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 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.
Van Boven
M
M
Laboratory of Toxicology and Food Chemistry, Katholieke Universiteit Leuven, Van Evenstraat 4, Belgium. maurits.vanboven@pharm.kuleuven.ac.be
Laga
M
M
Leonard
S
S
Busson
R
R
Holser
R
R
Decuypere
E
E
Flo
G
G
Lievens
S
S
Cokelaere
M
M
D000097:Acetonitriles / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003510:Cyclohexanes; D004355:Drug Stability; D005947:Glucose / Q000032:analysis / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry*; D006207:Half-Life; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry*; D008745:Methylation; D012639:Seeds / Q000737:chemistry*; D012972:Sodium Hydroxide / Q000494:pharmacology*
D000097:Acetonitriles; D003510:Cyclohexanes; D005960:Glucosides; D012972:Sodium Hydroxide; D005947:Glucose; C089377:simmondsin