Extraction, isolation and characterization of oleanolic acid and its analogues from Syzygium aromaticum (cloves) and evaluation of their biological activities

Pathogenic microorganisms have serious impact on people's lives. Every year, millions of people around the world die of bacterial infections. Resistance to common antibacterial drugs has proven to be a challenging problem in control of bacterial infections. In an attempt to develop an effective and affordable treatment for bacterial infections, oleanolic acid isolated from syzygium aromaticum conjugates incorporating other pharmaceutical scaffolds such as chloroquine derivatives, curcumin, and ergocalciferol etc have been developed. Based on the previous successes of testing combination of antimicrobial drugs and pharmaceutical drugs which appeared to be the promising strategy to overcome treatment failure; a series of hybrid compounds containing oleanolic acid and other pharmaceutical scaffolds were synthesized. 4- Aminoquinoline derivatives were first hybridized with selected organic compounds to form a class of hybrid compounds containing either amide bond or ester bond as a linker between the precursor molecules. Analogues/hybrid compounds can overcome the disadvantages of combination therapy such as drug-drug interaction. The structural effects of this type of conjugation of oleanolic acid and other pharmaceutical scaffolds were characterised by FTIR, Mass Spec and NMR spectroscopy. These compounds were studied along with the monosubstituted oleanolic acid analogues and the organic components in order to compare the effects of the substitution on their biological response.‖ All the synthesized analogues were tested against 11 bacterial strains on both Gram-positive and Gram-negative bacteria. The synthesized compounds showed selectivity and higher activity against Enterococcus faecalis (EF), Klebsiella oxytoca (KO), Escherischia coli (EC), Staphylococcus aureous (SA), Proteus vulgaris (PV) and Bacillus subtilis (BS) with MIC values; ranging between of 1.25 mg/mL to 0.072 mg/m