The fragrance chemical β-caryophyllene—air oxidation and skin sensitization

Sköld, Maria; Karlberg, Ann‐Therése; Matura, Mihály; Börje, Anna

doi:10.1016/j.fct.2005.08.028

Cited by 179 publications

(120 citation statements)

References 20 publications

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“…13) During its metabolism, BC can originate hydroperoxides as primary oxidation products; these, however, are rapidly converted to caryophyllene oxide, which is a low reactive and more stable product. 4) This process, together with efficient DNA repair and detoxification by mouse, may be involved in the absence of a significant number of micronuclei induced by the chemical. In summary, the results obtained in the present experiment suggest using BC safely for industrial and therapeutic purposes, although this should be confirmed in other test models.…”

Section: Resultsmentioning

confidence: 99%

“…4) Therefore, they deserve to be solidly scrutinized as regards their toxic and genotoxic effects to assure their safe use. Studies on the group have given varying results: for example, in a bacterial assay linalool and BC showed no mutagenicity but lynalil acetate did; on the other hand, linalool was not antimutagenic whereas BC gave positive results; and finally, the toxicity of linalool and lynalil acetate proved to be stronger than BC.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Clastogenicity of Beta-Caryophyllene in Mouse

Molina-Jasso

Álvarez-González

Madrigal-Bujaidar

2009

Biological & Pharmaceutical Bulletin

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Clastogenicity of Beta-Caryophyllene in Mouse

Molina-Jasso

Álvarez-González

Madrigal-Bujaidar

2009

Biological & Pharmaceutical Bulletin

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“…1). Because of its weak aromatic taste, (E)-BCP is commercially used as a food additive and in cosmetics (6). (E)-BCP is also a major component (up to 35%) in the essential oil of Cannabis sativa L (7).…”

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confidence: 99%

Beta-caryophyllene is a dietary cannabinoid

Gertsch

Leonti

Raduner

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

713

583

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The psychoactive cannabinoids from Cannabis sativa L. and the arachidonic acid-derived endocannabinoids are nonselective natural ligands for cannabinoid receptor type 1 (CB1) and CB2 receptors. Although the CB1 receptor is responsible for the psychomodulatory effects, activation of the CB2 receptor is a potential therapeutic strategy for the treatment of inflammation, pain, atherosclerosis, and osteoporosis. Here, we report that the widespread plant volatile (E) Cannabis ͉ CB2 cannabinoid receptor ͉ foodstuff ͉ inflammation ͉ natural product P lant essential oils are typically composed of volatile aromatic terpenes and phenylpropanoids. These lipophilic volatiles freely cross cellular membranes and serve various ecological roles, like plant-insect interactions (1, 2). The sesquiterpene (E)-␤-caryophyllene [(E)-BCP] (Fig. 1) is a major plant volatile found in large amounts in the essential oils of many different spice and food plants, such as oregano (Origanum vulgare L.), cinnamon (Cinnamomum spp.) and black pepper (Piper nigrum L.) (3-5). In nature, (E)-BCP is usually found together with small quantities of its isomers (Z)-␤-caryophyllene [(Z)-BCP or isocaryophyllene] and ␣-humulene (formerly ␣-caryophyllene) or in a mixture with its oxidation product, BCP oxide (Fig. 1). Because of its weak aromatic taste, (E)-BCP is commercially used as a food additive and in cosmetics (6). (E)-BCP is also a major component (up to 35%) in the essential oil of Cannabis sativa L (7). Although Cannabis contains Ͼ400 different secondary metabolites, including Ͼ65 cannabinoid-like natural products, only ⌬ 9 -tetrahydrocannabinol (THC), ⌬ 8 -tetrahydrocannabinol, and cannabinol have been reported to activate cannabinoid receptor types 1 (CB 1 ) and 2 (CB 2 ) (8). Here, we show that the essential oil component (E)-BCP selectively binds to the CP55,940 binding site (i.e., THC binding site) in the CB 2 receptor, leading to cellular activation and antiinflammatory effects. CB 1 and CB 2 cannabinoid receptors are GTP-binding protein (G protein) coupled receptors that were first cloned in the early 1990s (9, 10). Although the CB 1 receptor is expressed in the central nervous system and in the periphery, the CB 2 receptor is primarily found in peripheral tissues (11). In vivo, CB receptors are activated by arachidonic acid-derived endocannabinoids, such as 2-arachidonoyl ethanolamine (anandamide or AEA) and 2-arachidonoylglycerol (2-AG) (12, 13). In addition to a wide range of primarily CB 1 receptor-mediated physiological effects on the central nervous system, different cannabinoid ligands have been reported to modulate immune responses (14). In particular, CB 2 receptor ligands have been shown to inhibit inflammation and edema formation (15), exhibit analgesic effects (16), and play a protective role in hepatic ischemia-reperfusion injury (17). In the gastrointestinal tract, CB 2 receptor agonists have been shown to prevent experimental colitis by reducing inflammation (18). Moreover, the CB 2 receptor has been described as a potential ...

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“…The literature has also reported caryophylene oxide as an artefact from the oxidation of b-caryophylene. 31 For the L. alba chemotype II (limonene-citral) the essential oil (OE-LAQII) presented eighteen compounds while HS-SPME extraction (CVF-LAQII) yielded twenty-six constituents (Table 1). In this case, only thirteen (44.83%) are common to both methods of extraction.…”

Section: Resultsmentioning

confidence: 99%

HS-SPME as an efficient tool for discriminating chemotypes of Lippia alba (Mill.) N. E. Brown

Silva¹,

Barbosa²,

Mafezoli³

et al. 2016

Quim. Nova

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Recebido em 15/04/2016; aceito em 15/07/2016; publicado na web em 26/08/2016 HS-SPME AS AN EFFICIENT TOOL FOR DISCRIMINATING CHEMOTYPES OF Lippia alba (Mill.) N. E. Brown. Lippia alba (Mill.) N. E. Brown (Verbenaceae) is a medicinal plant for which several biological activities are reported, such as sedative, anxiolytic, anti-ulcer, antifungal, antimicrobial, antioxidant, antispasmodic, anti-nociceptive and anti-inflammatory. It is characterized by the production of essential oils which have been used to classify the plant in different chemotypes. In the Northeast region of Brazil, the presence of three chemotypes are reported: myrcene-citral (chemotype I), limonene-citral (chemotype II) and carvone-limonene (chemotype III). In this work, headspace-solid phase microextraction (HS-SPME) was used on the analysis of the volatile organic compounds (VOCs) of three chemotypes of L. alba from the Northeast region of Brazil, and compared to the essential oils of the plants extracted by hydrodistillation. Volatile compounds from each chemotype were more effectively differentiated when extracted by HS-SPME than by hydrodistillation.

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The fragrance chemical β-caryophyllene—air oxidation and skin sensitization

Cited by 179 publications

References 20 publications

Clastogenicity of Beta-Caryophyllene in Mouse

Clastogenicity of Beta-Caryophyllene in Mouse

Beta-caryophyllene is a dietary cannabinoid

HS-SPME as an efficient tool for discriminating chemotypes of Lippia alba (Mill.) N. E. Brown

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