Toluene (ACS grade, ≥99%) and the analytical standards (myrcene, caryophyllene, farnesene, humulene) used for GC-MS analyses were purchased from Sigma-Aldrich (St. Louis, MO, USA).
Farnesene
Manufactured by Merck Group
Sourced in United States
Farnesene is a naturally occurring isoprenoid compound produced by various plants and microorganisms. It is a colorless liquid with a mild odor. Farnesene is used as a precursor in the production of various chemical compounds and materials.
Automatically generated - may contain errors
Lab products found in correlation
Limonene, by Merck Group (3 mentions)
Linalool, by Merck Group (3 mentions)
Myrcene, by Merck Group (2 mentions)
α pinene, by Merck Group (2 mentions)
γ terpinene, by Merck Group (2 mentions)
Methyl salicylate, by Merck Group (2 mentions)
β myrcene, by Merck Group (2 mentions)
Ocimene, by Merck Group (2 mentions)
Caryophyllene, by Merck Group (1 mentions)
Humulene, by Merck Group (1 mentions)
Nonanal, by Merck Group (1 mentions)
Geraniol, by Merck Group (1 mentions)
Eugenol, by Merck Group (1 mentions)
Decanal, by Merck Group (1 mentions)
P anisaldehyde, by Merck Group (1 mentions)
3 methylbutanal, by Merck Group (1 mentions)
Methyl anthranilate, by Merck Group (1 mentions)
Methyl isonicotinate, by Merck Group (1 mentions)
4 acetylpyridine, by Merck Group (1 mentions)
Z 3 hexenol, by Merck Group (1 mentions)
10 protocols using farnesene
1
GC-MS analysis of terpenes
2
Thrips Attractants from Tea and Plants
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Twenty types of compounds, derived from tea plants and plant-derived semiochemicals attracted to other thrips, were used in our trials [4 (link),24 (link),25 (link),26 (link)]. In particular, 4-acetylpyridine, p-anisaldehyde, decanal, eugenol, farnesene (mixture of isomers, α-farnesene, and (E)-β-farnesene), geraniol, (Z)-3-hexenol, (Z)-3-hexenyl butyrate, limonene, methyl anthranilate, methyl benzoate, 3-methyl butanal, methyl isonicotinate, methyl salicylate, β-myrcene, nonanal, (E)-β-ocimene, (−)-α-pinene, (+)-α-pinene, and γ-terpinene were all purchased from Sigma-Aldrich (St. Louis, MO, United States) (Table S1 ). Hexane (HPLC grade, CNW Technologies GmbH (Düsseldorf, Germany)) was chosen as solvent, and the abovementioned synthetic volatiles were diluted to a specific concentration.
3
Quantifying Antioxidant Potential of Terpenes
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The terpenes (−)-isopulegol (≥99%), menthol (≥99%), p-cymene (≥99%), eucalyptol (≥99%), (R)-(+)-pulegone (97%), γ-terpinene (97%), α-terpinene (≥95%), linalool (≥97%), (S)-(+)-carvone (≥96%), citronellal (≥95%), (−)-terpinene-4-ol (≥95%), citral (≥95%), menthone (≥90%), farnesene (mixtures of isomers, ≥90%), α-phellandrene (≥90%), β-myrcene (≥90%), and TPTZ (2,4,6-Tri(2-pyridyl)-s-triazine)) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Acetic acid (ACS), FeCl3 × 6H2O, FeSO4 × 7H2O, phosphoric acid (ACS), hydrochloric acid (ACS), chloroform (ACS), ethyl acetate (ACS), 2-butanone (ACS), and methanol (analytic purity grade) were obtained from Polish Reagents (Gliwice, Poland). The standards trolox ((±)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid, 97%) and gallic acid (>98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA).
4
SPME Fiber Cleaning and Validation
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Twenty-four SPME fibers (DVB/CARBOXEN/PDMS 50/30 μm, SupelcoTM, Bellefonte, PA) were cleaned by heating in a gas chromatograph injector at 250°C for five minutes with helium as the carrier flow. Cleaning efficiency had been previously checked in similar conditions: blank analyses confirmed that there was no carryover from the previous analysis. Fibers were controlled by GC-MS analysis after incubation in a headspace vial containing a mixture of the standard compounds ocimene, limonene, methyl salicylate caryophyllene and farnesene (Sigma-Aldrich, Saint-Quentin Fallavier, France). The variability expressed as the ratio between the mean and the standard deviation of compounds’ areas were 41, 13, 9, 22 and 30% respectively. Fibers were then wrapped in aluminum foil and stored in individual screw-capped Pyrex glass tubes until use.
5
Characterization of Chemical Compounds
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White Coat was purchased from Shiraishi Calcium. Calcium carbonate, dodecane, pentadecane, hexadecane, heptadecane, nonyl acetate, dichloromethane, tetramethylsilane, and deuterated chloroform were obtained from Wako Pure Chemicals (Osaka, Japan). Other standards were obtained as follows: tridecane and tetradecane (Tokyo Chemical Industry, Tokyo, Japan), farnesene (mixture of isomers) and hexyl 2-methylbutanoate (Sigma-Aldrich, St. Louis, MO, USA), TXIB (Matrix Scientific, Columbia, SC, USA), texanol (Santa Cruz Biotechnology, Dallas, TX, USA).
