journal article·2019-12-11Open access

β-Caryophyllene: A Sesquiterpene with Countless Biological Properties

Fabrizio Francomano, Anna Caruso, Alexia Barbarossa, Alessia Fazio, Chiara La Torre, Jessica Ceramella, Rosanna Mallamaci, Carmela Saturnino, Domenico Iacopetta, Maria Stefania Sinicropi

Applied Sciences· Volume 9· Issue 24

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.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Plant-derived Lignans Synthesis and Bioactivity · Phytochemistry and Biological Activities · Natural product bioactivities and synthesis

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, Italy

Department of Biosciences, Biotechnology and Biopharmaceutics, University of Bari, Via Orabona 4, 70124 Bari, Italy

Department of Science, University of Basilicata, 85100 Potenza, Italy

References (86)

Show source-provided references
1. Biochemical and chemical characterization of Cynara cardunculus L. extract and its potential use as co-adjuvant therapy of chronic myeloid leukemia10.1016/j.jep.2017.03.026 ↗
2. Bergamot (Citrus bergamia Risso) Flavonoids and Their Potential Benefits in Human Hyperlipidemia and Atherosclerosis: An Overview10.2174/1389557515666150709110222 ↗
3. Assessment of antioxidant, antitumor and pro-apoptotic effects of Salvia fruticosa Mill. subsp. thomasii (Lacaita) Brullo, Guglielmo, Pavone & Terrasi (Lamiaceae)10.1016/j.fct.2017.05.040 ↗
4. Anchusa azurea Mill. (Boraginaceae) aerial parts methanol extract interfering with cytoskeleton organization induces programmed cancer cells death10.1039/C9FO00582J ↗
5. Resveratrol and Its Analogs As Antitumoral Agents For Breast Cancer Treatment10.2174/1389557516666160321113255 ↗
6. Role of Calabrian Black Rice in Metabolic Syndrome: In vitro Evaluation of Oryza sativa L. Indica Biological Properties10.2174/1573401313666170405153603 ↗
7. Chimento, A., De Amicis, F., Sirianni, R., Sinicropi, M.S., Puoci, F., Casaburi, I., Saturnino, C., and Pezzi, V. (2019). Progress to Improve Oral Bioavailability and Beneficial Effects of Resveratrol. Int. J. Mol. Sci., 20.10.3390/ijms20061381 ↗
8. Plastina, P., Apriantini, A., Meijerink, J., Witkamp, R., Gabriele, B., and Fazio, A. (2018). In Vitro Anti-Inflammatory and Radical Scavenging Properties of Chinotto (Citrus myrtifolia Raf.) Essential Oils. Nutrients, 10.10.3390/nu10060783 ↗
9. A systematic review on the neuroprotective perspectives of beta-caryophyllene10.1002/ptr.6199 ↗
10. Non-clinical toxicity of beta-caryophyllene, a dietary cannabinoid: Absence of adverse effects in female Swiss mice10.1016/j.yrtph.2017.12.013 ↗
11. Chemical Composition and Antimicrobial Activity of the Essential Oils from Annona cherimola (Annonaceae)
12. Beta-caryophyllene is a dietary cannabinoid10.1073/pnas.0803601105 ↗
13. beta-caryophyllene and beta-caryophyllene oxide-natural compounds of anticancer and analgesic properties10.1002/cam4.816 ↗
14. Cannabis sativa and Hemp
15. Cannabinoid signalling10.1016/j.lfs.2005.05.055 ↗
16. N-Alkyl Carbazole Derivatives as New Tools for Alzheimer’s Disease: Preliminary Studies10.3390/molecules19079307 ↗
17. Constrained analogues of tocainide as potent skeletal muscle sodium channel blockers towards the development of antimyotonic agents10.1016/j.ejmech.2008.01.023 ↗
18. Multifaceted properties of 1,4-dimethylcarbazoles: Focus on trimethoxybenzamide and trimethoxyphenylurea derivatives as novel human topoisomerase II inhibitors10.1016/j.ejps.2016.09.039 ↗
