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).
Humulene
Manufactured by Merck Group
Sourced in United States, Australia
Humulene is a naturally occurring organic chemical compound found in the essential oils of various plants, including hops, cannabis, and certain essential oils. It is a bicyclic sesquiterpene with the chemical formula C₁₅H₂₄. Humulene exhibits a distinct earthy, woody, and spicy aroma, and it is commonly used in the flavoring and fragrance industries.
Automatically generated - may contain errors
Lab products found in correlation
Linalool, by Merck Group (5 mentions)
β myrcene, by Merck Group (5 mentions)
Caryophyllene, by Merck Group (3 mentions)
D limonene, by Merck Group (3 mentions)
β caryophyllene, by Merck Group (3 mentions)
α farnesene, by Merck Group (2 mentions)
β ocimene, by Merck Group (2 mentions)
Geraniol, by Merck Group (2 mentions)
Ethyl hexanoate, by Merck Group (2 mentions)
Farnesene, by Merck Group (1 mentions)
Myrcene, by Merck Group (1 mentions)
Absolute ethanol, by Carlo Erba (1 mentions)
Trichloroacetic acid, by Carlo Erba (1 mentions)
Ferric chloride, by Carlo Erba (1 mentions)
Acetonitrile, by Avantor (1 mentions)
Methanol, by Avantor (1 mentions)
Rosmarinic acid, by Merck Group (1 mentions)
Acetic acid, by Avantor (1 mentions)
2 2 diphenyl 1 picrylhydrazyl dpph 6 hydroxy 2 5 7 8 tetramethylchroman 2 carboxylic acid trolox, by Merck Group (1 mentions)
α pinene, by Avantor (1 mentions)
7 protocols using humulene
1
GC-MS analysis of terpenes
2
Antioxidant Phytochemicals Analysis
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Ethanol absolute was obtained from Carlo Erba (Milan, Italy). Acetic acid, acetonitrile, methanol, and water (high performance liquid chromatography—HPLC grade) were purchased from VWR (Milan, Italy).
α-pinene, β-pinene, linalool, β-myrcene, terpinolene, caryophyllene, humulene, and β-bisabolene, gallic acid, p-OH benzoic acid, chlorogenic acid, vanillic acid, caffeic acid, syringic acid, ferulic acid, and rosmarinic acid (from Sigma-Aldrich, Darmstadt, Germany) standards were employed. Working standard mixtures were prepared by appropriate dilution of the standards in methanol. All solutions were stored at −20 °C in the dark.
Folin–Ciocâlteu’s reagent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,2-diphenyl-1-picrylhydrazyl (DPPH˙), and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS˙+) were purchased from Sigma-Aldrich (Darmstadt, Germany). Sodium carbonate, potassium persulfate, potassium hexacyanoferrate(III), trichloroAcetic acid, ferric chloride, and potassium phosphate monobasic were obtained from Carlo Erba (Milan, Italy).
α-pinene, β-pinene, linalool, β-myrcene, terpinolene, caryophyllene, humulene, and β-bisabolene, gallic acid, p-OH benzoic acid, chlorogenic acid, vanillic acid, caffeic acid, syringic acid, ferulic acid, and rosmarinic acid (from Sigma-Aldrich, Darmstadt, Germany) standards were employed. Working standard mixtures were prepared by appropriate dilution of the standards in methanol. All solutions were stored at −20 °C in the dark.
Folin–Ciocâlteu’s reagent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,2-diphenyl-1-picrylhydrazyl (DPPH˙), and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS˙+) were purchased from Sigma-Aldrich (Darmstadt, Germany). Sodium carbonate, potassium persulfate, potassium hexacyanoferrate(III), trichloroAcetic acid, ferric chloride, and potassium phosphate monobasic were obtained from Carlo Erba (Milan, Italy).
