Characterization of aroma-active compounds in rainbow trout (Oncorhynchus mykiss) eliciting an off-odor

The aroma-active and off-flavor compounds of cooked rainbow trout (Oncorhynchus mykiss) were analyzed by sensory and instrumental analyses. Sensory analysis shows that the aromatic extract obtained by vacuum steam distillation was representative of rainbow trout odor. To obtain more information on odorants of volatile compounds, analyses were conducted on two gas chromatography columns of different polarities (DB-5 and DB-Wax). The results of the gas chromatography-olfactometry analysis showed that 38 odorous compounds were perceived when the DB-5 column was used and 36 with the DB-Wax column. Of these, 31 with the DB-5 and 28 with the DB-Wax were identified. (E)-2-Nonenal, 2-ethyl-1-hexanol, 2-methylisoborneol, geosmin, 2-methylnaphthalene, and 8-heptadecene were described as off-flavor compounds by the sniffing assessors. The most powerful off-flavor compounds identified in the extract were 2-methylisoborneol and geosmin, which were described as strong musty and earthy odors, respectively.     

Algicidal activity of stilbene analogues

Continuing our search for natural product and natural product-based compounds for the control of off-flavor in catfish, 29 stilbene analogues were synthesized and evaluated for algicidal activity against the 2-methylisoborneol (MIB)-producing cyanobacterium Oscillatoria perornata. The cis and trans isomers of 4-(3,5-dimethoxystyryl)aniline showed moderate and selective algicidal activity toward O. perornata with the lowest observed inhibitory concentration and lowest complete inhibition concentrations of 10 muM. This is the first report on selective stilbene algicidal activity toward a MIB-producing cyanobacteria species.     

Determination of 2-methylisoborneol and geosmin produced by Streptomyces sp. and Anabaena PCC7120

A new sample preparation and enrichment technique, headspace liquid-phase microextraction (HS-LPME) linked to gas chromatography-mass spectrometry (GC-MS), was developed for the determination of the off-flavor odorants, 2-methylisoborneol and geosmin, produced by Streptomyces sp. and Anabaena PCC7120. Some of the factors that influence the extraction efficiency of HS-LPME, such as the type of extraction solvent, ionic strength of sample solution, and sample agitation rate, were studied and optimized by a single factor test. Other factors, including extraction temperature, extraction time, microdrop volume, and headspace volume were optimized by orthogonal array design. Extraction of 2-methylisoborneol and geosmin was conducted by exposing 2.5 microL of 1-hexanol for 9 min at 50 degrees C in the headspace of a 20 mL vial with a 10 mL of sample solution saturated by NaCl and stirred at 800 rpm. The developed protocol demonstrated good repeatability (relative standard deviations (RSDs) < 5%), wide linear ranges (10-5000 ng/L, r2 > 0.999), and low limits of detection (LODs) for 2-methylisoborneol and geosmin (0.05 ng/L for both analytes). Subsequently, the method was successfully applied to extract the analytes in bacterial cultures with high recoveries (from 94% to 98%). Compared with headspace solid-phase microextraction (HS-SPME), HS-LPME demonstrates better linearity, precision, and recovery. Importantly, the sensitivity is about 1 order of magnitude higher than that of most HS-SPME. The results showed that HS-LPME coupled with GC-MS is a simple, convenient, rapid, sensitive, and effective method for the qualitative and quantitative analysis of 2-methylisoborneol and geosmin.     

