Metals Complexes Formed with Oleanolic Acid — Oak Academic Publishing
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Metals Complexes Formed with Oleanolic Acid
IFMT, Rondonópolis, Brazil
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Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
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Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
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Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
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Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
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North Carolina State University, Research Campus, Kannapolis, NC, USA
1 IFMT, Rondonópolis, Brazil
2 Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
3 Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
4 Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
5 Chemistry Department, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n Campus Universitário, Viçosa, Minas Gerais, Brazil
6 North Carolina State University, Research Campus, Kannapolis, NC, USA
The oleanolic acid possesses diverse pharmacological properties, it is considered as a good starting material for creating new compounds. The oleanolic acid isolated of Plumeria obtusa leaves was used as raw material to obtained calcium, magnesium, zinc, nickel and copper complexes. The structures of complexes were confirmed by HRMS, 1 H NMR, and 13 C NMR. Five new compounds were synthesized to promote increased biological activity of oleanolic acid and PCR assays for the different type of cancer.
KeywordsOleanolic AcidComplexPCR
Liu, J. (1995) Pharmacology of Oleanolic Acid and Ursolic Acid. Journal of Ethnopharmacology, 49, 57-68. https://doi.org/10.1016/0378-8741(95)90032-2
Joger, S., Trojan, H., Kopp, T., Laszczyk, M.N. and Scheffler, A. (2009) Pentacyclic Triterpene Distribution in Various Plants—Rich Sources for a New Group of Multi-Potent Plant Extracts. Molecules, 14, 2016-2031. https://doi.org/10.3390/molecules14062016
Shanmugam, M.K., Dai, X., Kumar, A.P., Tan, B.K.H., Sethi, G. and Bishayee, A. (2014) Oleanolic Acid and Its Synthetic Derivatives for the Prevention and Therapy of Cancer: Preclinical and Clinical Evidence. Cancer Letters, 346, 206-216. https://doi.org/10.1016/j.canlet.2014.01.016
He, X. and Rui, H.L. (2007) Triterpenoids Isolated from Apple Peels Have Potent Antiproliferative Activity and May Be Partially Responsible for Apple’s Anticancer Activity. Journal of Agricultural and Food Chemistry, 55, 4366-4370. https://doi.org/10.1021/jf063563o
Gambhava, N.S., Ezhava, S.B., Rathod, I.S., Chhabria, M.T. and Patwari, A.H. (2013) Estimation of Ursolic Acid and Oleanolic Acid from Leaves of Plumeria Obtuse by HPTLC Method after Iodine Derivatization. Der Pharma Chemica, 5, 44-50.
Ovesna, Z., Kozics, K. and Slamenova, D. (2006) Protective Effects of Ursolic Acid and Oleanolic Acid in Leukemic Cells. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 600, 131-137. https://doi.org/10.1016/j.mrfmmm.2006.03.008
Lee, W., Yang, E.J., Ku, S.K., Song, K.S. and Bae, J.S. (2013) Anti-Inflammatory Effects of Oleanolic Acid on LPS-Induced Inflammation in vitro and in vivo. Inflammation, 36, 94-102. https://doi.org/10.1007/s10753-012-9523-9
Hsu, H.Y., Yang, J.J. and Lin, C.C. (1997) Effects of Oleanolic Acid and Ursolic Acid on Inhibiting Tumor Growth and Enhancing the Recovery of Hematopoietic System Postirradiation in Mice. Cancer Letters, 111, 7-13. https://doi.org/10.1016/S0304-3835(96)04481-3
Mengoni, F., Lichtner, M., Battinelli, L., Marzi, M., Mastroianni, C.M., Vullo, V., et al. (2002) In vitro Anti-HIV Activity of Oleanolic Acid on Infected Human Mononuclear Cells. Planta Medica, 68, 111-114. https://doi.org/10.1055/s-2002-20256
Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., et al. (2006) Pharmacological Activities of Natural Triterpenoids and Their Therapeutic Implications. Natural Product Reports, 23, 394-411. https://doi.org/10.1039/b515312n
Liu, J. (2005) Oleanolic Acid and Ursolic Acid: Research Perspectives. Journal of Ethnopharmacology, 100, 92-94. https://doi.org/10.1016/j.jep.2005.05.024
Chen, J., Gong, Y., Liu, J., Hua, W., Zhang, L. and Sun, H. (2008) Synthesis and Biological Evaluation of Novel-Pyrazolo [4,3-b]Oleanane Derivatives as Inhibitors of Glycogen Phosphorylase. Chemistry and Biodiversity, 5, 1304-1312. https://doi.org/10.1002/cbdv.200890117
Place, A.E., Suh, N., Williams, C.R., Risingsong, R., Honda, T., Honda, Y., et al. (2003) The Novel Synthetic Triterpenoid, CDDO-Imidazolide, Inhibits Inflammatory Response and Tumor Growth in vivo. Clinical Cancer Research, 9, 2798-2806.
