Stigmasterin; Wulzen anti-stiffness factor
3D model (JSmol)
|Molar mass||g·mol−1 412.702|
|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 – a plant sterol (phytosterol) – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes. In the European Union, it is a food additive listed with E number E499, and may be used in food manufacturing to increase the phytosterol content, potentially lowering the levels of LDL cholesterol.
Stigmasterol is an unsaturated phytosterol occurring in the plant fats or oils of numerous plants, such as soybean, calabar bean, and rape seed, and in herbs used in herbalism practices, including the Chinese herbs Ophiopogon japonicus (Mai men dong), in Mirabilis jalapa.
Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union. It is 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.
As one of the major phytosterols, stigmasterol is included among sterol compounds in the diet having potential to reduce the risk of cardiovascular diseases. Consumption of 2 grams per day of plant sterols is associated with a reduction in blood LDL cholesterol of 8-10%, possibly lowering cardiovascular disease risk. 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.
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
- Stigmasterol, ChemicalLand21.com
- Ferrer, Albert; Altabella, Teresa; Arró, Montserrat; Boronat, Albert (2017). “Emerging roles for conjugated sterols in plants (Review)”. Progress in Lipid Research. 67: 27–37. doi:10.1016/j.plipres.2017.06.002. ISSN 0163-7827. PMID 28666916.
- Cabral, Carlos Eduardo; Klein, Márcia Regina Simas Torres (2017). “Phytosterols in the treatment of hypercholesterolemia and prevention of cardiovascular diseases”. Arquivos Brasileiros de Cardiologia. 109 (5): 475–482. doi:10.5935/abc.20170158. ISSN 0066-782X. PMC 5729784. PMID 29267628.
- “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. doi:10.1016/S0895-3988(09)60001-5. PMID 19263798.
- “EU-approved additives and E Numbers”. Food Standards Agency, UK. 1 March 2018. Retrieved 21 February 2019.
- Sundararaman P, Djerassi C (1977). “A convenient synthesis of progesterone from stigmasterol”. J Org Chem. 42 (22): 3633–3634. doi:10.1021/jo00442a044. PMID 915584.
- “Nova Transcripts: Forgotten Genius”. PBS.org. February 6, 2007.
- “Giants of the Past”. lipidlibrary.aocs.org. Archived from the original on 2012-04-15.
- Kametani T, Furuyama H (1987). “Synthesis of vitamin D3 and related compounds”. Med Res Rev. 7 (2): 147–171. doi:10.1002/med.2610070202. PMID 3033409.
- Hogg, John A. (1992). “Steroids, the steroid community, and Upjohn in perspective: A profile of innovation”. Steroids. 57 (12): 593–616. doi:10.1016/0039-128X(92)90013-Y. PMID 1481225.
- Soy Infocenter (2009). History of Soybean and Soyfoods in Mexico and Central America (1877-2009). ISBN 9781928914211.
- G. Gallina; G. Ferretti; R. Merlanti; C. Civitareale; F. Capolongo; R. Draisci; 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. doi:10.1021/jf071097c. PMID 17844992.
- 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. doi:10.1080/02652030701216727. PMID 17613052.
- 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. doi:10.1016/j.aca.2007.01.026. PMID 17386709.