WHAT TERPENES ARE?

Terpenes are plant compounds, highly volatile, naturally present in all plants. They account for the different flavours, tastes and beneficial effects of the plants.

They are FUNCTIONAL MOLECULES responsible for natural beneficial properties of essential oils.

Terpenes have been shown to activate the olfactory receptors of our body, which are more widely distributed in many different tissues throughout the human body and to influence many physiological processes of our cells.

TERPENES and CANNABIS: THE ENTOURAGE EFFECT

Terpenes are well known because they can modulate the action of phytocannabinoids in order to bring benefits and implement them when treating different conditions, such as pain, inflammation, depression, anxiety, addiction, fungal and bacterial infections.

Several studies suggest possible synergic effects of cannabinoids associated with terpenes: the so-called ENTOURAGE EFFECT.

Terpenes are rather powerful. They show unique therapeutic properties that can widely contribute to the ENTOURAGE EFFECT in combination with medicine extracts of CBD, CBG and other cannabinoids. Some research has showed that, using cannabinoids as single molecules, you couldn’t fully obtain all the desired effects.

Some example of ENTOURAGE EFFECT:

Moreover, isolated terpenes show many therapeutic properties such as anti-inflammatory, analgesic, relaxing, anxiolytic and many others. Some scientists define them as the new frontier of aromatherapy, but with higher beneficial effects.

LET’S DISCOVER ALL EXTRAORDINARY NATURAL PROPERTIES OF TERPENES FOR OUR HEALTH AND WELLBEING!

mango utile per dormire

Myrcene is the terpene mainly present in Cannabis Sativa, but we can find it also in apricot, mango and hop. It plays a very important role in the entourage effect. For example, in some cannabis varieties, it is responsible for the so-called “couch-lock effect”, induced by its interaction with the THC.

Many references report that its use can be useful to give relief to muscular tension and protect articulation, thanks to its muscle-relaxant and anti-inflammatory action. It has also a balanced sedative action.

Linalool is the main terpene contained in the essential oil of Lavender and it is well-known for its characteristic beneficial properties. It can also be found in mint and bergamot. Its characteristic fragrance conveys a pleasant sense of tranquillity and serenity.

Linalool performs an anti-anxiety and sedative effect and it is useful as modulator of the mood, thanks to its action on the monoaminergic system, and in particular on the levels of serotonine and noradrenaline.

Limonene is present in high quantity in the citrus fruits and it can improve the assimilation of other molecules and terpenes in our body.

It is known for being the main component responsible for the digestive virtues of the essential oils of lemon, orange, mandarin and citrus fruits in general.

Limonene performs important biological activities: in particular, some studies show its ability to neutralize acidity of the gastric acid in the stomach and to improve issues connected to gastro-esophageal reflux, thanks to a protective action of the gastric mucosa.

Beta Caryophillene is characteristic of spicy plants like black pepper, oregano, and cloves.

Among terpenes, it is the only one that can be classified as a phytocannabinoid: in fact it can interact with CB2 receptors of the Endocannabinoid System, without having any psychoactive effect. This mechanism of action suggests a modulator role of beta caryophillene useful to improve certain states of physical and mental discomfort.

Several studies highlight its anti-inflammatory and anaesthetic properties.

The α-pinene is the most common terpene in nature and it appears in pine and conifers.
The literature acknowledges that Alpha Pinene has beneficial effects on the respiratory system, thanks to its espectorant and broncodilatatory action due to its balsamic notes, which help in case of nasal congestion and cold.

Furthermore, some studies demonstrate that Alpha Pinene can help memory and learning process, thanks to its ability to increase levels of Acetilcoline, an important neurotransmitter released in the brain during learning, crucial for the acquisition of new memories.

Nerolidol can be found in neroli, ginger and jasmine plants. It conveys sweet, relaxing and inebriating sensations.

It is known for its important antioxidant and protective qualities against many types of bacteria, fungi and parasites.

Geraniol is the natural terpene responsible for the delicate sweet and floral notes of Geranium, Mirtle and Melissa. Many references show its antifungal and antibacterial properties, especially against the Candida Albicans. Moreover, some studies demonstrate its modulating action on the level of triglycerides and cholesterol.

Terpineol is contained in the pine tree and the tea tree plant.

Scientific literature provides valid support to its antioxidant effect, useful to fight against damages caused by oxidative stress. Moreover, it shows a beneficial effect on hypertension and a Brazialian study also suggests that terpineol can exert a rebalancing action on the intestinal flora.

β-pinene is a common terpene in pine and conifers, with fresh and balsamic aroma. As its isomer (alpha pinene), Beta pinene has expectorant and bronchodilatory properties that can help breathing.

