ABSTRACT
The present study was carried out to investigate the anti-inflammatory activities of bioactive secondary metabolites of Artemisia pallens Wall, an aromatic herb from family Asteraceae. The results provide evidence for the topical anti-inflammatory properties of Artemisia pallens Wall. The compounds were isolated from the acetone extract of the plant material. The isolates were tested on Swiss albino mice using 12-O-tetradecanoyl phorbol-13-acetate (TPA) induced ear edema. One of the molecules from the extract indicated potent anti-inflammatory activity equivalent to indometacin (CAS 53-86-1). Elucidation of the molecular structures by single crystal x-ray diffraction studies revealed the conformational differences that the six membered rings in both the molecules are at an angle of 28.79 degrees. Presence of hydroxy function for compound 2 may be responsible for higher potency.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Artemisia/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Acetone , Animals , Chromatography, High Pressure Liquid , Crystallography, X-Ray , Edema/chemically induced , Edema/prevention & control , Female , Hydrogen Bonding , Indomethacin/pharmacology , Lactones/chemistry , Magnetic Resonance Spectroscopy , Male , Mice , Models, Molecular , Plant Extracts/chemistry , Solvents , Tetradecanoylphorbol Acetate/pharmacologyABSTRACT
A sex hormone, 3beta-acetoxy-17beta-hydroxy-androst-5-ene (1) (CAS 1639-43-6), was isolated from aerial parts of Acacia nilotica. This compound is reported to have anti-inflammatory activity. In view of this, considering this molecule as a lead molecule different androstene compounds were synthesized to study their potency and structure-activity relationship with respect to local anti-inflammatory activity. The experiments indicated that 17 ketonic compounds were more active towards inflammation than their oxime analogues. Similarly, for the compounds containing an acetyl group fixed at C-3 position a decreasing trend of activity was observed in the order of ketonic, hydroxyl, oxime and acetyl group, respectively, when these groups are at C-17 position.