Bednarczyk-Cwynar, B., Zaprutko, L., Ruszkowski, P. and Hladoń, B. (2012) Anticancer Effect of A-Ring or/and C-Ring Modified Oleanolic Acid Derivatives on KB, MCF-7 and HeLa Cell Lines. Organic & Biomolecular Chemistry, 10, 2201-2205. https://doi.org/10.1039/c2ob06923g
Garcia-Granados, A., López, P.E., Melguizo, E., Parra, A. and Simeó, Y. (2006) Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive-Pressing Residues. Synthetic Communications, 36, 3001-3018. https://doi.org/10.1080/00397910600773858
Chen, H., Gao, Y., Wang, A., Zhou, X., Zheng, Y. and Zhou, J. (2015) Evolution in Medicinal Chemistry of Ursolic Acid Derivatives as Anticancer Agents. European Journal of Medicinal Chemistry, 92, 648-655. https://doi.org/10.1016/j.ejmech.2015.01.031
Zhang, H., Li, X., Ding, J., Xu, H., Dai, X., Hou, Z., et al. (2013) Delivery of Ursolic Acid (UA) in Polymeric Nanoparticles Effectively Promotes the Apoptosis of GASTRIC CANCER CELLs through Enhanced Inhibition of Cyclooxygenase 2 (COX-2). International Journal of Pharmaceutics, 441, 261-268. https://doi.org/10.1016/j.ijpharm.2012.11.034
Acebey-Castellon, I.L., Voutquenne-Nazabadioko, L., Doan Thi Mai, H., Roseau, N., Bouthagane, N., Muhammad, D., et al. (2011) Triterpenoid Saponins from Symplocos Lancifolia. Journal of Natural Products, 74, 163-168. https://doi.org/10.1021/np100502y
Masullo, M., Pizza, C. and Piacente, S. (2017) Oleanane Derivatives for Pharmaceutical Use: A Patent Review (2000-2016). Expert Opinion on Therapeutic Patents, 27, 237-255. https://doi.org/10.1080/13543776.2017.1253680
Suh, N., Wang, Y., Honda, T., Gribble, G.W., Dmitrovsky, E., Hickey, W.F., et al. (1999) A Novel Synthetic Oleanane Triterpenoid, 2-Cyano-3,12-Dioxoolean-1,9-Dien-28-Oic Acid, with Potent Differentiating, Antiproliferative, and Anti-Inflammatory Activity. Cancer Research, 59, 336-341.
Partal Urena, F., Moreno, J.R.A. and López González, J.J. (2009) Conformational Study of (R)-(+)-Limonene in the Liquid Phase Using Vibrational Spectroscopy (IR, Raman, and VCD) and DFT Calculations. Tetrahedron: Asymmetry, 20, 89-97. https://doi.org/10.1016/j.tetasy.2009.01.024
Tabrizi, L. and Chiniforoshan, H. (2016) Ruthenium(II) p-Cymene Complexes of Naphthoquinone Derivatives as Antitumor Agents: A Structure Activity Relationship Study. Journal of Organometallic Chemistry, 822, 211-220. https://doi.org/10.1016/j.jorganchem.2016.09.003
Bukhari, S.B., Memon, S., Mahroof-Tahir, M. and Bhanger, M.I. (2009) Synthesis, Characterization and Antioxidant Activity Copper-Quercetin Complex. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71, 1901-1906. https://doi.org/10.1016/j.saa.2008.07.030
Jadeja, R.N., Vyas, K.M., Gupta, V.K., Joshi, R.G. and Ratna Prabha, C. (2012) Syntheses, Characterization and Molecular Structures of Calcium(II) and Copper(II) Complexes Bearing O2-Chelate Ligands: DNA Binding, DNA Cleavage and Anti-Microbial Study. Polyhedron, 31, 767-778. https://doi.org/10.1016/j.poly.2011.11.004
Hench, L.L. and West, J.K. (1990) The Sol-Gel Process. Chemical Reviews, 90, 33-72. https://doi.org/10.1021/cr00099a003
Tubert-Brohman, I., Sherman, W., Repasky, M. and Beuming, T. (2013) Improved Docking of Polypeptides with Glide. Journal of Chemical Information and Modeling, 53, 1689-1699.
Manente, F.A., De Almeida Mello, L.R., Khalil, O.A.K., De Carvalho, C.T., Bannach, G. and Vellosa, J.C.R. (2011) Efeito da complexacao de metais aos antiinflamatórios na acao contra agentes oxidativos e radicais livres: Acao do cetoprofeno. Ecletica Quimica, 36, 107-127. https://doi.org/10.1590/S0100-46702011000200006
Novotny, L., Abdel-Hamid, M.E., Hamza, H., Masterova, I. and Grancai, D. (2003) Development of LC-MS Method for Determination of Ursolic Acid: Application to the Analysis of Ursolic Acid in Staphylea holocarpa Hemsl. Journal of Pharmaceutical and Biomedical Analysis, 31, 961-968. https://doi.org/10.1016/S0731-7085(02)00706-9
Kalodera, Z. and Sofic, E. (2009) Identification and Isolation of Pharmacologically Active Triterpenes in Betula Cortex, Betula Pendula Roth., Betulaceae. Bosnian Journal of Basic Medical Sciences, 9, 31-38. https://doi.org/10.17305/bjbms.2009.2853
Kim, H.J., Jee, H.J. and Yun, J. (2011) DNA Damage Induces Down-Regulation of PEPCK and G6P Gene Expression through Degradation of PGC-1. Acta Biochimica et Biophysica Sinica, 43, 589-594. https://doi.org/10.1093/abbs/gmr053
Nordgren, J., Nitiema, L.W., Sharma, S., Ouermi, D., Traore, A.S., Simpore, J., et al. (2012) Emergence of Unusual G6P Rotaviruses in Children, Burkina Faso, 2009-2010. Emerging Infectious Diseases, 18, 589-597. https://doi.org/10.3201/eid1804.110973