Antiviral activity of simalikalactone D, a quassinoid from Quassia africana.
After removing lipophilic material, the ground root bark of Quassia africana Baill. (Simaroubaceae) was extracted with ethanol 95 %. Partitioning between chloroform, ethyl acetate and water yielded three crude extracts. Pronounced activities were shown by the chloroform and ethyl acetate crude extracts against Herpes simplex, Semliki forest, Coxsackie and Vesicular stomatitis viruses. By repeated column chromatography and preparative thin layer chromatography on silica gel, two quassinoids, i. e., quassin and simalikalactone D were isolated. Structures of the pure compounds were established primarily using NMR spectroscopy. Mass spectral information confirmed the assigned structures. Simalikalactone D was responsible, at least in part, for the high antiviral activity observed for the chloroform crude extract. Quassin showed no activity. For quassinoids the ester group at C-15 and the epoxymethano bridge between C-8 and C-13 appeared to be important structural features in order to exhibit a pronounced antiviral activity.
Apers
Sandra
S
Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium. Sandra.Apers@ua.ac.be
Cimanga
Kanyanga
K
Vanden Berghe
Dirk
D
Van Meenen
Els
E
Longanga
Albert Otshudi
AO
Foriers
André
A
Vlietinck
Arnold
A
Pieters
Luc
L
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005900:Glaucarubin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018259:Herpesvirus 1, Human / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D016488:Medicine, African Traditional; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D036702:Quassins; D029641:Simaroubaceae
D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D010936:Plant Extracts; D036702:Quassins; C024970:simalikalactone D; D005900:Glaucarubin