afzelechin and proanthocyanidin

Two benzophenone glucosides (

Topics: Benzophenones; Cassia; Crystallography, X-Ray; Dimerization; Glucosides; Molecular Structure; Proanthocyanidins; Proton Magnetic Resonance Spectroscopy; Trypanocidal Agents; Trypanosoma

Chamaecrista nictitans (L) extract possesses antiviral properties; it acts against the herpes simplex virus, and this may be attributed to its constituent phenolics. Here, high-resolution LC-ESI-MS/MS is used to identify the phenolic components of the most potent fraction of the extract. The fraction is a complex mixture rich in oligomeric proanthocyanidins with a high content of monohydroxyphenol moieties ((epi)fisetinidol, (epi)afzelechin and (epi)guibourtinidol) and A-type linkages, uncommon in other proanthocyanidin-rich phenolic extracts, such as those from grape seeds or pine bark. As monohydroxyphenolic structures and A-type linkages have been related to antiviral effects, particularly through the inhibition of late transcription, we suggest that the fraction of C. nictitans extract exerts its action through a particularly effective combination of proanthocyanidins that include these two structural features.

Topics: Antiviral Agents; Chamaecrista; Chemistry, Pharmaceutical; Chromatography, Liquid; DNA, Viral; Flavones; Flavonoids; Free Radical Scavengers; Herpes Simplex; Humans; Phenols; Plant Extracts; Polyphenols; Proanthocyanidins; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship; Tandem Mass Spectrometry