Volatile metabolites from actinomycetes

Twenty-six Streptomyces spp. were screened for their volatile production capacity on yeast starch agar. The volatile organic compounds (VOCs) were concentrated on a porous polymer throughout an 8-day growth period. VOCs were analyzed by gas chromatography with flame ionization detection and identified or characterized by gas chromatography-mass spectrometry. A total of 120 VOCs were characterized by retention index and mass spectra. Fifty-three compounds were characterized as terpenoid compounds, among which 18 could be identified. Among the VOCs were alkanes, alkenes, alcohols, esters, ketones, sulfur compounds, and isoprenoid compounds. Among the most frequently produced compounds were isoprene, acetone, 1-butanol, 2-methyl-1-propanol, 3-methyl-3-buten-1-ol, 3-methyl-1-butanol, 2-methyl-1-butanol, cyclopentanone, dimethyl disulfide, dimethyl trisulfide, 2-phenylethanol, and geosmin. The relationship between the excretion of geosmin and the production of spores was examined for one isolate. A good correlation between headspace geosmin and the number of spores was observed, suggesting that VOCs could be used to indicate the activity of these microorganisms in heterogeneous substrates.     

Multiple compound quality index for cold-smoked salmon (Salmo salar) developed by multivariate regression of biogenic amines and pH

Production of biogenic amines during chill storage of 12 lots of cold-smoked salmon was studied. These data allowed for a multiple compound quality index to be developed by multivariate regression (partial least square regression). The quality index was based on concentrations of cadaverine, histamine, putrescine, and tyramine and pH and showed good correlation with sensory assessments. Biogenic amines were indicators of spoilage rather than casual agents of spoilage off-flavors. Four different biogenic amine profiles were found at the time of spoilage in cold-smoked salmon. These were the results of differences in the spoilage microflora. Histamine was detected above regulatory limits but below toxic levels. Measurements of salt and dry matter for calculation of water phase salt could be substituted by rapid water activity measurements.     

Characterization of volatile compounds in chilled cod (Gadus morhua) fillets by gas chromatography and detection of quality indicators by an electronic nose

Volatile compounds in cod fillets packed in Styrofoam boxes were analyzed during chilled storage (0.5 degrees C) by gas chromatography (GC)-mass spectrometry and GC-olfactometry to screen potential quality indicators present in concentrations high enough for detection by an electronic nose. Photobacterium phosphoreum dominated the spoilage bacteria on day 12 when the fillets were rejected by sensory analysis. Ketones, mainly 3-hydroxy-2-butanone, were detected in the highest level (33%) at sensory rejection, followed by amines (TMA) (29%), alcohols (15%), acids (4%), aldehydes (3%), and a low level of esters (<1%). The electronic nose's CO sensor showed an increasing response with storage time coinciding with the production of ethanol and 2-methyl-1-propanol that were produced early in the storage, followed by the production of 3-methyl-1-butanol, 3-methyl-butanal, 2,3-butandiol, and ethyl acetate. Lipid-derived aldehydes, like hexanal and decanal, were detected in similar levels throughout the storage time and contributed to the overall sweet odors of cod fillets in combination with other carbonyls (3-hydroxy-2-butanone, acetaldehyde, 2-butanone, 3-pentanone, and 6-methyl-5-heptene-2-one).     

Volatile compounds in Hispánico cheese manufactured using a mesophilic starter,a thermophilic starter,and bacteriocin-producing Lactococcus lactis subsp. lactis INIA 415

The effect of the addition of Lactococcus lactis subsp. lactis INIA 415, a strain harboring the structural genes of nisin Z and lacticin 481, on the formation of volatile compounds in Hispánico cheese manufactured with a mesophilic starter or with the mesophilic starter and a thermophilic starter was investigated. Addition of bacteriocin-producing L. lactis subsp. lactis INIA 415 to milk enhanced the formation of 2-methyl-propanal, 2-methylbutanal, 3-methylbutanal, 2-methyl-1-propanol, 3-methyl-1-butanol, 1-octanol, 2-butanone, and 2,3-butanedione. On the other hand, addition of thermophilic starter enhanced the formation of acetaldehyde, ethanol, 3-methyl-2-buten-1-ol, ethyl butanoate, ethyl hexanoate, 2-butanone, and 2,3-butanedione in Hispánico cheese. Stepwise discriminant analysis using the relative abundances of volatile compounds classified cheeses by type of starter, with function 1 related to thermophilic starter and function 2 to bacteriocin producer.     

