Structure Elucidation of a Glycosylated Benzyl Ester of Salicylic Acid from the North American Prairie Plant Oligoneuron rigidum

The organic extract from Oligoneuron rigidum displayed anti-microbial activity, indicating a potential future use as a natural food preservative. Three novel compounds were isolated from the active extract. The skeletal structure of the three compounds was determined by spectral methods, and the final structural component that remained to be determined was the locations of the acetate groups. Neutral permethylations were performed on the compounds as the first step in determining the locations of the acetate groups; however, the permethylation technique proved to be ineffective, causing cleavage of the native compounds. The structure elucidation will be complete when a non-degradable method of permethylation is established. Basic permethylation, followed by reductive cleavage and acetylation, confirmed the presence of the expected products: 1-acetyl-2-methylbenzene, a di-anhydro-tri-methoxy-D-arabitol, a dianhydro-tetra-methoxy-D-glucitol and a di-acetyl-di-anhydro-di-methoxy-glucitol.