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1.
Pyrazine formation from serine and threonine.   总被引:4,自引:0,他引:4  
The formation of pyrazines from L-serine and L-threonine has been studied. L-Serine and L-threonine, either alone or combined, were heated at 120 degrees C as low temperature for 4 h or at 300 degrees C as high temperature for 7 min. The pyrazines formed from each reaction were identified by GC/MS, and the yields (to the amino acid used, as parts per million) were determined by GC/FID. It was found that pyrazine, methylpyrazine, ethylpyrazine, 2-ethyl-6-methylpyrazine, and 2,6-diethylpyrazine were formed from serine, whereas 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, trimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, and 2-ethyl-3, 5-dimethylpyrazine were formed from threonine. Mechanistically, it is proposed that the thermal degradation of serine or threonine is composed of various complex reactions. Among these reactions, decarbonylation followed by dehydration is the main pathway to generate the alpha-aminocarbonyl intermediates leading to the formation of the main product, such as pyrazine from serine or 2, 5-dimethylpyrazine from threonine. Also, deamination after decarbonylation generates more reactive intermediates, alpha-hydroxycarbonyls. Furthermore, aldol condensation of these reactive intermediates provides alpha-dicarbonyls. Subsequently, these alpha-dicarbonyls react with the remaining serine or threonine by Strecker degradation to form additional alpha-aminocarbonyl intermediates, which then form additional pyrazines. In addition, decarboxylation and retroaldol reaction may also involve the generation of the intermediates.  相似文献   

2.
The delta15N(AIR) and delta2H(VSMOW) data for several alkylpyrazines formed during the roasting process of coffee are reported. Samples of commercially available roasted (n = 9) as well as self-roasted (n = 8) coffee beans (Coffea arabica L. and Coffea canephora var. robusta) of different origins were investigated. By use of extracts prepared by simultaneous distillation extraction (SDE) and subsequently fractionated by liquid chromatography on silica gel, on-line capillary gas chromatography-isotope ratio mass spectrometry was employed in the combustion (C) and pyrolysis (P) modes (HRGC-C/P-IRMS) to determine the delta15N(AIR) and delta2H(VSMOW) values, respectively. In addition to the constituents of coffee beans, data for commercial synthetic alkylpyrazines and substances declared to be "natural" were determined. The delta15N(AIR) data for coffee alkylpyrazines under study-2-ethyl-5-methylpyrazine (1) and 2-ethyl-6-methylpyrazine (2) (measured as sum 1/2), 2-ethyl-3-methylpyrazine (3), 2-methylpyrazine (4), 2,5-dimethylpyrazine (5) and 2,6-dimethylpyrazine (6) (measured as sum 5/6), and 2,3-dimethylpyrazine (7), as well as 2,3,5-trimethylpyrazine (8)-varied in the range from +8.3 to -10.2 per thousand, thus revealing their biogeneration from amino acids (delta15N(AIR) ranging from +8 per thousand to -10 per thousand). The delta2H(VSMOW) values were determined in the range from -5 per thousand to -127 per thousand. Owing to the analytical differentiation observed between coffee alkylpyrazines and synthetic/"natural" samples of 3, 4, and 7, authenticity assessment of coffee-flavored products seems to be promising, provided that extended data will be available in the future. In the literature, there were no IRMS data available for the alkylpyrazines (1-8) under study.  相似文献   

3.
Some important edible oils (extra virgin olive oil, canola oil, and sunflower oil) were added to aqueous glucose-lysine or xylose-lysine model systems to investigate their effect on the formation of volatiles from the Maillard reaction (MR). The volatile compounds were extracted by a Likens-Nickerson apparatus and quantified. Pyrazines, Maillard reaction products with an important impact on food flavor, appeared to be particularly sensitive to the presence of the oils in both the xylose-lysine and glucose-lysine model systems. The unsubstituted pyrazine was formed more with olive oil, less with canola oil, and even less with sunflower oil, whereas 2-methylpyrazine, 2,5-methylpyrazine, and 2,3-dimethylpyrazine were formed less with olive oil, more with canola oil, and even more with sunflower. The oxidative states of the oils and their fatty acid fingerprints were determined: the results indicated that the relative amounts of the pyrazines are sensitive to the degree of unsaturation of the oil. The autoxidation of the volatile compounds generated from the MR, investigated by the addition of free radical modulators (antioxidants alpha-tocopherol, 2,6-di-tert-butyl-4-methylphenol, and rosemary extract; or pro-oxidant alpha,alpha'-azobis-isobutyronitrile, a free radical initiator), was limited in respect to aqueous model systems.  相似文献   

