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1.
Neohesperidin dihydrochalcone (NHDC), a sweet compound derived from citrus fruits, was modified to a series of its oligosaccharides by transglycosylation activity of Bacillus stearothermophilus maltogenic amylase (BSMA). Maltotriose as a donor was reacted with NHDC as an acceptor to glycosylate for the purpose of increasing the solubility of NHDC. Maltosyl-NHDC was a major transglycosylation product among the several transfer products by TLC analysis. The structure of the major transglycosylation product was determined to be maltosyl-alpha-(1,6)-neohesperidin dihydrochalcone by MALDI-TOF/MS and (1)H and (13)C NMR. Maltosyl-NHDC was 700 times more soluble in water and 7 times less sweet than NHDC.  相似文献   

2.
The enzymatic modification of genistin to enhance its water solubility was studied using two glycosyltransferases, cyclodextrin glucanotransferase from alkalophilic Bacillus sp. I-5 and 4-alpha-glucanotransferase from Thermus scotoductus. Two different catalytic reactions, the transglycosylation and cyclization activities, were observed when the reaction was performed with soluble starch as a donor and genistin as an acceptor. The reaction products were isolated and identified as [Glc(alpha1-4)](1-22)-Glc(beta1-7)-genisteins and cycloamylose with DP 8-12 by HPLC and MALDI-TOF MS. A beta-amylase treatment revealed inclusion complexes composed of Glc(alpha1-4)-Glc(beta1-7)-genistein/Glc(alpha1-4)-Glc(alpha1-4)-Glc(beta1-7)-genistein and cycloamylose with DP 8-12. The results indicated that the cycloamylose formed by the cyclization reaction of the enzyme included Glc(alpha1-4)-Glc(beta1-7)-genistein/Glc(alpha1-4)-Glc(alpha1-4)-Glc(beta1-7)-genistein. The presence of cycloamylopectin, in which the Glc(alpha1-4)-Glc(beta1-7)-genistein/Glc(alpha1-4)-Glc(alpha1-4)-Glc(beta1-7)-genistein was enclosed, was also observed with HPLC, HPSEC-MALLS, and MALDI-TOF MS analyses. The solubility of genistin was highly improved, and the solution containing glycosylated genistin and the inclusion complex demonstrated excellent properties of transparency and stability during storage at 4 degrees C.  相似文献   

3.
Isoflavones are novel nutraceutical constituents of soybeans, but considerable amounts are lost in the whey during conventional tofu manufacturing. In this study, in a small-scale process, 2 mL of koji enzyme extract (soybean koji/deionized water, 1/3, w/v) was combined with 600 mL of soy milk, and 30 mL aliquots were incubated at 35 degrees C for 0, 30, 60, 120, and 300 min, for enzyme pretreatment. After each treatment time, soy milk was heated to 85 degrees C, CaSO4 was added to aggregate protein, and the mixture was centrifuged to separate the solids (tofu) from the whey. The tofu yield and moisture contents from soy milk treated for 30 or 60 min were higher than those from soy milk treated for 0 (control), 120, or 300 min. The protein content of freeze-dried tofu varied in a limited range, and native PAGE and SDS-PAGE patterns revealed slight quantitative and qualitative variations among products. Soy milk daidzein and genistein contents increased while daidzin and genistin contents decreased as the time of enzyme pretreatment of the soy milk increased. After 30 min of pretreatment, daidzin, genistin, daidzein, and genistein contents recovered in tofu products were higher than those of the control. In a pilot-scale process, aliquots (3 L) of soy milk were enzyme-treated for 30 min, aggregated with CaSO4, and hydraulically pressed to remove the whey. As in pretreatments, soy milk daidzein and genistein contents increased while daidzin and genistin contents decreased. In a comparison of the control and enzyme-treated tofu products, the total recoveries of daidzin, genistin, daidzein, and genistein in the tofu products increased from 54.9% to 64.2%. When the tofu products were subjected to a sensory panel test, both products were judged acceptable.  相似文献   

4.
Naringin, a bitter compound in citrus fruits, was transglycosylated by Bacillus stearothermophilus maltogenic amylase reaction with maltotriose to give a series of mono-, di-, and triglycosylnaringins. Glycosylation products of naringin were observed by TLC and HPLC. The major glycosylation product was purified by using a Sephadex LH-20 column. The sturcture was determined by using MALDI-TOF MS, methylation analysis, and (1)H and (13)C NMR. The major transglycosylation product was maltosylnaringin, in which the maltose unit was attached by an alpha-1-->6 glycosidic linkage to the D-glucose moiety of naringin. This product was 250 times more soluble in water and 10 times less bitter than naringin.  相似文献   

