Stigmasterin; Wulzen anti-stiffness factor
3D model (JSmol)
|Molar mass||412.70 g·mol−1|
|Melting point||160 to 164 °C (320 to 327 °F; 433 to 437 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Stigmasterol (also known as Wulzen anti-stiffness factor) is a plant sterol, or phytosterol.
Stigmasterol is an unsaturated phytosterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong), in Mirabilis jalapa and American Ginseng.
Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. Pasteurization will inactivate stigmasterol. Edible oils contains higher amount than vegetables. Phytosterols normally are broken down in the bile.
Stigmasterol has been identified as a precursor suitable for the manufacture of semisynthetic progesterone, a valuable human hormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D3.
Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate, breast, and colon cancers. Studies have also indicated that a diet high in phytoesterols may inhibit the absorption of cholesterol and lower serum cholesterol levels by competing for intestinal absorption. Studies with laboratory animals fed stigmasterol found that both cholesterol and sitosterol absorption decreased 23% and 30%, respectively, over a 6-week period. It also possesses potent antioxidant, hypoglycemic and thyroid inhibiting properties.
Potential precursor of boldenone
Being a steroid, stigmasterol is precursor of anabolic steroid boldenone. 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.
- Charantin, a stigmasteryl glucoside found in the bitter melon plant.
- Stigmastanol, a closely related phytosterol
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