiessuch as antimutagenic, antioxidant and antiviral effects. Given the many beneficial effects and the great interest in the development of new pharmacological products from natural sources, the aim of this work was to investigate the phytochemistry of this species and to elucidate the structure of the main bioactive principles. Besides the presence of several known polyphenols, the major constituent was hitherto not described. The chemical structure of this compound, here named Fideloside, was elucidated by means of HR-ESIMS/MSn, 1D/2D NMR, FT-IR, and ECD as (2R,3R)-(−)-3’,4′,5,7-tetrahydroxydihydroflavonol-8-C-β-D-glucopyranoside. The compound, as well as the plant aqueous preparations, showed promising bioactive properties, i.e., anti-inflammatory capacity in human explanted monocytes, corroborating future pharmacological use for this new natural C-glycosyl flavanonol.

Keywords

• <i>Phyllanthus orbicularis</i>
• <i>C</i>-glycoside
• flavonoid
• natural products
• traditional medicine
• Cuba
• <i>Phyllanthus chamacristoides</i>
• chromatography
• mass spectrometry
• NMR
• circular dichroism
• stereochemistry
• Fideloside
• cytokines
• anti-inflammatory activity