5.
The present study investigated the changes of the bioavailable isoflavones, including daidzin, genistin, daidzein, and genistein, during the making of tofu. The amount of extracted daidzin and genistin in soy milk increased with increasing water-to-bean ratios from 5 to 9 and reached the maximum level at the ratios of 9-11. On the other hand, the amount of extracted free isoflavones (daidzein and genistein) was not affected by the water-to-bean ratio at the range of 5-11, and their extracted amounts in soy milk were 2-4-fold those in raw soybean. It is suggested that these free isoflavones are mainly derived from daidzin, genistin, malonyldaidzin, and malonylgenistin through enzymatic hydrolysis during the making of soy milk. Tofu made with water-to-bean ratios of 9:1 and 10:1 had the maximal retentions of daidzin and genistin, which were due to the fine homogeneous network microstructure that is supposed to be more effectively retained through hydrophilic interaction with protein. On the contrary, the retained amount of free isoflavones decreased significantly as the water-to-bean ratio increased from 7 to 11, due to their weakening hydrophobic interaction with protein. In this study it was found that the homogeneous microstructure of tofu improved the retention of hydrophilic daidzin and genistin and that the increased amount of drained water does not significantly reduce their retention in the final tofu products as generally imagined.  相似文献   

6.
Piceid is widely used in food, cosmetics, and pharmaceuticals because of its therapeutic benefits. However, the use of piceid as a drug is limited because of its low solubility. To increase solubility, we synthesized piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii . The MTase gene was cloned and expressed in Escherichia coli . The enzyme had a unique transfer specificity to the transfer of maltosyl units. Four piceid transglycosylation products were present and identified by thin-layer chromatography and recycling preparative high-performance liquid chromatography. The major product was purified by C(18) and gel filtration chromatography, and its molecular structure was determined using nuclear magnetic resonance spectroscopy to be α-d-maltosyl-(1→4)-piceid. The solubility of maltosyl piceid was 8.54 × 10(3) and 1.86 × 10(3) times those of natural resveratrol and piceid, respectively, suggesting that the transglycosylation greatly increased the water solubility. This suggests that dietary intake of this compound can enhance the bioavailability of resveratrol in the human body.  相似文献   

7.
The soy isoflavones daidzin, glycitin, and genistin were purified from defatted soy flour using preparative-scale reverse-phase HPLC. The stabilities of the three isoflavones at different heating temperatures were investigated. Daidzin, glycitin, and genistin were lost at a rate of 26, 27, and 27% of their original concentration, respectively, after 3 min at 185 degrees C. At 215 degrees C, decreases of daidzin, glycitin, and genistin were 65, 98, and 74% after 3 min and 91, 99, and 94% after 15 min, respectively. The order of the thermal stabilities, from lowest to highest, was glycitin, genistin, and daidzin. Acetyl daidzin and acetyl genistin, daidzein, glycitein, and genistein were produced during heating at temperatures above 135 degrees C. The rate of binding of an acetyl group to form acetyl daidzin and acetyl genistin from daidzin and genistin was higher than the rate of loss of a glucoside group to form daidzein and genistein. However, acetyl daidzin and acetyl genistin decreased sharply at temperatures above 200 degrees C, while daidzein, glycitein, and genistein were relatively stable over 30 min. The stability of daidzein was higher than that of glycitein or genistein.  相似文献   

