Norsesquiterpene hydrocarbon, chemical composition and antimicrobial activity of Rhaponticum carthamoides root essential oil

Havlík, Jaroslav; Budêšínský, Miloś; Klouček, Pavel; Kokoška, Ladislav; Valterová, Irena; Vašíčková, Soňa; Zelený, Václav

doi:10.1016/j.phytochem.2008.12.018

Cited by 28 publications

(33 citation statements)

References 14 publications

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“…Aplotaxene has also previously been found to dominate in essential oil from R. carthamoides roots and rhizomes by Havlik et al [17]. In addition, nardosina-1(10),11-diene and dauca-4(11),8-diene, petasitene, and trans - α -bergamotene were found for the first time in the Rhaponticum carthamoides root essential oil in the present study.…”

Section: Discussionsupporting

confidence: 84%

“…The levels of these components were significantly higher than those evaluated in the SGR essential oil. Interestingly, Havlik et al [17] found similar results for essential oil isolated from R. carthamoides roots and rhizomes of commercial material and also showed that 13-norcypera-1(5),11(12)-diene (22.6%) and cyperene (17.9%) were the major compounds in this essential oil. Cadalene was identified for the first time in R. carthamoides root essential oil in this work.…”

Section: Discussionsupporting

confidence: 55%

“…The oil yields were higher than those obtained previously from roots and rhizomes of R. carthamoides from the Czech Republic (0.04%) [17] and similar to those from the roots and rhizomes of plants growing in Poland (0.07–0.11%) [23]. In the present study, it was found that the essential oils from hairy roots and roots of soil-grown plants of R. carthamoides differed significantly in their compositions.…”

Section: Discussionsupporting

confidence: 54%

“…The sesquiterpene hydrocarbons were also the major group of the components in R. carthamoides essential oil obtained by Havlik et al [17]. In contrast, Geszprych and Weglarz [23] found that oils from the roots and rhizomes of this species growing in Poland were abundant in monoterpenes.…”

Section: Discussionmentioning

confidence: 93%

“…were as previously reported [14]. The identification of the compounds was based on the comparison of their RIs and MS spectra with those stored in the NIST 98.1, Wiley 8th Ed., and MassFinder 4.1. computer libraries as well as literature data [15–17]. …”

Section: Methodsmentioning

confidence: 99%

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The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

Skała

Rijo

García

et al. 2016

Oxidative Medicine and Cellular Longevity

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The essential oils were isolated by hydrodistillation from the hairy roots (HR) and roots of soil-grown plants (SGR) of Rhaponticum carthamoides and were analyzed by GC-MS method. In the both essential oils 62 compounds were identified. The root essential oils showed the differences in the qualitative and quantitative composition. The sesquiterpene hydrocarbons (55–62%) dominated in both essential oils. The major compounds of HR essential oil were cyperene, 13-norcypera-1(5),11(12)-diene, and cadalene while aplotaxene, nardosina-1(10),11-diene, and dauca-4(11),8-diene dominated in SGR essential oil. Both essential oils showed antibacterial activity especially against Enterococcus faecalis (ATCC 29212) and Pseudomonas aeruginosa (ATCC 27853) (MIC value = 125 µg/mL). HR and SGR essential oils also decreased the expression of IL-1β, IL-6, and TNF-α and the ROS level in LPS-treatment astrocytes. This is the first report to describe the chemical composition of R. carthamoides essential oil from hairy roots, its protective effect against LPS-induced inflammation and ROS production in astrocytes, and its antimicrobial potential. The results show that R. carthamoides hairy roots may be a valuable source of the essential oil and may be an alternative to the roots of soil-grown plants.

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Section: Discussionsupporting

confidence: 84%

Section: Discussionsupporting

confidence: 55%

Section: Discussionsupporting

confidence: 54%

Section: Discussionmentioning

confidence: 93%

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

Skała

Rijo

García

et al. 2016

Oxidative Medicine and Cellular Longevity

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Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrencea nd biosynthesis of germacrene Ai nN ature and its peculiar chemistry will be highlighted , followed by ad iscussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolutec onfiguration, if it is known,a nd the reasoning for its assignment is presented. 2. Germacrene A 2.1. Occurrence in Nature (À)-Germacrene A(1,S cheme 2) was first isolated in 1970 from the gorgonian Eunicea mammosa. [7] Its absolute configuration was established as (S)-(À)-1 through its Cope rearrangement to (+ +)-b-elemene (2)f or which the configurational assignment was performed by chemical correlation of (À)-elemol(3)t o (À)-2. [8, 9] Compound (À)-1 is also believed to occur in the soft coral Lobophytum, [10] andi st he alarm pheromone of the aphid Terioaphis maculata. [11, 12] In the course of this work it was noticed that the optical rotation([ a] D 25 = À26.8, c 1.0, CCl 4)w as significantly highert han initially reported ([a] D 25 = À3.2, c 14.4, CCl 4), [7] which is explainableb yapartial rearrangement of purified (À)-1 to (+ +)-2,o ra lternatively, 1 isolated from E. mammosa was not enantiomerically pure. However,the opticalrotation of (+ +)-2 ([a] D 25 =+15.1, neat) reported in this initial study [7] matches the reported value for (À)-2 ([a] D 25 = À15.8, c 0.50, CHCl 3)o btainedb yC ope rearrangement of (+ +)-1, [13] thus disfa-Scheme1.Te rpene cyclisation modes for FPP. Scheme2.Structure of 1 and its absolute configurationbyc hemicalcorrelation.

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A review on recent research results (2008–2010) on essential oils as antimicrobials and antifungals. A review.

Lang

Buchbauer

2011

Flavour & Fragrance J

345

209

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The antimicrobial activity of essential oils is discussed in this review taking in account studies which were published in the period of time from 2008 until September 2010. Furthermore, the most important methods to examine the antimicrobial efficiency of essential oils are presented. The studies are divided into the following two groups, namely antibacterial and antifungal active agents depending on the activity of the applied essential oil against the test microorganisms. Various interesting possible applications are revealed such as the use of essential oils instead of synthetic drugs to circumvent the increasing resistance of some pathogens. Moreover, they could not only be used for the therapy of infectious illnesses, but also as preservatives in the food industry. A further possibility is, among others, the application of essential oils in skin products in order to treat or avoid dermal infections. Additionally, the prevalent constituents of the individual antimicrobial active essential oils are elaborated.

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Norsesquiterpene hydrocarbon, chemical composition and antimicrobial activity of Rhaponticum carthamoides root essential oil

Cited by 28 publications

References 14 publications

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

A review on recent research results (2008–2010) on essential oils as antimicrobials and antifungals. A review.

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