Germacrenes in Citrus Peel Oils

Feger, Wolfgang; Brandauer, Herbert; Ziegler, Herta

doi:10.1080/10412905.2001.9699692

Cited by 19 publications

(8 citation statements)

References 11 publications

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“…The EO should only be obtained either by distillation (water steam distillation or Clevenger hydrodistillation) or cold pressing. To prevent confusion, an organic extract from Citrus peel should not be named EO, (Alissandrakis et al, 2003; Chisholm et al, 2003b) although it could simply be named oil (Feger et al, 2001b; Buettner et al, 2003; Craske et al, 2005; Fisher et al, 2008). In fact, medium polarity solvents (diethyl ether, dichloromethane or ethyl acetate) extract more polar and higher MW compounds such as hexadecanal (Naef and Velluz, 2001; Gancel et al, 2002; Chisholm et al, 2003a,b; Cannon et al, 2015), squalene (Cheong et al, 2011b; Jiang et al, 2011), linoleic acid (Cheong et al, 2011b, 2012; Jiang et al, 2011), heptadecanoic acid (Delort and Jaquier, 2009; Jiang et al, 2011) or neophytadiene (Delort and Jaquier, 2009; Delort et al, 2015) than distillation or cold press extraction, and it fails to extract many monoterpene and sesquiterpene compounds which are characteristic of Citrus EOs (Jiang et al, 2011).…”

Section: Techniques To Extract Citrus Volatile Compoundsmentioning

confidence: 99%

Volatile Compounds in Citrus Essential Oils: A Comprehensive Review

González‐Mas¹,

Rambla²,

et al. 2019

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The essential oil fraction obtained from the rind of Citrus spp. is rich in chemical compounds of interest for the food and perfume industries, and therefore has been extensively studied during the last decades. In this manuscript, we provide a comprehensive review of the volatile composition of this oil fraction and rind extracts for the 10 most studied Citrus species: C. sinensis (sweet orange), C. reticulata (mandarin), C. paradisi (grapefruit), C. grandis (pummelo), C. limon (lemon), C. medica (citron), C. aurantifolia (lime), C. aurantium (bitter orange), C. bergamia (bergamot orange), and C. junos (yuzu). Forty-nine volatile organic compounds have been reported in all 10 species, most of them terpenoid (90%), although about half of the volatile compounds identified in Citrus peel are non-terpenoid. Over 400 volatiles of different chemical nature have been exclusively described in only one of these species and some of them could be useful as species biomarkers. A hierarchical cluster analysis based on volatile composition arranges these Citrus species in three clusters which essentially mirrors those obtained with genetic information. The first cluster is comprised by C. reticulata, C. grandis, C. sinensis, C. paradisi and C. aurantium, and is mainly characterized by the presence of a larger abundance of non-terpenoid ester and aldehyde compounds than in the other species reviewed. The second cluster is comprised by C. junos, C. medica, C. aurantifolia, and C. bergamia, and is characterized by the prevalence of mono- and sesquiterpene hydrocarbons. Finally, C. limon shows a particular volatile profile with some sulfur monoterpenoids and non-terpenoid esters and aldehydes as part of its main differential peculiarities. A systematic description of the rind volatile composition in each of the species is provided together with a general comparison with those in leaves and blossoms. Additionally, the most widely used techniques for the extraction and analysis of volatile Citrus compounds are also described.

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Section: Techniques To Extract Citrus Volatile Compoundsmentioning

confidence: 99%

Volatile Compounds in Citrus Essential Oils: A Comprehensive Review

González‐Mas¹,

Rambla²,

et al. 2019

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“…It is noteworthy that the elemenes ( δ , β , γ ) were derived ( γ ‐elemene totally, and δ ‐ and β ‐ in part) from the Cope rearrangement of the germacrenes in the hot injector (250°C) . A certain amount of germacrene B remained untransformed, along with germacrene D, due to a high thermal stability.…”

Section: Resultsmentioning

confidence: 99%

“…Such co‐elutions, which are caused by insufficient peak capacity and/or a lack of selectivity, have been discussed recently by Dugo et al In such cases, the reliable identification and quantification of minor SH constituents becomes an excessive challenge, especially for those oils in which the overall SH fraction is present in low amounts. Finally, possible rearrangements can occur in hot GC injectors (e.g., germacrenes) which can cause the generation of incorrect analytical data …”

