Limonene

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Introduction

Limonene is the terpene that gives citrus fruits and turpentine their characteristic taste/smell but it can also be found in many cannabis strains. Preclinical research indicates that limonene can be therapeutic in many diseases. However, it must be noted that limonene is only present in trace amounts (0.01-1%) in cannabis flowers which may not be enough to exert therapeutic effects on its own. Still limonene may prove to be of therapeutic value at higher concentrations (extracts) or in combination with other cannabinoids and terpenes found in cannabis.

Chemical Name

1-Methyl-4-(1-methylethenyl)-cyclohexene

Wikipedia Entry

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Literature Discussion

Preclinical research has shown limonene to be therapeutic in the following diseases:

  • Anti-inflammatory (Piccinelli et al., 2017)
  • Anti-inflammatory in lung allergy model (Hansen et al., 2016)
  • Anti-inflammatory in ulcerative colitis model (Yu et al., 2017)
  • Anti-inflammatory in wound healing (Keskin et al., 2017)
  • Antioxidant and anti-cancer in a human Lung Cancer cell line A549 and prostate cancer cell line 22RV-1 (Yang et al., 2017)
  • Antioxidant and anti-microbial (Ben Hsouna et al., 2017)
  • Anxiolytic (Lima et al., 2013)(de Almeida et al., 2014)
  • Colon cancer (Chidambara Murthy et al., 2012)
  • Local nociception but systemic anti-nociception (Kaimoto et al., 2016)
  • Mosquito repellent (Jaleta et al., 2016)
  • obesity (Lone and Yun, 2016)(Jing et al., 2013)
  • Sedation (Park et al., 2011)(Yun, 2014)
  • T-cell modulator (Lappas and Lappas, 2012)

References:

de Almeida, A.A.C., de Carvalho, R.B.F., Silva, O.A., de Sousa, D.P., and de Freitas, R.M. (2014). Potential antioxidant and anxiolytic effects of (+)-limonene epoxide in mice after marble-burying test. Pharmacol. Biochem. Behav. 118, 69–78.

Ben Hsouna, A., Ben Halima, N., Smaoui, S., and Hamdi, N. (2017). Citrus lemon essential oil: chemical composition, antioxidant and antimicrobial activities with its preservative effect against Listeria monocytogenes inoculated in minced beef meat. Lipids Health Dis. 16, 146.

Chidambara Murthy, K.N., Jayaprakasha, G.K., and Patil, B.S. (2012). D-limonene rich volatile oil from blood oranges inhibits angiogenesis, metastasis and cell death in human colon cancer cells. Life Sci. 91, 429–439.

Hansen, J.S., Nørgaard, A.W., Koponen, I.K., Sørli, J.B., Paidi, M.D., Hansen, S.W.K., Clausen, P.A., Nielsen, G.D., Wolkoff, P., and Larsen, S.T. (2016). Limonene and its ozone-initiated reaction products attenuate allergic lung inflammation in mice. J. Immunotoxicol. 13, 793–803.

Hódi, Á., Földesi, I., Hajagos-Tóth, J., Ducza, E., and Gáspár, R. (2014). [The effect of R(+) limonene on β - adrenerg signaling: the significance of oxidative stress index]. Acta Pharm. Hung. 84, 111–119.

Jaleta, K.T., Hill, S.R., Birgersson, G., Tekie, H., and Ignell, R. (2016). Chicken volatiles repel host-seeking malaria mosquitoes. Malar. J. 15, 354.

Jing, L., Zhang, Y., Fan, S., Gu, M., Guan, Y., Lu, X., Huang, C., and Zhou, Z. (2013). Preventive and ameliorating effects of citrus D-limonene on dyslipidemia and hyperglycemia in mice with high-fat diet-induced obesity. Eur. J. Pharmacol. 715, 46–55.

Kaimoto, T., Hatakeyama, Y., Takahashi, K., Imagawa, T., Tominaga, M., and Ohta, T. (2016). Involvement of transient receptor potential A1 channel in algesic and analgesic actions of the organic compound limonene. Eur. J. pain Lond. Engl. 20, 1155–1165.

Keskin, I., Gunal, Y., Ayla, S., Kolbasi, B., Sakul, A., Kilic, U., Gok, O., Koroglu, K., and Ozbek, H. (2017). Effects of Foeniculum vulgare essential oil compounds, fenchone and limonene, on experimental wound healing. Biotech. Histochem. Off. Publ. Biol. Stain Comm. 92, 274–282.

Lappas, C.M., and Lappas, N.T. (2012). D-Limonene modulates T lymphocyte activity and viability. Cell. Immunol. 279, 30–41.

Lima, N.G.P.B., De Sousa, D.P., Pimenta, F.C.F., Alves, M.F., De Souza, F.S., Macedo, R.O., Cardoso, R.B., de Morais, L.C.S.L., Melo Diniz, M. de F.F., and de Almeida, R.N. (2013). Anxiolytic-like activity and GC-MS analysis of (R)-(+)-limonene fragrance, a natural compound found in foods and plants. Pharmacol. Biochem. Behav. 103, 450–454.

Lone, J., and Yun, J.W. (2016). Monoterpene limonene induces brown fat-like phenotype in 3T3-L1 white adipocytes. Life Sci. 153, 198–206.

Park, H.M., Lee, J.H., Yaoyao, J., Jun, H.J., and Lee, S.J. (2011). Limonene, a natural cyclic terpene, is an agonistic ligand for adenosine A(2A) receptors. Biochem. Biophys. Res. Commun. 404, 345–348.

Piccinelli, A.C., Morato, P.N., Dos Santos Barbosa, M., Croda, J., Sampson, J., Kong, X., Konkiewitz, E.C., Ziff, E.B., Amaya-Farfan, J., and Kassuya, C.A.L. (2017). Limonene reduces hyperalgesia induced by gp120 and cytokines by modulation of IL-1 β and protein expression in spinal cord of mice. Life Sci. 174, 28–34.

Yang, C., Chen, H., Chen, H., Zhong, B., Luo, X., and Chun, J. (2017). Antioxidant and Anticancer Activities of Essential Oil from Gannan Navel Orange Peel. Mol. Basel Switz. 22.

Yu, L., Yan, J., and Sun, Z. (2017). D-limonene exhibits anti-inflammatory and antioxidant properties in an ulcerative colitis rat model via regulation of iNOS, COX-2, PGE2 and ERK signaling pathways. Mol. Med. Rep. 15, 2339–2346.

Yun, J. (2014). Limonene inhibits methamphetamine-induced locomotor activity via regulation of 5-HT neuronal function and dopamine release. Phytomedicine Int. J. Phytother. Phytopharm. 21, 883–887.