19. Benzothienoquinazolinones as new multi-target scaffolds: Dual inhibition of human Topoisomerase I and tubulin polymerization10.1016/j.ejmech.2019.111583 ↗
20. Carbazole derivatives: A promising scenario for breast cancer treatment10.2174/1389557515666150709111342 ↗
21. Quercetin and its derivative Q2 modulate chromatin dynamics in adipogenesis and Q2 prevents obesity and metabolic disorders in rats10.1016/j.jnutbio.2019.03.019 ↗
22. beta-Caryophyllene, a phytocannabinoid attenuates oxidative stress, neuroinflammation, glial activation, and salvages dopaminergic neurons in a rat model of Parkinson disease10.1007/s11010-016-2733-y ↗
23. Antinociceptive and anti-inflammatory effects of the essential oil from Eremanthus erythropappus leaves10.1211/jpp.60.6.0013 ↗
24. Protective effect of beta-caryophyllene, a natural bicyclic sesquiterpene, against cerebral ischemic injury10.1089/jmf.2012.2283 ↗
25. Trans-caryophyllene suppresses hypoxia-induced neuroinflammatory responses by inhibiting NF-kappaB activation in microglia10.1007/s12031-014-0243-5 ↗
26. Trans-caryophyllene inhibits amyloid beta (Abeta) oligomer-induced neuroinflammation in BV-2 microglial cells10.1016/j.intimp.2017.07.009 ↗
27. Microglia-specific localisation of a novel calcium binding protein, Iba110.1016/S0169-328X(98)00040-0 ↗
28. Ultrastructural study of remyelination in an experimental lesion in adult cat spinal cord10.1083/jcb.10.1.67 ↗
29. beta-Caryophyllene (BCP) ameliorates MPP plus induced cytotoxicity10.1016/j.biopha.2018.03.168 ↗
30. Viveros-Paredes, J.M., Gonzalez-Castaneda, R.E., Gertsch, J., Chaparro-Huerta, V., Lopez-Roa, R.I., Vazquez-Valls, E., Beas-Zarate, C., Camins-Espuny, A., and Flores-Soto, M.E. (2017). Neuroprotective Effects of beta-Caryophyllene against Dopaminergic Neuron Injury in a Murine Model of Parkinson’s Disease Induced by MPTP. Pharmaceuticals, 10.10.3390/ph10030060 ↗
31. Oncogene-induced Nrf2 transcription promotes ROS detoxification and tumorigenesis10.1038/nature10189 ↗
32. beta-Caryophyllene protects in vitro neurovascular unit against oxygen-glucose deprivation and re-oxygenation-induced injury10.1111/jnc.13833 ↗
33. beta-Caryophyllene protects the C6 glioma cells against glutamate-induced excitotoxicity through the Nrf2 pathway10.1016/j.neuroscience.2014.08.043 ↗
34. The cannabinoid beta-caryophyllene (BCP) induces neuritogenesis in PC12 cells by a cannabinoid-receptor-independent mechanism10.1016/j.cbi.2016.11.015 ↗
35. Chemical composition and analgesic activity of Senecio rufinervis essential oil10.3109/13880209.2010.491083 ↗
36. Antiallodynic effect of beta-caryophyllene on paclitaxel-induced peripheral neuropathy in mice10.1016/j.neuropharm.2017.07.015 ↗
37. Involvement of peripheral cannabinoid and opioid receptors in beta-caryophyllene-induced antinociception10.1002/j.1532-2149.2012.00242.x ↗
38. Alberti, T.B., Barbosa, W.L., Vieira, J.L., Raposo, N.R., and Dutra, R.C. (2017). (-)-beta-Caryophyllene, a CB2 Receptor-Selective Phytocannabinoid, Suppresses Motor Paralysis and Neuroinflammation in a Murine Model of Multiple Sclerosis. Int. J. Mol. Sci., 18.10.3390/ijms18040691 ↗
39. Evaluation of anxiolytic and sedative effect of essential oil and hydroalcoholic extract of Ocimum basilicum L. and chemical composition of its essential oil
40. Sedative effects of essential oils obtained from Baccharis uncinella10.3109/13880209.2011.634423 ↗
41. beta-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice10.1016/j.physbeh.2014.06.003 ↗
