Semi-synthetic Derivatives of Limonin A: Synthesis Using Basic Hydrolysis and Reduction with NaBH4

Abstract

Abstract Limonin A (L-A) was obtained from seeds of Citrus sinensis that were dried, grounded, and extracted using Soxhlet equipment. Initially, 100% hexane was used to eliminate fats, and finally, 100% dichloromethane was used in order to concentrate and isolate the compound. L-A recrystallization was performed using acetic acid. The purified fraction was identified as limonin according to spectral nuclear magnetic resonance (NMR) data. Two reactions were performed from L-A: Basic hydrolysis that acted on the A' lactone ring producing a sodium salt of the lactone, and reduction with NaBH 4 to reduce the carbonyl of carbon C-7 and generate the corresponding alcohol limonol. The structural modification of abundant secondary metabolites can become a source of new products with biological activity, useful in the pharmaceutical, cosmetic, and agrochemical industries of natural origin.

Keywords

• limonin, semisynthetic derivates, bioactive compounds, non-timber forest products.