Volatiles from Fusarium verticillioides (Sacc.) nirenb. and their attractiveness to nitidulid beetles

It is known that sap beetles (Coleoptera: Nitidulidae) can vector the fungus Fusarium verticillioides (Sacc.) Nirenb. (= F. moniliforme Sheldon), which causes an important ear-rot disease in corn and also produces fumonisin mycotoxins. The volatiles produced by this fungus were studied to establish whether they could attract sap beetles. Such an association would suggest more than just an incidental role in transmission of the fungus by the beetles. F. verticillioides consistently produces a blend of five alcohols (ethanol, 1-propanol, 2-methyl-1-propanol, 3-methyl-1-butanol, and 2-methyl-1-butanol), acetaldehyde, and ethyl acetate. Ethanol is the most abundant alcohol. The fungus also produces four phenolic compounds (the most abundant of which is ethylguaiacol), a series of presently unidentified sesquiterpene hydrocarbons, and an unidentified compound that is probably a 10-carbon ketone. Solid-phase microextraction was the key technique used in volatile analysis. The volatile profiles change over time and differ somewhat among fungal strains: The alcohols, aldehyde, and ester always appeared first and were present for each strain. Production of the phenolics lagged by several days, and in some strains these compounds were barely detectable. Volatile production eventually diminished in all strains. All strains were attractive to the sap beetle, Carpophilus humeralis (F.), in wind-tunnel bioassays. Attraction was correlated primarily to the presence of the alcohols, acetaldehyde, and ethyl acetate, rather than to the phenolics. To verify that the identified culture volatiles were responsible for beetle attraction, cultures were quantitatively simulated with synthetic chemicals, and the cultures and corresponding synthetic mixtures were then compared by bioassay. The comparisons were favorable. Volatile emission patterns from cultures were fairly robust with respect to inoculum level or incubation temperature, but some manipulation was possible. For example, after freeze-drying and rehydrating (a rapid simulation of winter/spring conditions), F. verticillioides produced ethyl acetate and other esters at unusually high levels. The fungus produced attractive volatiles following ear inoculation of milk-stage field corn as well as on sterile, mature kernels in the laboratory.     

Interactions between artificial saliva and 20 aroma compounds in water and oil model systems

The interactions between saliva components and 20 aroma compounds in water and oil model systems were systematically evaluated as a function of saliva composition and saliva/model system ratio. Air/liquid partition coefficients of dimethyl sulfide, 1-propanol, diacetyl, 2-butanone, ethyl acetate, 1-butanol, 2-pentanol, propyl acetate, 3-methyl-1-butanol, ethyl butyrate, hexanal, butyl acetate, 1-hexanol, 2-heptanone, heptanal, alpha-pinene, 2-octanone, octanal, 2-nonanol, and 2-decanone were determined by static headspace gas chromatography. Chain length of compounds within the homologous series determined the extent of interactions with the model system or saliva. Salts in the artificial saliva hardly interacted with aroma compounds. On the other hand, saliva proteins lowered retention of highly volatile compounds and increased retention of less volatile, hydrophobic compounds. Significant differences in volatility of compounds when artificial saliva or water was added indicated that saliva could not be sufficiently replaced by water. The model system/saliva ratio influenced air/liquid partitioning of the aroma compounds significantly for both model systems. Although saliva composition affected volatility of the aroma compounds, the saliva/model system ratio was of much greater influence.     

