Leaf essential oils were obtained by hydrodistillation (100 g leaves) using a Clevenger type apparatus for 3 h. The essential oils were collected in dichloromethane, dried over silica gel, and stored at 4 °C in amber glass vials until analysis. Essential oil yield was calculated on a moisture-free basis as 0.08–0.19% (w/w). GC-MS used an Agilent technologies 7820A instrument with a HP-5 capillary columns (30 m × 0.32 mm I.D. covered with a 0.25 µm of 5:95 phenyl-dimethylpolysiloxane plate). The mobile phase was helium at 1 mL min−1 flow rate and 180 °C injector temperature; the oven program was from 60 °C for 3 min, 75 °C for 5 min, 150 °C for 10 min, and up to 250 °C for 20 min. Software was set for 30–600 m/z range, and the mass spectra was recorded at 70 eV. The relative retention index (RRI) was calculated with a standard mix of C8–C20n-alkanes (Sigma-Aldrich Co., St Louis, MO, USA) under identical conditions [74 (link)]. Data were compared with the NIST 2.0 database, with authentic d-limonene, β-linalool, β-caryophyllene, caryophyllene oxide, and (+) aromadendrene standards (Sigma-Aldrich Co., St Louis, MO, USA) and related literature [75 ,76 ]. The percentage of abundance was calculated from GC chromatograms.
Caryophyllene oxide
Manufactured by Merck Group
Sourced in United States, Germany, Italy, Australia
Caryophyllene oxide is a naturally occurring chemical compound found in various plants. It is a colorless, crystalline solid that is commonly used as a reference standard or analytical tool in laboratory settings.
Automatically generated - may contain errors
Lab products found in correlation
Linalool, by Merck Group (16 mentions)
β caryophyllene, by Merck Group (15 mentions)
β pinene, by Merck Group (14 mentions)
α pinene, by Merck Group (13 mentions)
Limonene, by Merck Group (13 mentions)
α humulene, by Merck Group (12 mentions)
Camphene, by Merck Group (10 mentions)
P cymene, by Merck Group (10 mentions)
α terpineol, by Merck Group (9 mentions)
γ terpinene, by Merck Group (7 mentions)
Myrcene, by Merck Group (6 mentions)
Sabinene, by Merck Group (5 mentions)
Terpinen 4 ol, by Merck Group (5 mentions)
E caryophyllene, by Merck Group (4 mentions)
1 8 cineole, by Merck Group (4 mentions)
Geraniol, by Merck Group (4 mentions)
Camphor, by Merck Group (4 mentions)
Bornyl acetate, by Merck Group (4 mentions)
Thymol, by Merck Group (4 mentions)
Borneol, by Merck Group (4 mentions)
39 protocols using caryophyllene oxide
1
Leaf Essential Oil Extraction and Analysis
2
Antioxidant Activity of Plant Extracts
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The standard substances α-pinene (98%), sabinene (95%), p-cymene (99%), limonene (97%), linalool (97%), γ-terpinene (96%), (E)-β-caryophyllene (98.5%), germacrene D (90%), α-humulene (96%), caryophyllene oxide (95%) (98%), p-hydroxybenzoic acid (99%), caffeic acid (98%), o-hydroxybenzoic acid (99%), rosmarinic acid (97%), rutin (94%), AAPH (97%), and fluorescein (99%) were purchased from Sigma Aldrich (St. Louise, MO, USA), and luteolin-7-O-glucoside (98%), kaempferol-3-O-rutinoside (98%), and salvigenin (98%) were purchased from ChemFaces (Wuhan, China); vitexin (≥95%) was purchased from PhytoLab GmbH (Vestenbergsgreuth, Bavaria, Germany). Solvents and other reagents used in the extraction process, GC/FID grade dichloromethane, ammonium formate (99%), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), formic acid HPLC grade, potassium persulfate (99%), and absolute ethanol (96%) were purchased from Merck (Darmstadt, Germany); commercial ethanol (96%) was acquired from SUQUIN (Bucaramanga, Santander, Colombia).
3
Identification of Volatile Compounds
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For the identification of volatiles, the following analytical standards purchased from Sigma Aldrich (Milan, Italy) were used: α-pinene, β-pinene, sabinene, 1,8-cineole, camphene, myrcene, α-phellandrene, δ-3-carene, p-cymene, limonene, γ-terpinene, terpinolene, linalool, trans-pinocarveol, terpinen-4-ol, α-terpineol, myrtenal, citronellol, isobornyl acetate, (E)-caryophyllene, α-humulene, (E)-β-ionone, and caryophyllene oxide. The reference drug suramin was purchased from Sigma Aldrich.
4
Comprehensive Phytochemical Profiling of Extracts
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All the chemicals and reagents involved in the extraction processes, total polyphenolic content, antioxidant activity experiments and the chemical standards (1-hexanol, 2-Thujene, 3-octanone, 5-Amino-1-ethylprazole, Allylbenzene, Camphene, Caryophyllene oxide, Decanoic acid, Docosane, Germacrene D, Hexadecane, HexaDecanoic acid, Lavandulol, Limonene, Linalool, Linalool acetate, Nerol, Nerolidol, Ninanal, TetraDecanoic acid, Tricosane, α-Copaene, α-Humulene, α-Ter-pinene, β-Bourbonene, β-Caryophyllene, β-Copaene, β-Cubenene, β-Farnesene, β-Gurjunene, β-Myrcene, β-Pinene) used in the identification of phenolic and aromatic compounds from the extracts were acquired from Sigma Aldrich Company (St. Louis, MO, USA).