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References:

Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects, Ethan B Russo GW Pharmaceuticals, Salisbury, Wiltshire, UK

MYRCENE

Central effects of citral, myrcene and limonene, constituents of essential oil chemotypes from Lippia alba (Mill.) n.e. Brown. Do Vale TG, Furtado EC, Santos JG Jr, Viana GS (2002). Phytomed 9: 709–714
https://www.ncbi.nlm.nih.gov/pubmed/12587690

Herbal Drugs and Phytopharmaceuticals: A Handbook for Practice on A Scientific Basis, 3rd edn. Bisset NG, Wichtl M (2004). Medpharm Scientific Publishers: Stuttgart; CRC Press: Boca Raton, FL
https://onlinelibrary.wiley.com/doi/abs/10.1002/ffj.2730100512

Evaluation of the anti-inflammatory, anti-catabolic and pro-anabolic effects of E-caryophyllene, myrcene and limonene in a cell model of osteoarthritis. Rufino, A.T., Ribeiro, M., Sousa, C., Judas, F., Salgueiro, L., Cavaleiro, C. and Mendes, A.F. (2015) Eur. J. Pharmacol., 750, 141–150.
https://www.ncbi.nlm.nih.gov/pubmed/25622554

Effect of myrcene on nociception in mice. Rao, V. S. N., A. M. S. Menezes, and G. S. B. Viana. Journal of pharmacy and pharmacology 42.12 (1990): 877-878.

https://www.ncbi.nlm.nih.gov/pubmed/1983154

Myrcene mimics the peripheral analgesic activity of lemongrass tea. Lorenzetti, Berenice B., et al. Journal of Ethnopharmacology 34.1 (1991): 43-48.

https://www.ncbi.nlm.nih.gov/pubmed/1753786

LINALOOL

Linalool bioactive properties and potential applicability in drug delivery systems. Pereira I, Severino P, Santos AC, Silva AM and Souto EB, Colloids Surface B: Biointerfaces 171:566–578 (2018)
https://www.ncbi.nlm.nih.gov/pubmed/30098535

Lavandula angustifolia Essential Oil and Linalool Counteract Social Aversion Induced by Social Defeat. Caputo L, Reguilon MD, Minarro J, De Feo V., Arias MR. Molecules  2018,23,2694 (2018)
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222471/

Linalool odor-induced anxiolytic effects in mice. H. Harada, H. Kashiwadani, Y. Kanmura, and T. Kuwaki. Frontiers in Behavioral Neuroscience, vol. 12, p. 241, 2018
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6206409/

Effects of inhaled Linalool in anxiety, social interaction and aggressive behavior in mice. Linck VM, da Silva AL, Figueiró M, Caramão EB, Moreno PR, Elisabetsky E. Phytomedicine. 2010 Jul;17(8-9):679-83.

https://www.ncbi.nlm.nih.gov/pubmed/19962290

LIMONENE

Limonene: aroma of innovation in health and disease. Vieira AJ, Beserra FP, Souza MC, et al. Chem Biol Interact. 2018 Mar;1(283):97–106
https://www.ncbi.nlm.nih.gov/pubmed/29427589

Gastroprotective effect of limonene in rats: Influence on oxidative stress, inflammation and gene expression. De Souza MC, Vieira AJ, Beserra FP, Pellizzon CH, Nóbrega RH, Rozza AL. Phytomedicine. 2019;53:37‐42.
https://www.ncbi.nlm.nih.gov/pubmed/30668410

Effects of limonene and essential oil from Citrus aurantium on gastric mucosa: role of prostaglandins and gastric mucus secretion. T. M. Moraes, H. Kushima, et al. Chemico-Biological Interactions, vol. 180, no. 3, pp. 499-505, 2009.
https://www.ncbi.nlm.nih.gov/pubmed/19410566

D-Limonene: safety and clinical applications. Sun J. Altern Med Rev. 2007 Sep;12(3):259-64.
https://www.ncbi.nlm.nih.gov/pubmed/18072821

Healing actions of essential oils from Citrus aurantium and d-limonene in the gastric mucosa: the roles of VEGF, PCNA, AND COX-2 in cell proliferation. T.M. Moraes, A.L. Rozza, H. Kushima, C.H. Pellizzon, L.R. Rocha, C.A. J. Med. Food, 16 (2013), pp. 1162-1167
https://www.ncbi.nlm.nih.gov/pubmed/24328705

