MOLECULE

Stigmast-4-en-3-one

Stigmast-4-en-3-one belongs to the class of organic compounds known as stigmastanes and derivatives. These are steroid-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. Stigmast-4-en-3-one is a naturally occurring phytosterol found in plants. Phytosterols consist of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits (PMID: 28702423). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423). They may also have a role in cancer prevention and treatment (PMID: 26086253). Stigmast-4-en-3-one is one of several phytosterols found in cannabis plants (PMID: 6991645).