4.
Application of the aroma extract dilution analysis on a concentrate of volatiles obtained by solvent extraction and high vacuum distillation from roasted seeds (180 degrees C; 15 min) of wild mango (Irvingia gabonensis) revealed 32 odor-active compounds with flavor dilution (FD) factors ranging from 8 (low odor activity) to 2048 (high odor activity). The identification experiments based on the use of reference odorants revealed methional (cooked potato-like) followed by 2-acetyl-1-pyrroline (roasty, popcorn-like), butan-2,3-dione, pentan-2,3-dione, 2-ethyl-3,5-dimethylpyrazine, and 2,3-diethyl-5-methylpyrazine as the key aroma compounds among the 27 odorants identified. All odorants are reported for the first time as components of roasted wild mango seeds.  相似文献   

5.
This paper describes the composition of sesame seed oils obtained from seeds collected from five countries that are major suppliers of traded sesame seed oil. Oils were extracted from the seeds using small-scale industry pressing equipment and analyzed using standard methods for fatty acids, fatty acids in the triglyceride 2-position, tocopherols and tocotrienols, triglycerides, sterols, steradienes, and iodine value. Values for the composition of the sterols, triglycerides, fatty acids, iodine value, and tocopherol composition were generally in good agreement with the results published elsewhere. All of the oils from roasted seeds contained low levels of the sterol degradation products stigmasta-3,5-diene and campesta-3,5-diene, which were probably formed by dehydration of the parent sterols during roasting.  相似文献   

6.
This research aims to optimize roasted green tea (Houjicha) processing by using roasting treatments to achieve acrylamide mitigation without compromising the quality. 2-Ethyl-3,5-dimethylpyrazine and 2-ethyl-3,6-dimethylpyrazine were identified as potent odorants by aroma extract dilution analysis. In preliminary sensory experiments, the desirable Houjicha flavor was produced in products roasted at 160 degrees C for 30 min and at 180 degrees C for 15 min. Under these conditions, potent odorants were formed at levels adequate for contributing to the Houjicha flavor. Acrylamide amounts in tea infusions were 2.0 and 4.0 microg/L by roasting at 160 degrees C for 30 min and at 180 degrees C for 15 min, respectively. Compared to roasting at 180 degrees C, the degradation of tea catechins was suppressed by roasting at 160 degrees C. Hence, roasting at 160 degrees C for is recommended for Houjicha processing for acrylamide mitigation, formation of potent odorants, and suppression of degradation of tea catechins.  相似文献   

7.
The volatiles in the headspace above a solution of [(13)C(6)]fructose and alanine in glycerol/water, heated in a closed vial at 130 degrees C for 2 h, were analyzed by solid-phase microextraction in tandem with GC-MS. Carbonyl compounds and pyrazines were among the detected components. The examination of their mass spectra showed that most of the 1-hydroxy-2-propanone and 2,3-pentanedione were (13)C(3)-labeled, the majority of the 2-methylpyrazine and 2-ethyl-3-methylpyrazine were (13)C(5)-labeled, and 2,5-dimethylpyrazine and 3-ethyl-2,5-dimethylpyrazine were mainly (13)C(6)-labeled. This is in agreement with the literature, and corresponds to the incorporation of fructose carbons, and in the case of 2,3-pentanedione, 2-ethyl-3-methylpyrazine, and 3-ethyl-2,5-dimethylpyrazine alanine carbons, into the molecules. However, minority fractions of 1-hydroxy-2-propanone (10%) and 2,3-pentanedione (14%) were found unlabeled, 2-methylpyrazine (10%) and 2-ethyl-3-methylpyrazine (11%) only doubly labeled, and 2,5-dimethylpyrazine (20%) and 3-ethyl-2,5-dimethylpyrazine (27%) only triply labeled, suggesting they contain carbons originating from the solvent glycerol. This could be confirmed by reaction of fructose and alanine in [(13)C(3)]glycerol/water, which produced the same volatiles, with 11-27% existent in their (13)C(3)-labeled form. Hence, glycerol participated not only as a solvent but also as a precursor in the reaction.  相似文献   

