Insights into the Phytochemistry of the Cuban Endemic Medicinal Plant Phyllanthus orbicularis: Fideloside, a Novel Bioactive 8-C-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.

Hitting the sweet spot: A systematic review of the bioactivity and health benefits of phenolic glycosides from medicinally used plants

“…Two of the remaining studies did not report results from a positive control (Francioso et al, 2019; Kim et al, 2018), while Pendota et al (2018) found that the antiinflammatory activity of the glycoside tiliroside was somewhat less than that of curcumin, the positive control.…”

A Prospective of Multiple Biopharmaceutical Activities of Procyanidins‐Rich Uapaca togoensis Pax Extracts: HPLC‐ESI‐TOF‐MS Coupled with Bioinformatics Analysis

“…Therefore, eight procyanidin C trimer isomer were identified (peaks 3, 5, 7, 8, 12, 16, 17 and 34) evaluating their molecular formula (C 45 H 38 O 18 ) and their characteristic MS/MS pattern which displayed two intense ion fragments at 287 and 407 [35] . These compounds were earlier detected in Phyllanthaceae plants [25] . Peak 4, 9 and 20 gave a molecular formula C 60 H 50 O 24 and a ion fragment at 287, 407, 575 and 863 enabling their identification as procyanidin D tetramer isomers [36] .…”

Chemophenetic Significance of Anomalocalyx uleanus Metabolites Are Revealed by Dereplication Using Molecular Networking Tools

“…One C-glycosylated flavonoid, isovitexin (20), was also detected in the extracts of A. uleanus. This class of compound is found in some genera of Euphorbiaceae, such as Aleurites [38], Croton [39], Jatropha [40], and Phyllanthus [41]. One biflavonoid was also annotated as 3′′′-O-methylfukugetin (21).…”