Once called Wulzen factor in the mid-20th century, stigmasterol was discovered by the University of California physiologist Rosalind 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 by Percy Lavon Julian for industrial large-scale manufacture of semisyntheticprogesterone,[8][9][10] 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.[11]
The Upjohn company used stigmasterol as the starting raw material for commercial synthesis of cortisone in 1959.[12][13]
Research
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 blood LDL 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]
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.[15][16][17]
^ abcdFerrer A, Altabella T, Arró M, Boronat A (July 2017). "Emerging roles for conjugated sterols in plants". Progress in Lipid Research. 67: 27–37. doi:10.1016/j.plipres.2017.06.002. PMID 28666916.
^ abCabral CE, Klein MR (November 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. PMC5729784. PMID 29267628.
^"Rosalind Wulzen (b. 1886)". Archives, Manuscripts and Photographs catalog. Smithsonian Institution. Retrieved 14 October 2015.
^Siddiqui S, Siddiqui BS, Adil Q, Begum S (1990). "Constituents of Mirabilis jalapa". Fitoterapia. 61 (5): 471.
^Han JH, Yang YX, Feng MY (December 2008). "Contents of phytosterols in vegetables and fruits commonly consumed in China". Biomedical and Environmental Sciences. 21 (6): 449–53. 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 (October 1977). "A convenient synthesis of progesterone from stigmasterol". The Journal of Organic Chemistry. 42 (22): 3633–4. doi:10.1021/jo00442a044. PMID 915584.
^"Nova Transcripts: Forgotten Genius". PBS.org. 6 February 2007.
^. lipidlibrary.aocs.org. Archived from the original on 15 April 2012.
^Kametani T, Furuyama H (1987). "Synthesis of vitamin D3 and related compounds". Medicinal Research Reviews. 7 (2): 147–71. doi:10.1002/med.2610070202. PMID 3033409. S2CID 20538461.
^Hogg JA (December 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. S2CID 21779154.
^Soy Infocenter (2009). History of Soybean and Soyfoods in Mexico and Central America (1877-2009). ISBN9781928914211.
^Kangsamaksin T, Chaithongyot S, Wootthichairangsan C, Hanchaina R, Tangshewinsirikul C, Svasti J (12 December 2017). Ahmad A (ed.). "Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor-α". PLOS ONE. 12 (12): e0189628. Bibcode:2017PLoSO..1289628K. doi:10.1371/journal.pone.0189628. PMC5726636. PMID 29232409.
^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. PMID 17844992.
^Ros MM, Sterk SS, Verhagen H, Stalenhoef AF, de Jong N (July 2007). "Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted" (PDF). Food Additives and Contaminants. 24 (7): 679–84. doi:10.1080/02652030701216727. PMID 17613052. S2CID 38614535.
^Draisci R, Merlanti R, Ferretti G, Fantozzi L, Ferranti C, Capolongo F, Segato S, Montesissa C (March 2007). "Excretion profile of boldenone in urine of veal calves fed two different milk replacers". Analytica Chimica Acta. 586 (1–2): 171–6. doi:10.1016/j.aca.2007.01.026. PMID 17386709.
January 20, 2023
stigmasterol, plant, sterol, phytosterol, among, most, abundant, plant, sterols, having, major, function, maintain, structure, physiology, cell, membranes, european, union, food, additive, listed, with, number, e499, used, food, manufacturing, increase, phytos. 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 2 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 3 Stigmasterol NamesIUPAC name Stigmasta 5 22 dien 3b olPreferred IUPAC name 1R 3aS 3bS 7S 9aR 9bS 11aR 1 2R 3E 5S 5 Ethyl 6 methylhept 3 en 2 yl 9a 11a dimethyl 2 3 3a 3b 4 6 7 8 9 9a 9b 10 11 11a tetradecahydro 1H cyclopenta a phenanthren 7 olOther names Stigmasterin Wulzen anti stiffness factorIdentifiersCAS Number 83 48 7 Y3D model JSmol Interactive imageChEBI CHEBI 28824 NChEMBL ChEMBL400247 YChemSpider 4444352 YECHA InfoCard 100 001 348PubChem CID 5280794UNII 99WUK5D0Y8 YInChI InChI 1S C29H48O c1 7 21 19 2 3 9 8 20 4 25 12 13 26 24 11 10 22 18 23 30 14 16 28 22 5 27 24 15 17 29 25 26 6 h8 10 19 21 23 27 30H 7 11 18H2 1 6H3 b9 8 t20 21 23 24 25 26 27 28 29 m1 s1 YKey HCXVJBMSMIARIN PHZDYDNGSA N YInChI 1 C29H48O c1 7 21 19 2 3 9 8 20 4 25 12 13 26 24 11 10 22 18 23 30 14 16 28 22 5 27 24 15 17 29 25 26 6 h8 10 19 21 23 27 30H 