8.
Volatiles were obtained from commercially prepared and laboratory-prepared rice cakes using high-flow dynamic headspace isolation with Tenax trapping. Analysis was carried out by capillary GC/MS. More than 60 compounds were identified. Major volatiles included 1-hydroxy-2-propanone, furfuryl alcohol, 2, 5-dimethylpyrazine, 2-methylpyrazine, pyrazine, hexanal, furfural, pentanol, 3-hydroxy-2-butanone (acetoin), and ethyl-3, 6-dimethylpyrazine. Although not ideally applicable to a dry product, concentration/threshold ratios indicated that the compounds with a high probability of contributing to the aroma and flavor included 3-methylbutanal, dimethyl trisulfide, 2-ethyl-3,5-dimethylpyrazine, 4-vinylguaiacol, hexanal, (E,E)-2,4-decadienal, 2-methylbutanal, 2-acetyl-1-pyrroline, 1-octen-3-ol, and 1-octen-3-one.  相似文献   

9.
Aroma compounds in Chinese "Wuliangye" liquor were identified by gas chromatography-olfactometry (GC-O) after fractionation. A total of 132 odorants were detected by GC-O in Wuliangye liquor on DB-wax and DB-5 columns. Of these, 126 aromas were identified by GC-mass spectrometry (MS). Aroma extract dilution analysis (AEDA) was further employed to identify the most important aroma compounds in "Wuliangye" and "Jiannanchun" liquors. The results showed that esters could be the most important class, especially ethyl esters. Various alcohols, aldehydes, acetals, alkylpyrazines, furan derivatives, lactones, and sulfur-containing and phenolic compounds were also found to be important. On the basis of flavor dilution (FD) values, the most important aroma compounds in Wuliangye and Jiannanchun liquors could be ethyl butanoate, ethyl pentanoate, ethyl hexanoate, ethyl octanoate, butyl hexanoate, ethyl 3-methylbutanoate, hexanoic acid, and 1,1-diethoxy-3-methylbutane (FD > or = 1024). These compounds contributed to fruity, floral, and apple- and pineapple-like aromas with the exception of hexanoic acid, which imparts a sweaty note. Several pyrazines, including 2,5-dimethyl-3-ethylpyrazine, 2-ethyl-6-methylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, and 3,5-dimethyl-2-pentylpyrazine, were identified in these two liquors. Although further quantitative analysis is required, it seems that most of these pyrazine compounds had higher FD values in Wuliangye than in Jiannanchun liquor, thus imparting stronger nutty, baked, and roasted notes in Wuliangye liquor.  相似文献   

10.
Caneberries (Rubus spp. L.) are grown primarily throughout the Pacific Northwestern United States and Canada. Processing of caneberry fruit typically removes the seed, and the development of a value-added use of seeds could expand the market for caneberries and the profit margins for growers. An initial step toward the use of the seeds is a characterization of seed and oil. Our investigation has described compositional characteristics for seeds of five commonly grown caneberry species: red raspberry, black raspberry, boysenberry, Marion blackberry, and evergreen blackberry. Seeds from all five species had 6-7% protein and 11-18% oil. The oils contained 53-63% linoleic acid, 15-31% linolenic acid, and 3-8% saturated fatty acids. The two smaller seeded raspberry species had higher percentages of oil, the lowest amounts of saturated fatty acid, and the highest amounts of linolenic acid. Antioxidant capacities were detected both for whole seeds and for cold-pressed oils but did not correlate to total phenolics or tocopherols. Ellagitannins and free ellagic acid were the main phenolics detected in all five caneberry species and were approximately 3-fold more abundant in the blackberries and the boysenberry than in the raspberries.  相似文献   

