Analysis of volatile constituents from Meyer lemon oil

Moshonas, Manuel G.; Shaw, Philip E.; Veldhuis, M. K.

doi:10.1021/jf60182a018

Cited by 22 publications

(22 citation statements)

References 7 publications

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“…[66,67] Compounds 4 and 5 were identified from various plant sources. [49,57,58,[60][61][62][63][66][67][68][69][70][71][72][73][74][75][76] In some cases 2 was also isolated, [58,68,69] sometimes with determined absolute configuration of (À)-2, [61][62][63] whichs upports (+ +)-1 as ab iosynthetic intermediate, but 1 could also be the true naturalp roduct, while 4 and 5 may have been formed spontaneously from 1 during compound isolation (Scheme 4).…”

Section: Eudesmanes From Cation H1mentioning

confidence: 99%

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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Section: Eudesmanes From Cation H1mentioning

confidence: 99%

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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“…Volatile compounds in Meyer lemon (Moshonas et al, 1972), Italian lemon (Allegrone et al, 2006) and petitgrain Eureka lemon essential oil (Baaliouamer et al, 1985) have been reported, except Eureka lemon. Many studies showed the common volatile compounds in lemon.…”

Section: Introductionmentioning

confidence: 99%

“…d-Limonene plays a potential role in preventing breast cancer (Miller et al, 2011), and the antioxidant activity of lemon essential oils has been confirmed (Di et al, 2010). Lemon products are also important for food industry and health care (González-Molina et al, 2010).Volatile compounds in Meyer lemon (Moshonas et al, 1972), Italian lemon (Allegrone et al, 2006) and petitgrain Eureka lemon essential oil (Baaliouamer et al, 1985) have been reported, except Eureka lemon. Many studies showed the common volatile compounds in lemon.…”

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confidence: 99%

Free and Bound Volatile Compounds in Juice and Peel of Eureka Lemon

Zhong

Ren

Chen

et al. 2014

FSTR

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Free and glycosidically bound volatile compounds in different parts of Eureka lemon were studied. Free volatile compounds were extracted by solid phase microextraction (SPME). Bound volatile compounds were isolated from juice by adsorption onto an Amberlite XAD-2 column, and then hydrolyzed by almond β-glucosidase. Both the free volatile compounds and the released aglycones were analyzed by using gas chromatography-mass spectromerty (GC-MS). Gas chromatography-olfactometry (GC-O) was also used to determine the aroma-active compounds in juice and peel. Totally 29 and 34 free volatiles were found in juice and peel, respectively. Terpenes and aldehydes were the most abundant compounds in free fractions. Four and six bound volatile compounds were found in juice and peel with a total concentration of 127.8 and 1161.52 μg/L. Benzenic and terpenic compounds were the main bound volatiles found in Eureka lemon fruit. Mannose and glucose were found as sugar moiety in juice, and glucose was found the only sugar linked to bound volatiles in peel.Keywords: eureka lemon, volatile compounds, glycosides, enzymatic hydrolysis, aroma active compounds IntroductionEureka lemon originated in America and grew widely under tropical and sub-tropical climatic conditions, including many countries such as Australia, Israel and southern China. It is a common lemon species in the world (Ford, 1942). It is called "the true 'better' lemon" and has large quantity of juice and acid content.Eureka lemon has not been got much attention. The fruit is elliptic in shape, bright yellow and medium thickness of the skin.It is more acidic than Meyer lemon, its peel is thicker, and also the juice is less than Lisbon lemon, a lemon similar to Eureka lemon.Generally speaking, Meyer lemon and Lisbon lemon are more used as juice production, cooking and eating. But the characters of Eureka lemon make it better to be a good material to produce essential oil and other aroma products. The luxuriant aroma compounds of lemon are applied in many fields. d-Limonene plays a potential role in preventing breast cancer (Miller et al., 2011), and the antioxidant activity of lemon essential oils has been confirmed (Di et al., 2010). Lemon products are also important for food industry and health care (González-Molina et al., 2010).Volatile compounds in Meyer lemon (Moshonas et al., 1972), Italian lemon (Allegrone et al., 2006) and petitgrain Eureka lemon essential oil (Baaliouamer et al., 1985) have been reported, except Eureka lemon. Many studies showed the common volatile compounds in lemon. Several studies showed that the main volatile compounds in lemon essential oil were monoterpenes, such as limonene, γ-terpinene and β-myrcene (Fan et al., 2009a;Verzera et al., 2004). Limonene was the most abundant compound in lemon. Additionally, aldehydes, ketones and esters were the other important volatile compounds in lemon (Lota et al., 2004;Moufida et al., 2003). The free volatile compounds and particular character compounds of Eureka lemon have not been reported yet. The boun...

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“…1) основные компоненты, % содержание, которых в эфирном масле преобладает: лимонен и γ-терпинен [21];…”

Section: рис 1 схема установки для сверхкритической углекислотной эunclassified

Production and Analysis of the Composition of Supercritical Carbon Dioxide Extracts From Exocarpy Citrus Meyeri Tan.

Molokhova¹,

Ponomareva²,

Кудинов³

2020

JCPRM

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The purpose of this work is to evaluate the effectiveness of using supercritical carbon dioxide extraction to obtain essential oils from exocarpy of Meyer lemon in comparison with the pressing method. The plant material is represented by the exocarpy of Meyer lemon Citrus meyeri Tan., Rutovye family – Rutaceae, collected in the vicinity of Khujand (Republic of Tajikistan), in November 2014. Supercritical carbon dioxide extracts (CO2 extracts) were obtained at the Research Center for Ecological GORO resources (Rostov-on-Don) at the KOERS1 installation. As a comparison, we used the essential oil obtained by direct pressing on hydraulic presses without heating. Qualitative and quantitative analysis of the components was carried out by gas chromatography with chromatography-mass spectrometric detection. As a result of the study, it was found that the optimal parameters of CO2 extraction, which provide the highest content of limonene and γ-terpinene in the extract, are: 50 °С, 16 MPa, and 30 min. A comparative analysis of the content of extract components showed that the yield of limonene during supercritical extraction, compared with traditional technology, increased by 7.5%, the γ-terpinene content was 1.5 times. In addition, significant differences were found in the qualitative and quantitative composition of the essential oil and the CO2 extract of Meyer lemon. In essential oil, the content is higher: α- and β-pinene, p-cumene, geranial, and others. In the CO2 extract, the content is higher: sabinene, α-humulene, β-bisabolene and other low-volatile compounds, with an additional 9 components: α-thuen, terpenolene, geranyl acetate, etc., which indicates the need for an additional pharmacological study of the CO2-extract of Meyer lemon.

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Analysis of volatile constituents from Meyer lemon oil

Cited by 22 publications

References 7 publications

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Free and Bound Volatile Compounds in Juice and Peel of Eureka Lemon

Production and Analysis of the Composition of Supercritical Carbon Dioxide Extracts From Exocarpy Citrus Meyeri Tan.

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