Alpha phellandrene

Standards used include cis-3,7-dimethyl-2,6-octadien-1-ol (Aldrich, 268909-5ML), α-pinene (Aldrich, P-7408), β-myrcene (Sigma, M-0382), 1,8-cineole (Aldrich, C8,060-1), γ-terpinene (Aldrich, T2134), limonene (Sigma-Aldrich, 62118), camphene (Sigma-Aldrich, 456055), alpha-phellandrene (Sigma-Aldrich, W285611), 2-carene (Sigma-Aldrich, 232386), beta-phellandrene (Carbosynth, FB158830), linalool (Aldrich, L2602), and a 70% sabinene solution (kindly donated by VIORYL S.A., Athens, Greece). Phusion High-Fidelity DNA Polymerase (New England BioLabs, M0530S) and MyTaq DNA polymerase (BIO-21105, Bioline) were used in PCR amplifications. The QIAquick Gel Extraction Kit (#28704, Qiagen) was used for gel extraction and DNA purification. The NucleoSpin Plasmid Kit (740588.250, Macherey-Nagel) was used for plasmid DNA purification. Restriction enzymes used were from New England BioLabs.

The flavonoids aglycones luteolin, chrysoeriol and kaempferol were obtained from Extrasynthèse S.A. (Lyon, France). Vitexin-2-O-rhamnoside, apigenin-7-O-glucuronide, apigenin, quercetin, cannabigerolic acid (CBGA), tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA) were purchased from Sigma-Aldrich Chemie GmbH (Buchs, Switzerland) and luteolin-7-O-glucuronide from HWI-group (Rülzheim, Germany). (+)-alpha-Pinene, (−)-beta-Pinene, beta-Myrcene, Ocimene, L-Linalool, (E)-beta-Caryophyllene, alpha-Humulene, (−)-alpha-Bisabolol, S(−)-Limonene, alpha-Phellandrene, 1.8-Cineol, Terpinolene and gamma-Terpinene were purchased from Sigma-Aldrich Chemie GmbH (Buchs, Switzerland).
Acetonitrile (LC-MS grade) was supplied by VWR International GmbH (Dietikon, Switzerland). Water (LC-MS grade) and methanol (HPLC grade) were supplied by Carl Roth AG (Arlesheim, Switzerland). Trifluoroacetic acid (TFA) and dimethysulfoxide (DMSO) were supplied by Sigma-Aldrich Chemie GmbH (Buchs, Switzerland).