Chemistry:Ursolic acid

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Short description: Pentacyclic chemical compound found in fruits
Ursolic acid
Ursolic acid.svg
Names
IUPAC name
3β-Hydroxyurs-12-en-28-oic acid
Systematic IUPAC name
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Other names
Prunol, Malol, β-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
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).
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Infobox references
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Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-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.

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 and holy basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, and prunes). Apple peels contain large quantities of ursolic acid and related compounds.[3]

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,[4][5] and may also decrease proliferation of cancer cells and induce apoptosis.[6] 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.[7] Ursolic acid is a weak aromatase inhibitor (IC50 = 32 μM),[8] 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.[9] Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).[10] It has been found to reduce muscle atrophy and to stimulate muscular growth in mice,[11] also shows a potential cardioprotection.[12]

In mice, ursolic acid induces neural regeneration after sciatic nerve injuries and recently found to have COVID preventative capabilities. More research in this recent finding is underway.[13] In mice with chronic multiple sclerosis, ursolic acid has reduced further damage to neurons and helped rebuild the protective sheaths covering neurons, apparently by suppressing Th17 immune cells and activating precursor cells that mature into myelin-sheath-making cells, called oligodendrocytes.[14] Ursolic acid improves domoic acid-induced cognitive deficits in mice.[15] Ursolic acid improves high fat diet-induced cognitive impairments by blocking endoplasmic reticulum stress and IκB kinase β/nuclear factor-κB-mediated inflammatory pathways in mice.[16] Ursolic acid attenuates lipopolysaccharide-induced cognitive deficits in mouse brain through suppressing p38/NF-κB mediated inflammatory pathways.[17] Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D-galactose.[18] Ursolic acid enhances mouse liver regeneration after partial hepatectomy.[19] Ursolic acid enhances the cellular immune system and pancreatic beta-cell function in streptozotocin-induced diabetic mice fed a high-fat diet.[20] Ursolic acid increased skeletal muscle mass, as well as grip strength and exercise capacity, improved endurance, reduced the expression of the genes involved in the development of muscle atrophy, and decreased indicators of accumulated fatigue and exercise-induced stress.[21]

In rats, ursolic acid ameliorated high-fat diet-induced hepatic steatosis and improved metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease.[22]

Uses

Ursolic acid can be found in plants that are used for cosmetics additives.[23] It can serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents.[24]

