Difference in the volatile composition of pine-mushrooms (Tricholoma matsutake Sing.) according to their grades

The differences in volatile components of pine-mushrooms (Tricholoma matsutake Sing.) according to their grades were observed by applying multivariate statistical methods to GC-MS data sets. A total of 35 and 37 volatile components were identified in raw and cooked pine-mushrooms, respectively. The volatile components in pine-mushrooms were primarily composed of C8 species, such as 3-octanol, 1-octen-3-ol, 1-octanol, (E)-2-octen-1-ol, 3-octanone, 1-octen-3-one, (E)-2-octenal, and octanoic acid. The levels of ethyl octanoate, junipene, and 3-methyl-3-buten-2-one were much higher in raw pine-mushroom of higher grades, whereas the reverse was true for C8 components. On the other hand, furfuryl alcohol, benzyl alcohol, phenylethyl alcohol, dihydro-5-methyl-2(3H)-furanone, 2(5H)-furanone, (E)-2-methyl-2-butenal, furfural, phenylacetaldehyde, benzoic acid methyl ester, camphene, and beta-pinene were the major components of cooked mushrooms. These volatile components formed by various thermal reactions could be mainly responsible for the difference in volatile components of cooked pine-mushrooms according to their grades.     

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 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.     

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.     

Characterization of volatiles and aroma-active compounds in honeybush (Cyclopia subternata) by GC-MS and GC-O analysis

Volatile organic compounds (VOCs) in fermented honeybush, Cyclopia subternata, were sampled by means of a high-capacity headspace sample enrichment probe (SEP) and analyzed by gas chromatography-mass spectrometry (GC-MS). Stereochemistry was determined by means of enantioselective GC-MS with derivatized β-cyclodextrin columns as chiral selectors. A total of 183 compounds, the majority of which are terpenoids (103; 56%), were identified by comparing their mass spectra and retention indices with those of reference compounds or tentatively identified by comparison with spectral library or literature data. Of these compounds, 37 were determined by gas chromatography-olfactometry (GC-O), using detection frequency (DF) and aroma extract dilution analysis (AEDA), to be odor-active (FD ≥ 2). (E)-β-Damascenone, (R/S)-linalool, (E)-β-damascone, geraniol, (E)-β-ionone, and (7E)-megastigma-5,7,9-trien-4-one were identified with the highest FD factors (≥512). The odors of certain compounds, that is, (6E,8Z)-megastigma-4,6,8-trien-3-one, (6E,8E)-megastigma-4,6,8-trien-3-one, (7E)-megastigma-5,7,9-trien-4-one, 10-epi-γ-eudesmol, epi-α-muurolol, and epi-α-cadinol, were perceived by GC-O assessors as typically honeybush-like.     

Characterization of volatile aroma compounds in cooked black rice

Black rice ( Oryza sativa L.), an aromatic specialty rice popular in Asia, has a unique flavor, the volatile chemistry of which has not been reported. The objectives of this research were to study volatile profiles of cooked black rice and to characterize the odor-active compounds. Thirty-five volatile compounds were identified by gas chromatography-mass spectrometry using a dynamic headspace system with Tenax trapping. Aldehydes and aromatics were quantitatively in the greatest abundance, accounting for 80.1% of total relative concentration of volatiles. The concentration of 2-acetyl-1-pyrroline (2-AP) was high, exceeded only by hexanal, nonanal, and 2-pentylfuran. A total of 25 odor-active compounds, determined by gas chromatography-olfactometry, were applied to principal component analysis, demonstrating significant differences between a black and a traditional white rice cultivar in terms of aroma and explaining 93.0% of the total variation. 2-AP, guaiacol, indole, and p-xylene largely influenced the difference between the aroma in cooked black and white rice. 2-AP and guaiacol were major contributors to the unique character of black rice based on odor thresholds, relative concentrations, and olfactometry.     

