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Ursolic acid

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"Malol" redirects here. For the language, see Malol language.
Ursolic acid
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.941 Edit this at Wikidata
  • 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 checkY
    Key: WCGUUGGRBIKTOS-GPOJBZKASA-N checkY
  • 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
  • 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
Properties
C30H48O3
Molar mass 456.711 g·mol−1
Melting point 285 to 288 °C (545 to 550 °F; 558 to 561 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ursolic acid (sometimes referred to as urson, prunol, malol, or 3-beta-3-hydroxy-urs-12-ene-28-oic-acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.[citation needed]

Natural occurrence

Ursolic acid is present in many plants, such as Mirabilis jalapa,[2] as well as in many fruits and herbs used in daily life (e.g. 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.[citation needed]

Potential biochemical effects

A number of potential biochemical effects of ursolic acid have been investigated, but there has been no clinical study demonstrating benefits to human health. In vitro, ursolic acid inhibits the proliferation of various cancer cell types by inhibiting the STAT3 activation pathway,[3][4] and may also decrease proliferation of cancer cells and induce apoptosis.[5] 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.[6] Ursolic acid is a weak aromatase inhibitor (IC50 = 32 μM),[7] and 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.[8] Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).[9] It has been found to reduce muscle atrophy and to stimulate muscular growth in mice,[10] also shows a potential cardioprotection.[11]

Uses

Ursolic acid is used as a cosmetics additive.[citation needed] Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents.[12]

See also

References

  1. ^ a b CID 64945 from PubChem
  2. ^ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
  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" (PDF). 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. {{cite journal}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  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 Full-text pdf
  6. ^ Kaewthawee, Narawan; Brimson, Sirikalaya (February 2013). "The Effects of Ursolic Acid on Cytokine Production via the MAPK Pathways in Leukemic T-Cells" (PDF). EXCLI. 12 (February): 102–114.
  7. ^ 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.
  8. ^ 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. doi:10.1371/journal.pone.0039332.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  9. ^ Jilani K, Abed M, Zelenak C, Lang E, Qadri SM, Lang F (2011). "Triggering of erythrocyte cell membrane scrambling by ursolic acid". J Nat Prod. 74 (10): 2181–2186. doi:10.1021/np2005133. PMID 21923134.
  10. ^ 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. doi:10.1016/j.cmet.2011.03.020. PMC 3120768. PMID 21641545.
  11. ^ 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
  12. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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