Isolation and characterization of dibutyl phthalate from leaves of Ipomoea carnea

Chemistry of Natural Compounds
2012.0

Abstract

Ipomoea carnea, a nonwoody plant belonging to the family Colvolvulaceae (commonly called Mahananda in Marathi) and a source of high-quality fibers, has been previously reported to exhibit antifungal activity (chloroform and methanol extracts against 11 pathogenic and nonpathogenic fungi), HIV type I reverse transcriptase inhibitory activity (water extract in combination with other extracts), and antimicrobial activity of metal complexes derived from its leaf proteins. In this study, the ethyl acetate extract of I. carnea leaves was tested for larvicidal activity against the 4th instar larvae of Aedes aegypti (a vector of Dengue fever) and Culex quinquifasciatus (a vector of filariasis), showing significant activity. Column chromatography using nonpolar n-hexane and polar ethanol as solvent systems was carried out to isolate molecules from the extract. The n-hexane fraction of the ethyl acetate extract yielded a crude product mixture, from which dibutyl phthalate (DBP), an aromatic ester, was isolated and purified by chromatographic techniques—this marks the first isolation of DBP from this plant source. DBP has previously been identified as a secondary metabolite in marine algae, bacteria, fungi, and various plants (including roots of Achyrathes bidentata, Rheum glabricaule, leaves of wheat cultivar "Mironovskaya 808", Alstonia scholaris, Torreya grandis, and the pericarp of Trichosanthes rosthornii). The isolated DBP is a colorless transparent liquid. Its structure was confirmed by: HPLC-LC-MS (molecular ion peak at m/z 279 in positive mode, corresponding to the molecular formula C₁₆H₂₂O₄); IR spectroscopy (peaks at 1728 cm⁻¹ for C=O and 1600/1579 cm⁻¹ for aromatic rings); ¹H NMR (500 MHz, CDCl₃) with signals for methyl (0.98 ppm, t, 6H), methylene (1.47 ppm, m, 4H; 1.74 ppm, m, 4H; 4.33 ppm, t, 4H), and aromatic protons (7.73 ppm, dd, 2H; 7.56 ppm, dd, 2H); ¹³C NMR (125 MHz, CDCl₃) for carbonyl (167.69 ppm, s), aromatic (132.35 ppm, s; 130.89 ppm, d; 128.84 ppm, d), and aliphatic carbons (13.70 ppm, q; 19.18 ppm, t; 30.59 ppm, t; 65.55 ppm, t); and saponification (new peaks of hydrolyzed products with decreased intensity of the molecular ion peak, confirmed by MS chromatograms of the hydrolyzed products).

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