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Title: Mechanism of simmondsin decomposition during sodium hydroxide treatment
Authors: Van Boven, Maurits ×
Laga, M
Leonard, Stefanie
Busson, Roger
Holser, R
Decuypere, Eddy
Flo, Gerda
Lievens, Sylvia
Cokelaere, Marnix #
Issue Date: Feb-2003
Series Title: Journal of Agricultural and Food Chemistry vol:51 issue:5 pages:1260-4
Abstract: Jojoba seed meal shows appetite-suppressing activity due to the presence of simmondsin. This pharmacological activity disappears with treatment of the meal with sodium hydroxide. To elucidate this mechanism of inactivation, the reaction of simmondsin in 1 N NaOH at 20 degrees C was monitored as a function of time. The end products of the reaction as well as intermediates were isolated and identified. The half-life of simmondsin was approximately 60 min with d-glucose and 2-hydroxy-3-methoxyphenylacetonitrile as reaction end products. The reaction mechanism could be elucidated by the isolation of isosimmondsin and a simmondsin lactone derivative. Those compounds were isolated and purified by a combination of column chromatography and HPLC and identified mainly by HRMS and NMR spectroscopy.
ISSN: 0021-8561
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Faculty of Medicine, Campus Kulak Kortrijk
Toxicology and Pharmacology
Practical Training, Faculty of Pharmaceutical Sciences
Medicinal Chemistry (Rega Institute)
Division of Livestock-Nutrition-Quality (-)
Interdisciplinary Research Facility Life Sciences, Campus Kulak Kortrijk
× corresponding author
# (joint) last author

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