See also

References

  1. ↑ 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. ↑ "Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties". Food Chem 220: 477–489. April 2017. doi:10.1016/j.foodchem.2016.10.029. PMID 27855928. 
  4. ↑ "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. 2003. PMID 12907607. http://crdd.osdd.net/open/930/1/majumdar2003.pdf. 
  5. ↑ 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. 
  6. ↑ 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
  7. ↑ 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. PMID 26417220. PMC 4531796. http://www.excli.de/vol12/Brimson_08022013_proof.pdf. 
  8. ↑ 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. 
  9. ↑ 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. PMID 22745735. Bibcode: 2012PLoSO...739332K. 
  10. ↑ "Triggering of erythrocyte cell membrane scrambling by ursolic acid". J Nat Prod 74 (10): 2181–2186. 2011. doi:10.1021/np2005133. PMID 21923134. 
  11. ↑ 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. PMID 21641545. 
  12. ↑ "Uncoupling and antioxidant effects of ursolic acid in isolated rat heart mitochondria". J. Nat. Prod. 74 (7): 1640–4. July 2011. doi:10.1021/np200060p. PMID 21648406. 
  13. ↑ Liu, Biao; Liu, Yan; Yang, Guang; Xu, Zemin; Chen, Jiajun (2013-09-25). "Ursolic acid induces neural regeneration after sciatic nerve injury". Neural Regeneration Research 8 (27): 2510–2519. doi:10.3969/j.issn.1673-5374.2013.27.002. ISSN 1673-5374. PMID 25206561. 
  14. ↑ Zhang, Yuan; Li, Xing; Ciric, Bogoljub; Curtis, Mark T.; Chen, Wan-Jun; Rostami, Abdolmohamad; Zhang, Guang-Xian (6 April 2020). "A dual effect of ursolic acid to the treatment of multiple sclerosis through both immunomodulation and direct remyelination". Proceedings of the National Academy of Sciences 117 (16): 9082–9093. doi:10.1073/pnas.2000208117. PMID 32253301. 
  15. ↑ Wu, Dong-mei; Lu, Jun; Zhang, Yan-qiu; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Li, Meng-qiu (2013-09-01). "Ursolic acid improves domoic acid-induced cognitive deficits in mice". Toxicology and Applied Pharmacology 271 (2): 127–136. doi:10.1016/j.taap.2013.04.038. ISSN 1096-0333. PMID 23707761. 
  16. ↑ Lu, Jun; Wu, Dong-mei; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Shan, Qun (2011-11-01). "Ursolic acid improves high fat diet-induced cognitive impairments by blocking endoplasmic reticulum stress and IκB kinase β/nuclear factor-κB-mediated inflammatory pathways in mice". Brain, Behavior, and Immunity 25 (8): 1658–1667. doi:10.1016/j.bbi.2011.06.009. ISSN 1090-2139. PMID 21708244. 
  17. ↑ Wang, Yong-Jian; Lu, Jun; Wu, Dong-mei; Zheng, Zi-hui; Zheng, Yuan-Lin; Wang, Xiao-hui; Ruan, Jie; Sun, Xiao et al. (2011-09-01). "Ursolic acid attenuates lipopolysaccharide-induced cognitive deficits in mouse brain through suppressing p38/NF-κB mediated inflammatory pathways". Neurobiology of Learning and Memory 96 (2): 156–165. doi:10.1016/j.nlm.2011.03.010. ISSN 1095-9564. PMID 21496491. 
  18. ↑ Lu, Jun; Zheng, Yuan-Lin; Wu, Dong-Mei; Luo, Lan; Sun, Dong-Xu; Shan, Qun (2007-10-01). "Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D-galactose". Biochemical Pharmacology 74 (7): 1078–1090. doi:10.1016/j.bcp.2007.07.007. ISSN 0006-2952. PMID 17692828. 
  19. ↑ Jin, Yong-Ri; Jin, Jing-Ling; Li, Cheng-Hao; Piao, Xi-Xu; Jin, Nan-Ge (2012-04-01). "Ursolic acid enhances mouse liver regeneration after partial hepatectomy". Pharmaceutical Biology 50 (4): 523–528. doi:10.3109/13880209.2011.611143. ISSN 1744-5116. PMID 22136205. 
  20. ↑ Jang, Sun-Mi; Yee, Sung-Tae; Choi, Jina; Choi, Myung-Sook; Do, Gyeong-Min; Jeon, Seon-Min; Yeo, Jiyoung; Kim, Myung-Joo et al. (2009-01-01). "Ursolic acid enhances the cellular immune system and pancreatic beta-cell function in streptozotocin-induced diabetic mice fed a high-fat diet". International Immunopharmacology 9 (1): 113–119. doi:10.1016/j.intimp.2008.10.013. ISSN 1567-5769. PMID 19013541. 
  21. ↑ Jeong, Ji-Woong; Shim, Jae-Jung; Choi, Il-Dong; Kim, Sung-Hwan; Ra, Jehyeon; Ku, Hyung Keun; Lee, Dong Eun; Kim, Tae-Youl et al. (2015-12-01). "Apple Pomace Extract Improves Endurance in Exercise Performance by Increasing Strength and Weight of Skeletal Muscle". Journal of Medicinal Food 18 (12): 1380–1386. doi:10.1089/jmf.2014.3401. ISSN 1557-7600. PMID 26331671. 
  22. ↑ Li, Songtao; Liao, Xilu; Meng, Fanyu; Wang, Yemei; Sun, Zongxiang; Guo, Fuchuan; Li, Xiaoxia; Meng, Man et al. (2014-01-01). "Therapeutic role of ursolic acid on ameliorating hepatic steatosis and improving metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease rats". PLOS ONE 9 (1): e86724. doi:10.1371/journal.pone.0086724. ISSN 1932-6203. PMID 24489777. Bibcode: 2014PLoSO...986724L. 
  23. ↑ Herbal Principles in Cosmetics: Properties and Mechanisms of Action. CRC Press. 2010-06-23. pp. 73–. ISBN 978-1-4398-1214-3. https://books.google.com/books?id=MaAZMbSxNt4C&pg=PA73. 
  24. ↑ "The cytotoxic activity of ursolic acid derivatives". Eur J Med Chem 40 (6): 582–9. June 2005. doi:10.1016/j.ejmech.2005.01.001. PMID 15922841. 



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