Humulene

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Introduction

Humulene is the terpene that gives hops their characteristic taste/smell but it can also be found in many cannabis strains. Preclinical research indicates that humulene can be therapeutic in many diseases. However, it must be noted that humulene 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 humulene may prove to be of therapeutic value at higher concentrations (extracts) or in combination with other cannabinoids and terpenes found in cannabis.

Chemical Name

2,6,6,9-Tetramethyl-1,4-8-cycloundecatriene

Wikipedia Entry

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Diseases

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Literature Discussion

Preclinical research has shown that humulene has the following therapeutic properties:

  • Anti-inflammatory (Coté et al., 2017)(Fernandes et al., 2007)(Rogerio et al., 2009)
  • Anti-tumor in MCF-7, PC-3, A-549, DLD-1, M4BEU and CT-26 cell lines (Legault et al., 2003)(Legault and Pichette, 2007)
  • Anti-tumor in LNCaP cells (Loizzo et al., 2007)
  • Oviposition deterrent for mosquitos (da Silva et al., 2015)(Bezerra-Silva et al., 2016)b
  • Boost of IL-8 secretion / neutrophil attraction (Satsu et al., 2004)
  • Mosquito larvicidal (Govindarajan and Benelli, 2016)

 

References:

Bezerra-Silva, P.C., Dutra, K.A., Santos, G.K.N., Silva, R.C.S., Iulek, J., Milet-Pinheiro, P., and Navarro, D.M.A.F. (2016). Evaluation of the Activity of the Essential Oil from an Ornamental Flower against Aedes aegypti: Electrophysiology, Molecular Dynamics and Behavioral Assays. PloS One 11, e0150008.

Coté, H., Boucher, M.-A., Pichette, A., and Legault, J. (2017). Anti-Inflammatory, Antioxidant, Antibiotic, and Cytotoxic Activities of Tanacetum vulgare L. Essential Oil and Its Constituents. Med. Basel Switz. 4.

Fernandes, E.S., Passos, G.F., Medeiros, R., da Cunha, F.M., Ferreira, J., Campos, M.M., Pianowski, L.F., and Calixto, J.B. (2007). Anti-inflammatory effects of compounds alpha-humulene and (-)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea. Eur. J. Pharmacol. 569, 228–236.

Govindarajan, M., and Benelli, G. (2016). α-Humulene and β-elemene from Syzygium zeylanicum (Myrtaceae) essential oil: highly effective and eco-friendly larvicides against Anopheles subpictus, Aedes albopictus, and Culex tritaeniorhynchus (Diptera: Culicidae). Parasitol. Res. 115, 2771–2778.

Legault, J., and Pichette, A. (2007). Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel. J. Pharm. Pharmacol. 59, 1643–1647.

Legault, J., Dahl, W., Debiton, E., Pichette, A., and Madelmont, J.-C. (2003). Antitumor activity of balsam fir oil: production of reactive oxygen species induced by alpha-humulene as possible mechanism of action. Planta Med. 69, 402–407.

Loizzo, M.R., Tundis, R., Menichini, F., Saab, A.M., Statti, G.A., and Menichini, F. (2007). Cytotoxic activity of essential oils from labiatae and lauraceae families against in vitro human tumor models. Anticancer Res. 27, 3293–3299.

Rogerio, A.P., Andrade, E.L., Leite, D.F.P., Figueiredo, C.P., and Calixto, J.B. (2009). Preventive and therapeutic anti-inflammatory properties of the sesquiterpene alpha-humulene in experimental airways allergic inflammation. Br. J. Pharmacol. 158, 1074–1087.

Satsu, H., Matsuda, T., Toshimitsu, T., Mori, A., Mae, T., Tsukagawa, M., Kitahara, M., and Shimizu, M. (2004). Regulation of interleukin-8 secretion in human intestinal epithelial Caco-2 cells by alpha-humulene. BioFactors Oxf. Engl. 21, 137–139.

da Silva, R.C.S., Milet-Pinheiro, P., Bezerra da Silva, P.C., da Silva, A.G., da Silva, M.V., Navarro, D.M. do A.F., and da Silva, N.H. (2015). (E)-Caryophyllene and α-Humulene: Aedes aegypti Oviposition Deterrents Elucidated by Gas Chromatography-Electrophysiological Assay of Commiphora leptophloeos Leaf Oil. PloS One 10, e0144586.