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Chemical Compound Review

AC1LDIKX     10-hydroxy-2,2,6a,6b,9,9,12a- heptamethyl-1...

Synonyms: AGN-PC-008ILS, SureCN13395360, BBL009966, STK801366, AKOS005613008, ...
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Disease relevance of OLEANOLIC ACID

  • Results obtained show that oleanolic acid inhibits the HIV-1 replication in all the cellular systems used (EC50 values: 22.7 microM, 24.6 microM and 57.4 microM for in vitro infected PBMC, naturally infected PBMC and M/M, respectively) [1].
  • Compounds, oleanolic acid, and 6'-(beta-sitosteryl-3- O-beta- D-glucopyranosidyl) pentadecanoate showed marginal cytotoxicity against Hep G2 cells (human liver cancer cells) with IC50 values of 14.4, 17.4, 4.9, 8.0, and 9.2 microg/mL, respectively [2].
  • The highest cicatrizant activity in mice was obtained by applying 40 microg of oleanolic acid per gram of body weight [3].
  • Effects of oleanolic acid glycosides on gastrointestinal transit and ileus in mice [4].
  • Of the isolated compounds, 3-oxotirucalla-7, 24-dien-21-oic acid (2), oleanolic acid (4), and 6 were found to be inhibitory substances against human immunodeficiency virus (HIV-1) protease, with their 50% inhibitory concentrations (IC(50)) being 20, 10, and 70 microg/mL, respectively [5].

Psychiatry related information on OLEANOLIC ACID

  • The active principles of the extract were isolated and purified by repeated column chromatography and their structures were identified as oleanolic acid glycosides known as momordin I, Id, and Ie [6].

