Isolation and characterization of an aliphatic saturated ester from Ipomoea carnea leaves

Chemistry of Natural Compounds
2012.0

Abstract

India has a rich traditional background in herbal medicines. Ipomoea carnea belongs to the family Convolvulaceae, is native to South America, occurs in tropical areas worldwide, and is abundant in India with uses such as biogas production, pulp for the paper industry, and synergistic effect with insecticides against malarial vectors. Compound 1 was isolated from an ethyl acetate extract of air shade-dried and pulverized I. carnea leaves using a Soxhlet extractor. Broad fractionation was performed via column chromatography, and Compound 1 was isolated from the n-hexane–ethyl acetate (9.5:0.5) fraction, then purified by repeated crystallization. Its structure was determined by spectral methods (mass spectrum, IR, PMR, 13C NMR, COSY) as octadecanoic acid eicosyl ester (eicosyl stearate), which was isolated for the first time from this plant source. Compound 1 is a white amorphous solid with a melting point of 132°C, molecular formula C38H76O2, and characteristic spectral data: mass spectrum showing [M + 1]+ at m/z 565 amu and base peak at m/z 267 amu; IR spectrum with peaks at 1747 (ester carbonyl), 1140, 849 cm–1; PMR spectrum with signals at 0.87 (6H, t, CH3-18, 20), 1.25 (62H, m, methylenes), 1.60 (4H, m, CH2-3, 2), 2.28 (2H, t, CH2-2), 4.05 (2H, t, CH2-1); 13C NMR spectrum with signals at 168 (C-1), 64.43 (C-1), 34.44 (C-2), 26.71 to 30.19 (middle methylenes), and 14.20 (C-18 and C-20). This compound was isolated for the first time from I. carnea.

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