Analysis of volatile compounds as spoilage indicators in fresh king salmon (Oncorhynchus tshawytscha) during storage using SPME-GC-MS

A method was developed for the analysis of salmon volatiles using solid-phase microextraction and gas chromatography-mass spectrometry. This method was used to monitor the volatiles of fresh king salmon (Oncorhynchus tshawytscha) stored in ambient air or in a 40:60 (v/v) mixture of CO2:N2 over time. The levels of several of the volatile compounds were found to change during storage, with some showing a clear difference between storage in air and storage in CO2:N2. Of these, several alcohols (cyclopentanol, Z-2-penten-1-ol, 1-penten-3-ol, and 1-octen-3-ol) and aldehydes (hexanal, octanal, E-2-pentenal, and E-2-hexenal) were identified as potential markers for salmon freshness. Several other volatiles (acetoin, ethyl benzene, propyl benzene, styrene, 3-methyl butanoic acid, and acetic acid) were identified as potential markers for salmon spoilage. A comparison of salmon harvested with and without the "rested harvesting" technique showed that E- and Z-isoeugenol levels were increased by the use of the isoeugenol based anesthetic. The use of the anesthetic did not affect the levels of any of the other compounds identified.     

Volatile compounds of Aspergillus strains with different abilities to produce ochratoxin A

Volatile compounds emitted by Aspergillus strains having different abilities to produce ochratoxin A were investigated. Thirteen strains of Aspergillus ochraceus, three belonging to the A. ochraceus group, and eight other species of Aspergillus were examined for their abilities to produce volatile compounds and ochratoxin A on a wheat grain medium. The profiles of volatile compounds, analyzed using SPME, in all A. ochraceus strains, regardless of their toxeginicity, were similar and comprised mainly of 1-octen-3-ol, 3-octanone, 3-octanol, 3-methyl-1-butanol, 1-octene, and limonene. The prevailing compound was always 1-octen-3-ol. Mellein, which forms part of the ochratoxin A molecule, was found in both toxigenic and nontoxigenic strains. Volatile compounds produced by other Aspergillus strains were similar to those of A. ochraceus. Incubation temperatures (20, 24, and 27 degrees C) and water content in the medium (20, 30, and 40%) influenced both volatile compounds formation and ochratoxin A biosynthesis efficiency, although conditions providing the maximum amount of volatiles were different from those providing the maximum amount of ochratoxin A. The pattern of volatiles produced by toxigenic A. ochraceus strains does not facilitate their differentiation from nontoxigenic strains.     

Aromatic profile of aqueous banana essence and banana fruit by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O)

Gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O) were used to determine the aromatic composition and aroma active components of commercial banana essence and fresh banana fruit paste. Totals of 43 and 26 compounds were quantified in commercial banana essence and fresh banana fruit paste, respectively. Five new components in commercial banana essence were identified as methyl butyrate, 2,3-butanediol diacetate, 2-hydroxy-3-methylethylbutyrate, 1-methylbutyl isobutyrate, and ethyl 3-hydroxyhexanoate. A total of 42 components appear to contribute to the aromatic profile in banana. Isoamyl acetate, 2-pentanol acetate, 2-methyl-1-propanol, 3-methyl-1-butanol, 3-methylbutanal, acetal, isobutyl acetate, hexanal, ethyl butyrate, 2-heptanol, and butyl butyrate had high concentrations and were most detected by GC-O panelists in the commercial banana essence. Volatile components found only in fresh banana fruit paste that were detected by aroma panelists include E-2-hexenal, limonene, and eugenol.     

Odor-active headspace components in fermented red rice in the presence of a monascus species

Headspace components from rice and agar with (experimental) and without (control) inoculation with a Monascus spp. were investigated. Kinetics studies were carried out. Using rice as a substrate, 10 and 19 compounds were found for the control and the experimental groups, respectively, at day 14. Experimental group compounds were composed mainly of alcohols, ketones, and esters, whereas control group compounds were composed of aldehydes and ketones. With agar as a substrate, only five and three components were found in the control and experimental groups, respectively. Five alcohols, four esters, two ketones, and one furan with odor activity values (OAV) >1 dominated the overall flavor of the product. With liquid inoculation, the first six components with high OAVs were in the following order: 3-methyl-1-butanol (17) > ethanol (14) > ethyl acetate (10) > 2-methyl-1-propanol (15) > ethyl butanoate (11) > 3-methylbutyl acetate (13). Kinetic studies showed that most compounds reached their maximum concentrations at 10-12 days. Many compounds identified in the model red rice were reported in commercial red sufus, and several appeared to contribute solely by red rice.     

