Volatile constituents of uncooked rhubarb (Rheum rhabarbarum L.) stalks

Volatiles of rhubarb (Rheum rhabarbarum L.) stalks were isolated by means of vacuum headspace method and analyzed by capillary gas chromatography-mass spectrometry. Fifty-nine components were reported for the first time in rhubarb. A striking feature of the extracts obtained is the preponderance (approximately 65%) of compounds with C(6) skeletons. In addition to unsaturated C(6) aldehydes and alcohols, substantial amounts of the less common (E)-2- and (E)-3-hexenoic acid were detected. Gas chromatography-olfactometry and determination of odor activity values revealed the sensory importance of the C(6) compounds to the aroma of rhubarb. Comparative experiments involving the inhibition of enzyme activities revealed that the initial spectrum of C(6) components is changed due to subsequent isomerization and reductions. Thus, contributions of (Z)-3-hexenal and the unsaturated acids decrease, and (E)-2-hexenal/(E)-2-hexenol play major sensory roles.     

Characterization of volatiles in strawberry guava (Psidium cattleianum Sabine) fruit.

Volatile compounds were isolated from strawberry guava fruit by simultaneous steam distillation-solvent extraction according to Likens-Nickerson. Compounds were identified by capillary GC-MS and sensorially characterized by sniffing GC. Two hundred and four compounds were identified in the aroma concentrate, of which ethanol, alpha-pinene, (Z)-3-hexenol, (E)-beta-caryophyllene, and hexadecanoic acid were found to be the major constituents. The presence of many aliphatic esters and terpenic compounds is thought to contribute to the unique flavor of the strawberry guava fruit.     

Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.)

Extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.) were obtained using two methods: steam distillation under reduced pressure followed by dichloromethane extraction (DRP) and simultaneous purging and extraction (SPSE). A total of 192 volatile chemicals were identified in the extracts obtained by both methods using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). They included 47 monoterpenoids (oxygenated monoterpenes), 26 aromatic compounds, 19 aliphatic esters, 18 aliphatic alcohols, 17 monoterpenes (hydrocarbon monoterpenes), 17 sesquiterpenes (hydrocarbon sesquiterpenes), 13 sesquiterpenoids (oxygenated sesquiterpenes), 12 aliphatic aldehydes, 8 aliphatic hydrocarbons, 7 aliphatic ketones, and 9 miscellaneous compounds. The major volatile constituents of the extract by DRP were borneol (10.27 ppm), alpha-thujone (3.49 ppm), artemisia alcohol (2.17 ppm), verbenone (1.85 ppm), yomogi alcohol (1.50 ppm), and germacren-4-ol (1.43 ppm). The major volatile constituents of the extract by SPSE were 1,8-cineole (8.12 ppm), artemisia acetate (4.22 ppm), alpha-thujone (3.20 ppm), beta-caryophyllene (2.39 ppm), bornyl acetate (2.05 ppm), borneol (1.80 ppm), and trans-beta-farnesene (1. 78 ppm).     

Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. variety spalter select) based on GC-olfactometry and odor dilution techniques

Application of aroma extract dilution analysis on the volatiles obtained from dried cones of Spalter Select hops grown in the German hop-growing area of Hallertau revealed 23 odorants in the flavor dilution (FD) factor range of 16-4096, 20 of which could be identified. On the basis of high FD factors, trans-4, 5-epoxy-(E)-2-decenal, linalool, and myrcene were identified as the most potent odorants, followed by ethyl 2-methylpropanoate, methyl 2-methylbutanoate, (Z)-1,5-octadien-3-one, nonanal, (E,Z)-1,3, 5-undecatriene, 1,3(E),5(Z),9-undecatetraene, propyl 2-methylbutanoate, 4-ethenyl-2-methoxyphenol, and 1-octen-3-one. Ten of the high-impact hop aroma compounds had previously not been identified as hop constituents and, in particular, 1,3(E),5(Z), 9-undecatetraene has not yet been reported as a food odorant. In an extract obtained from fresh hops, in addition to the odorants found in dry hops, (Z)-3-hexenal was characterized as a further key odorant rendering an additional green aroma note to the fresh material.     

