ABSTRACT
The antiherpes virus properties of Phyllanthus orbicularis Kunth, a Cuban-endemic medicinal plant, have been reported previously but data on its phytochemical profile and identification of antiviral metabolites as well as their mechanisms of action are still lacking. In this work, a bioactivity-guided phytochemical analysis was performed in order to isolate anti HSV-2 compounds. P. orbicularis contained mainly phenolic acids derivatives and flavonoids. The antiviral effects were attributed to (-)-epicatechin-3-O-gallate (EC(50) = 11.7 µg/mL), procyanidins B1 and B2 (EC(50) = 32.8 µg/mL and 24.2 µg/mL, respectively) as well as oligomeric and polymeric procyanidins and their gallate derivatives. The antiviral mechanisms of the active P. orbicularis extracts and fractions were also investigated and the inhibition of several HSV-2 early replication events and DNA synthesis were observed. This is the first study of extensive fractionation and phytochemical characterization of phenolic compounds from this species.
Subject(s)
Antiviral Agents/pharmacology , Herpesvirus 2, Human/drug effects , Phyllanthus/chemistry , Plant Extracts/pharmacology , Animals , Catechin/analogs & derivatives , Catechin/isolation & purification , Catechin/pharmacology , Chemical Fractionation , Chlorocebus aethiops , Plant Extracts/chemistry , Plants, Medicinal/chemistry , Proanthocyanidins/isolation & purification , Proanthocyanidins/pharmacology , Vero CellsABSTRACT
The flavone glycosides, named scutellarein-7-O-beta-D-apiofuranoside and apigenin-7-O-beta-D-apiofuranosyl-(1-->2)-beta-D-apiofuranoside, and the flavone celtidifoline (5,6,4',5'-tetrahydroxy-7,3'-dimethoxyflavone), along with other 11 known compounds, were isolated from leaves of the ethyl acetate extract of Lantana trifolia L. using step gradient High Speed Countercurrent Chromatography (HSCCC) and High Performance Liquid Chromatography (HPLC), respectively. Their structures were elucidated by spectroscopic methods, including 2D NMR and mass spectrometry (ESI-MS) techniques. The ethanolic and ethyl acetate extracts produced an intense sedative effect in mice, one hour after oral administration of 1 mg/kg. This effect was neither due to a benzodiazepine-like effect of the three flavone derivatives neither of the phenylpropanoids, betonyoside F and verbascoside, that were tested for their affinity for the [3H] flunitrazepam binding sites.