8.
Soybeans were soaked with water for 4 h, steam-cooked, inoculated with the conidia of Aspergillus oryzae, and incubated for 3 days for koji preparation. The koji was then mixed with water-soaked and steam-cooked soybeans (1:2, w/w), ground into paste, and supplemented with 15% ethanol and 12.5% NaCl or 3% ethanol and 6% NaCl for miso fermentation at 30 degrees C. Daidzin, genistin, daidzein, and genistein contents were extracted from the lyophilized and pulverized soybean powder or from the miso homogenate by a developed one-tube procedure and analyzed with an HPLC. After water soaking, daidzein and genistein contents increased markedly, whereas daidzin and genistin contents decreased. Further increases of daidzein and genistein contents and decreases of daidzin and genistin contents were observed after koji mold growth. During fermentation, fungal and lactic acid bacterial (LAB) growth in the miso products was inhibited, whereas soluble protein contents increased much more rapidly in the low-salt miso products supplemented with 3% ethanol and 6% NaCl than the other products. When the 4- and 8-week-fermented miso products were cooked with tofu for sensory evaluation, flavor ratings of the low-salt products were higher than that of a popular commercial product. In both products, the most daidzins and genistins were hydrolyzed after 4 weeks of fermentation. The hydrolytic enzymes contributing to isoflavone transformation originated from soybeans after water soaking and from koji with mold growth. It was of merit that the low-salt fermented products were fairly acceptable in flavor rating and rich in daidzein and genistein contents after 4 weeks of fermentation.  相似文献   

9.
Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an alpha-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and (13)C NMR analyses revealed that the structures of the transfer products were 6-O-alpha-D-glucosyl- (2) and 6-O-alpha-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-alpha-acarviosine-D-glucosyl- (4) and 2-O-alpha-acarviosine-D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu(2+) ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.  相似文献   

10.
The oxidative metabolism of the major soy isoflavones daidzein and genistein was investigated using liver microsomes from Aroclor-treated male Wistar rats. Both daidzein and genistein were extensively metabolized and are therefore excellent substrates for cytochrome P450 enzymes. The identity of the metabolites was elucidated using high-performance liquid chromatography (HPLC) with diode array detection, gas chromatography-mass spectrometry (GC/MS), and HPLC/atmospheric pressure ionization electrospray mass spectrometry (API-ES MS) as well as reference substances. Daidzein was converted to nine metabolites, comprising four monohydroxylated, four dihydroxylated, and one trihydroxylated metabolite. Genistein was metabolized to four monohydroxylated and two dihydroxylated products. With both isoflavones the additional hydroxy groups are exclusively introduced into the ortho positions of existing phenolic hydroxy groups. The major metabolites of daidzein were identified as 6,7,4'-trihydroxyisoflavone, 6,7,3',4'-tetrahydroxyisoflavone, 7,8, 4'-trihydroxyisoflavone, and 5,6,7,4'-tetrahydroxyisoflavone. The main microsomal metabolites of genistein were 5,6,7, 4'-tetrahydroxyisoflavone and 5,7,8,4'-tetrahydroxyisoflavone. Furthermore, the GC/MS and HPLC/API-ES MS analysis support the conclusion that one monohydroxylated metabolite of daidzein and genistein is hydroxylated at the aliphatic position C-2 of the C-ring. The UV-vis, GC/MS, and HPLC/MS data of all detected metabolites as well as the derived chemical structure of the metabolites are presented. Most metabolites are reported in this paper for the first time. On the basis of these findings it is suggested that hydroxylation reactions may also play an important role in the in vivo metabolism of the soy isoflavones daidzein and genistein.  相似文献   

11.
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) is a new technique having a number of advantages for food analysis. This study is the first to demonstrate the use of MALDI-TOF MS to identify isoflavones in soy samples. 2',4',6'-Trihydroxyacetophenone (THAP) and 2,5-dihydroxybenzoic acid (DHB) were both good matrices for isoflavones, but DHB was chosen as the best because it worked well for sample extracts, with good spot-to-spot repeatability. Isoflavones were predominantly ionized in a protonated form with a very small amount of sodium or potassium adduct ions. Fragmentation occurred only through loss of glycosidic residues. Daidzin showed more than twice the response of genistin using MALDI-TOF MS. A simple solid phase extraction of isoflavones from soy samples was developed for MALDI-TOF MS analysis. MALDI-TOF MS can provide an isoflavone profile in 2 min and serves as a powerful tool to identify and study processing changes of isoflavones in soy products.  相似文献   

12.
Profiles of genistein, daidzein, genistin, daidzin, and their acetyl- and malonyl-beta-glycosides were determined in tofu as affected by temperature and time. Tofu was heated in water at 80, 90, and 100 degrees C for 0 (control), 10, 20, 30, and 40 min, and the contents of the isoflavones of interest were quantified using reversed-phase HPLC. Total isoflavone content decreased most likely due to leaching of isoflavones into the water. Because the content of the isoflavones of the genistein series was little affected by the treatments, the decrease in the total isoflavone content was almost exclusively due to a decrease of the daidzein series. Changes in the profile of the daidzein series suggest little decarboxylation of the malonylglycoside to the acetylglycoside, but considerable de-esterification of the malonyl- and acetylglycoside to the beta-glucoside. Strongly temperature dependent decreases of the aglycon suggest possible thermal degradation of daidzein in addition to losses due to leaching.  相似文献   

