Isolation and characterization of Maclura (Maclura pomifera) extracts obtained by supercritical fluid extraction

The chemical composition of the CO2 extract of Madura fruit (Osage orange) was analyzed. The major constituents of the CO2 extracts were triterpene alcohol esters, along with the triglycerides of C-16 and C-18 fatty acids. Column chromatography of the CO2 extract yielded lupeol ester of hexadecanoic acid (2), lupeol ester of 3-hydroxyhexadecanoic acid (beta-hydroxy palmitic acid) (3) trace of lupeol (1), butyrospermol ester of hexadecanoic acid (5), butyrospermol acetate (6) and trace of butyrospermol (4) as the least polar components. By consequent extraction with acetone of the lipid free Madura material an extract was obtained, in which isoflavonoids osajin (7) and pomiferin (8) (natural antioxidant) were found in high yields. The structure of isolated compounds was established by spectroscopic data (IR, H-1 and C-13 NMR and MS) and some chemical reactions. The 3 is new natural product, not yet described in literature. (C) 2015 Elsevier B.V. All rights reserved.