High impact information on OLEANOLIC ACID


Chemical compound and disease context of OLEANOLIC ACID


Biological context of OLEANOLIC ACID


Anatomical context of OLEANOLIC ACID


Associations of OLEANOLIC ACID with other chemical compounds


Gene context of OLEANOLIC ACID


Analytical, diagnostic and therapeutic context of OLEANOLIC ACID


  1. In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells. Mengoni, F., Lichtner, M., Battinelli, L., Marzi, M., Mastroianni, C.M., Vullo, V., Mazzanti, G. Planta Med. (2002) [Pubmed]
  2. New cytotoxic 6-oxygenated 8,9-dihydrofurocoumarins, hedyotiscone A - C, from Hedyotis biflora. Chen, Y.H., Chang, F.R., Wu, C.C., Yen, M.H., Liaw, C.C., Huang, H.C., Kuo, Y.H., Wu, Y.C. Planta Med. (2006) [Pubmed]
  3. In vivo wound-healing activity of oleanolic acid derived from the acid hydrolysis of Anredera diffusa. Moura-Letts, G., Villegas, L.F., Marçalo, A., Vaisberg, A.J., Hammond, G.B. J. Nat. Prod. (2006) [Pubmed]
  4. Effects of oleanolic acid glycosides on gastrointestinal transit and ileus in mice. Li, Y., Matsuda, H., Yoshikawa, M. Bioorg. Med. Chem. (1999) [Pubmed]
  5. Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia. Ma, C., Nakamura, N., Hattori, M., Kakuda, H., Qiao, J., Yu, H. J. Nat. Prod. (2000) [Pubmed]
  6. Momordins inhibit both AP-1 function and cell proliferation. Lee, D.K., Kim, B., Lee, S.G., Gwon, H.J., Moon, E.Y., Hwang, H.S., Seong, S.K., Lee, M., Lim, M.J., Sung, H.J., Shin, D.H., Yoon, S.J., Yang, C.H. Anticancer Res. (1998) [Pubmed]
  7. Extremely potent triterpenoid inducers of the phase 2 response: correlations of protection against oxidant and inflammatory stress. Dinkova-Kostova, A.T., Liby, K.T., Stephenson, K.K., Holtzclaw, W.D., Gao, X., Suh, N., Williams, C., Risingsong, R., Honda, T., Gribble, G.W., Sporn, M.B., Talalay, P. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  8. Olive Fruit Extracts Inhibit Proliferation and Induce Apoptosis in HT-29 Human Colon Cancer Cells. Juan, M.E., Wenzel, U., Ruiz-Gutierrez, V., Daniel, H., Planas, J.M. J. Nutr. (2006) [Pubmed]
  9. Phytocomponents of triterpenoids, oleanolic acid and ursolic acid, regulated differently the processing of epidermal keratinocytes via PPAR-alpha pathway. Lee, H.K., Nam, G.W., Kim, S.H., Lee, S.H. Exp. Dermatol. (2006) [Pubmed]
  10. Release of acetylcholine to raise insulin secretion in Wistar rats by oleanolic acid, one of the active principles contained in Cornus officinalis. Hsu, J.H., Wu, Y.C., Liu, I.M., Cheng, J.T. Neurosci. Lett. (2006) [Pubmed]
  11. Search for possible antitumor promoters by inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation; ursolic acid and oleanolic acid from an anti-inflammatory Chinese medicinal plant, Glechoma hederaceae L. Ohigashi, H., Takamura, H., Koshimizu, K., Tokuda, H., Ito, Y. Cancer Lett. (1986) [Pubmed]
  12. Effects of pharmacological preconditioning by emodin/oleanolic acid treatment and/or ischemic preconditioning on mitochondrial antioxidant components as well as the susceptibility to ischemia-reperfusion injury in rat hearts. Du, Y., Ko, K.M. Mol. Cell. Biochem. (2006) [Pubmed]
  13. 3beta-Hydroxyolean-12-en-27-oic Acid: A Cytotoxic, Apoptosis-Inducing Natural Drug against COLO-205 Cancer Cells. Tu, J., Sun, H.X., Ye, Y.P. Chem. Biodivers. (2006) [Pubmed]
  14. Hydroxylation of Oleanolic Acid to Queretaroic Acid by Cytochrome P450 from Nonomuraea recticatena. Fujii, Y., Hirosue, S., Fujii, T., Matsumoto, N., Agematu, H., Arisawa, A. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
  15. The effects of 10 triterpenoid compounds on experimental liver injury in mice. Liu, J., Liu, Y., Mao, Q., Klaassen, C.D. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1994) [Pubmed]
  16. Inhibitory effect of oleanolic acid on 12-O-tetradecanoylphorbol-13-acetate-induced gene expression in mouse skin. Oguro, T., Liu, J., Klaassen, C.D., Yoshida, T. Toxicol. Sci. (1998) [Pubmed]
