Study of the Local Reactivity of Valeric Acid and its derivatives in the context of PDT

Authors

  • Nicol Flores-Mancilla Molecular Engineering Research Center, Catholic University of Santa María. Arequipa, Peru.
  • Pamela Gamero-Begazo Molecular Engineering Research Center, Catholic University of Santa María. Arequipa, Peru.

DOI:

https://doi.org/10.21754/tecnia.v28i1.193

Keywords:

Valerenic acid, Fukui functions, nucleophiles

Abstract

The valeric acid derivatives were studied, both derived amines (07) and esters (04). The structures were optimized to their fundamental state, which were characterized by respective frequency calculations. The analysis of the global and local reactivity of all the structures was performed, finding little relevance in the information of the global indexes. The local reactivity indexes, such as the Fukui Functions, were really enriching of the knowledge of the valeric acid systems, for their potential in the reaction with the GABA receptor. Likewise, now report that the substituting effect is only carried out for the case of reactions with nucleophiles, but it is not very relevant in the reactions with electrophiles, being the electron attractors the ones that help in an improvement of the center reactivity power

Downloads

Download data is not yet available.

References

[1] S. Bent, A. Padilla, D. Moore, M. Patterson, and W. Mehllng, "Valerian for sleep: a systematic review and meta-analysis," The American journal of medicine, vol. 119,pp. 1005-1012, 2006.

[2] J. E. Pizzorno, M. T. Murray, and H. Joiner-Bey, "45 - Insomnia," in The Clinician's Handbook of Natural Medicine (THIRD EDITION), ed Edinburgh: Churchill Livingstone, 2016, pp. 565-573.

[3] G. M. Kapalka, "Chapter 9 - Sleep," In Nutritional and Herbal Therapies for Children and Adolescents, ed San Diego: Academic Press, 2010, pp. 259-289.

[4] T. L. Dog, "CHAPTER 12 - Insomnia," in Women's Health in Complementary and Integrative Medicine, ed Saint Louis: Churchill Livingstone, 2005,pp. 187-200.

[5] J. R. Jamison, "Chapter 32 - Insomnia," in Clinical Cuide to Nutrition & Dietary Supplements in Disease Management, ed Saint Louis: Churchill Livingstone, 2003,pp. 339-344.

[6] S. Khom, J. Hintersteiner, D. Luger, M. Haider, G. Pototschnig, M. Mihovilovic, et al., "Analysis of (3-Subunit-dependent GABAA Receptor Modulation and Behavioral Effects of Valerenic Acid Derivatives," Journal of Pharmacology and Experimental Therapeutics, vol. 357,pp. 580-590, 2016.

[7] S. S. Cicek, S. Khom, B. Taferner, S. Hering, and H. Stuppner, "Bioactivity-Guided Isolation of GABAA Receptor Modulating Constituents from the Rhizomes of Actaea racemosa," Journal of Natural Products, vol. 73,pp. 2024-2028, 2010/12/27 2010.

[8] F. Crestani and U. Rudolph, "Chapter Two - Behavioral Functions of GABAA Receptor Subtypes The Zurich

Experience," in Advances in Pharmacology. vol. Volume 72, R. Uwe, Ed., ed: Academic Press, 2015, pp. 37-51.

[9] S. Kopp, R. Baur, E. Sigel, H. Mohler, and K.-H. Altmann, "Highly Potent Modulation of GABAA Receptors by Valerenic Acid Derivatives," ChemMedChem, vol. 5, pp. 678-681, 2010.

[10] D. C. Rueda, M. De Mieri, S. Hering, and M. Hamburger, "HPLCBased Activity Profiling for GABAA Receptor Modulators in Adenocarpus cincinnatus," Journal of Natural Products, vol. 77, pp. 640-649, 2014/03/28 1993.

[11] F. Moradi-Afrapoli, S. N. Ebrahimi, M. Smiesko, and M. Hamburger,"HPLC-Based Activity Profiling for GABAA Receptor Modulators In Extracts: Validation of an Approach Utilizing a Larval Zebraflsh Locomotor Assay," Journal of Natural Products, 2017/05/09 2017.

