Caryophyllene and caryophyllene oxide: a variety of chemical transformations and biological activities

Gyrdymova, Yu. V.; Рубцова, С. А.

doi:10.1007/s11696-021-01865-8

Cited by 22 publications

(11 citation statements)

References 122 publications

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“…The major constituent is used as a flavoring agent in various products of the food and cosmetics industries [ 44 ] and has several properties reported in the literature, such as antibacterial, antioxidant, anti-inflammatory, antimycobacterial, antiproliferative, cytotoxic, and insecticidal properties [ 45 , 46 , 47 , 48 , 49 , 50 , 51 ]. Gyrdymova and Rubtsova [ 52 ] state that caryophyllene oxide is an important compound for organic and medicinal chemistry due to its specific structure that favors the production of several other biologically active structures with analgesic, anti-inflammatory, sedative, cytotoxic, and leishmanicidal potentials [ 53 , 54 , 55 , 56 ].…”

Section: Resultsmentioning

confidence: 99%

Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

et al. 2023

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The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and β-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region.

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Section: Resultsmentioning

confidence: 99%

Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

et al. 2023

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“…The results of tobacco transformation further verified the above conclusion, with OfCYP142 overexpression significantly elevating some floral VOCs including linalool, leaf alcohol, and (-)-caryophyllene oxide in tobacco flowers ( Figure 9 E–H). Leaf alcohol is present in a wide range of foods, beverages, and fine fragrances, due to its characteristic intense smell of fresh cut grass or leaves [ 48 , 49 ]; and (-)-caryophyllene oxide is a major representative sesquiterpenoid, and an important resource for organic and medicinal chemistry [ 50 , 51 ]. Many CYP genes have been reported to participate in sesquiterpene biosynthesis [ 52 ].…”

Section: Discussionmentioning

confidence: 99%

Insights into the Cytochrome P450 Monooxygenase Superfamily in Osmanthus fragrans and the Role of OfCYP142 in Linalool Synthesis

Liu

Shen

et al. 2022

IJMS

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Osmanthus fragrans flowers have long been used as raw materials in food, tea, beverage, and perfume industries due to their attractive and strong fragrance. The P450 superfamily proteins have been reported to widely participate in the synthesis of plant floral volatile organic compounds (VOCs). To investigate the potential functions of P450 superfamily proteins in the fragrance synthesis of O. fragrans, we investigated the P450 superfamily genome wide. A total of 276 P450 genes were identified belonging to 40 families. The RNA-seq data suggested that many OfCYP genes were preferentially expressed in the flower or other organs, and some were also induced by multiple abiotic stresses. The expression patterns of seven flower-preferentially expressed OfCYPs during the five different flower aroma content stages were further explored using quantitative real-time PCR, showing that the CYP94C subfamily member OfCYP142 had the highest positive correlation with linalool synthesis gene OfTPS2. The transient expression of OfCYP142 in O. fragrans petals suggested that OfCYP142 can increase the content of linalool, an important VOC of the O. fragrans floral aroma, and a similar result was also obtained in flowers of OfCYP142 transgenic tobacco. Combined with RNA-seq data of the transiently transformed O. fragrans petals, we found that the biosynthesis pathway of secondary metabolites was significantly enriched, and many 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway genes were also upregulated. This evidence indicated that the OfCYP proteins may play critical roles in the flower development and abiotic response of O. fragrans, and that OfCYP142 can participate in linalool synthesis. This study provides valuable information about the functions of P450 genes and a valuable guide for studying further functions of OfCYPs in promoting fragrance biosynthesis of ornamental plants.

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“…Figure 2 displays the chromatogram obtained from the GC-MS analysis of clove oil. Based on their mass to charge (m/z) ratio, the chromatogram displayed twenty-four (24) peaks that corresponded to twentytwo ( 22) distinct compounds. The spectra data identified four major components: Benzofuran-2-methyl, Caryophyllene, trans-Isoeugenol, and Caryophyllene oxide.…”

Section: Gc-ms Analysismentioning

confidence: 99%

“…Caryophyllene and caryophyllene oxide are essential natural sesquiterpenoids for organic and medicinal chemistry. Due to their peculiar structure, these sesquiterpenoids can be regarded as a universal platform for obtaining compounds with a variety of structures, including biologically active compounds [24] . It is known that caryophellene oxide has analgesic and anti-inflammatory properties [25] .…”

Section: Scheme 1: Synthetic Route To Isoeugenol and Vanillinmentioning

confidence: 99%

Phytochemical Screening and Chemical Analysis of Cloves (Syzygium Aromaticum) Flower Buds

2022

IRJMETS

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Syzygium aromaticum flower buds commonly referred to as cloves are used as seasoning in food cuisines and display an array of ethno-medicinal properties making it beneficial for biological and chemical investigations. Phytochemical screening and chemical analysis of clove (Syzygium aromaticum) flower buds was performed systematically by steam distillation, Fourier Transform Infrared spectrophotometry and Gas Chromatography-Mass Spectrometry spectroscopic techniques. The extraction was carried out in triplicate using 200 g each of the pulverized and dried clove flower buds. At the end of the serial extractions and fractionation processes, 5.1% (w/w) yield of the total sample was obtained. The qualitative phytochemical analysis carried out on the crude extract revealed the presence of Balsams, Flavonoids, Steroids/Sterols, Terpenoids, Volatile oils and Carbohydrates. The Fourier Transform Infrared spectrophotometry spectral analysis revealed the presence of some major functional groups like hydroxyl, ethylene and ether. The Gas Chromatography-Mass Spectrometry results showed four major constituents; Benzofuran-2-methyl-, Caryophyllene, trans-Isoeugenol and Caryophyllene oxide. These compounds are known to possess a wide array of biological and medicinal properties ranging from anti-bacteria, anti-fungal, anti-oxidant, anti-depressant, anti-inflammatory, analgesics, anti-convulsant, antioxidant and radical scavenging ability supportive of the ethno-medicinal use of the plant in some Nigerian communities.

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Caryophyllene and caryophyllene oxide: a variety of chemical transformations and biological activities

Cited by 22 publications

References 122 publications

Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

Chemical Evaluation, Phytotoxic Potential, and In Silico Study of Essential Oils from Leaves of Guatteria schomburgkiana Mart. and Xylopia frutescens Aubl. (Annonaceae) from the Brazilian Amazon

Insights into the Cytochrome P450 Monooxygenase Superfamily in Osmanthus fragrans and the Role of OfCYP142 in Linalool Synthesis

Phytochemical Screening and Chemical Analysis of Cloves (Syzygium Aromaticum) Flower Buds

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