S-sulfonate contents in raw and cooked meat products

S-Sulfonates (R-S-SO3-) are compounds formed by the reaction between the sulfites added to foodstuffs and the disulfide bonds of cystine, peptides, and proteins. The content of S-sulfonates has been determined in raw sausages and burgers (n = 62). The range of variation in the contents of the determined S-sulfonates is very wide and varies between 47 and 267 microg of SO2/g. The degree of formation of S-sulfonates with regard to the determined sulfite (total SO2 + S-sulfonates) is similar in all of the samples and does not seem to be conditioned by the meat compound (chicken or beef) or by the process of elaboration or type of product (burgers or sausages). In grilled burgers (n = 20) significant losses are produced in the levels of the additive in any of its forms. The value for the S-sulfonates is 31 +/- 9.8%, 29 +/- 6.6% corresponding to the free sulfite and a very similar percentage to the total sulfite (free + reversibly bound) 28 +/- 6.7%. It is possible that during the cooking process cleavages of some bound compounds occur, releasing SO2 and reacting to form new adducts.     

Absorption and tissue distribution of an immunomodulatory alpha-D-glucan after oral administration of Tricholoma matsutake

Alpha-D-glucan (MPG-1) separated from Tricholoma matsutake (CM6271) has been reported to show immunomodulatory activities. In this study, the plasma concentration and tissue distribution of MPG-1 after CM6271 oral administration were investigated as part of the action mechanism analysis. When CM6271 was orally administered in a single dose to mice, MPG-1 was absorbed via the intestinal tract, appeared in plasma after 16 h, was gradually excreted from the blood, and fell to background level after 48 h. The time course analysis of MPG-1 in plasma showed the following pharmacokinetic parameters of MPG-1: tmax = 24 h; Cmax = 161.1 ng/mL; AUC(0-infinity) = 2559.7 ng x h/mL. Moreover, MPG-1 was confirmed to localize in Peyer's patches, mesenteric lymph nodes (MLN), and the spleen and to promote IL-12 p70 production and NK cell activity. These results suggest that MPG-1 stimulated the intestinal immune system through Peyer's patches; moreover, it was taken into the blood and stimulated the systemic immune system.     

The influences of litter cover and understorey vegetation on fruitbody formation of Tricholoma matsutake in southern Finland

Removing the litter layer from an area known to contain matsutake (Tricholoma matsutake) is believed to enhance mushroom productivity in Asian countries where it occurs. This study aimed to understand the effect of understorey vegetation and litter cover on matsutake fruitbody formation and to evaluate the utility of litter derived dissolved organic matter (DOM) as a growth medium. An inventory of understorey vegetation and litter cover was conducted in a productive forest site mainly including conifers that contained 15 plots in which fruitbodies had formed in successive years and 15 nearby control plots without fruitbodies. Litter composition of fruiting plots was investigated. Two T. matsutake isolates were incubated for one month in DOM derived from decomposing spruce or birch litter and mycelial growth was estimated by monitoring the concentration of ergosterol. Although plant diversity was rather uniform in the study site, total vegetation cover was substantially lower and litter cover was somewhat higher in fruiting plots. We concluded that litter derived carbon has a positive impact on T. matsutake fruitbody formation. This was confirmed by in vitro culture experiments where T. matsutake was able to grow in spruce litter derived DOM.     

Isolation and characterization of a novel immunomodulatory alpha-glucan-protein complex from the mycelium of Tricholoma matsutake in basidiomycetes

Tricholoma matsutake, a high-class edible mushroom in Japan, has been reported to have excellent biological activities, but difficulty in cultivating the fruit bodies and limited bulk availability have restricted detailed studies. We have developed a method of culturing in tanks, enabling the bulk supply of the mycelia. The preparation (CM6271) exerts modulative effects on the immune competence of mice and rats. In this study, a sodium hydroxide extract of CM6271 was defatted followed by fractionation with a combination of ion exchange chromatography and gel filtration in order to identify the components involved in the expression of the activity, and a single peak fraction (MPG-1) was obtained with reversed phase chromatography. MPG-1 was a glycoprotein (sugar:protein ratio, 94.3:5.7) with a relative molecular mass of 360 kDa, and the sugar moiety contained about 90% glucose. NMR spectra and methylation analysis revealed that the alpha-1,4-linkage was the predominant glucan linkage with alpha-1,6- and alpha-1,2-linkages in the minority. The amino acid composition in the protein moiety was rich in glutamine, alanine, asparagine, leucine, glycine, valine, serine, threonine, isoleucine, and proline. MPG-1 was resistant to degradation with amylase or protease. The oral administration of MPG-1 promoted, in a dose-dependent manner, the recovery of the mouse natural killer cell activity and serum IL-12 level that had been reduced by the loading of restraint stress. The dose of MPG-1 (25 mg/kg) required for the expression of the effect decreases to 1/12 of that of CM6271 (300 mg/kg). Furthermore, MPG-1 formed a complex with TGF-beta1 in vitro, modulating the biological activity of TGF-beta1 by binding to its active form. These results indicate that the mycelium of T. matsutake contains a novel alpha-glucan-protein complex with immunomodulatory activities.     