Gastroprotective mechanisms of citrus lemon (rutaceae) essential oil and its majority compounds limonene and beta-pinene: involvement of heat-shock protein-70, vasoactive intestinal peptide, glutathione, sulfhydryl compounds, nitric oxide and prostaglandin e(2). A.L. Rozza, M. Moraes Tde, H. Kushima, A. Tanimoto, M.O. Marques, T.M. Bauab, C.A. Hiruma-Lima, C.H. Pellizzon Chem. Biol. Interact., 189 (2011), pp. 82-89
https://www.ncbi.nlm.nih.gov/pubmed/20934418

BETA CARYOPHILLENE

β-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice. Bahi Amine; Al Mansouri Shamma; Al Memari Elyazia; Al Ameri Mouza; Nurulain Syed M.; Ojha Shreesh. Physiology & Behavior. 135: 119–124. 2014
https://www.ncbi.nlm.nih.gov/pubmed/24930711

Beta-caryophyllene is a dietary cannabinoid. Jürg Gertsch, Marco Leonti, Stefan Raduner, et al. Proc Natl Acad Sci U S A. 2008 Jul 1; 105(26): 9099–9104
https://www.ncbi.nlm.nih.gov/pubmed/18574142

Anti-Arthritic and Anti Inflammatory Activity of Beta Caryophyllene against Freund’s Complete Adjuvant Induced Arthritis in Wistar Rats. Vijayalaxmi A, Vasudha Bakshi, Nazia Begum, Kowmudi V, Naveen Kumar Y, Yogesh Reddy. Journal of Bone Reports & Recommendations. 2015
https://bone.imedpub.com/antiarthritic-and-anti-inflammatory-activity-of-beta-caryophyllene-against-freunds-complete-adjuvant-induced-arthritis-in-wistar-rats.php?aid=7220

The cannabinoid CB2 receptor-selective phytocannabinoid beta-caryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain. Klauke AL, Racz I, Pradier B, Markert A, Zimmer AM, Gertsch J, Zimmer A. Eur Neuropsychopharmacol. 2014 Apr;24(4):608-20
https://www.ncbi.nlm.nih.gov/pubmed/24210682

Local anaesthetic activity of beta-caryophyllene. Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A. Farmaco. 2001 May-Jul;56(5-7):387-9
https://www.ncbi.nlm.nih.gov/pubmed/11482764

Involvement of peripheral cannabinoid and opioid receptors in β-caryophyllene-induced antinociception. Katsuyama S.; Mizoguchi H.; Kuwahata H.; et al. European Journal of Pain. 17 (5): 664–675. 2013
https://www.ncbi.nlm.nih.gov/pubmed/23138934

ALPHA PINENE

Inhibition of acetylcholinesterase activity by bicyclic monoterpenoids. Miyazawa M, Yamafuji C (2005). J Agric Food Chem 53: 1765–1768.
https://www.ncbi.nlm.nih.gov/pubmed/15740071

In-vitro inhibition of human erythrocyte acetylcholinesterase by salvia lavandulaefolia essential oil and constituent terpenes. Perry NS, Houghton PJ, Theobald A, Jenner P, Perry EK (2000). J Pharm Pharmacol 52: 895–902.
https://www.ncbi.nlm.nih.gov/pubmed/10933142

Upper airway and pulmonary effects of oxidation products of (+)-alpha-pinene, d-limonene, and isoprene in BALB/c mice. Rohr A. C., Wilkins C. K., Clausen P. A., Hammer M., Nielsen G. D., Spengler J. D., Wolkoff P. Inhal. Toxicol. 2002; 14(7)663–684
https://www.ncbi.nlm.nih.gov/pubmed/12122569

NEROLIDOL

Anti-biofilm, anti-hemolysis, and anti-virulence activities of black pepper, cananga, myrrh oils, and nerolidol against Staphylococcus aureus. Lee K, Lee JH, Kim SI, Cho MH, Lee J. Appl Microbiol Biotechnol. 2014 Nov;98(22):9447-57. doi: 10.1007/s00253-014-5903-4. Epub 2014 Jul 16.
https://www.ncbi.nlm.nih.gov/pubmed/25027570

A novel nerolidol-rich essential oil from Piper claussenianum modulates Candida albicans biofilm. Curvelo JA, Marques AM et al. J Med Microbiol. 2014 May;63(Pt 5):697-702. doi: 10.1099/jmm.0.063834-0. Epub 2014 Feb 12.

https://www.ncbi.nlm.nih.gov/pubmed/24523158

Antifungal Effect of Eugenol and Nerolidol against Microsporum gypseum in a Guinea Pig Model. Lee S.-J et al. Biological & Pharmaceutical Bulletin 30(1):184-8
https://www.ncbi.nlm.nih.gov/pubmed/17202684

