Ursolic acid
| Ursolic acid | |
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(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 | |
| CAS number | 77-52-1  |
| PubChem | 64945 |
| ChemSpider | 58472 |
| ChEBI | CHEBI:9908 |
| ChEMBL | CHEMBL169 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C30H48O3 |
| Molar mass | 456.70 g mol−1 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ursolic acid (sometimes referred to as 3-beta-3-hydroxy-urs-12-ene-28-oic-acid, 3-β-hydroxy-urs-12-en-28-oic acid, urson, prunol, or malol) is a pentacyclic triterpene acid, used in cosmetics that is also capable of inhibiting various cancer cell types by inhibiting the STAT3 activation pathway,[2][3] one of which includes human fibrosarcoma by reducing expression of matrix metalloproteinase-9 via glucocorticoid receptors. It may also decrease proliferation of cancer cells and induce apoptosis.[4] 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.[5] Ursolic acid is present in many plants, including 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.[6]
Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as antitumor 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]
Ursolic acid was found to be a weak aromatase inhibitor (IC50 = 32 μM).[11]
Ursolic acid 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.[12]
See also [edit]
References [edit]
- ^ a b PubChem 64945
- ^ 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. Full-text pdf
- ^ 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.
- ^ 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
- ^ Kaewthawee, Narawan; Brimson, Sirikalaya (February 2013). "THE EFFECTS OF URSOLIC ACID ON CYTOKINE PRODUCTION VIA THE MAPK PATHWAYS IN LEUKEMIC T-CELLS". EXCLI 12 (February): 102–114.
- ^ MacRae, Fiona. "An apple a day keeps the doctor away... as long as you eat the peel". Daily Mail (London).
- ^ 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.
- ^ 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.
- ^ "Apple Ingredient Keeps Muscles Strong: Component of Apple Peels Found to Help Prevent Muscle Weakening in Mice". ScienceDaily, News, June 7, 2011, [1]
- ^ 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
- ^ 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.
- ^ Kunkel SD, Elmore CJ, Bongers KS, Ebert SM, Fox DK, et al. (2012) Ursolic Acid Increases Skeletal Muscle and Brown Fat and Decreases Diet-Induced Obesity, Glucose Intolerance and Fatty Liver Disease. PLoS ONE 7(6): e39332. doi:10.1371/journal.pone.0039332
