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A new hydrolysis technique for steroid glycoalkaloids with unstable aglycones from Solanum spp.
Author(s) -
Van Gelder Wim M. J.
Publication year - 1984
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.2740350503
Subject(s) - chemistry , aglycone , hydrolysis , glycoalkaloid , solasodine , chromatography , glycoside , steroid , acid hydrolysis , organic chemistry , solvolysis , biochemistry , solanum , botany , solanaceae , hormone , biology , gene
The acid hydrolysis of different types of Solanum steroid (glyco)alkaloids, solanine, solanidine, solasodine, demissine and tomatine was studied with various reaction times and acid concentrations. Recovery of aglycone varied considerably; in particular, the aglycones of solanine and tomatine were unstable, even under mild conditions. None of the procedures was suitable for the simultaneous hydrolysis of the different types of glycoalkaloids. A new hydrolysis technique was developed, using a two‐phase system. This system consisted of an aqueous acid phase, in which the substrate was hydrolysed, and an immiscible organic liquid phase. This apolar organic liquid served as a protective phase for the unstable apolar aglycones. The recoveries of the two‐phase hydrolyses were near 100%, regardless of the type and purity (presence or absence of tuber extracts) of glycoalkaloid. Varying the organic phase caused a controllable change in liquid‐liquid partition of glycoalkaloids, aglycones and dehydrated derivatives, allowing the quantitative formation of the desired hydrolysis product. This new hydrolysis technique will improve the current methods of estimating total glycoalkaloids in Solanum spp. The applicability of this technique in estimating cardiac glycosides and for the production of raw steroid material for the pharmaceutical industry is discussed.