[12] J. Singhuber, I. Baburin, G. F. Ecker, B. Kopp, and S. Hering, "Insights into structure-activity relationship of GABAA receptor modulating coumarins and furanocoumarins," European Journal of Pharmacology, vol. 668, pp. 57-64, 10/1/ 2011.

[13] B. Taferner, W. Schuehly, A. Huefner, I. Baburin, K. Wiesner, G. F. Ecker, et al , "Modulation of GABAA-Receptors by Honokiol and Derivatives: Subtype Selectivity and Structure-Activity Relationship," Journal of Medicinal Chemistry, vol. 54, pp. 5349-5361, 2011/08/11 2008.

[14] G. A. R. Johnston, J. R. Hanrahan, M. Chebib, R. K. Duke, and K. N. Mewett, "Modulation of Ionotropic GABA Receptors by Natural Products of Plant Origin," in Advances in Pharmacology. vol. Volume 54, ed: Academic Press, 2006,pp. 285-316.

[15] A. Manayi, S. M. Nabavl, M. Daglla, and S. Jafari, "Natural terpenoids as a promising source for modulation of GABAergic system and treatment of neurological diseases," Pharmacological Reports, vol. 68, pp. 671-679,8// 2016.

[16] M. Bernaskova, A. Schoeffmann, W. Schuehly, A. Hufner, I. Baburin, and S. Hering, "Nitrogenated honokiol derivatives allosterically modulate GABAA receptors and act as strong partial agonists," Bioorganic & Medicinal Chemistry, vol. 23, pp. 6757-6762,10/15/ 2015.

[17] J. Zaugg, E. Elckmeier, S. N. Ebrahimi, I. Baburin, S. Hering, and M. Hamburger, "Positive GABAA Receptor Modulators from Acorus calamus and Structural Analysis of (+)- Dloxosarcoguaiacol by 1D and 2D NMR and Molecular Modeling," Journal of Natural Products, vol. 74, pp. 1437-1443, 2011/06/24 2008.

[18] J. Ramharter and J. Mulzer, "Total Synthesis of Valerenic Acid, a Potent GABAA Receptor Modulator," Organic Letters, vol. 11,pp. 1151-1153, 2009/03/05 2009.

[19] S. Khom, B. Strommer, J. Ramharter, T. Schwarz,C. Schwarzer,T. Erker, et al., "Valerenic acid derivatives as novel subunit-selective GABAA receptor ligands -in vitro and in vivo characterization," British Journal of Pharmacology, vol.161,pp. 65-78, 2010.

[20] S. Khom, I. Baburin, E. Timln, A. Hohaus, G. Trauner, B. Kopp, et al., "Valerenic acid potentiates and inhibits GABAA receptors: Molecular mechanism and subunit specificity," Neuropharmacology, vol. 53, pp.178-187, 7II 2007.

[21] K. Shinomiya, K. Fujimura, Y. Kim, and C. Kamei, "Effects of valerian extract on the sleep-wake cycle in sleep-disturbed rats," Acta Medica Okayama, vol. 59, 2005.

[22] A. Becker, F. Felgentreff, H. Schroder, B. Meier, and A. Brattstróm,"The anxiolytic effects of a Valerian extract is based on Valerenic acid," BMC complementary and alternative medicine, vol. 14, p. 267, 2014.

[23] J. Patocka and J. Jakl, "Biomedically relevant chemical constituents of Valeriana officinalis," Journal of Applied Biomedicine, vol. 8,pp.11-18, // 2010.

[24] T. Minaml, T. Utsunomlya, S. Nakamura, M. Okubo, N. Kltamura, Y. Okada, et al., "Chemlnform Abstract: Intramolecular Ene Reaction of Vinylphosphonates. Synthetic Application to Bicycllc Compounds and Cadalane and Valerenic Acid Terpenoids," Chemlnform, vol. 26, pp. no-no,1995.