42. Antispasmodic effects of essential oil of Pterodon polygalaeflorus and its main constituent beta-caryophyllene on rat isolated ileum10.1111/j.1472-8206.2009.00800.x ↗
43. Anticonvulsant activity of beta-caryophyllene against pentylenetetrazol-induced seizures10.1016/j.yebeh.2015.12.040 ↗
44. Pharmacological characterization of the cannabinoid receptor 2 agonist, beta-caryophyllene on seizure models in mice10.1016/j.seizure.2018.03.009 ↗
45. The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene beta-Caryophyllene from the Essential Oil of Aquilaria crassna10.3390/molecules200711808 ↗
46. The Influence of Sesquiterpenes from Myrica rubra on the Antiproliferative and Pro-Oxidative Effects of Doxorubicin and Its Accumulation in Cancer Cells10.3390/molecules200815343 ↗
47. Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel10.1211/jpp.59.12.0005 ↗
48. beta-Caryophyllene potently inhibits solid tumor growth and lymph node metastasis of B16F10 melanoma cells in high-fat diet-induced obese C57BL/6N mice10.1093/carcin/bgv076 ↗
49. Synergistic interaction of beta-caryophyllene with aromadendrene oxide 2 and phytol induces apoptosis on skin epidermoid cancer cells
50. Amiel, E., Ofir, R., Dudai, N., Soloway, E., Rabinsky, T., and Rachmilevitch, S. (2012). β-Caryophyllene, a Compound Isolated from the Biblical Balm of Gilead (Commiphora gileadensis), Is a Selective Apoptosis Inducer for Tumor Cell Lines. Evid. Based Complement. Altern.10.1155/2012/872394 ↗
51. Effects of beta-caryophyllene on arginine ADP-ribosyltransferase 1-mediated regulation of glycolysis in colorectal cancer under high-glucose conditions
52. The combination of beta-caryophyllene, baicalin and catechin synergistically suppresses the proliferation and promotes the death of RAW267.4 macrophages in vitro10.3892/ijmm.2016.2801 ↗
53. Beta-caryophyllene protects against diet-induced dyslipidemia and vascular inflammation in rats: Involvement of CB2 and PPAR-gamma receptors10.1016/j.cbi.2018.10.010 ↗
54. Inhibitory effect of trans-caryophyllene (TC) on leukocyte-endothelial attachment10.1016/j.taap.2017.06.016 ↗
55. Acute administration of beta-caryophyllene prevents endocannabinoid system activation during transient common carotid artery occlusion and reperfusion10.1186/s12944-018-0661-4 ↗
56. β-Caryophyllene, the major constituent of copaiba oil, reduces systemic inflammation and oxidative stress in arthritic rats10.1002/jcb.27369 ↗
57. Anti-Inflammatory and Antioxidant Actions of Copaiba Oil Are Related to Liver Cell Modifications in Arthritic Rats10.1002/jcb.25998 ↗
58. The effect of beta-caryophyllene on nonalcoholic steatohepatitis10.1293/tox.2017-0018 ↗
59. Inhibitory effects of beta-caryophyllene on Streptococcus mutans biofilm10.1016/j.archoralbio.2018.01.009 ↗
60. Chemical composition and antibacterial activity of essential oil from Artemisia feddei
61. beta-Caryophyllene promotes osteoblastic mineralization, and suppresses osteoclastogenesis and adipogenesis in mouse bone marrow cultures in vitro10.3892/etm.2016.3818 ↗
62. Toxicological Evaluation of beta-Caryophyllene Oil: Subchronic Toxicity in Rats10.1177/1091581816655303 ↗
63. Gastric cytoprotection of the non-steroidal anti-inflammatory sesquiterpene, beta-caryophyllene10.1055/s-2006-957942 ↗
64. The inhibitory effects of beta-caryophyllene, beta-caryophyllene oxide and alpha-humulene on the activities of the main drug-metabolizing enzymes in rat and human liver in vitro10.1016/j.cbi.2017.10.021 ↗
65. Flavouring Group Evaluation 78 (FGE.78Rev2): Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromati hydrocarbons evaluated by EFSA in FGE.25Rev3
