Interaction of β-caryophyllene and β-caryophyllene oxide with phospholipid bilayers: Differential scanning calorimetry study

Sarpietro, Maria Grazia; Sotto, Antonella Di; Accolla, Maria Lorena; Castelli, Francesco

doi:10.1016/j.tca.2014.11.029

Cited by 49 publications

(32 citation statements)

References 28 publications

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“…On the other hand, because of their lipophilic nature, CRY and CRYO can also interact with the cell biomembranes and alter the phospholipid structure, so interfering with the uptake of CBE into cells. In support, in some permeation kinetic experiments by multilamellar vesicles of dimyristoylphosphatidylcholine, we highlighted that both compounds are able to bind the phospholipid bilayer, with a higher effect of CRY, and to diffuse across the biomembrane model (Sarpietro et al, ). We also found that CRY was able to inhibit in vitro the lipid peroxidation, so suggesting a potential protective effects on the biomembrane phospholipids (Di Sotto et al, unpublished data).…”

Section: Discussionsupporting

confidence: 72%

Mutagenicity of cigarette butt waste in the bacterial reverse mutation assay: The protective effects of β‐caryophyllene and β‐caryophyllene oxide

Giacomo

Mazzanti²,

Sotto

2015

Environmental Toxicology

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Cigarette filters pose a serious litter and toxic waste disposal problem, because of their not biodegradability and to the leaching of toxins in the environment. Therefore, cigarette butts need to be manipulated as special waste, with potential risks to human health and environment. In the present study, the genotoxic potential of a methanol extract from commonly discharged cigarette butts (CBE) was evaluated in the bacterial reverse mutation assay on Salmonella typhimurium TA98 and TA100 and Escherichia coli WP2uvrA strains, both in the absence and presence of the S9 exogenous metabolic activator. Furthermore, the ability of the natural sesquiterpenes β-caryophyllene (CRY) and β-caryophyllene oxide (CRYO) to inhibit the mutagenicity of CBE was studied as a possible preventive strategy. In order to identify the potential antimutagenic mechanisms, three different protocols (pretreatment, cotreatment, and posttreatment) were applied. CBE showed to increase the number of revertant colonies in all the strains tested in presence of S9, so resulting mutagenic. In the antimutagenicity assay, both CRY and CRYO significantly reduced the revertant colonies induced by CBE, although with different potency and specificity. For both sesquiterpenes, the antimutagenicity was strong in all experimental conditions, except for the cotreatment of CRY with CBE in WP2uvrA, which produced a moderate inhibition. Both desmutagenic and bioantimutagenic mechanisms seem to be involved in the antimutagenicity of the test substances. Taking into account the potential genotoxicity of cigarette butts, CRY and CRYO appear as possible further candidates as environmental decontaminants against this hazardous waste. © 2015 Wiley Periodicals, Inc. Environ Toxicol 31: 1319-1328, 2016.

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Section: Discussionsupporting

confidence: 72%

Mutagenicity of cigarette butt waste in the bacterial reverse mutation assay: The protective effects of β‐caryophyllene and β‐caryophyllene oxide

Giacomo

Mazzanti²,

Sotto

2015

Environmental Toxicology

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“…Both compounds exhibit low water solubility, thereby the aqueous medium such as biological fluids, impede their absorption to the cell. However, it was shown that both BCP and BCPO are able to interact with artificial lipid bilayer, which strongly suggests their high affinity to the cell membrane . The potential obstacles associated with poor solubility of these sesquiterpenes in aqueous fluids may be overcome through usage of liposomal drug delivery system, which provides much higher bioavailability of these compounds and by that ensures obtaining desired biological effects.…”