Odor thresholds of microbially induced off-flavor compounds in apple juice

Microbially derived off-flavor is a major problem in apple juice production as it diminishes the sensory quality of the juice significantly. Fifteen relevant off-flavor compounds that are formed in apple juice, for example, by the strains Alicyclobacillus acidoterrestris and Actinomycetes (Streptomyces ssp.) were investigated with respect to their sensory relevance. The odor threshold values (i.e., detection and recognition values) were determined for all compounds in the matrix apple juice. Odor threshold values for fenchyl alcohol are reported here for the first time. The obtained values were set in relation to the limits of detection and quantification of a previously published GC-MS method. Eight tainted apple juice samples were analyzed for the presence of the 2 strains and the 15 off-flavor compounds. Both strains could be found in the samples; the presence of Streptomyces ssp. as spoilage bacteria of apple juice is reported for the first time. In samples with distinct off-flavor, 2-isopropyl-3-methoxypyrazine, 2-isobutyl-3-methoxypyrazine, 2-methylisoborneol, 1-octen-3-ol, fenchyl alcohol, geosmin, and guaiacol as well as 2,6-dibromophenol were determined in concentrations higher than the detection threshold.     

Characterization of volatile compounds contributing to naturally occurring fruity fermented flavor in peanuts

Published research has indicated that ethyl 2-methylpropanoate, ethyl 2-methybutanaote, ethyl 3-methylbutanoate, hexanoic acid, butanoic acid, and 3-methylbutanoic acid are responsible for fruity fermented (FF) off-flavor; however, these compounds were identified in samples that were artificially created by curing immature peanuts at a constant high temperature. The objective of this study was to characterize the volatile compounds contributing to naturally occurring FF off-flavor. Volatile compounds of naturally occurring FF and no-FF samples were characterized using solvent-assisted flavor evaporation (SAFE), solid phase microextraction (SPME), gas chromatography-olfactometry (GC-O), and gas chromatography-mass spectrometry (GC-MS). Aroma extract dilution analysis (AEDA) identified 12 potent aroma active compounds, none of which were the previously identified esters, with no consistent differences among the aroma active compounds in no-FF and FF samples. Hexanoic acid alone was identified in the naturally occurring FF sample using the SAFE GC-MS methodology, whereas two of the three previously identified esters were identified in natural and artificially created samples. The same two esters were confirmed by SPME GC-MS in natural and artificially created samples. This study demonstrated the need for caution in the direct application of data from artificially created samples until those compounds are verified in natural samples. However, these results suggest that a laboratory method using SPME-GC techniques could be developed and correlated on an ester concentration versus FF intensity basis to provide an alternative to sensory analysis for detection of FF off-flavor in peanut lots.     

Composition and antibacterial activity of Pseudocytisus integrifolius (Salisb.) essential oil from Algeria

The essential oil composition of an endemic Algerian Cruciferae, Pseudocytisus integrifolius (Salisb.) Rehder, was analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). Eighty-three components representing more than 96.5% of the oil were identified. The major components were dimethyl disulfide (33.4%), dimethyl trisulfide (24.2%), and an unsaturated nitrile (31.7%). Fractionation on a silica gel column led to the identification of trace-level compounds, in particular, polar compounds such as nitriles and aldehydes, and to the isolation of dimethyl disulfide, dimethyl trisulfide, and an unsaturated nitrile. Structural analysis using high-resolution mass spectrometry (HRMS) and 1H,13C NMR techniques enabled the identification of pent-4-enenitrile. Variation in essential oil composition and yields was studied according to harvesting time, drying, and parts of the plant. The essential oil of aerial parts was tested for its antibacterial activity using a paper disk method. The oil was effective on the inactivation of Escherichia coli and Pseudomonas aeruginosa and ineffective on the inactivation of Staphylococcus aureus.     

Influence of some technological parameters on the formation of dimethyl sulfide, 2-mercaptoethanol,methionol, and dimethyl sulfone in port wines