[25] J. Ramharter and J. Mulzer, "Chemlnform Abstract: Total Synthesis of Valerenic Acid (VII), a Potent GABAA Receptor Modulator," Chemlnform, vol. 40, pp. no-no, 2009.

[26] J. Hintersteiner, M. Haider, D. Luger, C. Schwarzer, G. Reznlcek, W.Jager, et al., "Esters of valerenic acid as potential prodrugs," European journal of pharmacology, vol. 735,pp.123-131, 2014.

[27] D. Benke, A. Barberis, S. Kopp, K.-H. Altmann, M. Schubiger, K. E. Vogt, et al., "GABAA receptors as in vivo substrate for the anxiolytic action of valerenic acid, a major constituent of valerian root extracts," Neuropharmacology, vol. 56, pp. 174-181, til 2009.

[28] C.-S. Yuan, S. Mehendale, Y. Xiao, H. H. Aung, J.-T. Xie, and M. K. Ang-Lee, "The gamma-aminobutyric acidergic effects of valerian and valerenic acid on rat brainstem neuronal activity," Anesthesia & Analgesia, vol.98,pp. 353-358, 2004.

[29] A.Maier-Salamon,C.Trauner, R. Hiltscher, G. Reznicek, B. Kopp, T. Thalhammer , et al., "Hepatic metabolism and biliary excretion of valerenic acid in isolated perfused rat livers: Role of Mrp2 (Abcc2)," Journal of Pharmaceutical Sciences, vol. 98, pp. 3839-3849, 2009.

[30] A. Salimi, S. Fatemi, H. Zakizadeh Nei Nei, and A. Safaralie, "Mathematical Modeling of Supercritical Extraction of Valerenic Acid from Valeriana officinalis L," Chemical Engineering & Technology, vol. 31, pp.1470-1480, 2008.

[31] C. Bicchi, A. Binello, and P. Rubiolo, "Packed column SFC/UV versus HPLC/UV analysis of valerenic acids and valepotriates in extracts of Valeriana officinalis L," Phytochemical Analysis, vol.11 ,pp.179-183, 2000.

[32] G. D. Anderson, G. W. Elmer, E. D. Kantor, I. E. Templeton, and M. V. Vitiello, "Pharmacokinetics of valerenic acid after administration of valerian in healthy subjects," Phytotherapy Research, vol.19, pp. 801-803, 2005.

[33] D- M. Taibi, M. V. Vitiello, S. Barsness, G. W. Elmer, G. D. Anderson, and C. A. Landis, "A randomized clinical trial of valerian fails to improve self-reported, polysomnographic, and actigraphic sleep in older women with insomnia," Sleep Medicine, vol. 10, pp. 319-328, 3// 2009.

[34] D. Pade and S. Stavchansky, "Selection of Bioavailability Markers for Herbal Extracts Based on In Silico Descriptors and Their Correlation to In Vitro Permeability," Molecular Pharmaceutics, vol. 5, pp. 665-671, 2008/08/01 2008.

[35] B. M. Dietz, G. B. Mahady, G. F. Pauli, and N. R. Farnsworth,"Valerian extract and valerenic acid are partial agonists of the 5-HT 5a receptor in vitro," Molecular Brain Research, vol. 138, pp. 191-197, 2005.

[36] F. Felgentreff, A. Becker, B. Meier, and A. Brattstrom, "Valerian extract characterized by high valerenic acid and low acetoxy valerenic acid contents demonstrates anxiolytic activity," Phytomedicine, vol. 19, pp. 1216-1222, 2012.

[37] J. Ramharter and J. Mulzer, "From Planning to Optimization: Total Synthesis of Valerenic Acid and Some Bioactive Derivatives,” European Journal of Organic Chemistry, vol. 2012, pp. 2041-2053, 2012.

[38] D. Luger, G. Poli, M. Wieder, M. Stadler, S. Ke, M. Ernst, et al., "Identification of the putative binding pocket of valerenic acid on GABAA receptors using docking studies and site-directed mutagenesis," British Journal of Pharmacology, vol. 172, pp. 5403-5413, 2015.

