Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium
Department of Pharmacognosy and Ethnopharmacy, Usmanu Danfodiyo University, Sokoto, P.M.B 2346 Sokoto, Nigeria; Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, United Kingdom
3-Farnesyl-2-hydroxybenzoic acid is an antibacterial agent isolated from the leaves of Piper multiplinervium. This compound has activity against both Gram positive and Gram negative bacteria including Escherichia coli, Staphylococcus aureus and Helicobacter pylori. This research aimed to synthesize a natural antibacterial compound and its analogs. The synthesis of 3-Farnesyl-2-hydroxybenzoic acid consists of three steps: straightforward synthesis involving protection of phenolic hydroxyl group, coupling of suitable isoprenyl chain to the protected aromatic ring at ortho position followed by carboxylation with concomitant deprotection to give the derivatives of the salicylic acid. All the three prenylated compounds synthesized were found to exhibit spectrum of activity against S. aureus (ATCC) having MIC: 5.84 × 10- 3, 41.46 × 10- 2 and 6.19 × 10 - 1 μmol/ml respectively. The compounds also displayed activity against resistance strain of S. aureus (SA1119B) having MIC: 5.84 × 10- 3, 7.29 × 10- 3 and 3.09 × 10 - 1 μmol/ml respectively. This synthesis has been achieved and accomplished with the confirmation of it structure to that of the original natural product, thus producing the first synthesis of the natural product and providing the first synthesis of its analogs with 3-Farnesyl-2-hydroxybenzoic acid having biological activity higher than that of the original natural product. © 2014 Elsevier B.V.
1, 3 dibromo 2 methoxymethoxybenzene; 2 bromo 6 dimethlyallyl 1 methoxymethoxybenzene; 2 bromo 6 farnesyl 1 methoxymethoxybenzene; 2 bromo 6 geranyl 1 methoxymethoxybenzene; 3 dimethylallyl 2 hydroxybenzoic acid; 3 farnesyl 2 hydroxybenzoic acid; 3 geranyl 2 hydroxybenzoic acid; antiinfective agent; aromatic compound; natural product; norfloxacin; phenol; salicylic acid; unclassified drug; 3-farnesyl-2-hydroxybenzoic acid; antiinfective agent; farnesol; hydroxybenzoic acid derivative; antibacterial activity; article; biological activity; carboxylation; controlled study; deprotection reaction; drug isolation; drug screening; drug synthesis; Escherichia coli; Gram negative bacterium; Gram positive bacterium; Helicobacter pylori; isoprenylation; minimum inhibitory concentration; nonhuman; Piper (plant); Piper multiplinervium; plant leaf; prenylation; priority journal; Staphylococcus aureus; structure activity relation; analogs and derivatives; chemistry; medicinal plant; microbial sensitivity test; Piper (plant); synthesis; Anti-Bacterial Agents; Farnesol; Hydroxybenzoates; Microbial Sensitivity Tests; Piper; Plants, Medicinal