Volatile sulfur compounds of 15 young port wines and 12 old port wines were determined. As there is a great difference in the pool of sulfur compounds between the two groups of wines, an experimental protocol was performed to determine which technological parameter (dissolved O(2), free SO(2) levels, pH, and time/temperature) was related with the formation/consumption of these compounds. Four sulfur compounds were selected for this purpose: dimethyl sulfide, 2-mercaptoethanol, dimethyl sulfone, and methionol. The synergistic effects of increasing temperature and O(2) at lower pH had the largest impact. Dimethyl sulfide was formed during the experimental period in the presence of O(2). Dimethyl sulfone had the same behavior. Methionol decreased significantly in the presence of O(2), but no methional was formed. 2-Mercaptoethanol, considered to be an important "off-flavor" in dry wines, also decreased during the experimental period (54 days) in the presence of O(2), and the respective disulfide was formed. These results corroborate the fact that old port wine (barrel aged) never develops "off-flavors" associated with the presence of methionol (cauliflower), 2-mercaptoethanol (rubber/burnt), or methional (cooked potato). In fact, temperature and oxygen are the major factors in the consumption of these molecules. However, some notes of "quince" and "metallic" can appear during port wine aging, and these can be associated with the presence of dimethyl sulfide.     

Determination of the microbial origin of geosmin in Chinese liquor

Geosmin is the major cause of the common earthy off-flavor in light-aroma type Chinese liquor and, thus, highly detrimental to the aromatic quality. To find out its origin, the evolving process of geosmin in light-aroma type liquor making was monitored, and microbial analysis of Daqu containing geosmin was carried out. The results showed that geosmin appeared in all the fermented sorghums at different fermentation periods. About 57% geosmin in the fermented sorghums was distilled into liquor. During the distillation process, the peak of geosmin concentration appeared when alcohol content was 50-60% vol. More importantly, high geosmin content was observed during the Daqu-making process. Furthermore, five Streptomyces strains were isolated from different types of Daqu used for the fermentation of light-aroma type liquor. All of them produced only geosmin as the main volatile metabolite but no 2-methylisoborneol (2-MIB). It appears that microorganisms developing in Daqu are responsible for the presence of geosmin in liquor. Because of the relatively low detection threshold estimated at 110 ng/L in 46 vol % hydroalcoholic solution, the presence of geosmin in Daqu may pose a risk for Chinese liquor producers.     

Identification and sensory evaluation of volatile compounds in oxidized porcine liver

Headspace solid phase microextraction (HS-SPME) was used to isolate the off-flavor volatile compounds, which are formed during the oxidation of porcine liver induced by iron. Poly(dimethylsiloxane)/divinylbenzene fiber was used in the HS-SPME. Changes in the volatile compounds of oxidized porcine liver and unsaturated fatty acids induced by iron were examined. Results showed that 1-octen-3-one (metallic), hexanol (weak metallic), 1-octen-3-ol (mushroomlike), (E)-2-nonenal (cardboardlike), and (E,E)-2,4-decadienal (fatty, oily) were the main contributors to the overall off-flavor of porcine liver. The results of the sensory evaluation revealed that oxidized arachidonic acid has a major impact on metallic and liverlike off-flavor and that when liverlike off-flavor is perceived, metallic is also included. Oxidized linolenic acid was the most important contributor to the objectionable fishy off-flavor. Oxidized porcine liver exhibited distinct metallic, liverlike, and weak fishy background notes. Liverlike flavor had a high correlation coefficient with odor characteristics such as metallic (0.839) and fishy (0.777). In this study, it was clearly observed that the stronger the metallic and fishy off-flavor the higher the perception of liverlike off-flavor.     

Mousy off-flavor: a review

Although mousy off-flavor occurs infrequently in wine, it can be economically disastrous to the wine producer as, at worst, it can render the wine unpalatable or, at best, decrease the quality of the wine resulting in a lower sale price. Wines infected with either lactic acid bacteria (LAB) (particularly heterofermentative strains) or Dekkera/Brettanomyces yeast can potentially produce mousy off-flavor. There are three known compounds that cause mousy off-flavor: 2-ethyltetrahydropyridine, 2-acetyltetrahydopyridine, and 2-acetylpyrroline. Dekkera/Brettanomyces have been shown to be capable of producing at least two of these compounds, whereas LAB are capable of producing all three. The reason as to why mousy off-flavor forms in some wines and not in others is still not fully understood. The issue is further complicated by the fact that the compounds that have thus far been identified as necessary for off-flavor formation are all potentially available in wine (e.g., ethanol, L-lysine, L-ornithine, and metal ions). For these reasons, the microbe's metabolism probably plays a key role in mousy off-flavor formation. In the case of Dekkera/Brettanomyces-induced mousy off-flavor, it appears that oxygen may play a key role. Thus, a wine infected with Dekkera/Brettanomyces in the absence of oxygen may not become mousy unless exposed to oxygen via a processing or handling procedure.     