13.
The kudzu vine (Pueraria sp.) is a rich source of isoflavones. Dietary supplements based on kudzu have become commercially available. In the present study, liquid chromatography coupled with negative and positive electrospray ionization tandem mass spectrometry (MS/MS) and diode array detection (DAD) has been used for the detection and characterization of isoflavonoids in kudzu dietary supplements (KDS). The MS/MS spectrum of the protonated ion of puerarin showed characteristic product ions of the C-glycoside unit itself, whereas daidzin generated an abundant Y(0)(+) aglycon ion in its product ion spectrum. A base peak due to the loss of 120 Da [M + H - 120](+) is the diagnostic ion for C-glycosides. Neutral loss scans allowed for the detection of other C- and O-glycosides in the methanolic extract of KDS, and their structures have been proposed. The concentration of isoflavonoids in the methanolic extract of commercially available KDS was quantified by using DAD-HPLC. Puerarin, rather than daidzin, was the most abundant component (8.44-30.60 mg/capsule) in commercially available KDS.  相似文献   

14.
Puerarin and daidzin are the major isoflavone glucosides found in kudzu dietary supplements. In this study, we demonstrated that puerarin significantly improves glucose tolerance in C57BL/6J-ob/ob mice, an animal model of type 2 diabetes mellitus, blunting the rise in blood glucose levels after i.p. administration of glucose. In contrast, daidzin, the O-glucoside, had a significant but opposite effect, impairing glucose tolerance as compared to saline-treated controls. When they were administered i.p. with (14)C-glucose to C57BL/6J lean mice, puerarin inhibited glucose uptake into tissues and incorporation into glycogen, while daidzin stimulated glucose uptake, showing an opposite effect to puerarin. Puerarin also antagonized the stimulatory effect of decyl-beta-D-thiomaltoside, an artificial primer of glycogen synthesis, which increases (14)C-glucose uptake and incorporation into glycogen in mouse liver and heart. A liquid chromatography-tandem mass spectrometry procedure was used to investigate the metabolism and bioavailability of puerarin and daidzin. The blood puerarin concentration-time curve by i.p. and oral administration indicated that puerarin was four times more bioavailable via i.p. injection than via the oral route of administration. This may account for the increased hypoglycemic effect seen in the i.p. glucose tolerance test vs that seen orally. Our results suggest that puerarin is rapidly absorbed from the intestine without metabolism, while daidzin is hydrolyzed to the aglycone daidzein. The opposing effects of puerarin and daidzin on glucose homeostasis may have implications for the activity of dietary supplements that contain both of these isoflavonoids.  相似文献   

15.
Successful quantification of the glucose produced by enzyme hydrolysis of starch was achieved by a matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) protocol, using sorbitol as an internal standard. The starch contents measured by MALDI-TOF MS of corn starch, fiber-enriched oat flour derivatives, oat and barley flours, and barley flour/corn starch composites were evaluated in comparison to a widely accepted and validated method of starch determination, which relies on enzyme colorimetry (EC). The average starch content measured in a series of corn starch samples of different masses was 93 and 101% for EC and MALDI-TOF MS, respectively, values that represent the estimated purity of the sample. There was an agreement of 99% between the starch contents determined by the two analytical methods for complex flour-derived samples. Starch values estimated by MALDI-TOF MS consistently showed a greater degree of variability than those determined by EC, but this limitation was readily compensated by rapid acquisition of multiple mass spectra. This study is the first to report the quantification of glucose by MALDI-TOF MS, and it offers new perspectives into the potential utility of MALDI-TOF MS as a definitive tool for monosaccharide analysis and rapid starch determination in complex samples.  相似文献   

