Once calledWulzen factor in the mid-20th century, stigmasterol was discovered by the University of California physiologistRosalind Wulzen (born 1886).[4]
Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union.[7]
It was introduced as a precursor byPercy Lavon Julian for industrial large-scale manufacture ofsemisyntheticprogesterone,[8][9][10] a valuable humanhormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related toestrogen effects, as well as acting as an intermediate in the biosynthesis ofandrogens, estrogens, andcorticoids. It is also used as the precursor ofvitamin D3.[11]
TheUpjohn company used stigmasterol as the starting raw material for commercial synthesis ofcortisone in 1959.[12][13]
As one of the major phytosterols, stigmasterol is included among sterol compounds in the diet having potential to reduce the risk of cardiovascular diseases.[2] Consumption of 2 grams per day of plant sterols is associated with a reduction in bloodLDL cholesterol of 8–10%, possibly lowering cardiovascular disease risk.[3] As a factor in cellular processes of plants, stigmasterol may have roles in plant stress responses, metabolism, and enzymes involved in biosynthesis of plant cell membranes.[2] Stigmasterol has also been shown to exert anti-angiogenic and anti-cancer effects via the downregulation of TNF-alpha and VEGFR-2.[14]
Being a steroid, stigmasterol is precursor of anabolic steroidboldenone.Boldenone undecylenate is commonly used in veterinary medicine to induce growth in cattle, but it is also one of the most commonly abused anabolic steroids in sports. This led to suspicion that some athletes testing positive for boldenone didn't consume the steroid itself, but rather consumed foods rich in stigmasterol; this turned out not to be the case.[15][16][17]
^Sundararaman P, Djerassi C (October 1977). "A convenient synthesis of progesterone from stigmasterol".The Journal of Organic Chemistry.42 (22):3633–4.doi:10.1021/jo00442a044.PMID915584.
^Gallina G, Ferretti G, Merlanti R, Civitareale C, Capolongo F, Draisci R, Montesissa C (October 2007). "Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites".Journal of Agricultural and Food Chemistry.55 (20):8275–83.doi:10.1021/jf071097c.PMID17844992.
