The chemicals β-caryophyllene (≥98.5% purity), β-caryophyllene oxide (95% purity), and verapamil hydrochloride (≥98.0% purity) were purchased from Merck Life Science S.r.l. (Milan, Italy), while sorafenib tosylate (≥99.0% purity) and MK571 (≥96.0% purity) were purchased from Santa Cruz Biotechnology, Inc. (Santa Cruz, CA, USA). Dulbecco’s Modified Eagle’s medium (DMEM), Roswell Park Memorial Institute (RPMI) 1640 culture medium, fetal bovine serum, buffer, and cofactors were from Aurogene S.r.l. (Rome, Italy). EtOH (100% v/v) was used to dissolve β-caryophyllene and β-caryophyllene oxide, while DMSO (100% v/v) was used for sorafenib tosylate, verapamil hydrochloride, and MK571. Solvents were used up to 1% v/v nontoxic concentration.
β caryophyllene oxide
Manufactured by Merck Group
Sourced in United States
β-caryophyllene oxide is a chemical compound found in the essential oils of various plants. It is a colorless or pale yellow crystalline solid. β-caryophyllene oxide is used as a chemical standard and reference material in analytical applications.
Automatically generated - may contain errors
Lab products found in correlation
β caryophyllene, by Merck Group (5 mentions)
Dulbecco s modified eagle s medium dmem, by Aurogene (2 mentions)
Valencene, by Merck Group (2 mentions)
α humulene, by Merck Group (2 mentions)
Verapamil hydrochloride, by Merck Group (1 mentions)
Sorafenib tosylate, by Santa Cruz Biotechnology (1 mentions)
Fetal bovine serum (fbs), by Aurogene (1 mentions)
Mk 571, by Santa Cruz Biotechnology (1 mentions)
Gentamicin sulfate, by Thermo Fisher Scientific (1 mentions)
Doxorubicin, by Merck Group (1 mentions)
Fetal bovine serum (fbs), by Thermo Fisher Scientific (1 mentions)
Neutral red, by Merck Group (1 mentions)
Resazurin, by Merck Group (1 mentions)
N 2 hydroxyethylpiperazine n 2 ethanesulfonic acid hepes buffer, by Merck Group (1 mentions)
Rhodamine 123 rho 123, by Merck Group (1 mentions)
D glutamine, by Merck Group (1 mentions)
Mccoy s medium modified, by Merck Group (1 mentions)
Trans nerolidol, by Merck Group (1 mentions)
Rpmi 1640, by Merck Group (1 mentions)
Sodium pyruvate, by Merck Group (1 mentions)
8 protocols using β caryophyllene oxide
1
Compound Isolation and Solubilization
2
Enzymatic Synthesis of Terpene Derivatives
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Catechol, L-DOPA, trisodium citrate, HP-β-CD, and GlcDH from Bacillus sp. were purchased from FUJIFILM Wako Pure Chemical (Osaka, Japan). NTA•3Na•H 2 O, EDTA•2Na•2H 2 O, DTPA, phen, cyclam, and TPA were purchased from Tokyo Chemical Industry (Tokyo, Japan). (+)-Valencene, (+)-nootkatone, (-)isolongifolene, (-)-β-caryophyllene, and (-)-βcaryophyllene oxide were purchased from Merck (Darmstadt, Germany). (+)-Valencene oxide, (-)isolongifolene oxide, and (-)-isolongifolenone were synthesized and provided by T. Hasegawa (Kanagawa, Japan). (+)-Valencene oxide and (-)-isolongifolene oxide were synthesized using mCPBA from (+)-Valencene and (-)-isolongifolene by reference to previous studies [21, 22] . (+)-Valencene oxide was obtained as a mixture of diastereomers (α:β = 1:2) and used as the mixed authentic sample. (-)-Isolongifolenone was synthesized using chromium hexacarbonyl and tert-butyl hydroperoxide from (-)-isolongifolene, as previously reported [6] . All other chemicals were of analytical grade.
3
Cytotoxicity Evaluation of Sesquiterpenes
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McCoy’s modified medium, RPMI-1640, N-2-hydroxyethylpiperazine-N′-2-ethanesulfonic acid (HEPES) buffer, sodium pyruvate, d -glutamine, resazurin, rhodamine 123 (RHO 123) and neutral red were supplied by Sigma-Aldrich (Prague, Czech Republic). Fetal bovine serum and gentamicin sulfate were purchased from Invitrogen (Carlsbad, CA, USA) and bovine serum albumin (BSA) from Fluka (Prague, Czech Republic). Doxorubicin and pure sesquiterpenes (α-humulene, β-caryophyllene oxide, trans-nerolidol, valencene) were supplied by Sigma-Aldrich. Stock solutions of sesquiterpenes were prepared in dimethyl sulfoxide (DMSO) and stored in the dark at 4 °C. All other chemicals used were of HPLC or analytical grade and provided by Sigma-Aldrich.
4
Cannabinoids and Sesquiterpenes Characterization
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The chemicals β-caryophyllene (≥98.5% purity), β-caryophyllene oxide (≥99% purity), α-humulene (≥96.0% purity), cannabidiol (CBD, ≥99.0% purity), cannabichromene (CBC, ≥99.0% purity), 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide (MTT, ≥97.5% purity) were purchased from Sigma Aldrich Co (St. Louis, MO, USA), while AM281 (≥98.0% purity) and AM630 (≥98.0% purity) from Tocris bioscience (Bristol, UK). Dulbecco’s Modified Eagle’s Medium (DMEM) was provided by Aurogene (Rome, Italy).
