Variations in the essential oil composition in buds of six blackcurrant (Ribes nigrum L.) cultivars at various development phases

The variations in the content and the composition of dormant bud essential oil in six blackcurrant (Ribes nigrum L.) cultivars collected at various vegetation phases (from December 15, 2004 until April 19, 2005) were studied. Essential oil yield varied from 0.6% to 1.8%, except for the buds harvested in April, when the yield was considerably lower, 0.19–0.27%. Fifty volatile compounds were identified in the bud oils, hydrocarbon (38–55%) and oxygenated (on average 30%) terpenes being the major chemical constituents. Sabinene, δ-3-carene, terpinolene were dominant components, while cis- and trans-β-ocimene, α-thujene, α- and β-pinene, myrcene, α- and β-phellandrene, α- and γ-terpinene, p-cymene, cis- and trans-sabinene hydrate, terpinen-4-ol, α-terpineol, trans-piperitol, bornyl acetate, terpinyl acetate, citronellyl acetate, germacrenes D, β-caryophyllene, α-humulene, α-selinene, δ-cadinene and α-cadinol were found in reasonable amounts. Almiai may be considered as a superior cultivar, as possessing the most even content of oils ant the main constituents at all harvesting periods, except for April; however some other cultivars (Gagatai, Joniniai) accumulated higher amounts of oil at particular vegetation phases. January may be considered as a preferable harvesting time of buds; the amount of major terpenes at this phase was the highest in the all cultivars except for Joniniai. The concentration of the main oil compounds in buds harvested in April was 2–50 times lower than at other periods in the all six cultivars.     

酶解法制备柑橘皮渣膳食纤维的理化特性及抗氧化活性

分析6个不同香气型柑橘的果皮香气组分及关键香气物质成分,为柑橘果皮精油品质评价与发掘特殊香气柑橘精油提供依据。采用顶空-固相微萃取-气相色谱质谱联用法（HS-SPME-GCMS）分析柑橘果皮精油挥发性物质组成,结合相对气味活度值（relative odor activity value,ROAV）计算其关键香气物质构成。结果表明,从6个不同品种柑橘果皮精油中共鉴定出75种挥发性物质,其中单萜烯（73.82%~91.19%）含量最高,其次是醇类（4.32%~12.63%）和倍半萜烯（1.51%~10.20%）,它们共同作用形成柑橘果皮独特的香气。有23种化合物为6种柑橘果皮精油中共有,其含量达80.33%~94.59%。根据其化合物组成,可将6种柑橘果皮精油分为柠檬烯型、柠檬烯/γ-萜品烯型和柠檬烯/3-蒈烯型3个化学类型。ROAV法分析表明,芳樟醇是6种柑橘果皮精油风味贡献最大的物质。此外,衢州香橙、资阳香橙、青皮、南丰蜜橘、金秋砂糖橘和红美人果皮精油的关键香气物质种类存在明显不同,分别为8、14、11、8、13和18种,这些关键香气物质在柑橘果皮精油的独特香气形成中发挥重要作用。

     

Antibacterial activity of some Lamiaceae essential oils using resazurin as an indicator of cell growth

The aim of this work was to investigate the antibacterial activity of six Lamiaceae essential oils, against pathogenic and food spoilage bacteria. The chemical profiles of essential oils were evaluated by the means of GC and GC-MS. The major constituents of the oils were 1,8-cineol (29.2%), camphor (17.2%), α-pinene (11.5%) in Rosmarinus officinalis, citronellal (20.5%), β- geraniol (17.0%), β-citronellol (11.5%) in Melissa officinalis, 1,8-cineol (27.4%), α-thujone (16.3%), β-thujone (11.2%), borneol (10.4%), camphor (7.98%) in Salvia officinalis, linalool (25.1%), linalyl acetate (22.5%) in Lavandula angustifolia, thymol (52.4%), p-cymene (17.9%) in Thymus vulgaris and Patcholene alcohol (22.7%), α-bulnesene (17.1%), α-guaine (13.8%) in Pogostemon cablin. On quantitative basis, the amounts of 1,8-cineol, citronellal, 1,8-cineol, linalool, thymol and patchouli alcohol, calculated using calibrated curve with pure standard compounds, in the respective essential oils were found to be 28.4, 19.0, 26.7, 23.3, 51.1 and 21.1 g/100 g of oil, respectively. The modified resazurin microtitre-plate assay was used to evaluate the antibacterial activity of the essential oils and their principal components. All the essential oils analyzed presented inhibitory effects on most of the strains tested. Thymus vulgaris essential oil showed the highest inhibition. It was concluded that modified resazurin assay could be effectively used for reliable assessment of antibacterial activity of the tested essential oils against several Gram positive and negative bacterial taxa. The present results also demonstrated that Lamiaceae essential oils exhibiting higher antibacterial activity were generally rich in oxygenated monoterpens.     

