Mechanism of Simmondsin Decomposition during Sodium Hydroxide Treatment

• Published in: Journal of agricultural and food chemistry Vol. 51; no. 5; pp. 1260 - 1264
• Main Authors: Van Boven, M, Laga, M, Leonard, S, Busson, R, Holser, R, Decuypere, E, Flo, G, Lievens, S, Cokelaere, M
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 26.02.2003
• Subjects: Acetonitriles - chemistry; Biological and medical sciences; Chromatography, High Pressure Liquid; Cyclohexanes; Drug Stability; Feed and pet food industries; Food industries; Fruit and vegetable industries; Fundamental and applied biological sciences. Psychology; Glucose - analysis; Glucose - chemistry; Glucosides - chemistry; Half-Life; Hydrogen-Ion Concentration; Magnetic Resonance Spectroscopy; Magnoliopsida - chemistry; Methylation; Seeds - chemistry; Sodium Hydroxide - pharmacology; Purification; Jojoba seed; Decomposition; Identification; Sodium hydroxide; permethylsimmondsin; jojoba seed meal; Buxaceae; simmondsin decomposition; Chemical treatment; Dicotyledones; Antinutrient factor; Angiospermae; Reaction mechanism; Isolation; Spermatophyta; isosimmondsin; Simmondsia chinensis; Oil plant (vegetal)
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf025812o

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 °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 ∼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. Keywords: Simmondsia chinensis; jojoba seed meal; simmondsin decomposition; isosimmondsin; permethylsimmondsin