Synthesis of water-soluble 9,10-anthraquinone analogues with potent cyanobactericidal activity toward the musty-odor cyanobacterium Oscillatoria perornata

A series of water-soluble 9,10-anthraquinone analogues were prepared and evaluated for their selective toxicity toward Oscillatoria perornata, which grows in catfish production ponds and causes "musty" off-flavor in channel catfish ( Ictalurus punctatus). Water-soluble mono- and dicationic salts were prepared by conjugating various small amines directly or through a methylene or ethylene bridge to the 9,10-anthraquinone nucleus. One of the dicationic salts, 2-[ N-(1'-methyl-4'- N, N-diethylaminobutyl)aminometyl]anthraquinone diphosphate, exhibited very high water solubility and potent selective toxicity toward O. perornata. However, the tendency of this compound to potentially bind to suspended sediments may be the reason for its limitations in controlling O. perornata in catfish production ponds. The monocationic salt, 2-[ N-(1'-methylethyl)]aminomethyl]anthraquinone monophosphate, showed good solubility and high selective toxicity toward O. perornata. Neutral water-soluble analogues prepared by conjugating terta- or pentaethylene glycol directly or by a methylene bridge to the 9,10-anthraquinone nucleus had less activity than the parent compound.     

牛粪好氧发酵挥发性物质排放特征及恶臭物质分析

不同原料好氧发酵产生的臭气物质组分和浓度存在差异。以牛粪和玉米秸秆为原料研究好氧发酵过程挥发性有机物（Volatile Organic Compound，VOCs）的产排特征及主要致臭物质，开展牛粪好氧发酵试验，采用气相色谱-质谱法分析测定发酵升温期、高温期、降温期及腐熟期等不同发酵阶段的VOCs组分和浓度，硼酸溶液吸收，盐酸滴定法测定NH3，便携式检测器（Tion NH3-H2S 300 G）测定H2S，3点比较式臭袋法测定不同发酵阶段臭气浓度。结果表明，牛粪好氧发酵过程中共检出31种VOCs，其中含硫化合物42种，醇类1种，酯类1种，酮类1种，卤代烃4种，苯系物9种，烷烃类8种，烯烃3种；在好氧发酵高温期臭气浓度最高为724（无量纲），VOCs产生与排放主要在高温期。基于恶臭污染排放标准和恶臭物质气味活度值，并结合各物质检出率、GS-MS图谱及相关性分析，发现NH3、H2S、甲硫醚是牛粪好氧发酵过程的主要致臭物质；其次芳香族化合物对臭气浓度贡献也相对较大，应进行重点监测与控制。该研究可为牛粪好氧发酵过程臭气物质减控提供理论支撑。     

Light-induced off-flavor development in cloudy apple juice

Cloudy apple juice has been found to develop off-flavors during storage in daylight. The development of off-flavors and volatile compounds was monitored in reconstituted juice prepared from 'Golden Delicious' and 'Fuji' apple concentrates stored in glass bottles under fluorescent light (3000 lx, 8 degrees C). A strong metallic off-flavor was formed by photooxidation. A major contributor to the off-flavor was identified as 1-octen-3-one by gas chromatography-olfactometry. In addition, six volatile compounds, pentanal, 2-methyl-1-penten-3-one, hexanal, (E)-2-heptenal, 6-methyl-5-hepten-2-one, and (E)-2-octenal, increased significantly after light exposure and could contribute to the off-flavor. Except for pentanal and hexanal, these volatiles were found only after light exposure. Higher levels of volatiles were observed in juice from 'Golden Delicious' apples than in juice from 'Fuji' apples, and this difference was consistent with higher levels of suspended solids. When the suspended solids were removed by centrifugation, the development of volatiles on exposure to light was reduced significantly.     

