Abstract

EXTRACTION, ISOLATION AND ANALYTICAL CHARACTERISATION OF AEGELINE ENANTIOMERS FROM AEGLE MARMELOS

Sindhu Jose*, Dr. V. Ragunathan, Thangakumar Arunachalam, Milesh Joseph, Satish Madipatti

Abstract

Aegeline or N-[2-hydroxy-2(4-methoxyphenyl)-ethyl]-3-phenyl-2-propenamide is a main alkaloid isolated from the leaves of Aeglemarmelos (bael). The plant is extensively used in the Indian traditionalsystem of medicine viz. Ayurveda . It soothes impaired kapha, vata,body pain, poison, diarrhea, dysentery, vomiting and intermittent fever.Its leaves are known as a cure for asthma, inflammation, cough anddiabetes. The leaves are trifoliate and aromatic. They have a shape,intermediate between ovate and lanceolate with reticulate pinnatevenation. The present work was undertaken to provide an easy andreliable method for the extraction and isolation of Aegeline (N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenyl-2-propenamide) usinghigh performance liquid chromatography (HPLC). The study alsoincluded the separation of the two enantiomers of Aegeline using chiralHPLC, its crystallographic structure, activity of the two enantiomers on cervical cancer and anuclear magnetic resonance (NMR) method for the enantiomeric purity determination ofcollected fractions. Linear calibration curves were obtained over the range of 0.7 – 5mM forenantiomer-2 (R2 = 0.998). This study was undertaken with the intention to develop a fast andreliable method for the enantiomeric purity determination of Aegeline and relatedcompounds.

Keywords: Aegle marmelos, Chiral HPLC, crystallography, NMR.