Stigmasterin; Wulzen anti-stiffness factor
|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).
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Stigmasterol (also known as Wulzen anti-stiffness factor) is one of a group of plant sterols, or phytosterols, that include β-sitosterol, campesterol, brassicasterol, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol. Phytosterols are insoluble in water but soluble in most organic solvents and contain one alcohol functional group.
- Discovery 1
Natural occurrences 2
- Occurrences in food 2.1
- Uses 3
- Research 4
- Potential precursor of boldenone 5
- See also 6
- References 7
Wulzen factor, as it was first known, was discovered by University of California physiologist Rosalind Wulzen (born 1886).
Stigmasterol is an unsaturated plant sterol 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.
Occurrences in food
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 is used as a precursor in 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.
- Charantin, a stigmasteryl glucoside found in the bitter melon plant.
- Stigmastanol, a closely related phytosterol
- stigmasterol, ChemicalLand21.com
- "Rosalind Wulzen (b. 1886)". Archives, Manuscripts and Photographs catalog. Smithsonian Institution. Retrieved 14 October 2015.
- Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
- Han JH, Yang YX, Feng MY. (2008). "Contents of phytosterols in vegetables and fruits commonly consumed in China". Biomed Environ Sci. 21 (6): 449–453.
- Sundararaman P, Djerassi C. (1977). "A convenient synthesis of progesterone from stigmasterol". J Org Chem. 42 (22): 3633–3634.
- "Nova Transcripts: Forgotten Genius". PBS.org. February 6, 2007.
- "Giants of the Past". lipidlibrary.aocs.org.
- Kametani T, Furuyama H. (1987). "Synthesis of vitamin D3 and related compounds". Med Res Rev. 7 (2): 147–171.
- Hogg, John A. (1992). "Steroids, the steroid community, and Upjohn in perspective: A profile of innovation". Steroids 57 (12): 593–616.
- Soy Infocenter (2009). History of Soybean and Soyfoods in Mexico and Central America (1877-2009).
- Panda S, Jafri M, Kar A, Meheta BK. (2009). "Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma". Fitoterapia 80 (2): 123–126.
- G. Gallina, G. Ferretti, R. Merlanti, C. Civitareale, F. Capolongo, R. Draisci and C. Montesissa (2007). "Boldenone, Boldione, and Milk Replacers in the Diet of Veal Calves: The Effects of Phytosterol Content on the Urinary Excretion of Boldenone Metabolites". J. Agric. Food Chem. 55 (20): 8275–8283.
- Ros MM, Sterk SS, Verhagen H, Stalenhoef AF, de Jong N (2007). "Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted". Food Addit Contam. 24 (7): 679–684.
- R. Draisci, R. Merlanti, G. Ferretti, L. Fantozzi, C. Ferranti, F. Capolongo, S. Segato, C. Montesissa (2007). "Excretion profile of boldenone in urine of veal calves fed two different milk replacers". Analytica Chimica Acta 586 (1–2): 171–176.