Antileishmanial activity of the terpene nerolidol. Arruda D.C., D’Alexandri F.L., Katzin A.M., Uliana S.R.B. Antimicrob. Agents Chemother. 2005;49:1679-1687.
https://www.ncbi.nlm.nih.gov/pubmed/15855481

Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities. Weng-Keong Chan, Loh Teng-Hern Tan, Kok-Gan Chan OrcID, Learn-Han Lee and Bey-Hing Goh. Molecules 2016, 21(5), 529.
https://www.ncbi.nlm.nih.gov/pubmed/27136520

GERANIOL

Modulation by geraniol of gene expression involved in lipid metabolism leading to a reduction of serum-cholesterol and triglyceride levels. Phytomedicine, 22 (7) (2015), pp. 696-704

https://www.ncbi.nlm.nih.gov/pubmed/26141755

Effect of geraniol, a plant derived monoterpene on lipids and lipid metabolizing enzymes in experimental hyperlipidemic hamsters. Jayachandran M, Chandrasekaran B, Namasivayam N (2015) Mol Cell Biochem 398: 39–5

https://www.ncbi.nlm.nih.gov/pubmed/25218494

Fungicidal action of geraniol against Candida albicansis potentiated by abrogated CaCdr1p drug efflux and fluconazole synergism PLoS One.  S. Singh, Z. Fatima, K. Ahmad, S. Hameed, 13 (2018)
https://www.ncbi.nlm.nih.gov/pubmed/30157240

Investigating the antifungal activity and mechanism(s) of geraniol against Candida albicans strains. Leite MC, de Brito Bezerra AP, de Sousa JP, de Oliveira Lima E. Med Mycol. 2015 Apr;53(3):275-84. https://www.ncbi.nlm.nih.gov/pubmed/25480017

Anti-Candida activity of geraniol involves disruption of cell membrane integrity and function. Sharma Y, Khan LA, Manzoor N. J Mycol Med. 2016 Sep;26(3):244-54. https://www.ncbi.nlm.nih.gov/pubmed/27554866

Effect of geraniol on fatty acid and mevalonate metabolism in the human hepatoma cell line Hep G2 M.P. Polo, M.G. De Bravo Biochemistry and Cell Biology, 84 (2006), pp. 102-111
https://www.ncbi.nlm.nih.gov/pubmed/16462894

TERPINEOL

Evaluation of the antioxidant and antiproliferative potential of bioflavors. J.L. Bicas, I.A. Neri-Numa et al. Food and chemical toxicology 49 (2011); 1610-1615
https://www.ncbi.nlm.nih.gov/pubmed/21540069

α-Terpineol, a natural monoterpene: A review of its biological properties. Christina Khaleel, Nurhayat Tabanca, Gerhard Buchbauer. Open Chem., 2018; 16: 349–361 Journal 2017; 1 (2): 122–135
https://www.researchgate.net/publication/324790949_a-Terpineol_a_natural_monoterpene_A_review_of_its_biological_properties

Cardiovascular effects induced by a-terpineol in hypertensive rats. Sabino, C.K.; Ferreira-Filho, E.S.; et al. Flavour Fragr. J. 2013, 28, 333–339
https://onlinelibrary.wiley.com/doi/abs/10.1002/ffj.3159

Unravelling the cardiovascular effects induced by α-terpineol: A role for the nitric oxide–cGMP pathway. Thaís P Ribeiro Dayanne L Porto et al. Clinical and Experimental Pharmacology and Physiology, 2010
https://www.ncbi.nlm.nih.gov/pubmed/20374260

Antidiarrheal activity of α-terpineol in mice. 40 Polyanna dos Santos Negreirosa, Douglas Soares da Costaa, Valdelânia Gomes da Silvaa, et al. Biomedicine & Pharmacotherapy 110 (2019) 631–640
https://www.ncbi.nlm.nih.gov/pubmed/30540974

BETA PINENE

Fitoterapia: Impiego razionale delle droghe vegetali. Capasso, F., Grandolini, G., & Izzo, A. A. (2006). Springer Verlag Italia, pp 555-574

Antibacterial activity and mode of action of the Artemisia capillaris essential oil and its constituents against respiratory tract infection-causing pathogens. C. Yang, D.-H. Hu, and Y. Feng, Molecular Medicine Reports, vol. 11, no. 4, pp. 2852–2860, 2015
https://www.ncbi.nlm.nih.gov/pubmed/25522803

Comparative anti-infectious bronchitis virus (IBV) activity of (−)-pinene: Effect on nucleocapsid (N) protein. Yang, Z.; Wu, N.; Zu, Y.; Fu, Y. Molecules 2011, 16, 1044–1054.
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259611/