Essential oil composition of the turpentine tree (Pistacia terebinthus L.) fruits growing wild in Turkey

Constituents of essential oils from fruit samples of the turpentine tree (Pistacia terebinthus L.) collected from fifteen different localities of Turkey on August 2001 were identified by GC–MS. Twenty-eight compounds representing 92.3–100.0% of turpentine fruit oils were identified. The oil yields varied between 0.06% and 0.16%. The highest yield of oil was obtained from fruits of Antalya origin (Akba?-Serik) (0.16%). α-Pinene (51.3%), limonene (39.0%), p-cymen-8-ol (40.0%) and caryophyllene oxide (51.0%) were found as major components for different localities in Turkey. The predominant constituents in most samples were α-pinene (9.5–51.3%), limonene (tr-39.0%) and caryophyllene oxide (tr-51.5). Except for one collection (Manavgat-Antalya), which contained spathulenol (20.7%) and p-cymen-8-ol (40.0%), all the other samples yielded oils rich in α-pinene and limonene. β-Caryophyllene oxide is the most abundant compound in Hisarönü (?zmir), Alanya (Antalya) and Yaylada? (Hatay) oils. Results confirm the effect of locality on the oil content and composition.     

Characterization of the Key Aroma Compounds of Citrus flaviculpus Hort. ex Tanaka by Aroma Extraction Dilution Analysis

ABSTRACT: The key aroma compounds were identified in Citrus flaviculpus Hort. ex Tanaka (ki-mikan) by using aroma extraction dilution analysis (AEDA) and the sniff test. Ki-mikan peel oil was extracted by cold-pressing. The highest flavor dilution (FD) factor was found for limonene. β-Phellandrene, carvacrol, spathulenol, camphene, elemol, (+)- trans -limonene oxide, and tetradecane showed higher relative flavor activity. Results of the sniff test of the original essential oil and its oxygenated fraction revealed that tetradecane, linalool, and α-terpineol were regarded as the key aroma compounds of ki-mikan peel oil. A diluted solution of linalool and α-terpineol of 3 ppm gave a ki-mikan-like flavor, while a higher concentration near 100 ppm of tetradecane tended to produce a fresh and fruity aroma note similar to ki-mikan flavor.     

Chemical diversity in curry leaf (Murraya koenigii) essential oils

Wild and cultivated Murraya koenigii leaf essential oils collected from ten Indian locations were investigated for their chemical diversity. The essential oil yields ranged from 1.2–2.5 ml/kg biomass. GC and GC-MS analyses revealed ninety compounds, constituting 93.8–99.9% of the essential oils. The highest concentrations of α-pinene (55.7%) and β-pinene (10.6%) were found in the essential oil of wild plants. α-Pinene (13.5–35.7%) and/or β-phellandrene (14.7–50.2%) were the dominant essential oil constituents of seven locations. (E)-Caryophyllene (26.5%, 31.5%) and α-selinene (9.5%, 10.4%) were the principal essential oil components of two locations. The odour profiles of the essential oils were distinctly different. Tetradecanoic acid, hexadecanoic acid, piperitone, cada-1,4-diene,1,10-di-epi-cubenol, γ-eudesmol, α-muurolol, (Z,E)-farnesol and (Z,Z)-farnesol are identified for the first time in curry leaf essential oil. The chemical diversity of the oils offers opportunity to flavourists to choose curry leaves and essential oils with preferential flavour composition.     

