Ursolic acid

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Ursolic acid
IUPAC name (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)- 10-hydroxy-1,2,6a,6b,9,9,12a-hept

amethyl-
2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-
tetradecahydro-1H-picene-4a-car boxylic acid[1]
Other names Prunol

Malol
Urson[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]
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

Ursolic acid is also known as Prunol, Malol, Urson, beta-Ursolic acid, NSC4060, CCRIS 7123, CHEBI:9908, TOS-BB-0966, and 3beta-Hydroxyurs-12-en-28-oic acid. As medicine it is well tolerated and can be used topically and orally.

Ursolic acid is present in many plants, including apples, basil, bilberries, cranberries, elder flower, peppermint, lavender, oregano, thyme, hawthorn, prunes.

[edit] See also

[edit] References

  1. ^ a b c d e CID 64945 -- PubChem Compound Summary. pubchem.ncbi.nlm.nih.gov. Retrieved on 2008-03-14.
  2. ^ Ursolic acid at sabinsa.com
  3. ^ 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. 
  4. ^ 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:10.1158/1541-7786.MCR-06-0348. PMID 17855663.