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4 protocols using cannabigerolic acid

1

Quantification of Phytocannabinoids and Terpenoids

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Liquid chromatography-mass spectrometric (LC/MS) grade acetonitrile (catalog number 1.00029), methanol (1.06035), and water (1.15333); and gas chromatography (GC) headspace grade dimethyl sulfoxide (DMSO) (1.01900) were purchased from Mercury Scientific and Industrial Products Ltd. (Rosh Haayin, Israel). Ethanol, (catalog number 052541), acetic acid (010778) and n-Hexane (091484) were obtained from BioLab Ltd. (Jerusalem, Israel). Phytocannabinoid analytical standards (>98%) CBG, THC, CBD, CBC, CBN, Cannabigerolic acid (CBGA), TetrahydroCannabinolic acid (THCA), Cannabidiolic acid (CBDA), Cannabinolic acid (CBNA), Cannabichromenic Acid (CBCA), (-)-Δ8-trans-tetrahydrocannabinol (Δ8-THC), tetrahydrocannabivarin (THCV), Cannabidivarin (CBDV), Cannabidivarinic acid (CBDVA) and Cannabicyclol (CBL) were purchased from Sigma-Aldrich (Rehovot, Israel); Cannabichromevarin (CBCV) was purchased from Cayman Chemical (Ann Arbor, MI, United States). Terpenoid analytical standards (>95% unless stated otherwise) were purchased from Sigma-Aldrich (Rehovot, Israel); valencene (>80% pure), α- and β-curcumene (>90% pure), α-phellandrene, and sabinene were purchased from Extrasynthese (Genay, France); a mixture of n-alkanes was purchased from Sigma R 769 (40 mg/mL, C8-C20, Saint Louis, MO, United States) for semi-quantitative analysis.
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2

Comprehensive Cannabis Phytochemical Analysis

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PCL (Mw ∼ 14 000),
carboxymethylcellulose (CMC), Tween 20, cremophor, phosphate buffered
saline (PBS, pH 7.4), liquid chromatography–mass spectrometry
(LC/MS) grade acetic acid, and high-performance liquid chromatography
(HPLC) grade dichloromethane were purchased from Sigma-Aldrich (Rehovot,
Israel). LC/MS grade acetonitrile, methanol, and water, and HPLC grade
ethanol were obtained from Mercury Scientific and Industrial Products
Ltd. (Rosh Haayin, Israel) or Bio-Lab Ltd. (Jerusalem, Israel). (−)-trans9-tetrahydrocannabinolic acid9-THCA), cannabidiolic acid (CBDA), cannabigerolic acid (CBGA),
cannabichromenic acid (CBCA), cannabinolic acid (CBNA), cannabidivarinic
acid (CBDVA), Δ9-THC, CBD, cannabigerol (CBG), cannabichromene
(CBC), CBN, (−)-trans9-tetrahydrocannabivarin
9-THCV), cannabidivarin (CBDV), cannabichromevarin
(CBCV), Δ9-THC-d3, CBD-d3, and CBN-d3 were purchased
from Sigma-Aldrich (Rehovot, Israel). All the phytocannabinoid standards
were of analytical grade (>98%).
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3

Evaluation of Cannabinoid Compounds

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General chemicals were from VWR (West Chester, PA) and Sigma Aldrich (St. Louis, MO). PMA and Ionomycin were from Calbiochem (Gibbstown, NJ). IgE anti-DNP is from Sigma and KLH-DNP was from Calbiochem. Capsaicin and Capsazepine were from Sigma Aldrich. Cannabidivarin (CBDV), Cannabichromene (CBC), Cannabidiol (CBD), Cannabidiolic Acid (CBDA), Cannabigerol (CBG), Cannabigerolic Acid (CBGA), Cannabinol (CBN) were from Sigma Aldrich.
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4

Terpenoid and Cannabinoid Standards Catalogue

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The following terpenoid standards were purchased from Supelco: α-pinene, camphene, β-pinene, myrcene, 3-carene, α-terpinene, p-cymene, limonene, γ-terpinene, fenchone, terpinolene, linalool, camphor, isoborneol, borneol, menthol, α-terpineol, β-citronellol, neryl acetate, geranyl acetate, α-cedrene, β-caryophyllene, α-humulene, cis-nerolidol, geranyl isobutyrate, caryophyllene oxide, β-eudesmol, α-bisabolol, and phytol. Cannabinoid standards were purchased from Sigma Aldrich (1 mg/mL): cannabidiolic acid (CBD-A), cannabigerolic acid (CBG-A), cannabigerol (CBG), cannabidiol (CBD), cannabinol (CBN), Δ-9-tetrahydrocannabinol (Δ-9-THC), Δ-8-tetrahydrocannabinol (Δ-8-THC), cannabichromene (CBC), Δ-9-tetrahydrocannabinolic acid (Δ-9-THC-A), and cannabichromenic acid (CBC-A). Acid standards were dissolved in acetonitrile, and nonacid standards were dissolved in methanol. Hexane, ammonium format, and acetonitrile were purchased from Sigma Aldrich, methanol was purchased from J. T. Baker and formic acid was purchased from Scharlau. Chemical structures of essential oils and cannabinoids are presented in Supplementary Materials [37 ,38 ,39 ].
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