  17. Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase. Chen, J., Liu, J., Zhang, L., Wu, G., Hua, W., Wu, X., Sun, H. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  18. Structure-related inhibitory activity of oleanolic acid glycosides on gastric emptying in mice. Matsuda, H., Li, Y., Murakami, T., Yamahara, J., Yoshikawa, M. Bioorg. Med. Chem. (1999) [Pubmed]
  19. Dual activity of triterpenoids: apoptotic versus antidifferentiation effects. Cipak, L., Grausova, L., Miadokova, E., Novotny, L., Rauko, P. Arch. Toxicol. (2006) [Pubmed]
  20. Distribution of oleanolic acid glycosides in vacuoles and cell walls isolated from protoplasts and cells of Calendula officinalis leaves. Szakiel, A., Kasprzyk, Z. Steroids (1989) [Pubmed]
  21. Terpenoids of Salvia hydrangea: two new, rearranged 20-norabietanes and the effect of oleanolic acid on erythrocyte membranes. Sairafianpour, M., Bahreininejad, B., Witt, M., Ziegler, H.L., Jaroszewski, J.W., Staerk, D. Planta Med. (2003) [Pubmed]
  22. Five new oleanolic acid glycosides from Achyranthes bidentata with inhibitory activity on osteoclast formation. Li, J.X., Hareyama, T., Tezuka, Y., Zhang, Y., Miyahara, T., Kadota, S. Planta Med. (2005) [Pubmed]
  23. In vitro trypanocidal activity of triterpenes from miconia species. Cunha, W.R., Martins, C., da Silva Ferreira, D., Crotti, A.E., Lopes, N.P., Albuquerque, S. Planta Med. (2003) [Pubmed]
  24. Platelet anti-aggregating triterpenoids from the leaves of Acanthopanax senticosus and the fruits of A. sessiliflorus. Jin, J.L., Lee, S., Lee, Y.Y., Kim, J.M., Heo, J.E., Yun-Choi, H.S. Planta Med. (2004) [Pubmed]
  25. Glucuronide Saponins of Oleanolic Acid from Achyranthes fauriei Roots. Ida, Y., Katsumata Nee Ohtsuka, M., Satoh, Y., Shoji, J. Planta Med. (1994) [Pubmed]
  26. Biosynthesis of sterols and triterpenes in cell suspension cultures of Uncaria tomentosa. Flores-Sánchez, I.J., Ortega-López, J., del Carmen Montes-Horcasitas, M., Ramos-Valdivia, A.C. Plant Cell Physiol. (2002) [Pubmed]
  27. Solubilization of saponins of bupleuri radix with ginseng saponins: cooperative effect of dammarane saponins. Watanabe, K., Fujino, H., Morita, T., Kasai, R., Tanaka, O. Planta Med. (1988) [Pubmed]
  28. Platycodin D and D3 isolated from the root of Platycodon grandiflorum modulate the production of nitric oxide and secretion of TNF-alpha in activated RAW 264.7 cells. Wang, C., Schuller Levis, G.B., Lee, E.B., Levis, W.R., Lee, d.a. .W., Kim, B.S., Park, S.Y., Park, E. Int. Immunopharmacol. (2004) [Pubmed]
  29. Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus. Usia, T., Watabe, T., Kadota, S., Tezuka, Y. Biol. Pharm. Bull. (2005) [Pubmed]
  30. Cytokine-mediated induction of metallothionein in Hepa-1c1c7 cells by oleanolic acid. Kim, J.Y., Lee, K.J., Kim, D.H., Jeong, T.C., Lee, E.S., Choi, Y.M., Jeong, H.G. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  31. Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. Chiang, L.C., Ng, L.T., Chiang, W., Chang, M.Y., Lin, C.C. Planta Med. (2003) [Pubmed]
  32. In vitro activity of hederacolchisid A1 compared with other saponins from Hedera colchica against proliferation of human carcinoma and melanoma cells. Barthomeuf, C., Debiton, E., Mshvildadze, V., Kemertelidze, E., Balansard, G. Planta Med. (2002) [Pubmed]
  33. Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry. Modugno, F., Ribechini, E., Colombini, M.P. Rapid Commun. Mass Spectrom. (2006) [Pubmed]
  34. Determination of oleanolic acid in human plasma and study of its pharmacokinetics in Chinese healthy male volunteers by HPLC tandem mass spectrometry. Song, M., Hang, T.J., Wang, Y., Jiang, L., Wu, X.L., Zhang, Z., Shen, J., Zhang, Y. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  35. Quantification of eugenol, luteolin, ursolic acid, and oleanolic acid in black (Krishna Tulasi) and green (Sri Tulasi) varieties of Ocimum sanctum Linn. using high-performance thin-layer chromatography. Anandjiwala, S., Kalola, J., Rajani, M. Journal of AOAC International (2006) [Pubmed]
  36. Oleanolic acid nanosuspensions: preparation, in-vitro characterization and enhanced hepatoprotective effect. Chen, Y., Liu, J., Yang, X., Zhao, X., Xu, H. J. Pharm. Pharmacol. (2005) [Pubmed]
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