Aroma Impact Compounds in Three Citrus Oils: Cross-matching Test and Correspondence Analysis Approach

ABSTRACT Twenty‐three odor chemicals from 3 Citrus essential oils (lemon, Valencia orange, and Citrus sudachi) were selected as the potent character‐impact compounds on the basis of their limited odor unit values, and then every chemical was cross‐matched by sensory test to the 3 oils to attribute each aroma character to 1 of the 3 Citrus oils. The matching‐frequency data (ratio data) obtained was subjected to correspondence analysis and graphed on a diagram. Consequently, it was found that the aroma character of lemon oil was mainly represented by citral, with a high matching frequency of 0.89 (59 counts out of 66 trials, x²_o= 93.36). The orange character consisted mostly of linalool and nonanal. α, β‐Pinene, α‐sinensal and myrcene were related to the aroma of C. sudachi oil. The application of the cross‐matching test and correspondence analysis in the characterization of food aromas has never been reported in the literature to date, and the validity of these methods was successfully demonstrated by our study.     

Chemical composition and antimicrobial properties of essential oils of three Australian Eucalyptus species

The chemical composition and antimicrobial properties of the essential oils of three common Australian Eucalyptus species, namely E. olida, E. staigeriana and E. dives were determined by gas chromatography/mass spectrometry and the agar disc diffusion method, respectively. A total of 24 compounds were identified from the essential oil of E. dives, with the dominant compounds being piperitone (40.5%), α-phellandrene (17.4%), p-cymene (8.5%) and terpin-4-ol (4.7%). For E. staigeriana, 29 compounds were identified with 1,8-cineole (34.8%), neral (10.8%), geranial (10.8%), α-phellandrene (8.8%) and methyl geranate (5.2%) being the dominant ones. In contrast, a single compound, (E)-methyl cinnamate, accounted for 99.4% of the essential oils of E. oilda, although 20 compounds were identified. The essential oils displayed a variable degree of antimicrobial activity with E. staigeriana oil showing the highest activity. In general, Gram-positive bacteria were found to be more sensitive to the essential oils than Gram-negative bacteria. Staphylococcus aureus was the most sensitive strain while Pseudomonas aeruginosa was the most resistant.     

Identification of the odour-active aldehyde trans-4,5-epoxy-(E,Z)-2,7-decadienal in yuzu (Citrus junos Sieb. ex Tanaka)

Yuzu (Citrus junos Sieb. ex Tanaka) is a variety of sour citrus fruit that is popular in Japan. In this study, we investigated its aroma, which many people, especially in Japan, find appealing. Aroma extract dilution analysis was used to screen the odour-active compounds in the yuzu volatile oil. An unknown odorant with an albedo-like odour and a high flavour-dilution factor was detected. To identify this odorant, it was separated via flash column chromatography on silica gel and then fractionated by preparative high-performance liquid chromatography on a reverse-phase column. The volatile fraction, which contained a significant amount of the target unknown compound, was analysed by gas chromatography–mass spectrometry and gas chromatography–olfactometry to determine its mass spectrum, retention index, and odour quality. By comparing the resultant data with that of a synthesised authentic reference compound, it was evident that the unknown odorant was trans-4,5-epoxy-(E,Z)-2,7-decadienal (3); this is the first time that it has been identified as an odour-active unsaturated aldehyde in yuzu volatile oil. From the results of a model formation experiment, we propose that trans-4,5-epoxy-(E,Z)-2,7-decadienal originates from α-linolenic acid via 13(S)-hydroperoxy-(Z,E,Z)-9,11,15-octadecatrienoic acid (13(S)-HPOT), which is a lipoxygenase-induced oxidation product of α-linolenic acid.     