11.
Whole berries, seeds, and pulp/peel of goldenberry (Physalis peruviana L.) were compared in terms of fatty acids, lipid classes, triacylglyerols, phytosterols, fat-soluble vitamins, and beta-carotene. The total lipid contents in the whole berries, seeds, and seedless parts were 2.0, 1.8, and 0.2% (on a fresh weight basis), respectively. Linoleic acid was the dominating fatty acid followed by oleic acid as the second major fatty acid. Palmitic and stearic acids were the major saturates. In pulp/peel oil, the fatty acid profile was characterized by higher amounts of saturates, monoenes, and trienes than in whole berry and seed oils. Neutral lipids comprised >95% of total lipids in whole berry oil and seed oil, while neutral lipids separated in lower level in pulp/peel oil. Triacylglycerols were the predominant neutral lipid subclass and constituted ca. 81.6, 86.6, and 65.1% of total neutral lipids in whole berry, seed, and pulp/peel oils, respectively. Nine triacylglycerol molecular species were detected, wherein three species, C54:3, C52:2, and C54:6, were presented to the extent of approximately 91% or above. The highest level of phytosterols was estimated in pulp/peel oil that contained the highest level of unsaponifiables. In both whole berry and seed oils, campesterol and beta-sitosterol were the sterol markers, whereas Delta5-avenasterol and campesterol were the main 4-desmethylsterols in pulp/peel oil. The tocopherols level was much higher in pulp/peel oil than in whole berry and seed oils. beta- and gamma-tocopherols were the major components in whole berry and seed oils, whereas gamma- and alpha-tocopherols were the main constituents in pulp/peel oil. beta-Carotene and vitamin K(1) were also measured in markedly high levels in pulp/peel oil followed by whole berry oil and seed oil, respectively. Information provided by the present work is of importance for further chemical investigation of goldenberry oil and industrial utilization of the berries as a raw material of oils and functional foods.  相似文献   

12.
Cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils were evaluated for their fatty acid composition, carotenoid content, tocopherol profile, total phenolic content (TPC), oxidative stability index (OSI), peroxide value, and antioxidant properties. All tested seed oils contained significant levels of alpha-linolenic acid ranging from 19.6 to 32.4 g per 100 g of oil, along with a low ratio of n-6/n-3 fatty acids (1.64-3.99). The total carotenoid content ranged from 12.5 to 30.0 micromoles per kg oil. Zeaxanthin was the major carotenoid compound in all tested berry seed oils, along with beta-carotene, lutein, and cryptoxanthin. Total tocopherol was 260.6-2276.9 mumoles per kg oil, including alpha-, gamma-, and delta-tocopherols. OSI values were 20.07, 20.30, and 44.76 h for the marionberry, red raspberry, and boysenberry seed oils, respectively. The highest TPC of 2.0 mg gallic acid equivalents per gram of oil was observed in the red raspberry seed oil, while the strongest oxygen radical absorbance capacity was in boysenberry seed oil extract (77.9 micromol trolox equivalents per g oil). All tested berry seed oils directly reacted with and quenched DPPH radicals in a dose- and time-dependent manner. These data suggest that the cold-pressed berry seed oils may serve as potential dietary sources of tocopherols, carotenoids, and natural antioxidants.  相似文献   

13.
The effect of roasting on some nutritional characteristics of hazelnut lipidic fraction was investigated. Hazelnuts (Corylus avellana L.) were submitted to several different thermal treatments, comprising different temperatures (125-200 degrees C) and times of exposure (5, 15, and 30 min) and analyzed for their moisture and crude fat. Raw and roasted hazelnuts were also analyzed for their compositions in phytosterols and fatty acids (including trans isomers) by GC-FID, triacylglycerols by HPLC-ELSD, and tocopherols and tocotrienols by HPLC-DAD/fluorescence spectroscopy. Minor changes occurred in the fatty acid and triacylglycerol compositions. As temperatures and roasting periods increased, generally, a modest increase of oleic and saturated fatty acids and a decrease of linoleic acid, expressed as relative percentages, occurred. Similarly, an increase of triacylglycerols containing oleic acid moieties and a decrease of those containing linoleic acid moieties were found in the roasted samples. Roasting caused a modest decrease of the beneficial phytosterols (maximum 14.4%) and vitamin E homologues (maximum 10.0%) and a negligible increase of the trans fatty acids.  相似文献   