Volatile components of roots, stems, leaves, and flowers of Echinacea species.

The headspace volatile components of roots, stems, leaves, and flowers of Echinacea angustifolia,E. pallida, and E. purpurea were analyzed by capillary gas chromatography/mass spectrometry (GC/MS). Over 70 compounds were identified in the samples. All plant tissues, irrespective of the species, contain acetaldehyde, dimethyl sulfide, camphene, hexanal, beta-pinene, and limonene. The main headspace constituents of the aerial parts of the plant are beta-myrcene, alpha-pinene, limonene, camphene, beta-pinene, trans-ocimene, 3-hexen-1-ol, and 2-methyl-4-pentenal. The major headspace components of root tissue are alpha-phellandrene (present only in the roots of E. purpurea and E.angustifolia), dimethyl sulfide, 2-methylbutanal, 3-methylbutanal, 2-methylpropanal, acetaldehyde, camphene, 2-propanal, and limonene. Aldehydes, particularly butanals and propanals, make up 41-57% of the headspace of root tissue, 19-29% of the headspace of the leaf tissue, and only 6-14% of the headspace of flower and stem tissues. Terpenoids including alpha- and beta-pinene, beta-myrcene, ocimene, limonene, camphene, and terpinene make up 81-91% of the headspace of flowers and stems, 46-58% of the headspace of the leaf tissue, and only 6-21% of the roots. Of the 70 compounds identified, >50 are reported in Echinacea for the first time.     

Study of light-induced volatile compounds in goat's milk cheese

Light-induced volatile compounds in goat cheese were studied by a combination of solid phase microextraction (SPME)-gas chromatography (GC)-mass spectrometry (MS), headspace oxygen depletion, and sensory evaluation. Samples stored under fluorescent light for 2 days at 30 degrees C had 90% more volatile compounds and 4 times more headspace oxygen depletion than samples stored in the dark at 30 degrees C. The volatiles 1-heptanol, heptanal, nonanal, and 2-decenal were formed and increased only in the light-stored samples, which may be formed from singlet oxygen oxidation of unsaturated fatty acids. Sensory evaluation showed that samples stored under light had significantly more off-flavor than samples stored in the dark at 30 degrees C (P < 0.05), and 1-heptanol, heptanal, nonanal, and 2-decenal increased the goat cheese off-flavor significantly (P < 0.05).     

Se-enriched mycelia of Pleurotus ostreatus: distribution of selenium in cell walls and cell membranes/cytosol

The incorporation of Se to fungi has been studied, focusing on element distribution among different cellular compartments and, in particular, polysaccharide structures contained in cell walls. Se-enriched mycelia of Pleurotus ostreatus were obtained in submerged cultures. The incorporation of selenium from the growth medium to mycelia was observed with the relative distribution between cytosol plus cell membranes fraction (CCM) and cell walls fraction (CW) of about 44 and 56%, respectively. CCM fractions were analyzed by size exclusion chromatography with on-line UV (280 nm) and ICP-MS detection (80Se). The results obtained showed selenium binding to components of different molecular masses (about 24% of total selenium coeluted with the compounds of molecular mass > 10 kDa). A polysaccharide-containing fraction of mycelia was treated alternatively with Tris-HCl at pH 7.5 or with chitinase. Better solubility and increased contribution of low molecular mass compounds were observed in chitinase extracts (UV detection), confirming the degradation of polysacharides by the enzyme. The total area under the ICP-MS chromatogram of chitinase extract was 2 times higher with respect to the area for Tris-HCl extract. Furthermore, the relative contribution of selenium in the low molecular mass fraction (molecular mass < 1 kDa) in chitinase extract was 72% as compared to 45% in Tris-HCl extract (based on peak area measurements with respect to total area under the chromatogram). The results obtained suggest selenium binding to chitin-containing polysaccharide structures in fungi cell walls.     

