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Isolation and Characterization of Piperine from the Fruits of Black Pepper (piper Nigrum)

Mr. Kartik Chandra Saha
Professor
Department of Agricultural Chemistry, Bangladesh Agricultural University, Mymensingh-2202, Bangladesh

Abstract/ Executive Summary:

Black pepper (Piper nigrum) is a spice vine crop which is used as a food preservative and as an essential component in traditional medicines. The aim of this study was to extract, isolate and characterize the structure of piperine. The fruits of black pepper were extracted in ethanol and compounds present identified by TLC under iodine vapour. A compound (A₂) having R_f value 0.54 was isolated by column chromatography which may be responsible for the pungency of black pepper. After recrystallization of the isolate with benzene and chloroform mixture (7:1) gave pale yellow crystals of m.p. 128~129^oC (reported 130^oC). The IR, ¹H NMR and mass spectra of the pure crystalline compound (A₂) were recorded. The mass spectra of the compound (A₂) showed molecular ion peak M^+∙ at 284.5 which was similar to that of piperine (mol. wt. 285).

Keywords: Piperine, TLC, IR, NMR, Mass spectrometry

Location: Mymensingh.

Start Date: 01-01-2009

End Date: 31-12-2010

Program Area: Variety and Species

Commodity:

Objectives:

To extract, isolate and characterize the structure of piperine.

Methodology:

The work was performed at the Organic Chemistry laboratory, Department of Agricultural Chemistry, BAU, Mymensingh.Dried black pepper fruits were purchased from local market at Mymensingh, cleaned to free from stone and other undesirable matters and sun dried. Then the sun dried fruits were ground in an electrically operated grinder to fine particle size. Extraction and isolation were performed according to the method described by Lambein et al. (1993).Thin layer chromatography was carried out on glass plates coated with silica gel G type 60. The different column chromatographic fractions of ethanolic extract were analyzed with the help of thin layer chromatographic technique.

Source of Information: J. Bangladesh Agril. Univ. 11(1): 11–16, 2013, ISSN 1810-3030

Article Link (Online Journal):

Funding Source:

Total Budget (Tk.) :

Achievement/Findings:

IR spectroscopy provides a fast and effective way to identify functional groups present in a molecule by looking to absorption (bands) corresponding to the bond types present in the functional groups. A strong absorption band in the region around 1700 cm^-1 is due to the C=O stretching and the presence of this band indicates that the ketonic group (C=O) may be present in the compound. Compound A₂ showed absorption at 1699 cm^-1 which indicating the presence of ketonic (C=O) group. An ether group (methylene ether, –O–CH₂–O–) is distinctly clear from the strong band at 1230 cm^-1 where as the experimental data found at 1253 cm^-1 and 1134 cm^-1 for symmetric and asymmetric stretching of the same ether group respectively. Every type of proton has only a limited range of d-values over which it gives resonance. Hence the numerical value in d-units of the chemical shift for a proton gives a clue as to the type of proton originating the signal. Actually this shift is intermediate. The chemical shift of these protons is variable, depending not only on the chemical environment, but also on concentration, temperature and solvent.

Knowledge Management: Journal