新疆不同品种薰衣草精油特征香气成分及感官属性分析

通过水蒸汽蒸馏法对新疆五种薰衣草花中精油进行提取,采用气相色谱-质谱联用(GC-MS)技术对薰衣草精油中挥发性成分及特征香气成分进行了分析,并对其香气轮廓进行了感官评定。结果显示,五个品种的薰衣草精油(70-1、74262、杂花、法国兰、白花)中,70-1精油含量最高,为6.88%。经鉴定薰衣草精油中挥发性成分主要为萜烯类、酯类、醛类、酮类和醇类,其中白花精油中挥发性化合物种类最多,含量也最高,五种精油中挥发性物质含量差异最大的为萜烯类,分别为17.15%、12.36%、16.33%、16.16%、20.48%;五种精油中特征香气成分如芳樟醇及乙酸芳樟酯等含量具有较大差异。通过感官分析发现74262精油中花香、酯香气最浓郁,五种精油中花香,酯香、凉气、油蜡气和萜气均有较大差异,其原因主要是由于品种以及所含有的挥发性物质存在差异。     

Composition of peel essential oils from four selected Tunisian Citrus species: Evidence for the genotypic influence

The peel essential oils from four selected Tunisian Citrus species: sweet orange (Citrus sinensis Osbeck), mandarin (Citrus reticulata Blanco); sour orange (Citrus aurantium L.) and pummelo (Citrus grandis Osbeck), cultivated under the same pedoclimatic and cultural conditions have been analysed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The essential oils content ranged from 1.06% to 4.62% (w/w) in pummelo and mandarin, respectively. The qualitative and quantitative analysis led to the identification of 70 components in all oil samples. The analysed oils consist mainly in monoterpene hydrocarbons (97.59–99.3%), with limonene (92.52–97.3%) and β-pinene (1.37–1.82) being the major constituents. The remaining chemical classes were weakly represented (<1%). Both qualitative and quantitative differences between oil samples have been observed and numerous components have been proposed as marker compounds. Since the influence of different environmental factors has been eliminated, the observed chemical variability between the studied species and cultivars seems likely to results from the genetic variability.     

Phytochemical composition and antimicrobial activities of the essential oils from Satureja subspicata Vis. growing in Croatia

The present study describes the phytochemical profile and antimicrobial activity of Satureja subspicata Vis. essential oils, collected in Dalmatia (Croatia). Three samples of essential oils were obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC–MS. From the 24 compounds representing 97.47% of the oils, carvacrol (16.76%), α-pinene (13.58), p-cymene (10.76%), γ-terpinene (9.54%) and thymol methyl ether (8.83%) appear as the main components. The oils also contained smaller percentages of myrcene, linalool, β-caryophyllene, limonene, geranyl acetate, 1-Octen-3-ol, nerol, thymol and borneol. Furthermore, antimicrobial activity of the oil was evaluated using agar diffusion and broth microdilution methods. The antimicrobial test results showed that the oils had a great potential antimicrobial activity against all 13 bacteria and 9 fungal strains. Gram-positive bacteria are more sensitive to the investigated oil, with a range of 0.09 to 6.25 μl/ml than Gram-negative bacteria in the range which is significantly higher from 1.56 to 25.00 μl/ml. Results presented here may suggest that the essential oil of S. subspicata possesses antimicrobial properties, and is therefore a potential source of antimicrobial ingredients for the food and pharmaceutical industry.     

Comparison of key aroma-active composition and aroma perception of cold-pressed and roasted peanut oils

The difference in the aroma composition of cold-pressed and roasted peanut oils was investigated. There were 28 and 75 odorants with flavour dilution (FD) factors between 1 and 512 in cold-pressed and roasted peanut oils, respectively. Fifty-nine odorants were newly identified in peanut oils. Ten key odorants with odour activity value (OAV) ≥ 1 were identified in cold-pressed peanut oil, of which hexanal (OAV = 1,288, green), (E,E)-2,4-decadienal (OAV = 370, earthy and fried fat) and α-pinene (OAV = 34, woody) were the most important contributors to the overall aroma of cold-pressed peanut oil. 2,3-Pentanedione (OAV = 5,054, buttery), 2-methoxy-4-vinylphenol (OAV = 326, smoky), 2,5-dimethylpyrazine (OAV = 160, roasted and nutty) and 2-methylpyrazine (OAV = 92, roasted and nutty) were the most important contributors among the 26 key odorants to the aroma of roasted peanut oil. Roasting peanut seeds induced apparent changes in the formation of aromatic heterocycles, loss of terpenes and increase in lipid oxidation odorants in peanut oil. This study would provide important practical applications in aroma regulation and process optimisation of peanut oil.     

