Isolation and Characterization of a Novel Tertiary Substituted Amine from the Leaves of Sarcophrynium brachystachys (Benth.) K Schum

http://www.doi.org/10.26538/tjnpr/v7i7.32

Abstract

Sarcophrynium brachyatachys, commonly known as Yoruba soft cane or the praying plant, is traditionally used for packaging food items. Only a few natives recognize the usefulness of the leaves for the treatment of cough and bronchitis in herbal medicine. This study was designed to isolate and characterize a bioactive component. Successful percolation was carried out with 96 percent ethanol to get the crude extract. Afterwards, fractionation was carried out using chloroform and distilled water in a ratio of 1:1. The chloroform fraction was further fractionated with methanol and n-hexane. Column chromatography was carried out on the methanol portion of
the extract with organic solvents of different polarities to isolate a pure compound, which was ascertained by thin layer chromatography. The isolated component was characterized based on FT-IR, 1H and 13C NMR spectra, DEPT-135, HSQC, COSY and mass spectrometry. FTIR spectrum revealed a weakly intense peak at 3100 cm-1, which is typical of aromatic C-H. The 1HNMR spectrum of showed the chemical shift of six member ring aromatic protons as doublets at 7.23 ppm (1H, d), 7.27 ppm (1H, d), and 7.32 ppm (1H, d). The methine tertiary amine proton signal was observed at 3.26 ppm. In the 13CNMR spectrum, the tertiary methine amine carbon was observed at 62.62 ppm, while the tertiary methyl amine carbon resonated at 56.87 ppm. The isolated compound was identified as a tertiary substituted amine with the name 5-(2-(secbutyl)phenoxy)-N-(1-ethoxypropyl)-6-(2-is buthyl-2,3-imetylcyclopropoxy)-N-methyldec-1-en-2-amine.