Section: Introductionmentioning

confidence: 99%

Analysis of the sesquiterpene fraction of citrus essential oils by using the off‐line combination of high performance liquid chromatography and gas chromatography‐based methods: a comparative study

Zoccali

Bonaccorsi

Tranchida

et al. 2015

Flavour & Fragrance J

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The present investigation is based on the off-line combination of high-performance liquid chromatography (HPLC), with different high-resolution gas chromatography (GC) methods (LC//GC), for the analysis of the sesquiterpene hydrocarbon (SH) fraction of various Citrus essential oils. Attention was directed to such constituents because the SH profile is often highly specific and can vary considerably between different Citrus oil-types. The (normal phase) HPLC step was exploited for the separation of the hydrocarbons, from the oxygenated compounds, hence generating a simplified sub-sample. After, the hydrocarbon fraction was concentrated and subjected to analysis, using conventional GC-quadrupole mass spectrometry (qMS) and GC-flame ionization detection (FID), comprehensive two-dimensional GC-qMS and comprehensive two-dimensional GC-FID, and cold-injection GC-qMS. The latter approach was exploited to avoid and evaluate solute rearrangements occurring under hot-injection conditions. The data derived from each approach were compared, to evaluate each analytical approach. Apart from the comparative scopes, an overall highly-detailed view (both qualitative and quantitative) was attained on the SH fraction of each essential oil, with many constituents reported here for the first time.

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“… e δ ‐Elemene is reported to be generated by the thermally induced Cope rearrangement of germacrene C.[10–12] …”

Section: Resultsmentioning

confidence: 99%

“…Condition B (DB‐Wax): oven temperature programmed, 50°C to 100°C at 3°C/min, held isothermal (70 min) at 100°C, then increased to 220°C at 5°C/min, held isothermal (20 min) at 220°C, injector temperature, 100°C,[10–12] split ratio, 40:1 (GC), 20:1 (GC‐MS), carrier gas, helium, constant pressure, 30.00 psi, volume injected, 5 µ l, FID temperature, 250°C (GC), hydrogen flow, 30 ml/min (GC), air flow, 400 ml/min (GC).…”

Section: Methodsmentioning

confidence: 99%

New eudesmane‐type sesquiterpenoids and other volatile constituents from the roots of Gynura bicolor DC.

Shimizu

Imayoshi

Kato

et al. 2010

Flavour & Fragrance J

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Diethyl ether extracts from fresh, field-grown plant roots and the thin roots of the cultured plantlet were analysed by gas chromatography (GC) and GC-mass spectrometry (GC-MS), and their constituents were compared. Of the components identified, major components of the field-grown plant roots were revealed to be sesquiterpene hydrocarbons such as (E)-caryophyllene, a-humulene, and germacrenes A, B, and C. (E)-b-Farnesene and germacrene C were predominant in the roots of the cultured plantlet. Three new sesquiterpenoids, gynuradienol (1), hydroperoxy-gynuradiene (2), and gynurenol (3) were isolated from the field-grown plant roots and their chemical structures were elucidated by nuclear magnetic resonance (NMR) spectra together with five known sesquiterpenoids, eudesm-11-en-4a-ol (4), intermedeol (5), alismol (6), alismoxide (7), (2E,6E)-3-isopropyl-6-methyl-10-oxoundeca-2,6-dienal (8), and a polyacetylenic compound, 1-tridecene-3,5,7,9,11-pentayne (9). Furthermore, characteristic green, moldy, and earthy aromas of the field-grown plant roots, which were remarkably different from those of the thin roots of the cultured plantlet, were revealed to be contributed by four methoxypyrazines, 2-methoxy-3-isopropylpyrazine (10), 2-methoxy-3-sec-butylpyrazine (11), 2-methoxy-3-isopropyl-5-methylpyrazine (12), and 2-methoxy-3-sec-butyl-5-methoxypyrazine (14) using a combination of GC-MS and GC-olfactometry (GC-O).

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Germacrenes in Citrus Peel Oils

Cited by 19 publications

References 11 publications

Volatile Compounds in Citrus Essential Oils: A Comprehensive Review

Volatile Compounds in Citrus Essential Oils: A Comprehensive Review

Analysis of the sesquiterpene fraction of citrus essential oils by using the off‐line combination of high performance liquid chromatography and gas chromatography‐based methods: a comparative study

New eudesmane‐type sesquiterpenoids and other volatile constituents from the roots of Gynura bicolor DC.

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