Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium.
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.
Department of Pharmacognosy and Ethnopharmacy, Usmanu Danfodiyo University, Sokoto, P.M.B 2346 Sokoto, Nigeria. Electronic address: keepibinformed@yahoo.co.uk.
Ibrahim
I
Malami
Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.
Simon
S
Gibbons
Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.
John P
JP
Malkinson
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D005204:Farnesol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D062385:Hydroxybenzoates / Q000138:chemical synthesis*; D008826:Microbial Sensitivity Tests; D031701:Piper / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry
C521381:3-farnesyl-2-hydroxybenzoic acid; D000900:Anti-Bacterial Agents; D062385:Hydroxybenzoates; D005204:Farnesol
3-Farnesyl-2-hydroxybenzoic acid; Antibacterial; Piper multiplinervium; Prenylated salicylic acid; Staphylococcus aureus