Identification of aroma-active compounds in Jiashi muskmelon juice by GC-O-MS and OAV calculation

To identify aromatic compounds in Jiashi melon juice, gas chromatography-mass spectrometry-olfactometry (GC-MS-O) analysis was used. Odor activity values (OAVs) were also calculated on the basis of the qualitative and quantitative analysis of volatile compounds. Results showed that 42 volatiles were identified, among which 4 compounds, namely, diethyl carbonate, isophorone, 2-butoxyethyl acetate, and menthol, were identified or tentatively identified for the first time as volatiles in melon fruit. Twelve compounds, namely, (2E,6Z)-nona-2,6-dienal, (3Z,6Z)-nona-3,6-dien-1-ol, ethyl butanoate, ethyl 2-methylbutyrate, ethyl 2-methylpropanoate, (Z)-non-6-enal, (E)-2-nonenal, heptanal, methyl 2-methylbutyrate, nonanal, hexanal, and 2-methylpropyl acetate, were identified as the potent odorants of Jiashi melon juice by both OAV and detection frequency analysis (DFA). In addition, seven odorants were detected by all of the panelists and showed higher OAVs, indicating that DFA and OAV resulted in relatively similar "Jiashi" melon aroma patterns.     

Characterization and quantitation of phenolic compounds in new apricot (Prunus armeniaca L.) varieties

Thirty-seven apricot varieties, including four new releases (Rojo Pasión, Murciana, Selene, and Dorada) obtained from different crosses between apricot varieties and three traditional Spanish cultivars (Currot, Mauricio, and Búlida), were separated according to flesh color into four groups: white, yellow, light orange, and orange (mean hue angles in flesh were 88.1, 85.0, 77.6, and 72.4, respectively). Four phenolic compound groups, procyanidins, hydroxycinnamic acid derivatives, flavonols, and anthocyanins, were identified by HPLC-MS/MS and individually quantified using HPLC-DAD. Chlorogenic and neochlorogenic acids, procyanidins B1, B2, and B4, and some procyanidin trimers, quercetin 3-rutinoside, kaempferol 3-rhamnosyl-hexoside and quercetin 3-acetyl-hexoside, cyanidin 3-rutinoside, and 3-glucoside, were detected and quantified in the skin and flesh of the different cultivars. The total phenolics content, quantified as the addition of the individual compounds quantified by HPLC, ranged between 32.6 and 160.0 mg 100 g(-1) of edible tissue. No correlation between the flesh color and the phenolic content of the different cultivars was observed.     

Arsenosugars in raw and cooked edible seaweed: characterization and bioaccessibility

The aim of this study was to examine arsenic species contents in raw and cooked edible seaweed and the bioaccessibility (maximum soluble concentration in gastrointestinal medium) of arsenosugars (glycerol ribose, phosphate ribose, sulfonate ribose, and sulfate ribose). For the analysis, a new chromatographic separation was developed in anion exchange, coupled with thermooxidation-hydride generation-atomic fluorescence spectrometry. An in vitro digestion (pepsin, pH 2; pancreatin-bile extract, pH 7) was applied to estimate arsenosugar bioaccessibility. Cooking of Undaria pinnatifida and Porphyra sp. did not alter the arsenic species present in the methanol-water extract, but it produced a substantial increase (2 and 5 times) in the As(V) extracted from Hizikia fusiforme. In all of the seaweeds analyzed, arsenosugar bioaccessibility was high (>80%) and did not vary as a result of cooking. Arsenosugar degradation as a result of in vitro digestion was not observed.     