7 11 18H2 1 6H3 b9 8 t20 21 23 24 25 26 27 28 29 m1 s1Key HCXVJBMSMIARIN PHZDYDNGBLSMILES CCC C CC C C1CCC2C1 CCC3C2CC C4C3 CCC C4 O C C C C CPropertiesChemical formula C 29H 48OMolar mass 412 702 g mol 1Appearance White solid 1 Melting point 160 to 164 C 320 to 327 F 433 to 437 K 1 Solubility in water InsolubleExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Discovery 2 Natural occurrences 3 Uses 4 Research 5 Potential precursor of boldenone 6 See also 7 ReferencesDiscovery EditOnce called Wulzen factor in the mid 20th century stigmasterol was discovered by the University of California physiologist Rosalind Wulzen born 1886 4 Natural occurrences EditStigmasterol is an unsaturated phytosterol occurring in the plant fats or oils of numerous plants 2 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 5 Stigmasterol is a constituent of various vegetables legumes nuts seeds and unpasteurized milk Pasteurization will inactivate stigmasterol Edible oils contains higher amount than vegetables 6 Uses EditStigmasterol is a food additive in manufactured food products in the United Kingdom and European Union 7 It was introduced as a precursor by Percy Lavon Julian for industrial large scale manufacture of semisynthetic progesterone 8 9 10 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 11 The Upjohn company used stigmasterol as the starting raw material for commercial synthesis of cortisone in 1959 12 13 Research EditAs 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 blood LDL 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 Potential precursor of boldenone EditBeing 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 15 16 17 See also EditCharantin a stigmasteryl glucoside found in the bitter melon plant Stigmastanol a closely related phytosterol Sitosterol a commonly occurring phytosterolReferences Edit a b Stigmasterol ChemicalLand21 com a b c d Ferrer A Altabella T Arro M Boronat A July 2017 Emerging roles for conjugated sterols in plants Progress in Lipid Research 67 27 37 doi 10 1016 j plipres 2017 06 002 PMID 28666916 a b Cabral CE Klein MR November 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 PMC 5729784 PMID 29267628 Rosalind Wulzen b 1886 Archives Manuscripts and Photographs catalog Smithsonian Institution Retrieved 14 October 2015 Siddiqui S Siddiqui BS Adil Q Begum S 1990 Constituents of Mirabilis jalapa Fitoterapia 61 5 471 Han JH Yang YX Feng MY December 2008 Contents of phytosterols in vegetables and fruits commonly consumed in China Biomedical and Environmental Sciences 21 6 449 53 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 October 1977 A convenient synthesis of progesterone from stigmasterol The Journal of Organic Chemistry 42 22 3633 4 doi 10 1021 jo00442a044 PMID 915584 Nova Transcripts Forgotten Genius PBS org 6 February 2007 Giants of the Past lipidlibrary aocs org Archived from the original on 15 April 2012 Kametani T Furuyama H 1987 Synthesis of vitamin D3 and related compounds Medicinal Research Reviews 7 2 147 71 doi 10 1002 med 2610070202 PMID 3033409 S2CID 20538461 Hogg JA December 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 S2CID 21779154 Soy Infocenter 2009 History of Soybean and Soyfoods in Mexico and Central America 1877 2009 ISBN 9781928914211 Kangsamaksin T Chaithongyot S Wootthichairangsan C Hanchaina R Tangshewinsirikul C Svasti J 12 December 2017 Ahmad A ed Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor a PLOS ONE 12 12 e0189628 Bibcode 2017PLoSO 1289628K doi 10 1371 journal pone 0189628 PMC 5726636 PMID 29232409 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 PMID 17844992 Ros MM Sterk SS Verhagen H Stalenhoef AF de Jong N July 2007 Phytosterol consumption and the anabolic steroid boldenone in humans a hypothesis piloted PDF Food Additives and Contaminants 24 7 679 84 doi 10 1080 02652030701216727 PMID 17613052 S2CID 38614535 Draisci R Merlanti R Ferretti G Fantozzi L Ferranti C Capolongo F Segato S Montesissa C March 2007 Excretion profile of boldenone in urine of veal calves fed two different milk replacers Analytica Chimica Acta 586 1 2 171 6 doi 10 1016 j aca 2007 01 026 PMID 17386709 Retrieved from https en wikipedia org w index php title Stigmasterol amp oldid 1085893785, wikipedia, wiki, book, books, library,