茶叶挥发物对鞍形花蟹蛛觅食行为的影响

为了探明茶叶挥发物在鞍形花蟹蛛(Xysticus ephippiatus Simon)搜寻猎物——茶尺蠖(Ectropis obliqua Prout)过程中的作用,采用固相微萃取气相色谱质谱联用技术研究了茶尺蠖取食对茶树叶片挥发物释放的影响,并通过蜘蛛行为观测平台研究了蟹蛛在不同味源侧(觅食斑块)的活动行为。结果表明:对照叶片没有释放出挥发物,经茶尺蠖幼虫取食后的叶片能释放31种挥发物,其中有12种绿叶挥发物、9种萜类及其衍生物、4种芳香族挥发物和6种未知化合物。行为观测表明,雌、雄蟹蛛进入处理味源侧(茶尺蠖取食后的茶树叶片)和对照味源侧(未损伤茶树叶片)的初次选择均不存在差别(P>0.05),雌蛛进入处理味源侧和对照味源侧的频次分别为3.37±0.18和3.43±0.15,二者无明显区别(P>0.05);雄蛛进入两侧的频次分别为3.86±0.21和3.66±0.20,也无明显区别(P>0.05);雌蛛在处理味源侧和对照味源侧的停留时间分别为(922.57±19.59)s和(818.89±29.63)s,有极显著差异(P<0.01),雄蛛在两侧的停留时间分别为(937.97±18.05)s和(814.83±18.97)s,也有极显著差异(P<0.01),表明雌蛛、雄蛛在处理侧的停留时间明显延长。这说明,猎物取食诱导改变了茶树叶片挥发物的释放,而鞍形花蟹蛛能感知挥发物的变化并由此调整在不同觅食斑块中的停留时间。另外,本文还讨论了挥发物在蟹蛛搜寻猎物过程中的生态学意义。     

Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L

The volatiles of fresh leaves, buds, flowers, and fruits from bay (Laurus nolilis L.) were isolated by solvent extraction and analyzed by capillary gas chromatography-mass spectrometry. Their odor quality was characterized by gas chomatography-olfactometry-mass spectrometry (HRGC-O-MS) and aroma extract dilution analysis (AEDA). In fresh bay leaves 1,8-cineole was the major component, together with alpha-terpinyl acetate, sabinene, alpha-pinene, beta-pinene, beta-elemene, alpha-terpineol, linalool, and eugenol. Besides 1,8-cineole and the pinenes, the main components in flowers were alpha-eudesmol, beta-elemene, and beta-caryophyllene, in fruits (E)-beta-ocimene and biclyclogermacrene, and in buds (E)-beta-ocimene and germacrene D. The aliphatic ocimenes and farnesenes were absent in leaves. By using HRGC-O-MS 21 odor compounds were identified in fresh leaves. Application of AEDA revealed (Z)-3-hexenal (fresh green), 1,8-cineole (eucalyptus), linalool (flowery), eugenol (clove), (E)-isoeugenol (flowery), and an unidentified compound (black pepper) with the highest flavor dilution factors. Differences between buds, flowers, fruits, and leaves with regard to the identified odor compounds are presented.     

Volatiles from leaves,fruits, and virgin oil from Olea europaea Cv. Olivastra Seggianese from Italy

The volatiles produced by leaves and fruits of Olea europaea cv. Olivastra Seggianese have been analyzed in two different phenological stages. Furthermore, the volatiles of the virgin olive oil obtained from ripe fruits has been characterized. The volatiles were sampled by means of two different techniques: hydrodistillation and SPME. Differences were observed between the two different collection times, the different organs, and sampling techniques. The major constituents were often aldehydes, particularly (E)-2-hexenal (9.8-48.0%); however, also many terpenoids have been identified, mainly (E,E)-alpha-farnesene (0.2-27.0%), linalool (0-3.6%), beta-caryophyllene (0-8.1%), and valencene (0-2.5%). This is the first investigation on this cultivar.     

Comparison of volatile constituents of Persicaria odorata(Lour.) Soják (Polygonum odoratum Lour.) and Persicaria hydropiper L. Spach (Polygonum hydropiper L.)

Polygonum odoratum Lour. has been reclassified as Persicaria odorata (Lour.) Soják [Wilson, K. L. Polygonum sensu lato (Polygonaceae) in Australia. Telopea 1988, 3, 177-182]; other synonyms currently used are Vietnamese mint or Vietnamese coriander and, in Malaysia, Daun Laksa or Laksa plant. The aerial parts of Laksa plant are highly aromatic, and they contain many organic compounds such as (Z)-3-hexenal, (Z)-3-hexenol, decanal, undecanal, and dodecanal that are typical for green, citrus, orange peel, and coriander odors. In addition to these aldehydes, 3-sulfanyl-hexanal and 3-sulfanyl-hexan-1-ol were discovered for the first time in this herb. The fresh leaves are pungent when they are chewed, although the active compound has never been identified. The pungency of Persicaria hydropiper (L.) Spach (formerly Polygonum hydropiper L., synonym water pepper) is produced by polygodial, a 1,4-dialdehyde derived from drimane terpenoids. We also identified polygodial as the active pungent compound in P. odorata (Lour.) Soják.     

Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors in melón de olor fruit pulp (Sicana odorifera)

Free and glycosidically bound volatiles obtained from the fruit pulp of Sicana odorifera by liquid-liquid extraction and by chromatography, followed by enzymatic hydrolysis with Rohapect D5L, respectively, were analyzed by capillary gas chromatography (HRGC), HRGC-mass spectrometry (HRGC-MS), and HRGC-Olfatometry (HRGC-O) analyses. A total of 37 free volatiles was detected, with the major components being 3-methyl-2-butanol, 3-hydroxy-2-butanone, ethyl 3-hydroxybutanoate, and (Z)-3-hexenol. Among the 22 detected glycosidically bound compounds, 4-hydroxybenzyl methyl ether, 4-hydroxybenzyl alcohol, and 2-phenylethanol were found to be the major constituents. Additionally, two glucoconjugates were isolated in pure form by multilayer coil countercurrent chromatography (MLCCC) of the glycosidic extrac and further purification. Their structures were elucidated by MS and NMR analyses to be the novel [4-(beta-D-glucopyranosyloxy)benzyl] 2,3-dihydroxy-3-methylbutanoate 2, and the known 4-(beta-D-glucopyranosyloxy)benzyl alcohol 1. Compounds 1 and 2 are precursors of 4-hydroxybenzyl alcohol, one of the major volatiles generated by enzymatic hydrolysis of the glycosidic fraction.     

Identification of characteristic aroma-active compounds from water dropwort (Oenanthe javanica DC.)

Characteristic aroma components of water dropwort (Oenanthe javanica DC.) were evaluated by aroma extract dilution analysis and solid-phase microextraction-gas chromatography-olfactometry. Alpha-Terpinolene (plastic/cucumber-like) was the most intense aroma-active compound in water dropwort. Other potent aroma-active compounds included p-cymene (kerosene-like), alpha-terpinene (lemon), (E)-caryophyllene (woody), (Z,E)-alpha-farnesene (woody), hexanal (green), (Z)-3-hexenol (green), phenylacetaldehyde (honey), (E)-2-nonenal (cucumber), bornyl acetate (cooked vegetable), and gamma-terpinene (lemon). Of these, p-cymene was believed to be primarily responsible for the distinct kerosene-like aroma note of water dropwort. The aroma property of p-cymene was dependent on its concentration and was described as kerosene-like at relatively high concentrations but changed to citrus and green aroma notes at low concentrations.     

Characterization of the most odor-active volatiles in fresh, hand-squeezed juice of grapefruit (Citrus paradisi Macfayden)

By application of the aroma extract dilution analysis on an extract prepared from fresh grapefruit juice, 37 odor-active compounds were detected in the flavor dilution (FD) factor range of 4-256 and subsequently identified. Among them the highest odor activities (FD factors) were determined for ethyl butanoate, p-1-menthene-8-thiol, (Z)-3-hexenal, 4,5-epoxy-(E)-2-decenal, 4-mercapto-4-methylpentane-2-one, 1-heptene-3-one, and wine lactone. Besides the 5 last mentioned compounds, a total of 13 further odorants were identified for the first time as flavor constituents of grapefruit. The data confirmed results of the literature on the significant contribution of 1-p-menthene-8-thiol in grapefruit aroma but clearly showed that a certain number of further odorants are necessary to elicit the typical grapefruit flavor.     

Analysis of glycosidically bound aroma precursors in tea leaves. 1. Qualitative and quantitative analyses of glycosides with aglycons as aroma compounds

Twenty-six synthetic glycosides constituting aglycons of the main tea aroma compounds ((Z)-3-hexenol, benzyl alcohol, 2-phenylethanol, methyl salicylate, geraniol, linalool, and four isomers of linalool oxides) were synthesized in our laboratory as authentic compounds. Those compounds were used to carry out a direct qualitative and quantitative determination of the glycosides as aroma precursors in different tea cultivars by capillary gas chromatographic-mass spectrometric (GC-MS) analyses after trifluoroacetyl conversion of the tea glycosidic fractions. Eleven beta-D-glucopyranosides, 10 beta-primeverosides (6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside) with aglycons as the above alcohols, and geranyl beta-vicianoside (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) were identified (tentatively identified in the case of methyl salicylate beta-primeveroside) in fresh tea leaves and quantified on the basis of calibration curves that had been established by using the synthetic compounds. Primeverosides were more abundant than glucosides in each cultivar we investigated for making green tea, oolong tea, and black tea. Separation of the diastereoisomers of linalool and four isomers of linalool oxides by GC analyses is also discussed.     

Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim)

Volatile flavor compounds of miniature beefsteakplant (Mosla dianthera Maxim.) from Vietnam were analyzed through gas chromatography-mass spectrometry-olfactometry (GC-MS-O). Sixty-two compounds were identified by GC-MS. Of these, (+/-)-carvone and (+/-)-limonene were the most abundant, followed by (Z)-limonene oxide, beta-caryophyllene, and alpha-humulene. Twenty aroma-active compounds were detected by aroma extract dilution analysis conducted on two GC columns of different polarities (DB-5MS and DB-Wax). The most intense aroma-active compounds were linalool (floral/sweet/lemon), (-)-carvone (spearminty), and 1-octen-3-one (mushroom/earthy). Other predominant aroma-active compounds included (Z)-3-hexenol (grassy/leafy/metallic), (Z)-limonene oxide (lemon/floral), myrcene (plastic/sweet), (+)-limonene (orange/lemon), alpha-thujene (soy sauce/grassy), and (Z)-dihydrocarvone (spearminty/pepperminty). On the basis of the aroma characteristics and intensity, it was concluded that (-)-carvone was responsible for the characteristic aroma of miniature beefsteakplant.     

Isolation of some glycosides as aroma precursors in young leaves of Japanese pepper (Xanthoxylum piperitum DC.).

To clarify the formation mechanism for the major alcoholic aroma compounds in young leaves of Japanese pepper, the glycosides were isolated as aroma precursors. The presence of glycosides of the main alcoholic aroma constituents was indirectly determined by enzymatic hydrolysis and trifluoroacetylation (TFA) of the glycoside-containing fraction. After Amberlite XAD-2 column chromatography, ODS flash chromatography, and high-performance liquid chromatography (HPLC), two new compounds, namely, (3S,6S)-cis-linalool-3,7-oxide beta-D-glucopyranoside and 2-methylpropanyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, were isolated. In addition, (3S,6R)-cis-linalool-3,6-oxide beta-D-glucopyranoside, which absolute configuration was the first determined, and six known glycosides, citronellyl beta-D-glucopyranoside, linalyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, (Z)-3-hexenyl beta-D-glucopyranoside, benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, dendranthemoside A, and 3,6-dihydroxy-5,6-dihydro-beta-ionol 9-beta-D-glucopyranoside, were isolated. All of these glycosides were isolated for the first time from the leaves of Japanese pepper. Their structures were established on the basis of spectral data and chemical evidence. The ratios of stereoisomers of the aglycon moieties of citronellyl beta-D-glucopyranoside and linalyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside were investigated by a chiral GC analysis and compared with those of free citronellol and linalool in the aroma concentrate.     

Variation of major volatile constituents in various green teas from Southeast Asia

A total of 15 green tea samples were prepared from fresh tea leaves obtained from three different countries: two from Laos, seven from Myanmar, and six from Vietnam. The volatile aroma constituents of the 15 samples were analyzed by gas chromatography/mass spectroscopy. Eleven aroma constituents were chosen from over 100 chemicals found in the samples to compare differences among various teas. They were hexanal, 1-penten-3-ol, heptanal, 1-pentenal, (Z)-2-penten-1-ol, (Z)-3-penten-1-ol, linalool oxide (trans-furanoid), linalool oxide (cis-furanoid), linalool, linalyl propanoate, and geraniol. Generally, concentrations of linalool and hexanal seem to play an important role in the quality of green teas. Green teas from Laos and Myanmar contained heterocyclic compounds, such as pyridines and pyrazines, formed by high-temperature processing. The presence of these heterocyclic compounds suggested that the temperature used for tea processing plays an important role in the formation of aroma chemicals in green teas.     

Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis

"Spanish style" Moroccan green table olives were screened for potent odorants by gas chromatography-olfactometry/aroma extraction dilution analysis of a representative Likens-Nickerson extract. (Z)-3-Hexenal [flavor dilution factor (FD) = 256], (E,E)-2,4-decadienal (FD = 128), and (E,Z)-2,4-decadienal (FD = 64) were revealed to confer green and coriander/paraffin oil odors to both fruit and oil extracts, whereas guaiacol (FD = 128) imparted a bad olive, phenolic note. Methional (3-methylthiopropionaldehyde, FD = 128) and several terpenes (FD 相似文献   

Volatile composition of four southern highbush blueberry cultivars and effect of growing location and harvest date

