Mechanism of simmondsin decomposition during sodium hydroxide treatment

Mechanism of simmondsin decomposition during sodium hydroxide treatment

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 fu...

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Veröffentlicht in:Journal of Agricultural and Food Chemistry 2003-02, Vol.51 (5), p.1260-4
Hauptverfasser: Van Boven, Maurits, Laga, M, Leonard, Stefanie, Busson, Roger, Holser, R, Decuypere, Eddy, Flo, Gerda, Lievens, Sylvia, Cokelaere, Marnix
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container_end_page 4
container_issue 5
container_start_page 1260
container_title Journal of Agricultural and Food Chemistry
container_volume 51
creator Van Boven, Maurits
Laga, M
Leonard, Stefanie
Busson, Roger
Holser, R
Decuypere, Eddy
Flo, Gerda
Lievens, Sylvia
Cokelaere, Marnix
description 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.
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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. 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title Mechanism of simmondsin decomposition during sodium hydroxide treatment
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