Antimicrobial activity of the essential oils of Brazilian species of the genus Cunila against foodborne pathogens and spoiling bacteria

The essential oils from aerial parts of six Brazilian species of the genus Cunila Mill. (Lamiaceae) currently used in beverages and food preparation, and in folk medicine, were obtained by steam distillation and analyzed by GC and GC/MS. The main components of the oils were: Cunila galioides citral (citral −77.9%), C. galioides menthene (mentha-trans-2,8-dienol −20.0%, limonene −13.6%, trans-ocimene −13.0%), C. incisa (1,8-cineole −42.9%, α-terpineol −14.0%), C. spicata (1,8-cineole −47.9%, α-terpineol −37.5%), C. menthoides (menthene −77.8%), C. angustifolia (sabinene −41.4%, γ-terpinene −11.4%), and C. microcephala (menthofuran −94.90%). These oils were screened for antibacterial activity against 15 bacterial species. The oil of C. galioides citral efficiently controlled the growth of Bacillus sp., L. monocytogenes, S. aureus, A. hydrophila, and E. faecalis, showing both contact and gaseous activity. Although less efficient, the other essential oils studied were effective against Bacillus species, S. aureus, and other specific bacteria. MIC and MCC values support their popular use, and indicate that they can be an efficient alternative for the control of foodborne and spoiling bacteria.     

Authenticity control on lemon essential oils employing Gas Chromatography-Combustion-Isotope Ratio Mass Spectrometry (GC-C-IRMS)

Gas Chromatography-Combustion-Isotope Ratio Mass Spectrometry (GC-C-IRMS) can provide information useful to discriminate among essential oils of different geographical origin and to reveal frauds on essential oils by addition of synthetic or natural compounds from different botanical origin. The present work reports the combination of information obtained by GC-C-IRMS, Enantioselective Gas Chromatography (Es-GC), high resolution Gas Chromatography (GC-FID) and spectrophotometry (CD values). All these techniques represent useful tools to evaluate the authenticity control on lemon essential oils. The GC-C-IRMS was applied to determine the authenticity range of carbon stable isotope ratios in genuine Italian lemon essential oils industrially cold-pressed. Several commercial samples were evaluated to assess their genuineness. The IRMS results are discussed in function of the values also obtained by GC-FID, es-GC and CD values. Stable isotope ratio analysis, by GC-C-IRMS, proved to be useful to detect the presence of sophistications in lemon essential oils, even when other techniques of analysis fail. However for subtle sophistications (e.g. addition of distilled lemon oil) quality assessment must be performed by the auxiliary of more than one technique.     

Composition of the essential oil of Daucus gingidium L. ssp. gingidium

The essential oils obtained from leaves and fruits of Daucus gingidium ssp. gingidium have been studied. The main constituents of the essential oil from the leaves were sabinene (26.8%), α-pinene (10.8%), germacrene D (6.9%) and limonene (5.7%). Sabinene (60.6%) was the main compound identified in the essential oil of the fruits, followed by α-pinene (12.2%) and 4-terpineol (5.4%). Furthermore, qualitative and quantitative considerations about differences with literature data on Daucus carota have been made in order to confirm the species status of D. gingidium.     