The volatile composition of four southern highbush blueberry cultivars ('Primadonna', 'Jewel', 'Snowchaser', and 'FL02-40') grown in two locations (Gainesville and Haines City, FL) and harvested multiple times was investigated. A total of 42 volatiles were identified, including 8 esters, 12 terpenoids, 11 aldehydes, 7 alcohols, and 4 ketones. Twelve of these volatiles are reported for the first time in highbush blueberries, with 10 being positively identified: (Z)-3-hexenal, (E,E)-2,4-hexadienal, (E,Z)-2,6-nonadienal, (E,E)-2,4-nonedienal, methyl 2-methylbutanoate, butyl acetate, 2-methylbutyl acetate, and geranyl acetate. The dominant volatiles were aldehydes followed by terpenoids and esters, with distinct varietal profiles. 'Primadonna' was characterized by a large amount of esters and C-6 aldehydes. In contrast, fewer than 4 esters were found in 'FL02-40' and 'Snowchaser', respectively, but they produced more terpenoids than 'Primadonna' and 'Jewel'. Location and/or harvest date affected the production of volatiles in 'Primadonna', but not so much in the other cultivars.     

Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis

The volatiles present in fresh, pink-fleshed Colombian guavas ( Psidium guajava, L.), variety regional rojo, were carefully isolated by solvent extraction followed by solvent-assisted flavor evaporation, and the aroma-active areas in the gas chromatogram were screened by application of the aroma extract dilution analysis. The results of the identification experiments in combination with the FD factors revealed 4-methoxy-2,5-dimethyl-3(2 H)-furanone, 4-hydroxy-2,5-dimethyl-3(2 H)-furanone, 3-sulfanylhexyl acetate, and 3-sulfanyl-1-hexanol followed by 3-hydroxy-4,5-dimethyl-2(5 H)-furanone, ( Z)-3-hexenal, trans-4,5-epoxy-( E)-2-decenal, cinnamyl alcohol, ethyl butanoate, hexanal, methional, and cinnamyl acetate as important aroma contributors. Enantioselective gas chromatography revealed an enantiomeric distribution close to the racemate in 3-sulfanylhexyl acetate as well as in 3-sulfanyl-1-hexanol. In addition, two fruity smelling diastereomeric methyl 2-hydroxy-3-methylpentanoates were identified as the ( R,S)- and the ( S,S)-isomers, whereas the ( S,R)- and ( R,R)-isomers were absent. Seven odorants were identified for the first time in guavas, among them 3-sulfanylhexyl acetate, 3-sulfanyl-1-hexanol, 3-hydroxy-4,5-dimethyl-2(5 H)-furanone, trans-4,5-epoxy-( E)-2-decenal, and methional were the most odor-active.     

A hairy root culture of melon produces aroma compounds

Musk melon is the favorite fruit with a high market value in Japan, and the fragrance is one of the major factors determining the fruit quality of melon. In this study, mutant melon hairy roots which had been induced by means of the T-DNA insertion mutagenesis were found to produce volatile compounds with the fruity fragrance of mature melon. The volatile compounds were extracted and identified by GLC-mass spectrometry. Some essential oils such as (Z)-3-hexenol, (E)-2-hexenal, 1-nonanol, and (Z)-6-nonenol were stably synthesized by these hairy roots despite the increased number of subcultures. The productivity of these compounds by the best hairy root line was shown to be considerably higher than naturally ripened melon fruits.     

Characterization of (E,E,Z)-2,4,6-nonatrienal as a character impact aroma compound of oat flakes

To identify the compounds evoking the characteristic cereal-like, sweet aroma of oat flakes, an aroma extract dilution analysis (AEDA) was applied to a distillate prepared by solvent extraction/vacuum distillation from commercial oat flakes. Among the nine aroma-active compounds detected by gas chromatography-olfactometry and AEDA in the flavor dilution (FD) factor range of 4-1024, eight odorants, for example, (E)-beta-damascenone, (Z)-3-hexenal, and butanoic acid, showed only low FD factors. However, one odorant eliciting the typical cereal, sweet aroma of the flakes was detected with the highest FD factor of 1024. By mass spectrometry and nuclear magnetic resonance measurements followed by a synthesis, (E,E,Z)-2,4,6-nonatrienal, exhibiting an intense oat flake-like odor at the extremely low odor threshold of 0.0002 ng/L in air, was identified as the key odorant of the flakes. By means of a newly developed stable isotope dilution analysis using synthesized, carbon-13-labeled nonatrienal as the internal standard, a concentration of 13 mug of (E,E,Z)-2,4,6-nonatrienal per kilogram of the flakes was measured. Model studies suggested linolenic acid as the precursor of nonatrienal in oats.