solanidinebased

Solanidine-based compounds are chemical species that use solanidine as the aglycone—the non-sugar part of a glycoside. In plants of the Solanaceae family, solanidine serves as the core of major glycoalkaloids, such as α-solanine and α-chaconine, which are formed by attachment of sugar moieties to the solanidine skeleton. The term is used to describe both the aglycone itself and a range of glycoside derivatives.

Chemistry and occurrence: Solanidine is a steroidal alkaloid derived from cholesterol; glycosylation yields glycoalkaloids that occur in potatoes, tomatoes, eggplants, and other nightshades. The sugar portions commonly include solanose or chacotriose-like units, and the exact composition defines the name and properties of each compound.

Biology and safety: These compounds are biologically active and can bind to membrane cholesterol, disrupting membranes and, in higher concentrations, causing cell damage. In humans, consumption of solanidine-based glycoalkaloids from green or sprouted potatoes can cause nausea, vomiting, abdominal pain, and neurologic symptoms. Food safety guidelines emphasize avoiding elevated levels in tubers and careful handling to minimize sprouting and greening.

Research and applications: Some solanidine-based derivatives are studied as pharmaceutical scaffolds; researchers explore structure-activity relationships to separate therapeutic effects from toxicity and to improve solubility and selectivity. Because toxicity limits their direct use, most work focuses on controlled, pharmacological contexts or on developing safer synthetic analogs.