Phellandrenes and Some Species from Them - A DFT Treatment

  • Lemi Türker Department of Chemistry, Middle East Technical University, Üniversiteler, Eskişehir Yolu No: 1, 06800 Çankaya/Ankara, Turkey
Keywords: alpha-phellandrene, beta-phellandrene, density functional, stability, spectra


Phellandrenes are naturally occurring cyclic dienes belonging to cyclic monoterpene class and have many medicinal applications. In the present study, some resonance stabilized radicals from α- and β-phellandrene and also some closed shell structures from those radicals have been investigated within the constraints of density functional theory and basis set employed. For structure optimizations of the closed-shell and open-shell structures, B3LYP/6-311++G(d,p) and UB3LYP/6-311++G(d,p) level of theories have been adopted, respectively. All the systems considered have been found to be thermo chemically favorable and electronically stable. Various structural, quantum chemical and spectral properties of them have been obtained and discussed.


Thangaleela, S., Sivamaruthi, B.S., Kesika, P., Tiyajamorn, T., Bharathi, M., & Chaiyasut, C. (2022). A narrative review on the bioactivity and health benefits of alpha-phellandrene. Sci. Pharm., 90(4), 57.

Zhang, J‑H., Sun, H‑L., Chen, S‑Y, Zeng, L., & Wang, T‑T. (2017). Anti-fungal activity, mechanism studies on α-phellandrene and nonanal against Penicillium cyclopium. Bot. Stud., 58,13.

Zhang, P.Y., Chen, K.S., He, P.Q., Liu, S.H., & Jiang, W.F. (2008). Effects of crop development on the emission of volatiles in leaves of Lycopersicon esculentum and its inhibitory activity to Botrytis cinerea and Fusarium oxysporum. J. Integr. Plant Biol., 50(1), 84-91.

Tisserand, R., & Young, R. (2013). Essential oil safety: A guide for health care professionals; Amsterdam (The Netherlands): Elsevier Health Sciences. ISBN 0702054348.

Dhakad, A.K., Pandey, V.V., Beg, S., & Rawat, J.M. (2018). Biological, medicinal and toxicological significance of Eucalyptus leaf essential oil: A review. J. Sci. Food Agri., 98, 833-848.

LOTUS. Available online

Bizzo, R.H., Hovell, A.M.C., & Rezende, C.M. (2009). Brazilian essential oil: General view, developments, and perspectives. Quim. Nova, 32(3), 588-594.

Iscan, G., Kirimer, N., Demirci, F., Demirci, B., Noma, Y., & Başer, K.H. (2012). Biotransformation of (−)-(R)-α-phellandrene: Antimicrobial activity of its major metabolite. Chem. Biodivers., 9, 1525-1532.

Gaich, T., & Mulzer, J. (2012). Chiral pool synthesis: Starting from terpenes. In E.M. Carreira & H. Yamamoto (Eds.), Comprehensive Chirality (1st ed., Vol. 2, pp. 163-206). Amsterdam, The Netherlands: Elsevier.

Wu, C-C., Lin, C-L., Huang, C-Y., Hsieh, S., Liu, C-H., & Hsieh, S-L. (2019). α Phellandrene enhances the immune response and resistance against Vibrio alginolyticus in white shrimp (Litopenaeus vannamei). Fish & Shellfish Immunology, 84, 1108-1114.

Chaaban, A., Richardi, V.S., Carrer, A.R., Brum, J.S., Cipriano, R.R., Martins, M.A.N., Silva, C.E.N., Deschamps, C., & Molento, M.B. (2019). Insecticide activity of Curcuma longa (leaves) essential oil and its major compound α-phellandrene against Lucilia cuprina larvae (Diptera: Calliphoridae): Histological and ultrastructural biomarkers assessment. Pesticide Biochemistry and Physiology, 153, 17-27.

Oonmetta-Aree, J., Suzuki, T., Gasaluck, P., & Eumkeb, G. (2006). Antimicrobial properties and action of galangal (Alpinia galangal Linn.) on Staphylococcus aureus. LWT-Food Sci. Technol., 39, 1214-1220.

Oliveira, M.G., Marques, R.B., Santana, M.F., Santos, A.B., Brito, F.A., Barreto, E.O., Sousa, D.P., Almeida, F.R., Badauê-Passos, D., Antoniolli, A.R., & Quintans-Júnior, L.J. (2012). α-Terpineol reduces mechanical hypernociception and inflammatory response. Basic Clin. Pharmacol. Toxicol., 111, 120-125.

Kawata, J., Kameda, M.,& Miyazawa, M. (2008). Cyclooxygenase-2 inhibitory effects of monoterpenoids with a p-methane skeleton. Int. J. Essent. Oil Ther., 2(4), 145-148.

Siqueira, H.D.S., Neto, B.S., Sousa, D.P., Gomes, B.S., da Silva, F.V., Cunha, F.V.M., Wanderley, C., Pinheiro, G., Cândido, A., Wong, D., Ribeiro, R.A., Lima-Júnior, R.C.P., & Oliveira, F.A. (2016). α-Phellandrene, a cyclic monoterpene, attenuates inflammatory response through neutrophil migration inhibition and mast cell degranulation. Life Sci., 160, 27-33.