[39] S. P. Fernández, C. Wasowskl, A. C. Paladini, and M. Marder, "Synergistic interaction between hesperidin, a natural flavonold, and diazepam," European Journal of Pharmacology, vol. 512, pp.189-198, 4/11/ 2005.

[40] T. L. Gabel, "Chapter 20 - Sleep Pharmacology A2 - Barkoukis, Teri J," in Review of Sleep Medicine (Second Edition), A. Y. Avidan, Ed., ed Philadelphia: Butterworth-Heinemann, 2007, pp. 385-399.

[41] D. J. Buysse and S. Tyagi,"Chapter 42 - Clinical Pharmacology of Other Drugs Used as Hypnotics A2 - Kryger, Meir," in Principles and Practice of Sleep Medicine (Sixth Edition), T. Roth and W. C. Dement, Eds., ed: Elsevier, 2017,pp. 432-445.07.

[42] D. J. Buysse,"Chapter 43 - Clinical Pharmacology of Other Drugs Used as Hypnotics A2 - Kryger, Meir H," in Principles and Practice of Sleep Medicine (Fifth Edition), T. Roth and W. C. Dement, Eds., ed Philadelphia: W.B. Saunders, 2011, pp. 492-509.

[43] M. Adams, S.-V. Schneider, M. Kluge, M. Kessler, and M. Hamburger, "Epilepsy in the Renaissance: A survey of remedies from 16th and 17th century German herbáis," Journal of Ethnopharmacology, vol.143, pp.1-13,8/30/ 2012.

[44] P. J. Houghton, "Old Yet New—Pharmaceuticals from Plants," Journal of Chemical Education, vol. 78,p. 175, 2001/02/011993.

[45] R. K. Gilpin and L. A. Pachla, "Pharmaceuticals and related drugs," Analytical Chemistry, vol. 59, pp. 174-197, 1987/06/15 1993.

[46] S. Waldmann, M. Almukainzi, N. A. Bou-Chacra,G. L. Amidon, B.- J. Lee, J. Feng, et al., "Provisional Biopharmaceutical Classification of Some Common Herbs Used in Western Medicine," Molecular Pharmaceutics, vol. 9, pp. 815-822, 2012/04/02 2012.

[47] R. Dennington, T. A. Keith, and J. M. Millam, "GaussView," ed. Shawnee Mission, KS: Semichem Inc., 2016.

[48] T. Yanal, D. P. Tew, and N. C. Handy, "A new hybrid exchangecorrelation functional using the Coulomb-attenuating method (CAM-B3LYP),11 Chemical Physics Letters, vol. 393, pp. 51-57, 2004.

[49] G. W. T. M. J. Frisch, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmanl, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchlan, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann,O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G.

Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ó. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, "Gaussian 09," ed. Wallingford CT: Gaussian, Inc., 2009.

[50] A. Schafer, H. Horn, and R.Ahlrichs,"Fully optimized contracted Gaussian basis sets for atoms Li to Kr," The Journal of Chemical Physics, vol. 97, pp. 2571-2577,1992.

[51] A. Schafer, C. Huber, and R. Ahlrichs, "Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr," The Journal of Chemical Physics, vol. 100, pp. 5829-5835,1994.

[52] F. L. Hirshfeld, "Bonded-atom fragments for describing molecular charge densities," Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), vol. 44, pp.129-138,1977.

Downloads

Published

2018-06-01

How to Cite

[1]
N. Flores-Mancilla and P. Gamero-Begazo, “Study of the Local Reactivity of Valeric Acid and its derivatives in the context of PDT”, TEC, vol. 28, no. 1, pp. 37–44, Jun. 2018.

Issue

Vol. 28 No. 1 (2018)

Section

Articles

License

Copyright (c) 2018 TECNIA

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Articles published by TECNIA can be shared under the international Creative Commons license: CC BY 4.0. Permissions beyond this scope can be inquired via email at tecnia@uni.edu.pe.