14.
The Hibiscus genus encompasses more than 300 species, but kenaf (Hibiscus cannabinus L.) and roselle (Hibiscus sabdariffa L.) are the two most economically important species within the genus. Seeds from these two Hibiscus species contain a relatively high amount of oil with two unusual fatty acids: dihydrosterculic and vernolic acids. The fatty acid composition in the oil can directly affect oil quality and its utilization. However, the variability in oil content and fatty acid composition for these two species is unclear. For these two species, 329 available accessions were acquired from the USDA germplasm collection. Their oil content and fatty acid composition were determined by nuclear magnetic resonance (NMR) and gas chromatography (GC), respectively. Using NMR and GC analyses, we found that Hibiscus seeds on average contained 18% oil and seed oil was composed of six major fatty acids (each >1%) and seven minor fatty acids (each <1%). Hibiscus cannabinus seeds contained significantly higher amounts of oil (18.14%), palmitic (20.75%), oleic (28.91%), vernolic acids (VA, 4.16%), and significantly lower amounts of stearic (3.96%), linoleic (39.49%), and dihydrosterculic acids (DHSA, 1.08%) than H. sabdariffa seeds (17.35%, 18.52%, 25.16%, 3.52%, 4.31%, 44.72%, and 1.57%, respectively). For edible oils, a higher oleic/linoleic (O/L) ratio and lower level of DHSA are preferred, and for industrial oils a high level of VA is preferred. Our results indicate that seeds from H. cannabinus may be of higher quality than H. sabdariffa seeds for these reasons. Significant variability in oil content and major fatty acids was also detected within both species. The variability in oil content and fatty acid composition revealed from this study will be useful for exploring seed utilization and developing new cultivars in these Hibiscus species.  相似文献   

15.
Aroma-active compounds from a beeflike process flavor, produced by extrusion of enzyme-hydrolyzed vegetable protein (E-HVP), were analyzed using aroma extract dilution analysis. The number of aroma-active compounds and the aroma intensity were increased by the addition of aroma precursors prior to extrusion. The most intense compound was 2-methyl-3-furanthiol having a cooked rice/vitamin-like/meaty aroma note. Several sulfur-containing furans, such as 2-methyl-3-(methylthio)furan, 2-methyl-3-(methyldithio)furan, and bis(2-methylfuryl)disulfide, were detected with high flavor dilution (FD) factors. Some pyrazines, such as 2-ethyl-3,5-dimethylpyrazine, 2,6-diethylpyrazine, and 3,5-diethyl-2-methylpyrazine, also had high FD factors. It is hypothesized that sulfur-containing amino acids and thiamin were important precursors in aroma formation in process flavor from E-HVP.  相似文献   

16.
Although poppy seed oil is an expensive article of trade, no literature about identification methods for adulteration with cheaper vegetable oils, like sunflower oil, has been published. This kind of adulteration is a challenge for routine analytical methods, such as the determination of fatty acid composition, because of almost similar fatty acid ratios. The detection of adulteration of poppy seed oils with sunflower oils at different levels (5-40%, w/w) by using SPME-GC-MS and MALDI-ToF-MS is the subject of our investigation. With the mentioned SPME-GC-MS method, it was possible to detect an admixture of sunflower oils in all relevant (5-40%) amounts by using alpha-pinene as a marker compound. Admixture of sunflower oil with high levels of triolein (high-oleic acid type) could be undoubtedly detected by MALDI-MS down to the 5-10% level. In contrast, adulteration of pure poppy seed oil by "standard" sunflower oils remained indistinguishable using this MALDI-MS.  相似文献   

17.
Acrylamide levels in cooked/processed food can be reduced by treatment with citric acid or glycine. In a potato model system cooked at 180 degrees C for 10-60 min, these treatments affected the volatile profiles. Strecker aldehydes and alkylpyrazines, key flavor compounds of cooked potato, were monitored. Citric acid limited the generation of volatiles, particularly the alkylpyrazines. Glycine increased the total volatile yield by promoting the formation of certain alkylpyrazines, namely, 2,3-dimethylpyrazine, trimethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, tetramethylpyrazine, and 2,5-diethyl-3-methylpyrazine. However, the formation of other pyrazines and Strecker aldehydes was suppressed. It was proposed that the opposing effects of these treatments on total volatile yield may be used to best advantage by employing a combined treatment at lower concentrations, especially as both treatments were found to have an additive effect in reducing acrylamide. This would minimize the impact on flavor but still achieve the desired reduction in acrylamide levels.  相似文献   

