Stigmasterol

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Stigmasterol
IUPAC name

(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

Other names

Stigmasterin; Wulzen anti-stiffness factor

Identifiers
CAS number 83-48-7 YesY
PubChem 5280794
ChemSpider 4444352 YesY
UNII 99WUK5D0Y8 YesY
ChEBI CHEBI:28824 N
ChEMBL CHEMBL400247 YesY
Jmol-3D images Image 1
Properties
Molecular formula C29H48O
Molar mass 412.69 g mol−1
Appearance White solid[1]
Melting point 160 to 164 °C; 320 to 327 °F; 433 to 437 K ([1])
Solubility in water Insoluble
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Stigmasterol (also known as Wulzen anti-stiffness factor) is one of a group of plant sterols, or phytosterols, that include β-sitosterol, campesterol, ergosterol (provitamin D2), 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.

Natural occurrences

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[2] 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.[3] Phytosterols normally are broken down in the bile.

Uses

Stigmasterol is used as a precursor in the manufacture of semisynthetic progesterone,[4][5][6] 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.[7]

The Upjohn company used stigmasterol as the starting raw material for the synthesis of cortisone.[8][9]

Research

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 was demonstrated that it inhibits several pro-inflammatory and matrix degradation mediators typically involved in osteoarthritis-induced cartilage degradation.[10] It also possesses potent antioxidant, hypoglycemic and thyroid inhibiting properties.[11]

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.[12][13][14]

See also

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

References

  1. ↑ 1.0 1.1 stigmasterol, ChemicalLand21.com
  2. ↑ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
  3. ↑ 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. 
  4. ↑ 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. 
  5. ↑ "Nova Transcripts: Forgotten Genious". PBS.org. February 6, 2007. 
  6. ↑ "Giants of the Past". lipidlibrary.aocs.org. 
  7. ↑ 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. 
  8. ↑ 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. 
  9. ↑ Soy Infocenter (2009). History of Soybean and Soyfoods in Mexico and Central America (1877-2009). ISBN 9781928914211. 
  10. ↑ Gabay O, Sanchez C, Salvat C, Chevy F, Breton M, Nourissat G, Wolf C, Jacques C, Berenbaum F. (2010). "Stigmasterol: a phytosterol with potential anti-osteoarthritic properties". Am J Clin Nutr. 18 (1): 106–116. doi:10.1016/j.joca.2009.08.019. PMID 19786147. 
  11. ↑ 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. doi:10.1016/j.fitote.2008.12.002. PMID 19105977. 
  12. ↑ 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. doi:10.1021/jf071097c. PMID 17844992. 
  13. ↑ 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. 
  14. ↑ 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. 
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