16.
Sulfamethazine (SMT) and its major metabolite, N(4)-acetylsulfamethazine (NA-SMT), were each recovered from spiked water (0.1 ppb) and 10% (w/v) aqueous suspensions of soil (1 ppb) or composted manure (1 ppb), by using a three-stage solid phase immunoextraction (SPIE) system, followed by detection with matrix-assisted laser/desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). Sulfonamide recovery rates are reported for separate stages of the SPIE system and for trace-level sulfonamide SPIE extraction from the environmental samples. SPIE MALDI-TOF MS is a rapid and definitive technique with potentially better efficiency relative to other established trace-level sulfonamide analytical methods. SPIE MALDI-TOF MS required 1.5 h per batch (8-24 samples/batch) for sample enrichment, 5 min per batch for probe preparation, and 5 min per sample to acquire and process the spectrum. This is the first time MALDI-TOF MS has been reported as a potential means of detecting trace-level drug residues in complex environmental samples.  相似文献   

17.
The major constituents in grape seed and pine bark extracts are proanthocyanidins. To evaluate material available to consumers, select lots were analyzed using high-performance liquid chromatography, gas chromatography/mass spectrometry (GC/MS), liquid chromatography/mass spectrometry (LC/MS), gel permeation chromatography (GPC), and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Atmospheric pressure chemical ionization (APCI) LC/MS was used to identify monomers, dimers, and trimers present. GC/MS analyses led to the identification of ethyl esters of hexadecanoic acid, linoleic acid, and oleic acid, as well as smaller phenolic and terpene components. The GPC molecular weight (MW) distribution indicated components ranging from approximately 162 to approximately 5500 MW (pine bark less than 1180 MW and grape seed approximately 1180 to approximately 5000 MW). MALDI-TOF MS analyses showed that pine bark did not contain oligomers with odd numbers of gallate units and grape seed contained oligomers with both odd and even numbers of gallate. Reflectron MALDI-TOF MS identified oligomers up to a pentamer and heptamer, and linear MALDI-TOF MS showed a mass range nearly double that of reflectron analyses.  相似文献   

18.
Interest in the molecular composition of almonds is growing, due to their popularity in a wide variety of food formulations. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) is a powerful new technique that can be used to rapidly identify and quantify possible bioactive compounds in these popular tree nuts. Four flavonol glycosides were identified in almond seedcoats for the first time: isorhamnetin rutinoside, isorhamnetin glucoside, kaempferol rutinoside, and kaempferol glucoside. A MALDI-TOF MS methodology was developed using rutin (quercetin-3-rutinoside) as an internal standard to quantitatively determine each of the four flavonol glycosides. Results of MALDI-TOF MS analysis were verified by high performance liquid chromatography.  相似文献   

19.
Seven legume extracts containing phytoestrogens were analyzed for estrogenic activity. Methanol extracts were prepared from soybean (Glycine max L.), green bean (Phaseolus vulgaris L.), alfalfa sprout (Medicago sativa L.), mung bean sprout (Vigna radiata L.), kudzu root (Pueraria lobata L.), and red clover blossom and red clover sprout (Trifolium pratense L.). Extracts of kudzu root and red clover blossom showed significant competitive binding to estrogen receptor beta (ERbeta). Estrogenic activity was determined using an estrogen-dependent MCF-7 breast cancer cell proliferation assay. Kudzu root, red clover blossom and sprout, mung bean sprout, and alfalfa sprout extracts displayed increased cell proliferation above levels observed with estradiol. The pure estrogen antagonist, ICI 182,780, suppressed cell proliferation induced by the extracts, suggesting an ER-related signaling pathway was involved. The ER subtype-selective activities of legume extracts were examined using transiently transfected human embryonic kidney (HEK 293) cells. All seven of the extracts exhibited preferential agonist activity toward ERbeta. Using HPLC to collect fractions and MCF-7 cell proliferation, the active components in kudzu root extract were determined to be the isoflavones puerarin, daidzin, genistin, daidzein, and genistein. These results show that several legumes are a source of phytoestrogens with high levels of estrogenic activity.  相似文献   

20.
Beta-1,2,3,4,6-penta-O-galloyl-D-glucopyranose (PGG) and soluble complexes of PGG with bovine serum albumin (BSA) were characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). PGG was also characterized by electrospray ionization mass spectrometry (ESI-MS). Similar fragmentation patterns of PGG were found in ESI-MS and MALDI-TOF MS. The apparent stoichiometries of non-covalent BSA-PGG complexes were determined by MALDI-TOF MS.  相似文献   

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