18.
The concentrations of 19 odorants, recently characterized by GC-olfactometry and aroma extract dilution analysis as the most odor-active compounds in raw hazelnuts, were quantitated by stable isotope dilution assays (SIDA). Calculation of odor activity values (OAV) on the basis of odor thresholds in oil revealed high OAVs, in particular for linalool, 5-methyl-4-heptanone, 2-methoxy-3,5-dimethylpyrazine, and 4-methylphenol. A model mixture in sunflower oil containing the 13 odorants showing OAVs above 1 in their natural concentrations resulted in a good similarity compared to the overall nut-like, fruity aroma of the raw hazelnuts. Quantitation of the 25 most odor-active compounds in roasted hazelnut paste by SIDA showed clear changes in the concentrations of most odorants, and formation of new odor-active compounds induced by the roasting process was observed. The highest OAVs were calculated for 3-methylbutanal (malty), 2,3-pentanedione (buttery), 2-acetyl-1-pyrroline (popcorn), and (Z)-2-nonenal (fatty), followed by dimethyl trisulfide, 2-furfurylthiol, 2,3-butanedione, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone. The aroma of a model mixture containing the 19 odorants with OAVs above 1 in their actual concentrations in the roasted nut material was judged to elicit a very good similarity to the popcorn-like, coffee-like, and sweet-smoky aroma of the roasted hazelnut paste. New SIDAs were developed for the quantitation of 5-methyl-4-heptanone, 5-methyl-(E)-2-hepten-4-one, 2-thenylthiol, and 3,5,5-trimethyl-2(5H)-furanone.  相似文献   

19.
The contents of triacylglycerols and diacylglycerols in three kinds of olive fruit oils (pulp, seed, and whole fruit) were determined. The fatty acid composition and the quality ratios 1,2-diacylglycerols/1,3-diacylglycerols and 1,2-diacylglycerols/total diacylglycerols were also assessed. Seven major Italian olive varieties were considered. Results of univariate statistical analyses indicated that the above analytical parameters (glyceridic ratios excepted) were effective in discriminating between pulp and seed oils. The seed oil fraction did not determine any change in the glyceridic indices and the acylglycerol or fatty acid composition concerning the whole fruit oil (mixture of pulp and seed oil fractions), the weight (%) of seed ( approximately 2%) being by far lower than the weight (%) of pulp ( approximately 85%) (fruit weight basis). Based on the data of triacylglycerol or fatty acid composition, and using appropriate parametric or nonparametric multivariate statistics, the genetic origins (olive variety) of the three fruit oil kinds were characterized.  相似文献   

20.
The antioxidant properties of water extracts from Cassia tora L. (WECT) prepared under different degrees of roasting were investigated. The water extracts of unroasted C. tora L. (WEUCT) showed 94% inhibition of peroxidation of linoleic acid at a dose of 0.2 mg/mL, which was higher than that of alpha-tocopherol (82%). Water extracts prepared from C. tora L. roasted at 175 degrees C for 5 min and at 200 degrees C for 5 min exhibited 83% and 82%, respectively, inhibition of linoleic acid peroxidation. This result indicated that the antioxidant activities of WECT decreased with longer roasting time or higher roasting temperature. The IC(50) of WEUCT in liposome oxidation induced by the Fenton reaction was 0.41 mg/mL, which was higher than that of alpha-tocopherol (IC(50) = 0.55 mg/mL). WEUCT also exhibited good antioxidant activity in enzymatic and nonenzymatic microsome oxidative systems. The water extracts of roasted C. tora L. increased in the degree of browning and produced chemiluminescence when compared with the unroasted sample. However, the total polyphenolic compounds of WECT decreased after the roasting process finished. In conclusion, the decrease in the antioxidant activity of water extracts from roasted C. tora L. might have been due to the degradation of Maillard reaction products and the decrease of polyphenolic compounds.  相似文献   

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