Quantification of selected aroma-active compounds in Pinot noir wines from different grape maturities

Effect of grape maturity on aroma-active compounds in Pinot noir wine was investigated using stir bar sorptive extraction-gas chromatograph-mass spectrometry (SBSE-GC-MS). High correlation coefficient (> 0.95) and low standard deviation (< 10%) were obtained for all aroma-active compounds of interest. Two vintages of Pinot noir wines with three different grape maturities each were analyzed. Statistical analysis showed that both grape maturity and growing year significantly affected the aroma composition of the final wine. Analysis of wine samples from the same vintage indicated that grape maturity could affect aroma compounds in different ways, based on their biochemical formation in the wines. For most short-chain fatty acid esters, there were no obvious trends with grape maturity, however, the concentrations of ethyl 2-methylpropanoate and ethyl 3-methylbutanoate consistently decreased with grape maturity. The decreasing trend was also observed for other esters including ethyl cinnamate, ethyl dihydroxycinnamate, and ethyl anthranilate, with the exception of ethyl vanillate, while C13 norisoprenoids, monoterpenes, and guaiacols had increasing trends with grape maturation.     

Characterization of the key aroma compounds in cooked grey mullet (Mugil cephalus) by application of aroma extract dilution analysis

Aroma and aroma-active compounds of wild grey mullet ( Mugil cephalus ) were analyzed by gas chromatography-mass spectrometry-olfactometry (GC-MS-O). According to sensory analysis, the aromatic extract obtained by simultaneous distillation and extraction (SDE) was representative of grey mullet odor. A total of 50 aroma compounds were identified and quantified in grey mullet. Aldehydes were qualitatively and quantitatively the most dominant volatiles in grey mullet. Aroma extract dilution analysis (AEDA) was used for the determination of aroma-active compounds of fish sample. A total of 29 aroma-active compounds were detected in aromatic extract of grey mullet, of which 24 were identified. On the basis of the flavor dilution (FD) factor, the most powerful aroma active compounds identified in the extract were (Z)-4-heptenal and nonanal, which were described as the strong cooked fish and green-fruity odor, respectively.     

Formation of aroma-active strecker-aldehydes by a direct oxidative degradation of Amadori compounds

alpha-Dicarbonyls, generated by sugar degradation, catalyze the formation of the so-called Strecker aldehydes from alpha-amino acids. To check the effectiveness of Amadori compounds (suggested as important intermediates in alpha-dicarbonyl formation from carbohydrates) in Strecker aldehyde formation, the amounts of phenylacetaldehyde (PA) formed from either an aqueous solution of L-phenylalanine/glucose or the corresponding Amadori compound N-(1-deoxy-D-fructosyl-1-yl)-L-phenylalanine (ARP-Phe) were compared. The results revealed the ARP-Phe as a much more effective precursor in PA generation. On the contrary, a binary mixture of glucose/phenylalanine yielded preferentially phenylacetic acid, in particular, when reacted in the presence of oxygen and copper ions. Further model experiments gave evidence that a transition-metal-catalyzed oxidation of the ARP-Phe by air oxygen into the 2-hexosulose-(phenylalanine) imine is the key step responsible for the favored formation of phenylacetaldehyde from the Amadori compound. This mechanism might explain differences in the ratios of Strecker aldehydes and the corresponding acids depending on the structures of carbohydrate degradation products involved.     

Bioavailability and kinetics of sulforaphane in humans after consumption of cooked versus raw broccoli

The aim of this study was to determine the bioavailability and kinetics of the supposed anticarcinogen sulforaphane, the hydrolysis product of glucoraphanin, from raw and cooked broccoli. Eight men consumed 200 g of crushed broccoli, raw or cooked, with a warm meal in a randomized, free-living, open cross-over trial. Higher amounts of sulforaphane were found in the blood and urine when broccoli was eaten raw (bioavailability of 37%) versus cooked (3.4%, p ) 0.002). Absorption of sulforaphane was delayed when cooked broccoli was consumed (peak plasma time ) 6 h) versus raw broccoli (1.6 h, p ) 0.001). Excretion half-lives were comparable, 2.6 and 2.4 h on average, for raw and cooked broccoli, respectively (p ) 0.5). This study gives complete kinetic data and shows that consumption of raw broccoli results in faster absorption, higher bioavailability, and higher peak plasma amounts of sulforaphane, compared to cooked broccoli.