To perform the experiments, all the solutions were prepared in the appropriate solvent, sterilized, and stored at the recommended temperature for a conservation time. Nonintoxicating phytocannabinoids (i.e., cannabidiol and cannabichromene) and caryophyllane sesquiterpenes (i.e., β-caryophyllene, β-caryophyllene oxide, and α-humulene) were dissolved in EtOH 100% v/v, while the CB1 and CB2 receptor antagonists (i.e., AM281 and AM630) in DMSO 100% v/v. EtOH and DMSO were used at a maximum concentration of 1% v/v in cell medium to avoid any cytotoxicity.
To perform the experiments, all the solutions were prepared in the appropriate solvent, sterilized, and stored at the recommended temperature for a conservation time. Nonintoxicating phytocannabinoids (i.e., cannabidiol and cannabichromene) and caryophyllane sesquiterpenes (i.e., β-caryophyllene, β-caryophyllene oxide, and α-humulene) were dissolved in EtOH 100% v/v, while the CB1 and CB2 receptor antagonists (i.e., AM281 and AM630) in DMSO 100% v/v. EtOH and DMSO were used at a maximum concentration of 1% v/v in cell medium to avoid any cytotoxicity.
5
Standardization of Black Pepper for Analysis
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Black pepper (BP) was provided by Ottogi Vietnam Co., Ltd. and obtained from Shinyoung (Gwangju, Gyeonggi, Korea). These BP (5 mm, about 0.02 g) were harvested in 2020. They were dried to a moisture content of < 17%. The samples were stored in a shaded place until analysis. To obtain uniform-sized samples prior to analysis, the BP was ground using a high-speed blender for approximately 1 min. At this time, it was carefully and smoothly crushed to prevent any temperature increase. This is because, as the temperature increases, the quantity and quality of the components extracted from samples decrease (Liu et al., 2018 ). The crushed BP was sieved with a particle size of 425 µm to obtain a fine powder. It was used immediately to minimize the loss of the components in the sample.
Standard chemicals, including trans-caryophyllene (β-caryophyllene) and β-caryophyllene oxide, were purchased from Sigma-Aldrich (St. Louis, MO, USA). All chemicals and solvents were graded as gas chromatography. The solvent was mainly used from methanol (99.9% purity) and n-hexane (95% purity).
Standard chemicals, including trans-caryophyllene (β-caryophyllene) and β-caryophyllene oxide, were purchased from Sigma-Aldrich (St. Louis, MO, USA). All chemicals and solvents were graded as gas chromatography. The solvent was mainly used from methanol (99.9% purity) and n-hexane (95% purity).
6
Cytotoxicity Evaluation of Phytochemicals
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β-caryophyllene, humulene, β-caryophyllene oxide, zerumbone, thiazolyl blue tetrazolium bromide (MTT), thioflavin T, trypan blue, tert-butyl hydroperoxide (t-BHP), DMSO, Roswell Park Memorial Institute 1640 (RPMI) medium, non-essential amino acids (NEAA), penicillin/streptomycin, trypsin EDTA, foetal bovine serum (FBS), ascorbic acid, α-tocopherol, glutathione, AM251, SR144528 and phosphate buffered saline (PBS) were all supplied by Sigma-Aldrich (Sydney, Australia).
7
Pharmacological Modulation of Nociception
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Paracetamol, β-caryophyllene oxide, methiothepin, glibenclamide, [1 ,2 (link),4 (link)] oxadiazolo [4,3-a]quinoxalin-1-one (ODQ), N(G)-nitro-l -arginine methyl ester hydrochloride (l -NAME), and l -arginine were obtained from Sigma-Aldrich (St. Louis, MO, USA), and naloxone was acquired from Pisa Laboratories (Mexico City, Mexico). All drugs were suspended in carboxymethylcellulose (0.1%) and prepared minutes before being given to the animals. β-caryophyllene oxide and Paracetamol were administered orally (0.1 mL/10 g of body weight). Naloxone, methiothepin, l -NAME, ODQ, l -arginine, and glibenclamide were injected intraperitoneally (0.1 mL/10 g of body weight). Formalin (2%) was prepared by diluting aqueous formaldehyde to 37% from J.T. Baker (Matsonford Rd. Radnor Township, PA, USA).
8
Natural Sesquiterpenes and Doxorubicin Anticancer Effects
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All the chemicals, including β-caryophyllene (≥98.5% purity), β-caryophyllene oxide (95% purity), doxorubicin hydrochloride (98.0%–102.0% purity), rhodamine and ethanol (EtOH; ≥99.5% purity) were purchased from Sigma Aldrich Co (St. Louis, MO, USA). Dulbecco’s Modified Eagle’s Medium Ham’s F12 (DMEM-F12) was provided by Aurogene (Rome, Italy). The sources of antibodies and materials for molecular biology analysis were specified in the relative paragraphs. To perform the experiments, all solutions were prepared in the better solvent, sterilized and stored for a just conservation time at recommended temperature. The natural sesquiterpenes and doxorubicin were dissolved in EtOH 100% v/v and deionized water, respectively, and hence were diluted in the complete medium. In order to avoid any cytotoxicity, EtOH was used at a maximum concentration of 1% v/v in the medium.
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