ABSTRACT
Nimbolide 1, a potent molecule of biological significance, was isolated. Attempts were made to cleave the ether linkage in nimbolide using boron trifluoride etherate in the presence of tetrabutyl ammonium bromide so as to generate a ring-opened structure akin to azadirachtins, which are known to possess excellent antifeedant properties. However, a novel rearranged product was envisaged during the course of the reaction, which was determined as isonimbolide 2-a structural isomer of nimbolide through spectroscopic methods.
Subject(s)
Limonins/chemistry , Phytotherapy , Plants, Medicinal , Humans , Magnetic Resonance SpectroscopyABSTRACT
Nimbolide [systematic name: (4alpha,5alpha,6alpha,7alpha,15beta,17alpha)-7,15:21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-18,24-dinor-11,12-secochola-2,13,20,22-tetraene-4,11-dicarboxylic acid gamma-lactone methyl ester], C27H30O7, was isolated from the leaves of Azadirachta indica, and its isomer, isonimbolide [systematic name: (4alpha,5alpha,6alpha,7alpha,15alpha)-7,15:21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-18,24-dinor-11,12-secochola-2,16,20,22-tetraene-4,11-dicarboxylic acid gamma-lactone methyl ester], was prepared from a novel rearrangement reaction of nimbolide, using boron trifluoride etherate and tetrabutylammonium bromide. The reaction conditions are probably responsible for the ether cleavage, double-bond rearrangement and reformation of the ether linkage. As a result, there are conformational changes in two cyclopentane rings and the side-chain -CH2COOMe group. In isonimbolide, an R(4)(4)(24) hydrogen-bond motif is observed.