Lima, D.F., Brandão, M.S., Moura, J.B., Leitão, J.M., Carvalho, F.A., Miúra, L.M., Leite, J.R., Sousa, D.P., & Almeida, F.R.(2012). Antinociceptive activity of the monoterpene α-phellandrene in rodents: Possible mechanisms of action. J. Pharm. Pharmacol., 64, 283-292.

Yamamoto, S., Ohsawa, M., & Ono, H. (2013). Contribution of TRPV1 receptor- expressing fibers to spinal ventral root after-discharges and mechanical hyperalgesia in a spared nerve injury (SNI) rat model. J. Pharmacol. Sci., 121, 9-16.

Dhaka, A., Murray, A.N., Mathur, J., Earley, T.J., Petrus, M.J., & Patapoutian, A. (2007). TRPM8 is required for cold sensation in mice. Neuron, 54, 371-378.

Piccinelli, A.C., Santos, J.A., Konkiewitz, E.C., Oesterreich, S.A., Formagio, A.S., Croda, J.H., Ziff, E.B., & Kassuya, C.A. (2015). Antihyperalgesic and antidepressive actions of (R)-(+)-limonene, α-phellandrene, and essential oil from Schinus terebinthifolius fruits in a neuropathic pain model. Nutr. Neurosci., 18, 217-224.

Pinheiro-Neto, F.R., Lopes, E.M., Acha, B.T., Gomes, L., Dias, W.A., Reis Filho, A., Leal, B.S., Rodrigues, D., Silva, J., Dittz, D., Ferreira, P.M.P., & de Castro Almeida, F.R. (2021). α-Phellandrene exhibits antinociceptive and tumor-reducing effects in a mouse model of oncologic pain. Toxicol. Appl. Pharmacol., 418, 115497.

Heal, C.F., Banks, J.L., Lepper, P.D., Kontopantelis, E., & van Driel, M.L. (2016). Topical, antibiotics for preventing surgical site infection in wounds healing by primary intention. Cochrane Database Syst. Rev., 11, Cd011426.

Scherer, de C.M.M., Marques, F.M., Figueira, M.M., Peisino, M., Schmitt, E., Kondratyuk, T.P., Endringer, D.C., Scherer, R., & Fronza, M. (2019). Wound healing activity of terpinolene and α-phellandrene by attenuating inflammation and oxidative stress in vitro. J. Tissue. Viability, 28, 94-99.

Nedelec, B., Ghahary, A., Scott, P.G., & Tredget, E.E. (2000). Control of wound contraction. Basic and clinical features. Hand Clin., 16, 289-302.

Gonçalves, R.L.G., Cunha, F.V.M., Sousa-Neto, B.P.S., Oliveira, L.S.A., Lopes, M.E., Rezende, D.C., Sousa, I.J.O., Nogueira, K.M., Souza, L.K.M., Medeiros, J.V.R., Wong, D.V.T., Pereira, V.M.P., Lima-Júnior, R.C.P., Sousa, D.P., Oliveira, C.P.C., Almeida, F.R.C., & Oliveira, de F. A. (2020). α-Phellandrene attenuates tissular damage, oxidative stress, and TNF-α levels on acute model ifosfamide-induced hemorrhagic cystitis in mice. Naunyn-Schmiedeberg’s Arch Pharmaco., 393, 1835-1848.

Baldwin, J.E. & Krueger, S.M. (1969). Stereoselective photochemical electrocyclic valence isomerizations of .alpha.-phellandrene conformational isomers. J. Am. Chem. Soc., 91(23), 6444-6447.

Formighieri, C., & Melis, A. (2014). Carbon partitioning to the terpenoid biosynthetic pathway enables heterologous β-phellandrene production in Escherichia coli cultures. Arch Microbiol., 196, 853-861.

Lafever, R.E., & Croteau, R. (1993). Hydride Shifts in the Biosynthesis of the p menthane monoterpenes α-terpinene, γ-terpinene, and β-phellandrene. Archives of Biochemistry and Biophysics, 301(2), 361-366.

Miller, D.R., & Borden, J.H. (1990). β-Phellandrene: Kairomone for pine engraver, Ips pini (Say) (Coleoptera: Scolytidae). J. Chem. Ecol., 16, 2519-2531.

Stewart, J.J.P. (1989). Optimization of parameters for semi empirical methods I. J. Comput. Chem., 10, 209-220.

Stewart, J.J.P. (1989). Optimization of parameters for semi empirical methods II. J. Comput. Chem., 10, 221-264.

Leach, A.R. (1997). Molecular modeling. Essex: Longman.

Kohn, W., & Sham, L.J. (1965). Self-consistent equations including exchange and correlation effects. Phys. Rev., 140, 1133-1138.

Parr, R.G., & Yang, W. (1989). Density functional theory of atoms and molecules. London: Oxford University Press.

Becke, A.D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A, 38, 3098-3100.

Vosko, S.H., Wilk, L., & Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can. J. Phys., 58, 1200-1211.

Lee, C., Yang, W., & Parr, R.G. (1988). Development of the Colle-Salvetti correlation energy formula into a functional of the electron density. Phys. Rev. B, 37, 785-789. 37.785

SPARTAN 06 (2006). Wavefunction Inc. Irvine CA, USA.

How to Cite
Türker, L. (2023). Phellandrenes and Some Species from Them - A DFT Treatment. Earthline Journal of Chemical Sciences, 10(2), 167-183.