Potent aroma compounds of two red wine vinegars

Gas chromatography olfactometry (GCO) was used to determine key aroma compounds of two red wine vinegars. Sensory analysis was performed to choose the best neutralization agent of acetic acid (NaOH or MgO) and to test representativeness of four extracts obtained by different methods (dichloromethane extraction, XAD-2, mixture of XAD-2 and XAD-7, and Extrelut resins extraction). Neutralization with NaOH followed by dichloromethane extraction was selected to extract volatile compounds of vinegars. Key odorant compounds were determined by GCO based on detection frequency with 13 people. In the two red wine vinegars, 13 odors were perceived by at least 70% of the panelists, and 8 compounds among the 13 were identified: acetic acid, 3-methylbutyric acid, 2-phenyl-1-ethanol, 2, 3-butanedione, butyric acid, 2-methylbutyric acid, mixture of 2- and 3-methyl-1-butanol, and two newly identified compounds in vinegar, 3-hydroxy-2-pentanone and 3-(methylthio)-1-propanal. Quantification of all the volatile compounds was performed by GC-FID, and 10 other compounds were identified for the first time in wine vinegar.     

Flavor characterization of ripened cod roe by gas chromatography, sensory analysis, and electronic nose

Characterization of the flavors of ripened roe products is of importance to establish a basis for a standardized product. Flavor profiles of commercially processed ripened roe from Iceland and Norway were studied by sensory analysis, gas chromatography-olfactometry (GC-O), gas chromatography-mass spectrometry (GC-MS), and an electronic nose to characterize the headspace of ripened roe. Sensory analysis showed that ripened roe odor and flavor in combination with caviar flavor and whey/caramel-like odor give the overall positive effect of the complex characteristic roe flavor. Analysis of volatiles by GC-MS and electronic nose confirmed the presence of aroma compounds contributing to the typical ripening and spoilage flavors detected by the sensory analysis. Methional, 1-octen-3-ol, and 2,6-nonadienal were the most important compounds contributing to ripened roe odor. Spoilage flavors were partly contributed by 3-methyl-1-butanol and 3-methylbutanal, which can be measured by the electronic nose and are suggested as quality indicators for objectively assessing the ripening of roe. Principal component analysis of the overall data showed that GC-O correlated well with sensory evaluation and the electronic nose measurements.     

Comparison of volatiles of cultured and wild sea bream (Sparus aurata) during storage in ice by dynamic headspace analysis/gas chromatography-mass spectrometry

Cultured and wild sea bream were compared for differences in their volatile components over a 23 day storage period in ice. A total of 60 compounds in cultured and 78 compounds in wild sea bream were tentatively identified (in addition to this, there were 23 unknowns in cultured and 29 unknowns in wild sea bream volatiles). These included aldehydes, ketones, alcohols, aromatics, terpenes, furans, sulfur-containing compounds, an acid, and miscellaneous compounds. Although selection of best fish is a subjective matter, more aldehydes, ketones, aromatics, and terpenes were found in wild sea bream as compared to that of its cultured counterpart. Both sea bream samples exhibited complex volatile profiles over the entire storage period. The combination of several classes of volatile compounds, dependent upon their concentrations and odor thresholds, is responsible for the distinctive and unique flavor of fresh cultured and wild sea bream. Relative concentrations of several compounds (trimethylamine, piperidine, methanethiol, dimethyl disulfide, dimethyl trisulfide, 1-penten-3-ol, 3-methyl-1-butanol, and acetic acid) increased continually throughout the storage period, and these may have the potential to be used as indicators of sea bream quality.     

