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Chemical Compound Review

Merotaine     (1S,2R,4aS,6aR,6aS,6bR,8aR,10S ,12aS,14bR)...

Synonyms: Micromerol, Prunol, Malol, Urson, HNMR, ...
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Disease relevance of Prunol


Psychiatry related information on Prunol


High impact information on Prunol


Chemical compound and disease context of Prunol


Biological context of Prunol


Anatomical context of Prunol


Associations of Prunol with other chemical compounds

  • Treatment with ursolic acid suppressed PMA-mediated induction of COX-2 protein and synthesis of prostaglandin E2 [11].
  • Since the chemical structure of ursolic acid is very similar to that of dexamethasone, a synthetic glucocorticoid, we investigated whether ursolic acid acts through the glucocorticoid receptor [17].
  • With other pentacyclic triterpenes lacking the 11-keto function and/or the carboxyl function on ring A (e.g., amyrin and ursolic acid), no 5-lipoxygenase inhibition was observed [24].
  • The carboxy group at position 28 in the pentacyclic-ring system of the triterpenes contributes to binding to HLE, since replacement of this group with a hydroxy group, as in uvaol, the alcohol analogue of ursolic acid, reduces the potency of inhibition [19].
  • There were 31 and 17 genes repressed by 10 and 30 microg of ursolic acid/ml, respectively, and 12 genes were consistently repressed that have functions in cysteine synthesis (cysK) and sulfur metabolism (cysD), as well as unknown functions (such as hdeAB and yhaDFG) [3].

