Stigmasterol
| Stigmasterol | |
|---|---|
 |
|
|
(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  |
| PubChem | 5280794 |
| ChemSpider | 4444352 |
| UNII | 99WUK5D0Y8 |
| ChEBI | CHEBI:28824  |
| ChEMBL | CHEMBL400247 |
| Jmol-3D images | Image 1 |
|
|
|
|
| Properties | |
| Molecular formula | C29H48O |
| Molar mass | 412.69 g/mol |
| Boiling point |
160−164 °C |
| Solubility in water | Insoluble |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
Stigmasterol (also known as Wulzen anti-stiffness factor) is one of a group of plant sterols, or phytosterols, that include beta-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.
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) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. Pasteurization will inactivate stigmasterol. Edible oils contains higher amount than vegetables.[1]
Stigmasterol is used as a precursor in the manufacture of synthetic 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.[2] It is also used as the precursor of vitamin D3.[3]
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.[4] It also possesses potent antioxidant, hypoglycemic and thyroid inhibiting properties.[5]
Phytosterols normally are broken down in the bile.
[edit] See also
- Charantin, a stigmasteryl glucoside found in the bitter melon plant.
- Stigmastanol, a closely related phytosterol
[edit] References
- ^ 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.
- ^ Sundararaman P, Djerassi C. (1977). "A convenient synthesis of progesterone from stigmasterol". J Org Chem. 42 (22): 3633–3634. PMID 915584.
- ^ Kametani T, Furuyama H. (1987). "Synthesis of vitamin D3 and related compounds". Med Res Rev. 7 (2): 147–171. PMID 3033409.
- ^ 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.
- ^ 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.
[edit] External links
- Chemical Land
- Jieliang Extract Co., Ltd.
- top200foodsources
- U.S. Department of Agriculture, Agricultural Research Service
|
|||||
