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Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium.
Fitoterapia. 2014 Mar; 93:189-93.F

Abstract

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Malami I
Department of Pharmacognosy and Ethnopharmacy, Usmanu Danfodiyo University, Sokoto, P.M.B 2346 Sokoto, Nigeria. Electronic address: keepibinformed@yahoo.co.uk.
Gibbons S
Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.
Malkinson JP
Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, United Kingdom.

MeSH

Anti-Bacterial AgentsFarnesolHydroxybenzoatesMicrobial Sensitivity TestsPiperPlants, Medicinal

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24444894

Citation

Malami, Ibrahim, et al. "Synthesis and Antibacterial Evaluation of 3-Farnesyl-2-hydroxybenzoic Acid From Piper Multiplinervium." Fitoterapia, vol. 93, 2014, pp. 189-93.
Malami I, Gibbons S, Malkinson JP. Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium. Fitoterapia. 2014;93:189-93.
Malami, I., Gibbons, S., & Malkinson, J. P. (2014). Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium. Fitoterapia, 93, 189-93. https://doi.org/10.1016/j.fitote.2014.01.005
Malami I, Gibbons S, Malkinson JP. Synthesis and Antibacterial Evaluation of 3-Farnesyl-2-hydroxybenzoic Acid From Piper Multiplinervium. Fitoterapia. 2014;93:189-93. PubMed PMID: 24444894.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium. AU - Malami,Ibrahim, AU - Gibbons,Simon, AU - Malkinson,John P, Y1 - 2014/01/18/ PY - 2013/04/15/received PY - 2013/12/31/revised PY - 2014/01/09/accepted PY - 2014/1/22/entrez PY - 2014/1/22/pubmed PY - 2015/2/24/medline KW - 3-Farnesyl-2-hydroxybenzoic acid KW - Antibacterial KW - Piper multiplinervium KW - Prenylated salicylic acid KW - Staphylococcus aureus SP - 189 EP - 93 JF - Fitoterapia JO - Fitoterapia VL - 93 N2 - 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. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/24444894/Synthesis_and_antibacterial_evaluation_of_3_Farnesyl_2_hydroxybenzoic_acid_from_Piper_multiplinervium_ DB - PRIME DP - Unbound Medicine ER -