Ursolic acid

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 Y
PubChem	64945
ChemSpider	58472 Y
ChEBI	CHEBI:9908 N
ChEMBL	CHEMBL169 Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)[C@@H](C)[C@H](C)CC5
InChI InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 Y Key: WCGUUGGRBIKTOS-GPOJBZKASA-N Y InChI=1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 Key: WCGUUGGRBIKTOS-GPOJBZKABB
Properties
Molecular formula	C30H48O3
Molar mass	456.7 g mol−1
N acid (verify) (what is: Y/N?) 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. It may also decrease proliferation of cancer cells and induce apoptosis.^[5]

Ursolic acid is present in many plants, including apples, basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, prunes. Apple peels contain large quantities of ursolic acid and related compounds.^[6]

Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as anti-tumor agents.^[7] It has been found to reduce muscle atrophy and to stimulate muscle growth in mice.^[8][9] Ursolic acid has potential use as a cardioprotective compound.^[10]

Usolic acid was found to be a weak aromatase inhibitor (IC₅₀ = 32 μm).^[11]

Other names for ursolic acid include, 3-beta-3-hydroxy-urs-12-ene-28-oic-acid, 3-β-hydroxy-urs-12-en-28-oic acid, urson, prunol, and malol.

See also

• Betulinic acid
• Moronic acid
• Oleanolic acid

References

1. ^ ^{a b} PubChem 64945
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. 
5. ^ 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
6. ^ http://www.dailymail.co.uk/health/article-2000392/Apple-peel-helps-build-muscle-control-weight.html
7. ^ 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 (6): 582–589. doi:10.1016/j.ejmech.2005.01.001. PMID 15922841. 
8. ^ Kunkel, S. D.; Suneja, M.; Ebert, S. M.; Bongers, K. S.; Fox, D. K.; Malmberg, S. E.; Alipour, F.; Shields, R. K. et al. (2011). "MRNA Expression Signatures of Human Skeletal Muscle Atrophy Identify a Natural Compound that Increases Muscle Mass". Cell Metabolism 13 (6): 627–638. doi:10.1016/j.cmet.2011.03.020. PMC 3120768. PMID 21641545. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3120768.  edit
9. ^ "Apple Ingredient Keeps Muscles Strong: Component of Apple Peels Found to Help Prevent Muscle Weakening in Mice". ScienceDaily, News, June 7, 2011, [1]
10. ^ 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
11. ^ Gnoatto, SC; Dassonville-Klimpt, A; Da Nascimento, S; Galéra, P; Boumediene, K; Gosmann, G; Sonnet, P; Moslemi, S (2008). "Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition". European journal of medicinal chemistry 43 (9): 1865–77. doi:10.1016/j.ejmech.2007.11.021. PMID 18192087.