66. microRNAs to Monitor Pain-migraine and Drug Treatment10.2174/2211536606666170913152821 ↗
67. Gallelli, L., Cione, E., Peltrone, F., Siviglia, S., Verano, A., Chirchiglia, D., Zampogna, S., Guidetti, V., Sammartino, L., and Montana, A. (2019). Hsa-miR-34a-5p and hsa-miR-375 as Biomarkers for Monitoring the Effects of Drug Treatment for Migraine Pain in Children and Adolescents: A Pilot Study. J. Clin. Med., 8.10.3390/jcm8070928 ↗
68. Human kidney podocyte cell population as a novel biological target of nerve growth factor10.3109/08977194.2014.975799 ↗
69. New insights for the use of quercetin analogs in cancer treatment10.4155/fmc-2017-0118 ↗
70. 3-(Dipropylamino)-5-hydroxybenzofuro[2,3-f]quinazolin-1(2H)-one (DPA-HBFQ-1) plays an inhibitory role on breast cancer cell growth and progression10.1016/j.ejmech.2015.11.004 ↗
71. Novel Gold and Silver Carbene Complexes Exert Antitumor Effects Triggering the Reactive Oxygen Species Dependent Intrinsic Apoptotic Pathway10.1002/cmdc.201700634 ↗
72. N-heterocyclic carbene complexes of silver and gold as novel tools against breast cancer progression10.4155/fmc-2016-0160 ↗
73. Finding solutions for agricultural wastes: Antioxidant and antitumor properties of pomegranate Akko peel extracts and beta-glucan recovery10.1039/C8FO01394B ↗
74. N-thioalkylcarbazoles derivatives as new anti-proliferative agents: Synthesis, characterisation and molecular mechanism evaluation10.1080/14756366.2017.1419216 ↗
75. Proliferative and anti-proliferative effects of retinoic acid at doses similar to endogenous levels in Leydig MLTC-1/R2C/TM-3 cells10.1016/j.bbagen.2010.06.006 ↗
76. Synthesis, characterization and cytotoxic activity on breast cancer cells of new half-titanocene derivatives10.1016/j.bmcl.2013.03.059 ↗
77. Inhibition of human topoisomerase I and II and anti-proliferative effects on MCF-7 cells by new titanocene complexes10.1016/j.bmc.2015.10.030 ↗
78. Inhibition of Human Topoisomerase II by N,N,N-Trimethylethanammonium Iodide Alkylcarbazole Derivatives10.1002/cmdc.201800546 ↗
79. Old Drug Scaffold, New Activity: Thalidomide-Correlated Compounds Exert Different Effects on Breast Cancer Cell Growth and Progression10.1002/cmdc.201600629 ↗
80. Different 6-Aryl-Fulvenes Exert Anti-proliferative effects on Cancer Cells10.2174/1871520614666141019190855 ↗
81. Saturnino, C., Popolo, A., Ramunno, A., Adesso, S., Pecoraro, M., Plutino, M.R., Rizzato, S., Albinati, A., Marzocco, S., and Sala, M. (2017). Anti-Inflammatory, Antioxidant and Crystallographic Studies of N-Palmitoyl-ethanol Amine (PEA) Derivatives. Molecules, 22.10.3390/molecules22040616 ↗
82. Augimeri, G., Plastina, P., Gionfriddo, G., Rovito, D., Giordano, C., Fazio, A., Barone, I., Catalano, S., Ando, S., and Bonofiglio, D. (2019). N-Eicosapentaenoyl Dopamine, A Conjugate of Dopamine and Eicosapentaenoic Acid (EPA), Exerts Anti-inflammatory Properties in Mouse and Human Macrophages. Nutrients, 11.10.3390/nu11092247 ↗
83. Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products10.1016/j.foodchem.2018.12.007 ↗
84. Synthesis, inhibition of NO production and antiproliferative activities of some indole derivatives10.1080/14756360802693890 ↗
85. In vitro antioxidant activity of extracts of Sybaris liquorice roots from Southern Italy10.1080/14786419.2011.647022 ↗
86. Comparison of fatty acid profile and antioxidant potential of extracts of seven Citrus rootstock seeds10.1080/14786419.2011.647023 ↗