Gene context of Prunol


Analytical, diagnostic and therapeutic context of Prunol


  1. Anti-invasive activity of ursolic acid correlates with the reduced expression of matrix metalloproteinase-9 (MMP-9) in HT1080 human fibrosarcoma cells. Cha, H.J., Bae, S.K., Lee, H.Y., Lee, O.H., Sato, H., Seiki, M., Park, B.C., Kim, K.W. Cancer Res. (1996) [Pubmed]
  2. Ursolic acid induces apoptosis through mitochondrial intrinsic pathway and caspase-3 activation in M4Beu melanoma cells. Harmand, P.O., Duval, R., Delage, C., Simon, A. Int. J. Cancer (2005) [Pubmed]
  3. Differential gene expression for investigation of Escherichia coli biofilm inhibition by plant extract ursolic acid. Ren, D., Zuo, R., González Barrios, A.F., Bedzyk, L.A., Eldridge, G.R., Pasmore, M.E., Wood, T.K. Appl. Environ. Microbiol. (2005) [Pubmed]
  4. Ursolic acid inhibits neointima formation in the rat carotid artery injury model. Pozo, M., Castilla, V., Gutierrez, C., de Nicolás, R., Egido, J., González-Cabrero, J. Atherosclerosis (2006) [Pubmed]
  5. Ursolic Acid inhibits growth and metastasis of human colorectal cancer in an orthotopic nude mouse model by targeting multiple cell signaling pathways: chemosensitization with capecitabine. Prasad, S., Yadav, V.R., Sung, B., Reuter, S., Kannappan, R., Deorukhkar, A., Diagaradjane, P., Wei, C., Baladandayuthapani, V., Krishnan, S., Guha, S., Aggarwal, B.B. Clin. Cancer Res. (2012) [Pubmed]
  6. Effect of ursolic acid from epicuticular waxes of Jacaranda decurrens on Schizaphis graminum. Varanda, E.M., Zúñiga, G.E., Salatino, A., Roque, N.F., Corcuera, L.J. J. Nat. Prod. (1992) [Pubmed]
  7. Ursolic acid plays a role in Nepeta sibthorpii Bentham CNS depressing effects. Taviano, M.F., Miceli, N., Monforte, M.T., Tzakou, O., Galati, E.M. Phytotherapy research : PTR (2007) [Pubmed]
  8. Inhibitory effect of ursolic acid purified from Origanum majorana L on the acetylcholinesterase. Chung, Y.K., Heo, H.J., Kim, E.K., Kim, H.K., Huh, T.L., Lim, Y., Kim, S.K., Shin, D.H. Mol. Cells (2001) [Pubmed]
  9. A hypoxia-driven vascular endothelial growth factor/Flt1 autocrine loop interacts with hypoxia-inducible factor-1alpha through mitogen-activated protein kinase/extracellular signal-regulated kinase 1/2 pathway in neuroblastoma. Das, B., Yeger, H., Tsuchida, R., Torkin, R., Gee, M.F., Thorner, P.S., Shibuya, M., Malkin, D., Baruchel, S. Cancer Res. (2005) [Pubmed]
  10. 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. Shishodia, S., Majumdar, S., Banerjee, S., Aggarwal, B.B. Cancer Res. (2003) [Pubmed]
  11. Ursolic acid inhibits cyclooxygenase-2 transcription in human mammary epithelial cells. Subbaramaiah, K., Michaluart, P., Sporn, M.B., Dannenberg, A.J. Cancer Res. (2000) [Pubmed]
  12. Induction of differentiation in the cultured F9 teratocarcinoma stem cells by triterpene acids. Lee, H.Y., Chung, H.Y., Kim, K.H., Lee, J.J., Kim, K.W. J. Cancer Res. Clin. Oncol. (1994) [Pubmed]
  13. Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats. Shih, Y.H., Chein, Y.C., Wang, J.Y., Fu, Y.S. Neurosci. Lett. (2004) [Pubmed]
  14. Amelioration of obesity and glucose intolerance in high-fat-fed C57BL/6 mice by anthocyanins and ursolic acid in Cornelian cherry (Cornus mas). Jayaprakasam, B., Olson, L.K., Schutzki, R.E., Tai, M.H., Nair, M.G. J. Agric. Food Chem. (2006) [Pubmed]
  15. Protective effect of ursolic acid on ethanol-mediated experimental liver damage in rats. Saravanan, R., Viswanathan, P., Pugalendi, K.V. Life Sci. (2006) [Pubmed]
  16. Inhibitory effects of constituents from Cynomorium songaricum and related triterpene derivatives on HIV-1 protease. Ma, C., Nakamura, N., Miyashiro, H., Hattori, M., Shimotohno, K. Chem. Pharm. Bull. (1999) [Pubmed]
  17. Ursolic acid-induced down-regulation of MMP-9 gene is mediated through the nuclear translocation of glucocorticoid receptor in HT1080 human fibrosarcoma cells. Cha, H.J., Park, M.T., Chung, H.Y., Kim, N.D., Sato, H., Seiki, M., Kim, K.W. Oncogene (1998) [Pubmed]
  18. Intracellular Ca2+ release mediates ursolic acid-induced apoptosis in human leukemic HL-60 cells. Baek, J.H., Lee, Y.S., Kang, C.M., Kim, J.A., Kwon, K.S., Son, H.C., Kim, K.W. Int. J. Cancer (1997) [Pubmed]
  19. Inhibition of human leucocyte elastase by ursolic acid. Evidence for a binding site for pentacyclic triterpenes. Ying, Q.L., Rinehart, A.R., Simon, S.R., Cheronis, J.C. Biochem. J. (1991) [Pubmed]
  20. Apoptotic activity of ursolic acid may correlate with the inhibition of initiation of DNA replication. Kim, D.K., Baek, J.H., Kang, C.M., Yoo, M.A., Sung, J.W., Chung, H.Y., Kim, N.D., Choi, Y.H., Lee, S.H., Kim, K.W. Int. J. Cancer (2000) [Pubmed]
  21. Ursolic acid promotes the release of macrophage migration inhibitory factor via ERK2 activation in resting mouse macrophages. Ikeda, Y., Murakami, A., Ohigashi, H. Biochem. Pharmacol. (2005) [Pubmed]
  22. Ursolic acid, an antagonist for transforming growth factor (TGF)-beta1. Murakami, S., Takashima, H., Sato-Watanabe, M., Chonan, S., Yamamoto, K., Saitoh, M., Saito, S., Yoshimura, H., Sugawara, K., Yang, J., Gao, N., Zhang, X. FEBS Lett. (2004) [Pubmed]
  23. Characterization of ursolic acid as a lipoxygenase and cyclooxygenase inhibitor using macrophages, platelets and differentiated HL60 leukemic cells. Najid, A., Simon, A., Cook, J., Chable-Rabinovitch, H., Delage, C., Chulia, A.J., Rigaud, M. FEBS Lett. (1992) [Pubmed]
  24. Mechanism of 5-lipoxygenase inhibition by acetyl-11-keto-beta-boswellic acid. Safayhi, H., Sailer, E.R., Ammon, H.P. Mol. Pharmacol. (1995) [Pubmed]
  25. Ursolic acid enhances nitric oxide and tumor necrosis factor-alpha production via nuclear factor-kappaB activation in the resting macrophages. You, H.J., Choi, C.Y., Kim, J.Y., Park, S.J., Hahm, K.S., Jeong, H.G. FEBS Lett. (2001) [Pubmed]
  26. Regulation of the phosphatidylinositol 3-kinase-akt and the mitogen-activated protein kinase pathways by ursolic Acid in human endometrial cancer cells. Achiwa, Y., Hasegawa, K., Udagawa, Y. Biosci. Biotechnol. Biochem. (2007) [Pubmed]
  27. Novel triterpenoids suppress inducible nitric oxide synthase (iNOS) and inducible cyclooxygenase (COX-2) in mouse macrophages. Suh, N., Honda, T., Finlay, H.J., Barchowsky, A., Williams, C., Benoit, N.E., Xie, Q.W., Nathan, C., Gribble, G.W., Sporn, M.B. Cancer Res. (1998) [Pubmed]
  28. Evaluation of apparent formation constants of pentacyclic triterpene acids complexes with derivatized beta- and gamma-cyclodextrins by reversed phase liquid chromatography. Claude, B., Morin, P., Lafosse, M., Andre, P. Journal of chromatography. A. (2004) [Pubmed]
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