Characterization of the most odor-active volatiles of orange wine made from a Turkish cv. Kozan (Citrus sinensis L. Osbeck)

The aroma-active compounds of cv. Turkish Kozan orange wine were analyzed by sensory and instrumental analyses. Liquid-liquid extraction with dichloromethane was used for extraction of volatile components. According to sensory analysis, the aromatic extract obtained by liquid-liquid extraction was representative of orange wine odor. A total of 63 compounds were identified and quantified in orange wine. The results of the gas chromatography-olfactometry analysis showed that 35 odorous compounds were detected by the panelists. Of these, 28 aroma-active compounds were identified. Alcohols followed by terpenes and esters were the most abundant aroma-active compounds of the orange wine. Among these compounds, ethyl butanoate (fruity sweet), 3-methyl-1-pentanol (roasty), linalool (floral citrusy), gamma-butyrolactone (cheesy burnt sugar), 3-(methylthio)-propanol (boiled potato, rubber), geraniol (floral citrusy), and 2-phenylethanol (floral rose) were the most important contributors to the aroma of the orange wine because they were perceived by all eight panelists.     

Aroma active components in aqueous kiwi fruit essence and kiwi fruit puree by GC-MS and multidimensional GC/GC-O

Gas chromatography-mass spectrometry (GC-MS) and multidimensional gas chromatography olfactometry (GC/GC-O) were utilized to study the aroma profile and the aroma active components of commercial kiwi essence and the initial fresh fruit puree. Totals of 29 and 33 components were identified and quantified in the essence and the puree, respectively. Ten components were quantified for the first time as constituents of the kiwi fruit including 3-penten-2-ol, 3-hydroxy-2-butanone, 3-methyl-2-butenal, 2-hexanol, nonanal, 3-methyl-1-butanol, 2-methyl-1-butanol, 3-methyl-2-butanone, 3-methyl 3-buten-2-one, and octane. Analysis of these samples by multidimensional gas chromatography-olfactometry (GC-O) allowed for the identification of >80% of the aroma active components present at level traces in this fruit. A total of 35 components appear to contribute to the aroma of kiwi fresh puree and its aqueous essence. Components described for the first time as constituents of the aroma profile in this fruit were 2-ethylfuran, 3-methyl-1-butanol, 2-cyclohexen-1-one, (E,E)-2,6-nonadienal, diethyl succinate, and hexyl hexanoate.     

Long-term storage of Pink Lady apples modifies volatile-involved enzyme activities: consequences on production of volatile esters

Pink Lady apples were harvested at commercial maturity and stored at 1 degrees C and 92% relative humidity under either air or controlled atmosphere conditions (2 kPa O 2:2 kPa CO 2 and 1 kPa O 2:1 kPa CO 2) for 27 weeks. Data on the emission of volatile compounds and on the activity of some related enzymes in both skin and flesh tissues were obtained during subsequent shelf life at 20 degrees C. Major effects of storage atmosphere and poststorage period were observed on the emission of volatile esters and their precursors. Changes in the production of volatile esters were partly due to alterations in the activity of alcohol o-acyltransferase, but the specific esters emitted by fruit after storage also resulted largely from modifications in the supply of the corresponding substrates. Samples stored under air were characterized by higher availability of acetaldehyde, whereas those stored under CA showed enhanced emission of the alcohol precursors ethanol and 1-hexanol (2 kPa O 2) and 1-butanol (1 kPa O 2), with accordingly higher production of ethyl, hexyl, and butyl esters. Multivariate analysis revealed that a large part of the observed differences in precursor availability arose from modifications in the activity of the enzymes considered. Higher pyruvate decarboxylase activity in air-stored fruit possibly accounted for higher acetaldehyde levels in these samples, while storage under 1 kPa O 2 led to significantly decreased lipoxygenase activity and thus to lessened production of 1-hexanol and hexyl esters. Low acetaldehyde availability together with enhanced hydroperoxide lyase and alcohol dehydrogenase levels in these fruits are suggested to have led to higher emission of 1-butanol and butyl esters.     

