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Abstract

Although the structure of phytosterols is closely related to cholesterol, there is a gap in knowledge concerning the formation and occurrence of oxidation products from phytosterols. The main objective of this study was to isolate and characterize some side-chain oxidation products formed after autoxidation of stigmasterol. Another objective was to highlight the difficulties in the analysis of phytosterol and a mixture of their oxidation products by GC. Pure stigmasterol was oxidized at 120degreesC for 72 h in an air-ventilated oven. Preparative TLC separated the oxidation products, and the products were characterized with GC-MS and NMR. In addition to the common ring-structure oxidation compounds, three semipolar oxidation products-24-ethylcholest-5,22-dien-3beta,25-diol, 24-ethylcholest-5,22-dien-3beta,24-diol, and 24-ethyl-5,22-choladien-3beta-ol-24-one-were characterized for the first time by TLC, GC-MS, and NMR. Moreover, the results of the analysis of a large number of oxidation products from sitosterol, campesterol, and stigmasterol by capillary column GC indicated that further efforts and optimization are required in this area.

Keywords

autoxidation; campesterol; GC-MS; NMR; phytosterol oxidation product; sitosterol; stigmasterol; TLC

Published in

Journal of the American Oil Chemists' Society
2003, volume: 80, number: 8, pages: 777-783
Publisher: AMER OIL CHEMISTS SOC A O C S PRESS

SLU Authors

UKÄ Subject classification

Organic Chemistry

Publication identifier

  • DOI: https://doi.org/10.1007/s11746-003-0771-4

Permanent link to this page (URI)

https://res.slu.se/id/publ/602