AI Article Synopsis
- Jojoba seed meal contains simmondsin, which helps suppress appetite, but this effect is lost when treated with sodium hydroxide.
- Researchers studied how sodium hydroxide affects simmondsin over time, discovering that it has a half-life of about 60 minutes, leading to the formation of d-glucose and another compound.
- By isolating and analyzing intermediates like isosimmondsin and a lactone derivative using techniques like chromatography and spectroscopy, the team clarified the mechanism behind simmondsin's inactivation.
Article 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.
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| http://dx.doi.org/10.1021/jf025812o | DOI Listing |
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