Composition and antimicrobial activity of the essential oils of three Satureja species growing in Tanzania

Hydro-distilled volatile oils from the aerial parts of three Satureja species were investigated, mainly by a combination of GC and GC/MS. One hundred and thirteen compounds were identified, representing 82.9–92.0% of the total oil. Among the identified components, spathulenol, cis-piperitone oxide, α-bisabolol oxide-B, terpinen-4-ol, linalool, bornyl acetate, β-bourbonene, isomenthone, thymol, neoisomenthol and menthone were found as the main components. Furthermore, the essential oils were investigated for their antimicrobial activity, by the agar dilution technique. The antimicrobial test results showed that the oils had a high antimicrobial activity against two Gram-positive and four Gram-negative bacteria, two oral pathogens and three pathogenic fungi. Gram-positive bacteria were more sensitive to the investigated oils than were Gram-negative bacteria. These results could support the suggestion of Satureja species as a source of antimicrobial ingredients for the food industry.     

Comparative chemical composition,antioxidant and hypoglycaemic activities of Juniperus oxycedrus ssp. oxycedrus L. berry and wood oils from Lebanon

Juniper (Juniperus oxycedrus) is used in European cuisine for its distinguishing flavour. J. oxycedrus ssp. oxycedrus berry and wood essential oils were tentatively identified by GC and GC/MS. Fifty compounds were identified in the berry oil and 23 compounds were identified in the wood oil. The J. oxycedrus ssp. oxycedrus berry oil was characterised by high contents of α-pinene (27.4%) and β-myrcene (18.9%). Other important compounds were α-phellandrene (7.1%), limonene (6.7%), epi-bicyclosesquiphellandrene (2.3%) and δ-cadinene (2.2%) while, in the wood oil, δ-cadinene (14.5%) is a major main component, together with cis-thujopsene (9.2%) and α-muurolene (4.9%). In vitro evaluation of antioxidant activity by the DPPH method showed a significant activity for both oils with IC₅₀ values of 1.45 μl/ml for wood and 7.42 μl/ml for berries. Hypoglycaemic activity was investigated through the inhibition of α-amylase. The results revealed that oil obtained by hydrodistillation from J. oxycedrus ssp. oxycedrus wood exhibits an interesting activity with IC₅₀ of 3.49 μl/ml.     

Chemical composition and antioxidant and antimicrobial activity of two Satureja essential oils

Hydro-distilled volatile oils from the aerial parts of Satureja montana L., and Satureja subspicata Bartl. ex Vis., growing wild in Bosnia and Herzegovina, were analyzed by GC/MS. More than one hundred compounds were identified in both plant oils, representing 92.4–98.1% of the total oil. The major constituents of essential oils obtained from the plant material of S. montana, collected from two different localities, were thymol (31.7%), and geraniol (22.3%), respectively. The most abundant compounds in essential oils of S. subspicata, collected at two different stages of development, were thymol (28.6%), and spathulenol (37.6%), respectively. The screening of antimicrobial activity of essential oil samples was individually evaluated against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeruginosa and Bacillus subtilis using a paper disc diffusion method. All tested microorganisms were inhibited by essential oil samples. Antioxidant activity was tested using the DPPH radical-scavenging method. All samples showed activity comparable to thymol, which was used as a positive probe.     

Odor and taste thresholds of potential carry-over/off-flavor compounds in orange and apple juice

The odor and taste threshold values of six aroma substances known to be constituents of fruit juices and other fruit products, i.e. limonene, α-terpineol, carvone, methyl 2-methylbutanoate, ethyl 2-methylbutanoate, and γ-decalactone, were determined in various matrices, i.e. model sugar/acid solution, apple and orange juice, as well as apple and orange substitute (made by dilution of fruit juice concentrate with water). Whereas for α-terpineol thresholds in the 1.2-11 mg/l area were defined, limonene and carvone were determined to be sensorially effective each at 0.5 mg/l. Very low thresholds were measured for γ-decalactone, methyl 2-methylbutanoate and ethyl 2-methylbutanoate that showed sensory activity in the area of 20, 1.5, and 0.5 μg/l, respectively. In relation to the aroma composition determined by high resolution gas chromatography-mass spectrometry (HRGC-MS), these results provide an objective possibility to evaluate the sensory efficacy and/or an ‘off-flavor’ potential of these compounds in fruit juices.