3
Quantification of Volatile Compounds
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All 23 standard compounds used for the quantification analysis were purchased from Sigma-Aldrich (purity 99.0%, all chromatographic grade), including butanoic acid, acetic acid, thujone, methyl eugenol, p-cymene, α-pinene, diallyl disulphide, α-terpineol, β-caryophyllene, β-myrcene, 1,8-cineole, D-limonene, linalool, methional, nonanal, phenylethanal, ethyl caprylate, 4-methyl-5-thiazoleethanol, (E)-2-octenal, (E)-2-heptenal, humulene, acetophenone, and linalyl acetate. The internal standard (2,4,5-trimethylthiazole) and n-alkanes (C8–C30) used to calculate the retention index (RI) were of chromatographic grade and purchased from Sigma-Aldrich (St, Louis, MO, USA). Diethyl ether and n-pentane for dilution and preparation of sample were obtained from Thermo Fisher Scientific Inc. (Waltham, MA, USA). High purity helium (99.999% purity) and nitrogen (99.99% purity) were purchased and produced by Beijing Tianlirenhe Trading Co., Ltd. (Beijing, China).
4
Quantitative Analysis of Volatile Compounds
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The following reference standards were purchased from Sigma-Aldrich (St. Louis, MO, USA): C7-C30 saturated alkane mixed standard, (internal standard) 2-methyl-3-heptanone, 2-methylpropyl 2-methylpropanoate, β-myrcene, β-trans-ocimene, ethyl hexanoate, 3-octanone, hexyl acetate, 2-methylbutyl 2-methylbutanoate, (Z)-3-hexenyl acetate, (Z)-hex-3-en-1-ol, 2-nonanone, 3-octanol, ethyl octanoate, (Z)-3-hexenyl butanoate, α-gurgujene, linalool, β-caryophyllene, (Z)-3-hexenyl (E)-2-butenoate, 2-undecanone, methyl benzoate, (Z)-3-hexenyl hexanoate, ethyl benzoate, humulene, α-farnesene, (Z)-3-hexenyl benzoate, and β-ocimene. All chemicals were of analytical grade or higher.
5
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).
6
Hop Samples Analysis Protocol
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The chemical compounds and standards used in this work were hexane (HPLC grade), ethyl hexanoate (98%), and methanol (HPLC grade) from Merck (Darmstadt, Germany); 2-octanol (99%), undecane (99%), (+) camphene (80%), β-myrcene (90%), D-limonene (97%), linalool (95%), geraniol (98%), geranyl acetate (97%), humulene (96%), (−)-caryophyllene oxide (97%), and n-alkanes C8–C21 (99%) provided by Sigma Aldrich (Castle Hill, NSW, Australia); and α-pinene (95%), β-pinene (94%), and caryophyllene (90%) from TCI (Tokyo, Japan).
The hop samples Azacca (AZAC) and Loral (LORA) were kindly donated by Carlton & United Breweries (Asahi-CUB, Abbotsford, Australia) and the samples Cascade (CASC), Enigma (ENIG), and Zappa (ZAPP) were obtained from various other local suppliers. All samples were obtained in the format of pellet type 90, stored in the presence of nitrogen, and kept in a freezer until ready for analysis. More information about the hop samples is presented inTable S1 of the Supplementary Materials .
The hop samples Azacca (AZAC) and Loral (LORA) were kindly donated by Carlton & United Breweries (Asahi-CUB, Abbotsford, Australia) and the samples Cascade (CASC), Enigma (ENIG), and Zappa (ZAPP) were obtained from various other local suppliers. All samples were obtained in the format of pellet type 90, stored in the presence of nitrogen, and kept in a freezer until ready for analysis. More information about the hop samples is presented in
7
Analysis of Volatile Compounds in Tea
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Five-year-old tea plants of Camellia sinensis cv. “Shu Cha Zao” grown at the experimental farm of Anhui Agricultural University in Hefei, China, were used in this study. Standards of geranyl diphosphate (GDP), farnesyl diphosphate (FDP), β-myrcene, β-ocimene, linalool, geraniol, α-citral, β-citral, methyl geranate, nerol, D-limonene, trans-linalool oxide (furanoid), neryl acetate, L-terpineol, α-terpinen, geranyl acetone, thymol, (Z)-nerolidol, α-farnesene, β-farnesene, (E)-nerolidol, humulene, α-ionone, β-ionone, (E)-γ-bisabolene, cadinol and caryophyllene were purchased from Sigma-Aldrich (St. Louis, MO, USA).
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