:Stigmasterol

Once called Wulzen factor in the mid-20th century, stigmasterol was discovered by the University of California physiologist Rosalind Wulzen (born 1886).{{Cite web|url = http://siris-archives.si.edu/ipac20/ipac.jsp?&profile=all&source=~!siarchives&uri=full=3100001~!306595~!0#focus|title = Rosalind Wulzen (b. 1886)|access-date = 14 October 2015|website = Archives, Manuscripts and Photographs catalog|publisher = Smithsonian Institution}}

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.{{cite journal | vauthors = Siddiqui S, Siddiqui BS, Adil Q, Begum S | title = Constituents of Mirabilis jalapa | journal = Fitoterapia | date = 1990 | volume = 61 | issue = 5 | pages = 471 | url = http://www.cabdirect.org/abstracts/19910302341.html;jsessionid=196D9B7C532F29E40F2551F192CD3923 }}

Stigmasterol is a constituent of various vegetables, legumes, nuts, seeds, and unpasteurized milk. Pasteurization will inactivate stigmasterol. Edible oils contains higher amount than vegetables.{{cite journal | vauthors = Han JH, Yang YX, Feng MY | title = Contents of phytosterols in vegetables and fruits commonly consumed in China | journal = Biomedical and Environmental Sciences | volume = 21 | issue = 6 | pages = 449–53 | date = December 2008 | pmid = 19263798 | doi = 10.1016/S0895-3988(09)60001-5 | doi-access = | bibcode = 2008BioES..21..449H }}

Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union.{{cite web | title=EU-approved additives and E Numbers | website=Food Standards Agency, UK | url=https://www.food.gov.uk/business-guidance/eu-approved-additives-and-e-numbers |date=1 March 2018| access-date=21 February 2019}}

It was introduced as a precursor by Percy Lavon Julian for industrial large-scale manufacture of semisynthetic progesterone,{{cite journal | vauthors = Sundararaman P, Djerassi C | title = A convenient synthesis of progesterone from stigmasterol | journal = The Journal of Organic Chemistry | volume = 42 | issue = 22 | pages = 3633–4 | date = October 1977 | pmid = 915584 | doi = 10.1021/jo00442a044 }}{{cite web | url = https://www.pbs.org/wgbh/nova/transcripts/3402_julian.html | date = 6 February 2007 | title = Nova Transcripts: Forgotten Genius | publisher = PBS.org}}{{cite web | url = http://lipidlibrary.aocs.org/history/Julian/index.htm | title = Giants of the Past | publisher = lipidlibrary.aocs.org | url-status = dead | archive-url = https://web.archive.org/web/20120415001340/http://lipidlibrary.aocs.org/history/Julian/index.htm | archive-date = 15 April 2012 }} 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.{{cite journal | vauthors = Kametani T, Furuyama H | title = Synthesis of vitamin D3 and related compounds | journal = Medicinal Research Reviews | volume = 7 | issue = 2 | pages = 147–71 | year = 1987 | pmid = 3033409 | doi = 10.1002/med.2610070202 | s2cid = 20538461 }}

The Upjohn company used stigmasterol as the starting raw material for commercial synthesis of cortisone in 1959.{{cite journal | vauthors = Hogg JA | title = Steroids, the steroid community, and Upjohn in perspective: a profile of innovation | journal = Steroids | volume = 57 | issue = 12 | pages = 593–616 | date = December 1992 | pmid = 1481225 | doi = 10.1016/0039-128X(92)90013-Y | s2cid = 21779154 }}{{cite book | title = History of Soybean and Soyfoods in Mexico and Central America (1877-2009) | author = Soy Infocenter | url = https://books.google.com/books?id=MIcpYJgcnzoC&q=shurtleff+soybean+mexico+upjohn&pg=PA293 | isbn = 9781928914211 | year = 2009| publisher = Soyinfo Center }}

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. Stigmasterol has also been shown to exert anti-angiogenic and anti-cancer effects via the downregulation of TNF-alpha and VEGFR-2.{{cite journal | vauthors = Kangsamaksin T, Chaithongyot S, Wootthichairangsan C, Hanchaina R, Tangshewinsirikul C, Svasti J | title = Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor-α | journal = PLOS ONE | volume = 12 | issue = 12 | pages = e0189628 | date = 12 December 2017 | pmid = 29232409 | pmc = 5726636 | doi = 10.1371/journal.pone.0189628 | editor-first = Aamir | bibcode = 2017PLoSO..1289628K | editor-last = Ahmad | doi-access = free }}

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.{{cite journal | vauthors = Gallina G, Ferretti G, Merlanti R, Civitareale C, Capolongo F, Draisci R, Montesissa C | title = Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 20 | pages = 8275–83 | date = October 2007 | pmid = 17844992 | doi = 10.1021/jf071097c }}{{cite journal | vauthors = Ros MM, Sterk SS, Verhagen H, Stalenhoef AF, de Jong N | title = Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted | journal = Food Additives and Contaminants | volume = 24 | issue = 7 | pages = 679–84 | date = July 2007 | pmid = 17613052 | doi = 10.1080/02652030701216727 | s2cid = 38614535 | url = https://hal.archives-ouvertes.fr/hal-00577549/file/PEER_stage2_10.1080%252F02652030701216727.pdf }}{{cite journal | vauthors = Draisci R, Merlanti R, Ferretti G, Fantozzi L, Ferranti C, Capolongo F, Segato S, Montesissa C | title = Excretion profile of boldenone in urine of veal calves fed two different milk replacers | journal = Analytica Chimica Acta | volume = 586 | issue = 1–2 | pages = 171–6 | date = March 2007 | pmid = 17386709 | doi = 10.1016/j.aca.2007.01.026 | bibcode = 2007AcAC..586..171D }}

• Charantin, a stigmasteryl glucoside found in the bitter melon plant.
• Stigmastanol, a closely related phytosterol
• Sitosterol, a commonly occurring phytosterol

{{Reflist}}

{{Phytosterols}}

{{Cholesterol metabolism intermediates}}

Category:Phytosterols