Section: Introductionmentioning

confidence: 99%

β‐caryophyllene and β‐caryophyllene oxide—natural compounds of anticancer and analgesic properties

et al. 2016

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Natural bicyclic sesquiterpenes, β‐caryophyllene (BCP) and β‐caryophyllene oxide (BCPO), are present in a large number of plants worldwide. Both BCP and BCPO (BCP(O)) possess significant anticancer activities, affecting growth and proliferation of numerous cancer cells. Nevertheless, their antineoplastic effects have hardly been investigated in vivo. In addition, both compounds potentiate the classical drug efficacy by augmenting their concentrations inside the cells. The mechanisms underlying the anticancer activities of these sesquiterpenes are poorly described. BCP is a phytocannabinoid with strong affinity to cannabinoid receptor type 2 (CB 2), but not cannabinoid receptor type 1 (CB 1). In opposite, BCP oxidation derivative, BCPO, does not exhibit CB 1/2 binding, thus the mechanism of its action is not related to endocannabinoid system (ECS) machinery. It is known that BCPO alters several key pathways for cancer development, such as mitogen‐activated protein kinase (MAPK), PI3K/AKT/mTOR/S6K1 and STAT3 pathways. In addition, treatment with this compound reduces the expression of procancer genes/proteins, while increases the levels of those with proapoptotic properties. The selective activation of CB 2 may be considered a novel strategy in pain treatment, devoid of psychoactive side effects associated with CB 1 stimulation. Thus, BCP as selective CB 2 activator may be taken into account as potential natural analgesic drug. Moreover, due to the fact that chronic pain is often an element of cancer disease, the double activity of BCP, anticancer and analgesic, as well as its beneficial influence on the efficacy of classical chemotherapeutics, is particularly valuable in oncology. This review is focused on anticancer and analgesic activities of BCP and BCPO, the mechanisms of their actions, and potential therapeutic utility.

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“…20,31,32 Moreover, β-caryophyllene is able to interact with artificial lipid bilayer. 33 Citral reduced DENV-2 infection in the NS1 reduction assay in HepG-2 cells. Nevertheless, the same effect was not observed against this serotype and the others in the in-situ ELISA assay in Vero cells.…”

Section: Discussionmentioning

confidence: 93%

Evaluation of in vitro Antiviral Activity of Essential Oil Compounds Against Dengue Virus

Flechas¹,

Ocazionez²,

Stashenko³

2017

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Introduction:There are not effective drugs available for treatment of dengue fever despite intensive research on synthetic inhibitors. The search for active phytochemicals could serve for the discovery of new drugs. This study aims to evaluate the antiviral activity in vitro of compounds found in essential oils from medicinal plants. Materials and Methods: Nine synthetic-derived essential oil compounds were evaluated. Antiviral effect was screened measuring the reduction of viral NS1 and E proteins in HepG-2 and Vero cells. Results: β-Caryophyllene was identified as the most active compound, it reduced the virus serotype-2 replication in HepG-2 cells at IC 50 of 22 ± 5.6 µM, and blocked replication of all four serotypes in Vero cells at IC 50 between 8.0 µM and 15.0 µM. The selectivity indexes were between 5.3 and 10. According to results from time-in-addition assays, the antiviral effect of β-caryophyllene appears to be associated with interruption of early steps of the virus life cycle. Citral revealed modest antiviral effect, it reduced the virus serotype-2 (IC 50 of 31 ± 4.5 µM) replication but not the other three serotypes. Seven terpenes did not reveal antiviral activity at maximum concentration of 30 µM. Conclusion: Research on compounds found in essential oils can contribute to the drug discovery effort for dengue. β-Caryophyllene could serve as a starting point.

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Interaction of β-caryophyllene and β-caryophyllene oxide with phospholipid bilayers: Differential scanning calorimetry study

Cited by 49 publications

References 28 publications

Mutagenicity of cigarette butt waste in the bacterial reverse mutation assay: The protective effects of β‐caryophyllene and β‐caryophyllene oxide

Mutagenicity of cigarette butt waste in the bacterial reverse mutation assay: The protective effects of β‐caryophyllene and β‐caryophyllene oxide

β‐caryophyllene and β‐caryophyllene oxide—natural compounds of anticancer and analgesic properties

Evaluation of in vitro Antiviral Activity of Essential Oil Compounds Against Dengue Virus

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