Ursolic acid
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| Names | |
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| IUPAC name
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid[1]
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| Other names
Prunol, Malol, beta-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966, 3-beta-hydroxyurs-12-en-28-oic acid[1]
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| Identifiers | |
77-52-1  |
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| ChEBI | CHEBI:9908 |
| ChEMBL | ChEMBL169 |
| ChemSpider | 58472 |
| Jmol 3D model | Interactive image |
| PubChem | 64945 |
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| Properties | |
| C30H48O3 | |
| Molar mass | 456.71 g·mol−1 |
| Melting point | 285 to 288 °C (545 to 550 °F; 558 to 561 K) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Ursolic acid (sometimes referred to as urson, prunol, malol, or 3-beta-3-hydroxy-urs-12-ene-28-oic-acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.[citation needed]
Natural occurrence
Ursolic acid is present in many plants, such as Mirabilis jalapa,[2] as well as in many fruits and herbs used in daily life (e.g. apples, basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, and prunes). Apple peels contain large quantities of ursolic acid and related compounds.[citation needed]
Potential biochemical effects
A number of potential biochemical effects of ursolic acid have been investigated, but there has been no clinical study demonstrating benefits to human health. In vitro, ursolic acid inhibits the proliferation of various cancer cell types by inhibiting the STAT3 activation pathway,[3][4] and may also decrease proliferation of cancer cells and induce apoptosis.[5] Ursolic acid has also been shown to inhibit JNK expression and IL-2 activation of JURKAT leukemic T Cells leading to the reduction in proliferation and T cell activation.[6] Ursolic acid is a weak aromatase inhibitor (IC50 = 32 μM)[7] and has been shown to increase the amount of muscle and brown fat and decrease white fat obesity and associated conditions when added to diets fed to mice.[8] Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).[9] It has been found to reduce muscle atrophy and to stimulate muscular growth in mice,[10] also shows a potential cardioprotection.[11]
Uses
Ursolic acid is used as a cosmetics additive.[citation needed] Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents.[12]
See also
References
- ↑ 1.0 1.1 CID 64945 from PubChem
- ↑ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Wang X, Zhang F, Yang L, Mei Y, Long H, Zhang X, Zhang J, Qimuge-Suyila , Su X.,"Ursolic acid inhibits proliferation and induces apoptosis of cancer cells in vitro and in vivo", J Biomed Biotechnol. 2011;2011:419343 Full-text pdf
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
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- ↑ Liobikas J, Majiene D, Trumbeckaite S, Kursvietiene L, Masteikova R, Kopustinskiene DM, Savickas A, Bernatoniene J.,"Uncoupling and antioxidant effects of ursolic acid in isolated rat heart mitochondria", J Nat Prod. 2011 Jul 22;74(7):1640-4
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
