β-Caryophyllene: A Sesquiterpene with Countless Biological Properties

Abstract

β-Caryophyllene (BCP), a natural bicyclic sesquiterpene, is a selective phytocannabinoid agonist of type 2 receptors (CB2-R). It isn’t psychogenic due to the absence of an affinity to cannabinoid receptor type 1 (CB1). Among the various biological activities, BCP exerts anti-inflammatory action via inhibiting the main inflammatory mediators, such as inducible nitric oxide synthase (iNOS), Interleukin 1 beta (IL-1β), Interleukin-6 (IL-6), tumor necrosis factor-alfa (TNF-α), nuclear factor kapp a-light-chain-enhancer of activated B cells (NF-κB), cyclooxygenase 1 (COX-1), cyclooxygenase 2 (COX-2). Peroxisome proliferator-activated receptors alpha (PPAR-α) effects are also mediated by the activation of PPAR-α and PPAR-γ receptors. In detail, many studies, in vitro and in vivo, suggest that the treatment with β-caryophyllene improves the phenotype of animals used to model various inflammatory pathologies, such as nervous system diseases (Parkinson’s disease, Alzheimer’s disease, multiple sclerosis, amyotrophic lateral sclerosis, stroke), atherosclerosis, and tumours (colon, breast, pancreas, lymphoma, melanoma and glioma cancer). Furthermore, pre-clinical data have highlighted that BCP is potentially useful in Streptococcus infections, osteoporosis, steatohepatitis, and exerts anticonvulsant, analgesic, myorelaxing, sedative, and antidepressive effects. BCP is non-toxic in rodents, with a Lethal dose, 50% (LD50) greater than 5000 mg/kg. Nevertheless, it inhibits various cytochrome P450 isoforms (above all, CYP3A4), which metabolise xenobiotics, leading to adverse effects, due to drug levels over therapeutic window. All the reported data have highlighted that both pharmacological and toxicological aspects need to be further investigated with clinical trials.

Chemical composition, insecticidal and biochemical effects of two plant oils and their major fractions against Aedes aegypti, the common vector of dengue fever

“…As described in our study, β-caryophyllene, the bicyclic sesquiterpene of J. procera EO was a promising mosquitocide against A. aegypti . These results are in a good accordance with the findings of many authors, where β-caryophyllene is proved as insecticide and repellant against pest insects ( de Elguea-Culebras et al., 2017 ; Francomano et al., 2019 ).…”

Traditionally Used Sideritis cypria Post.: Phytochemistry, Nutritional Content, Bioactive Compounds of Cultivated Populations

“…Orhan et al (2006) also reported the anti-inflammatory activity of the compound, while reviewing the synergistic effect of a-pinene with b-caryophyllene, as anti-inflammatory compounds. Interestingly, b-caryophyllene alone is a compound which has been demonstrated to possess a great potential application for various pathological conditions, as central nervous system diseases (Parkinson's disease, Alzheimer's disease), osteoporosis, cancer, and antibacterial (Francomano et al, 2019). Importantly, it is also approved as food additive, taste enhancer, and flavoring agent by U.S. Food and Drug Administration (FDA) and European Food Safety Authority (EFSA) (Fidyt et al, 2016;Machado et al, 2018).…”

Terpenes/Terpenoids in <b><i>Cannabis</i></b>: Are They Important?

“…This compound is the only terpene known to interact with the body's endocannabinoid system (selectively binds to the CB 2 receptor) [57]. Caryophyllene has gastroprotective, analgesic, anticancerogenic, antifungal, antibacterial, antidepressant, anti-inflammatory, antiproliferative, antioxidant, anxiolytic, analgesic, and neuroprotective effects [58,59]. The presence of β-caryophyllene in many essential oils might contribute strongly to their antiviral ability.…”