6
Analytical Determination of Monoterpenes
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All reagents used throughout the study were of analytical grade. Limonene, α-pinene, farnesene, myrcene, and linalool were obtained from Sigma-Aldrich (St. Louis, MO, USA). Hydrochloric acid (37%) was supplied by Scharlau (Barcelona, Spain). Methanol and acetonitrile (both HPLC grade) were purchased from VWR Chemicals (Randnor, PA, USA). Stock solutions of the analytes (1000 µg mL−1) were prepared by dissolving the appropriate amounts of the commercial standards in methanol. Working solutions of the analytes and their mixtures were prepared by diluting the stock solutions with water.
Ultrapure water was obtained from an Adrona system (Adrona, Riga, Latvia). Water was filtered through 0.22 µm nylon membranes purchased from GVS (Sandford, ME, USA) before use. All solutions were stored at 4 °C until use.
Ultrapure water was obtained from an Adrona system (Adrona, Riga, Latvia). Water was filtered through 0.22 µm nylon membranes purchased from GVS (Sandford, ME, USA) before use. All solutions were stored at 4 °C until use.
7
Authentic Standards for Volatile Compounds
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Authentic standards of linalool, benzyl alcohol, E-nerolidol, farnesene, phenylethyl alcohol, methyl salicylate, indole, and ocimene were purchased from Sigma Aldrich.
8
Evaluating Nicotine and Farnesene Doses
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(–)-Nicotine hydrogen tartrate (product number 1463304) and farnesene (product number W383902-100G-K, lot number MKCB6021) were obtained from Sigma-Aldrich. We determined the relevant dose of farnesene in regard to mouse behavioral assay doses. According to Tierney et al. (2016) (link), flavorants range from 1- to 20-fold the amount of nicotine in the traditional cigarette as well as ENDS, with an average flavor concentration of ∼12 mg/ml (Omaiye et al., 2019 (link)). It has been confirmed that 0.5 mg/kg nicotine is rewarding for mice in conditioned place preference (CPP) assays (Tapper et al., 2004 (link); Henderson et al., 2016 (link), 2017 (link)). Given this dose of nicotine, we determined the clinically relevant dose of farnesene is 0.5–10 mg/kg and used a dosing range of 0.1, 1.0, and 10 mg/kg for this study.
9
Chemotaxis Assay with Various Compounds
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N-formyl-Met-Leu-Phe (fMLF), Trp-Lys-Tyr-Val-Met (WKYMVM), and farnesene (mixture of isomers) were from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). (±)-Bornyl acetate was from Cayman Chemical Company (Ann Arbor, MI, USA). Xanthoxylin was from TargetMol (Boston, MA, USA). Piperitone (mixture of isomers), (+)-camphor, and 1,8-cineole were from TCI America (Portland, OR, USA), and (−)-camphor was from Alfa Aesar (Ward Hill, MA, USA). Fluo-4AM was from Invitrogen (Carlsbad, CA, USA). Fetal bovine serum was from ATCC (Manassas, VA, USA). Hanks’ balanced salt solution without Ca2+ and Mg2+ (HBSS–) was from Life Technologies (Grand Island, NY, USA). We prepared HBSS+ by adding 1.3 mM CaCl2 and 1.0 mM MgSO4. Human interleukin-8 (IL-8) was purchased from Peprotech (Rocky Hill, NJ, USA).
10
Sesquiterpenoid Extraction and Quantification
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The clean tissue culture seedlings were dried at 37 °C for 36 h to constant weight. After grinding to powder in a mortar, a four-fold volume of cyclohexane (W: V) was added, followed by extraction in the dark for 8 h. The sesquiterpenoid content was detected by gas chromatography (GC). The Agilent 7890A GC (Agilent Technologies, Santa Clara, CA) with HP-5 capillary column (30 m × 0.32 mm × 0.10 μm) and flame ionization detector (FID) were used, and samples were tested according to the following heating program: 70 °C for 1 min, 8 °C min−1 to 200 °C, 20 °C min−1 to 300 °C for 5 min. The temperature of the sample was 240 °C, the temperature of the detector was 350 °C, the carrier gas was high-purity nitrogen, the flow rate was 0.92266 mL min−1, and the injection volume was 1 μL. Twelve kinds of sesquiterpenoids were analyzed by GC. Among them, caryophyllene oxide, cedrol, nerolidol, farnesene, β-caryophyllene and valencene were purchased from Sigma-Aldrich with purity > 99%; germacrene d and zingiberene were purchased from Chengdu MUST Bio-Technology Co., Ltd with purity > 95%; β-sesquiphellandrene was purchased from Toronto Research Chemicals with purity > 95%; Atractylone, β-eudesmol and hinesol were isolated and purified by our research group with purity > 95%.
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