Universiti Teknologi Malaysia Institutional Repository

Synthesis of piperine derivatives

Muhamad Isa, Mardiana (2012) Synthesis of piperine derivatives. Masters thesis, Universiti Teknologi Malaysia, Faculty of Science.

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Abstract

The berries of black pepper (P. nigrum) are well known for its pungent smell and biting taste. Piperine which is one of the major amide present in P. nigrum contributes to the medicinal properties of the species. Extraction of the berries through maceration process followed by isolation of piperine via treatment with ethanolic potassium hydroxide successfully produced piperine (5-(1,3-benzodioxol- 5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one). Several chemical modifications have been carried out to derivatize piperine. Acetal cleavage has afforded 5-(3,4- dihydroxyphenyl)-1-(1-piperidinyl)-2,4-pentadien-1-one. Basic hydrolysis of piperine then afforded piperic acid (5-(1,3-benzodioxol-5-yl)-2,4-pentadienoic acid) which had been used as the precursor to synthesize an aliphatic amide (5-(1,3- benzodioxol-5-yl)-1-(n-butylamine)-2,4-pentadien-1-one), an ester (5-(1,3- benzodioxol-5-yl)ethyl-2,4-pentadienoate) and an acid (1,3-benzodioxol-1-yl)- methanoic acid). The pure piperine and derivatives were characterized by using infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS). The screening for antimicrobial properties of the compounds were also carried out by using disc diffusion, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods against Grampositive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). Piperine and all derivatives were found to be active towards Gram-positive bacteria with MIC value ranging from 225-900 µg/mL.

Item Type:Thesis (Masters)
Additional Information:Thesis (Sarjana Sains (Kimia)) - Universiti Teknologi Malaysia, 2012; Supervisor : Assoc. Prof. Dr. Farediah Ahmad
Uncontrolled Keywords:piperine derivatives, black pepper (P. nigrum)
Subjects:Q Science > Q Science (General)
Divisions:Science
ID Code:32819
Deposited By: Narimah Nawil
Deposited On:25 Oct 2013 01:20
Last Modified:27 Apr 2018 01:47

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