Volatile compounds from potato-like model systems

The volatile reaction products of aqueous mixtures comprising combinations of methionine, glucose, linoleic acid, and starch heated in a modified Likens-Nickerson apparatus were extracted and analyzed by gas chromatography-mass spectrometry (GC-MS). The majority of volatile compounds were formed from linoleic acid degradation, hexanal, 2,4-decadienal, and 2-pentylfuran being identified in the greatest amounts. Dimethyl disulfide and dimethyl trisulfide were detected in every system containing methionine. 3-(Methylthio)propanal (methional) and other sulfur compounds were detected when methionine was heated with another precursor. No binding of volatile compounds to starch was observed; rather, starch appeared to act as an additional source of reactive carbohydrate. Almost all the components identified have been identified among the aroma components of cooked potato. No pyrazines, pyridines, or thiazoles were identified, probably due to the relatively low temperature/high moisture conditions.     

Aroma compound analysis of Eruca sativa (Brassicaceae) SPME headspace leaf samples using GC,GC-MS,and olfactometry

The aroma compounds of rocket salad (Eruca sativa) SPME headspace samples of fresh leaves were analyzed using GC, GC-MS, and olfactometry. More than 50 constituents of the Eruca headspace could be identified to be essential volatiles, responsible for the characteristic intense green; herbal; nutty and almond-like; Brassicaceae-like (direction of cabbage, broccoli, and mustard); and horseradish-like aroma of these salad leaves. As aroma impact compounds, especially isothiocyanates, and derivatives of butane, hexane, octane, and nonane were identified. 4-Methylthiobutyl isothiocyanate (14.2%), cis-3-hexen-1-ol (11.0%), cis-3-hexenyl butanoate (10.8%), 5-methylthiopentyl isothiocyanate (9.3%), cis-3-hexenyl 2-methylbutanoate (5.4%), and 5-methylthiopentanenitrile (5.0%) were found in concentrations higher than 5.0% (calculated as % peak area of GC analysis using a nonpolar column).     

贮藏过程中京甜紫花糯2号玉米软罐头的主要挥发性风味成分的变化

采用顶空固相微萃取和气相色谱-质谱联用（HS-SPME-GC/MS）技术,测定京甜紫花糯2号玉米软罐头贮存10个月的挥发性物质,并对主要挥发性物质的变化进行探讨;同时对京甜紫花糯2号玉米软罐头蒸煮香气和不良气味进行感官评定,使用偏最小二乘回归分析法（PLSR）研究感官测定结果与仪器测定结果的相关性。结果显示,京甜紫花糯...     

Effect of high-oxygen and high-carbon-dioxide atmospheres on strawberry flavor and other quality traits

The effect of high-oxygen atmospheres on strawberry flavor was studied. Strawberry fruits (Fragariax ananassa Duch. cv. Camarosa) were stored at 8 degrees C in four different atmospheres: air, 5% O(2)/20% CO(2), 80% O(2)/20% CO(2), and 90% O(2)/10% CO(2). Changes in several quality parameters were evaluated. Atmospheres combining high O(2) and high CO(2) were the most effective in preventing fungal growth and enhancing strawberry firmness. Other quality parameters such as color, titrable acidity, sugars and organic acids distribution, off-flavor development, and aroma were only mildly affected by superatmospheric O(2) levels. After one week of storage, unexpected high contents of off-flavor related compounds were found in the 80% O(2)/20% CO(2) and 90% O(2)/10% CO(2) atmospheres. Evidence of an altered ester biosynthesis was also found in fruits stored under these high-O(2) atmospheres. Data obtained suggest that stress induced by high CO(2) and stress induced by high O(2) have an additive effect on strawberry flavor alteration.