Teoretyczne badania właściwości konformacyjnych kannabidiolu i tetrahydrokannabinolu

• Autorzy: Buczek, Aneta , Rzepiela, Kacper

Warianty tytułu

EN

Theoretical studies on the conformational properties of cannabidiol and tetrahydrocannabinol

• Języki publikacji: PL

Abstrakty

EN

The conformational properties of cannabidiol and tetrahydrocannabinol are discussed on the basis of DFT calculations. For all conformers of CBD and THC the intramolecular interactions stabilizing each structure in the gas phase were determined. Additionally, dissociation energies of O-H bonds and selected C-H bonds were calculated to characterize the anti-radical properties of studied compounds. The lowest energy conformation of CBD, stabilized by O-H···π and CH···O hydrogen bonds, is consistent with the crystallographic structure of this compound and have comparable hydrogen bond parameters.

Słowa kluczowe

PL

kannabidiol; tetrahydrokannabinol; właściwości konformacyjne; wiązanie wodorowe; energia dysocjacji

EN

cannabidiol; tetrahydrocannabinol; conformational properties; hydrogen bonding; dissociation energy

• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2024
• Tom: [Z] 78, 5-6
• Strony: 527--543
• Opis fizyczny: Bibliogr. 38 poz., rys., tab.

Twórcy

autor

Buczek, Aneta

• Uniwersytet Opolski, Wydział Chemii, ul. Oleska 48, 45-052 Opole,

autor

Rzepiela, Kacper

• Uniwersytet Opolski, Wydział Chemii, ul. Oleska 48, 45-052 Opole

Bibliografia

• [1] S.A. Bonini, M. Premoli, S. Tambaro, A. Kumar, G. Maccarinelli, M. Memo, A. Mastinu, J. Ethnopharmacol., 2018, 227, 300.
• [2] S. Pisanti, M. Bifulco, J. Cell. Physiol., 2019, 234, 8342.
• [3] K.W. Hillig, P.G. Mahlberg, Am J Bot, 2004, 91, 966.
• [4] S. Pisanti, A.M. Malfitano, E. Ciaglia, A. Lamberti, R. Ranieri, G. Cuomo, M. Abate, G. Faggiana, M.C. Proto, D. Fiore, C. Laezza, M. Bifulco, Pharmacology & Therapeutics, 2017, 175, 133.
• [5] L. Calvi, D. Pentimalli, S. Panseri, L. Giupponi, F. Gelmini, G. Beretta, D. Vitali, M. Bruno, E. Zilio, R. Pavlovic, A. Giorgi, J. Pharm. Biomed. Anal., 2018, 150, 208.
• [6] C.P.L. Grof, Br J Clin Pharmacol, 2018, 84, 2463.
• [7] B. Farinon, R. Molinari, L. Costantini, N. Merendino, Nutrients, 2020, 12, 1935.
• [8] S.E. Kearney, A.J. Gangano, D.G. Barrus, K.J. Rehrauer, T.-E.R. Reid, P.V. Navaratne, E.K. Tracy, A. Roitberg, I. Ghiviriga, C.W. Cunningham, T. Gamage, A.J. Grenning, Journal of the American Chemical Society, 2023, 145, 13581.
• [9] M.N. Tahir, F. Shahbazi, S. Rondeau-Gagné, J.F. Trant, Journal of Cannabis Research, 2021, 3, 7.
• [10] F. Grotenhermen, G. Leson, 2002.
• [11] R. Adams, M. Hunt, J.H. Clark, Journal of the American Chemical Society, 1940, 62, 196.
• [12] R. Mechoulam, Y. Shvo, Tetrahedron, 1963, 19, 2073.
• [13] Y. Gaoni, R. Mechoulam, Journal of the American Chemical Society, 1964, 86, 1646.
• [14] E.S. Seltzer, A.K. Watters, D. MacKenzie, L.M. Granat, D. Zhang, Cancers, 2020, 12, 3203.