5
Sesquiterpene Evaluation in Cell Cultures
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Sesquiterpenes α-humulene, β-caryophyllene (CAR), caryophyllene oxide (CAO), farnesol (FAR), cis-nerolidol (cNER) and trans-nerolidol (tNER), rifampicin (RIF), methylcholanthrene (MC) and fetal bovine serum (FBS) were purchased from Sigma Aldrich (Prague, Czech Republic). All other chemicals were of analytical grade or higher. Stock solutions of sesquiterpenes (10 mM) were prepared in dimethyl sulfoxide (DMSO) and stored at 4 °C in the dark.
6
Extraction and Characterization of Essential Oils
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Bornyl acetate (99%), camphene (95%), camphor (96%), carvarol (98%), (−)-carveol (95%), (+)-carvone (96%), β-caryophyllene (98.5%), caryophyllene oxide (95%), β-citronellal (95%), citral (95%), 1,8-cineole (99%), p-cymene (99%), decyl chloroformate (97%), dodecanoic acid (98%), β-farnesene (90%), geranyl acetate (97%), geraniol (98%), isopulegol (98%), linalool (97%), limonene (97%), limonene oxide (97%), methyl linolenate (99%), myrcene (90%), myristic acid (99%), palmitic acid (99%), α-phellandrene (85%), α-pinene (98%), pivalic acid (99%), sabinene (75%), α-terpineol (90%), γ-terpinene (97%), 4-terpineol (95%), terpinolene (90%), and tymol (99%) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Achillea millefolium L. flowers, Citrus aurantium L. fruits, Leptospermum petersonii F. M. Bailey leaves, Ruta graveolens L. leaves, and Thymus vulgaris L. leaves were collected from a local store in Chonju, Korea. Sample specimens were authenticated by Jeongmoon Kim at Chonbuk National University, Korea. Essential oils of the five plants were obtained by steam distillation extraction, and finally dried over Na2SO4 to extract the pure essential oils (Table 1 ).
7
GC-MS Analysis of Essential Oils
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The GC analysis was performed on a Shimadzu gas chromatograph-model QP2010 Ultra (Kyoto, Japan). The oil was separated on a Rtx-5MS capillary column (30 m × 0.25 mm × 0.25 μm, Restek, Lisses, France). The column temperature program was: 50 °C/1.5 min, followed by a rate of 4 °C·min−1 to 200 °C, then a rate of 10 °C to 300 °C, and finally 300 °C/5 min. The injector temperature was 280 °C. The sample (1.0 μL in ethyl acetate) was injected with a 1:30 split ratio. The carrier gas was helium at 1.0 mL/min. Data processing of the obtained mass spectra was carried out with the GC-MS Solution Ver. 4.45 (Shimadzu Corporation, Kyoto, Japan). The identification of essential oil compounds was assigned by comparison of their retention time using caryophyllene oxide (Sigma-Aldrich, St. Louis, USA and a-humulene (Sigma-Aldrich, St. Louis, MO, USA) used as a reference standard, as well as by comparison of the mass spectra fragmentation patterns with the NIST—Mass Spectral Database, version 2.2, 2014 (NIST Standard Reference Data, USA).
8
Analytical Standards for Terpene Profiling
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Analytical standards were procured from Sigma Aldrich, Australia and included (+)-α-pinene (#80605), (-)-β-pinene (#80609), α-humulene (#12448), β-humulene (#53676), (-)-α-bisabolol (#95426), (-)-caryophyllene oxide (#91034) and (-)-trans-caryophyllene (#75541). Organic solvents n-hexane, methanol, ethanol, dichloromethane, diethyl ether and diethyl acetate were of HPLC grade and bought from Scharlau Australia.
9
Comprehensive Analysis of Plant Compounds
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The synthetic standards including (1R)-(+)-α-pinene, (-)-β-pinene, β-myrcene, (S)-(-)-limonene, linalool, octanal, nonanal, decanal, benzaldehyde, butylated hydroxytoluene, methyl benzoate, (-)-bornyl acetate, 6-methyl-5-hepten-2-one, geranyl acetone, decanoic acid, undecanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, myristoleic acid, palmitoleic acid, linoleic acid, oleic acid, (+)-longifolene, caryophyllene oxide, (E)–β-caryophyllene, undecane, dodecane, pentadecane, hexadecane and quercetin were obtained from Sigma-Aldrich (>98% purity).
10
Antitrichomonal Activity of Essential Oil Compounds
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After analyzing the composition of the EOs by GC-MS, products that fulfill the following criteria were selected to study their antitrichomonal activity in vitro: three more abundant in each of the selected active EO, abundance higher than 5%, and availability. Some of the major compounds that were excluded were not identified, not commercially available or not easy to obtain or isolate. Pure compounds (monoterpenes and sesquiterpenes) were obtained from commercial sources, except camphor that was previously isolated in our laboratory (ICA, CSIC). Linalool, thymol, α-pinene, α-terpineol, β-pinene, camphene, β- caryophyllene and caryophyllene oxide were obtained from Sigma Aldrich (Madrid, Spain); linalyl acetate, γ-terpinene, and p-cymene from Acros Organics (Madrid, Spain); 4-terpineol from Merck Life Sciences (Madrid, Spain); α and β thujone from Phytolab: borneol, 1,8-cineole, carvacrol and D-fenchone from Fluka (Madrid, Spain).
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