气调包装协同低温等离子体杀菌对狮子头保鲜效果的影响

为探究气调包装协同低温等离子体处理对狮子头品质及货架期的影响,本研究设置对照组(普通彩袋包装)、气调包装组(40%CO₂+60%N₂)以及气调包装协同不同处理时间的低温等离子体组(MAP-3 min、MAP-6 min、MAP-9 min),通过菌落总数、挥发性盐基氮(TVB-N)、硫代巴比妥酸反应物(TBARS)、感官评定及挥发性有机化合物等指标综合评价狮子头的贮藏品质。结果表明,气调包装协同低温等离子体处理使狮子头的初始微生物数量降低0.70~1.56 log CFU·g^-1,能有效减缓狮子头贮藏过程中TVB-N值的增加及脂质氧化。经低温等离子体处理后的新鲜狮子头中庚醇、1-己醇、1-丙醇、2-癸酮及壬酸等挥发性有机化合物增加。2-己酮、2-丁酮、苯乙烯、2-甲基吡嗪及八甲基三硅氧烷等挥发性有机化合物可能是狮子头腐败气味的主要成分。与对照组及其他处理组相比,MAP-6 min和MAP-9 min处理均可将狮子头货架期延长7 d,MAP-6 min和MAP-9 min 2组狮子头在贮藏7 d后微生物及TVB-N、TBARS等品质指标无显著差异。综合各项指标及能源成本,40%CO₂+60%N₂气调包装协同低温等离子体处理6 min可以在显著抑制微生物生长的同时保持狮子头的品质,将产品货架期延长至14 d。本研究结果为中式调理类肉丸制品新型保鲜技术的发展提供了理论参考。     

Evolution of volatile byproducts during wine fermentations using immobilized cells on grape skins

A biocatalyst was prepared by immobilization of Saccharomyces cerevisiae cells on grape skins. Repeated batch fermentations were conducted using this biocatalyst as well as free cells, at 25, 20, 15, and 10 degrees C. Solid phase microextraction (SPME) was used in monitoring the evolution of volatile byproducts. The effect of immobilization and temperature on evolution patterns of volatiles was obvious. The major part of esters was formed after consumption of 40-50% of the sugars. Similar processes were observed for amyl alcohols and 2-phenylethanol, whereas 1-propanol and 2-methyl-1-propanol were formed during the whole alcoholic fermentation period at an almost constant formation rate. Acetaldehyde and acetoin were synthesized in the early stages of fermentation. Afterward, their amount decreased. In most cases, immobilized cells exhibited higher formation rates of volatiles than free cells. The final concentration of esters was higher in wines produced by immobilized biocatalyst. Their amount increased with temperature decrease. The opposite was observed for higher alcohols.     

Influence of lipid fraction, emulsifier fraction, and mean particle diameter of oil-in-water emulsions on the release of 20 aroma compounds

The influence of compositional and structural properties of oil-in-water emulsions on aroma release was examined under mouth conditions. The lipid (0.40 and 0.65) and emulsifier fractions (0.007, 0.010, and 0.014) were varied, as well as the mean particle diameter of the dispersed phase (0.60, 0.73, 0.85, and 1.10 microm). Aroma compounds were isolated in a model mouth system and quantified by gas chromatography-mass spectrometry. Studies were carried out to separate effects on the thermodynamic and the kinetic components of aroma release using equilibrium headspace analysis to distinguish the thermodynamic component. The lipid phase of the emulsions was composed of sunflower oil and the emulsifier phase was Tween 20. The release of 20 aroma compounds was evaluated; the compounds included alcohols (1-propanol, 1-butanol, 3-methyl-1-butanol, 2-pentanol, 1-hexanol, and 2-nonanol), ketones (diacetyl, 2-butanone, 2-heptanone, 2-octanone, and 2-decanone), esters (ethyl acetate, propyl acetate, butyl acetate, and ethyl butyrate), aldehydes (hexanal, heptanal, and octanal), a terpene (alpha-pinene), and a sulfur compound (dimethyl sulfide). Decrease in lipid fraction and emulsifier fraction, as well as increase in particle diameter, increased aroma release under mouth conditions. Differences between groups of compounds and between compounds of homologous series with varying chain lengths were found. Changes in particle diameter had a considerable effect on the thermodynamic component of aroma release, whereas hardly any influence of the lipid fraction and emulsifier fraction was observed. Lipid fraction, emulsifier fraction, and particle diameter affected the kinetic component of aroma release, which could partially be attributed to changes in viscosity.