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Ursolic acid

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Title: Ursolic acid  
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Ursolic acid

Ursolic acid
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
ChEBI  YesY
ChEMBL  YesY
Jmol-3D images Image 1
Properties
Molecular formula C30H48O3
Molar mass 456.70 g mol−1
Melting point 285-288 °C
Boiling point 556.89 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

Ursolic acid (sometimes referred to as urson, prunol, malol, or 3-beta-3-hydroxy-urs-12-ene-28-oic-acid), 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 can serve as a starting material for synthesis of more potent bioactive derivatives, such as antitumor agents.[6] It has been found to reduce muscle atrophy and to stimulate muscle growth in mice.[7][8] Ursolic acid has potential use as a cardioprotective compound.[9]

Ursolic acid was found to be a weak aromatase inhibitor (IC50 = 32 μM).[10]

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.[11] Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).[12]

Contents

  • Natural occurrences 1
    • Occurrences in food 1.1
  • See also 2
  • References 3

Natural occurrences

Ursolic acid is present in many plants, such as Mirabilis jalapa.[13]

Occurrences in food

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.[14]

See also

References

  1. ^ a b PubChem 64945
  2. ^ 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.   Full-text pdf
  3. ^ 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.  
  4. ^ 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
  5. ^ 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. 
  6. ^ 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.  
  7. ^ Kunkel, S. D.; Suneja, M.; Ebert, S. M.; Bongers, K. S.; Fox, D. K.; Malmberg, S. E.; Alipour, F.; Shields, R. K.; Adams, C. M. (2011). "MRNA Expression Signatures of Human Skeletal Muscle Atrophy Identify a Natural Compound that Increases Muscle Mass". Cell Metabolism 13 (6): 627–638.  
  8. ^ "Apple Ingredient Keeps Muscles Strong: Component of Apple Peels Found to Help Prevent Muscle Weakening in Mice". ScienceDaily, News, June 7, 2011, [1]
  9. ^ 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
  10. ^ 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.  
  11. ^ Kunkel, Steven D. (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.  
  12. ^ PMID 21923134
  13. ^ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
  14. ^ MacRae, Fiona. "An apple a day keeps the doctor away... as long as you eat the peel". Daily Mail (London). 
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