• [15] E. Perucca, J Epilepsy Res, 2017, 7, 61.
• [16] B. Costa, Chemistry & Biodiversity, 2007, 4, 1664.
• [17] E. Papaseit, C. Pérez-Mañá, A.P. Pérez-Acevedo, O. Hladun, M.C. Torres-Moreno, R. Muga, M. Torrens, M. Farré, Int J Med Sci, 2018, 15, 1286.
• [18] A. Stasiłowicz, A. Tomala, I. Podolak, J. Cielecka-Piontek, International Journal of Molecular Sciences, 2021, 22, 778.
• [19] A.J. Hampson, M. Grimaldi, J. Axelrod, D. Wink, Proc. Natl, 1998, 95, 8268.
• [20] A.J. Hampson, M. Grimaldi, M. Lolic, D. Wink, R. Rosenthal, J. Axelrod, Ann. N.Y. Acad. Sci., 2000, 899, 274.
• [21] A.L. Dawidowicz, M. Olszowy-Tomczyk, R. Typek, Fitoterapia, 2021, 152, 104915.
• [22] S. Atalay, I. Jarocka-Karpowicz, E. Skrzydlewska, Antioxidants, 2020, 9, 21.
• [23] Q.V. Vo, P.C. Nam, N.M. Thong, N.T. Trung, C.-T.D. Phan, A. Mechler, ACS Omega, 2019, 4, 8935.
• [24] S.M. Baswan, A.E. Klosner, K. Glynn, A. Rajgopal, K. Malik, S. Yim, N. Stern, Clinical, Cosmetic and Investigational Dermatology, 2020, 13, 927.
• [25] P. Cerino, C. Buonerba, G. Cannazza, J. D'Auria, E. Ottoni, A. Fulgione, A. Di Stasio, B. Pierri, A. Gallo, Cannabis Cannabinoid Res, 2021, 6, 19.
• [26] C.J. Grassa, G.D. Weiblen, J.P. Wenger, C. Dabney, S.G. Poplawski, S. Timothy Motley, T.P. Michael, C.J. Schwartz, New Phytol, 2021, 230, 1665.
• [27] G. Baranović, J. Mol. Struct., 2021, 1244, 130945.
• [28] H. Chung, A. Fierro, C.D. Pessoa-Mahana, PLOS ONE, 2019, 14, e0220025.
• [29] R. Mechoulam, L.A. Parker, R. Gallily, J Clin Pharmacol, 2002, 42, 11s.
• [30] J. Manzanares, M. Julian, A. Carrascosa, Curr Neuropharmacol, 2006, 4, 239.
• [31] V.A.N. Bragança, T.G. França, A.C.S.P.S. de Jesus, I.C. Palheta, F.P.A. Melo, P.A.P.F.G. Neves, A.B. Lima, R.S. Borges, Chemical Data Collections, 2020, 26, 100345.
• [32] P.H. Reggio, R.D. Bramblett, H. Yuknavich, H.H. Seltzman, D.N. Fleming, S.R. Fernando, L.A. Stevenson, R.G. Pertwee, Life Sci., 1995, 56, 2025.
• [33] R.G. Parr, Y. Weitao, Density-Functional Theory of Atoms and Molecules. Oxford University Press, 1995.
• [34] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A.V. Marenich, J. Bloino, B.G. Janesko, R.
• Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, Williams, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski,
• J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M.J. Bearpark, J.J. Heyd, E.N. Brothers, K.N. Kudin, V.N. Staroverov, T.A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A.P. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman, D.J. Fox, Wallingford, CT, 2016.
• [35] Y. Zhao, D.G. Truhlar, Theor. Chem. Acc., 2008, 120, 215.
• [36] T. Mayr, T. Grassl, N. Korber, V. Christoffel, M. Bodensteiner, IUCrData, 2017, 2, x170276.
• [37] D. Loru, A. Vigorito, A.F.M. Santos, J. Tang, M.E. Sanz, Phys. Chem. Chem. Phys., 2019, 21, 26111.
• [38] E. Rosenqvist, T. Ottersen, Acta Chem Scand B, 1975, 29, 379.

Identyfikatory

DOI

10.53584/wiadchem.2024.05.5