| Ursolic acid | |
|---|---|
 |
|
| 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]
|
| Other names | Prunol, Malol, beta-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966, 3-beta-hydroxyurs-12-en-28-oic acid[1] |
| Identifiers | |
| CAS number | 77-52-1  |
| PubChem | 64945 |
| SMILES |
CC1CCC2(CCC3(C(=CCC4C3(CCC5C4 (CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O[1]
|
| Properties | |
| Molecular formula | C30H48O3[1] |
| Molar mass | 456.70 g/mol[1] |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
Ursolic acid is a pentacyclic triterpene acid, used in cosmetics,[2] that is also capable of inhibiting various types of cancer cells by inhibiting the STAT3 activation pathway[3][4] and human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9 by acting through the glucocorticoid receptor. As medicine, it is well tolerated and can be used topically and orally.[citation needed]
Ursolic acid is present in many plants, including apples, basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, prunes. Apple peels contain high quantity of ursolic acid and related compounds which are responsible for the anti-cancer activity of apple. Ursolic acid can also serve as a starting material for synthesis of more potent bioactive derivatives, such as anti-tumor agents.[5]
Other names for ursolic acid include 3-β-hydroxy-urs-12-en-28-oic acid, urson, prunol, and malol.
See also
References
- ^ a b c d e "CID 64945 -- PubChem Compound Summary". pubchem.ncbi.nlm.nih.gov. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=64945. Retrieved 2008-03-14.
- ^ Ursolic acid at sabinsa.com
- ^ Shishodia S, Majumdar S, Banerjee S, Aggarwal BB (2003). "Ursolic acid inhibits nuclear factor-kappaB activation induced by carcinogenic agents through suppression of IkappaBalpha kinase and p65 phosphorylation: correlation with down-regulation of cyclooxygenase 2, matrix metalloproteinase 9, and cyclin D1". Cancer Res. 63 (15): 4375–83. PMID 12907607.
- ^ Pathak AK, Bhutani M, Nair AS, et al. (2007). "Ursolic acid inhibits STAT3 activation pathway leading to suppression of proliferation and chemosensitization of human multiple myeloma cells". Mol. Cancer Res. 5 (9): 943–55. doi:. PMID 17855663.
- ^ Ma CM, Cai SQ, Cui JR, Wang RQ, Tu PF, Hattori M. Daneshtalab, M (2005). "The cytotoxic activity of ursolic acid derivatives". Eur. J. Med. Chem 40: 582–589. doi:.
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