植物源天然产物的抑菌作用、机理及在食品保藏中的应用

食源性致病菌引起的食品安全问题严重威胁着人们的身体健康,已经广泛引起人们的关注,因而如何安全有效地抑制食品中致病菌的生长成为食品领域中的研究热点。研究表明,植物源天然产物具有来源广泛、抑菌谱广、与化学防腐剂相比副作用小等特点,可作为一种天然防腐剂运用于食品中。本文综述了植物源天然产物对食源性致病菌的抑菌活性、机理以及在食品保藏中的应用,以期为减少食源性致病菌对食品的污染提供理论依据。     

Precursors to damascenone: synthesis and hydrolysis of isomeric 3,9-dihydroxymegastigma-4,6,7-trienes

A series of four isomeric 3,9-dihydroxymegastigma-4,6,7-trienes, 8, has been prepared. The (3S,6R,9S) isomer of 8 proved to be identical to an isomer of this compound tentatively identified as an intermediate in the formation of damascenone from an allene triol. Each of the four isomers, when hydrolyzed independently of each other at pH 3.0 and 25 degrees C, produced product mixtures in which the major product was damascenone (1). Contrary to expectation, 3-hydroxydamascone (5) was not observed in any of the hydrolyses. Consequently, the mechanism of formation of damascenone proposed earlier requires modification. In each hydrolysis, the product mixtures showed the presence of a second isomer of 8, produced by epimerization during hydrolysis. Chiral analysis on a Cyclosil B column revealed that this epimerization was occurring at C(3) in each of the hydrolyses.     

Phenolic constituents, furans, and total antioxidant status of distilled spirits.

The concentrations of 11 phenols and 5 furans were measured in 12 categories of distilled spirits by HPLC methodology, together with the total antioxidant status (TAS) of the same beverages. Ellagic acid was the phenol present in highest concentration in all beverages. Moderate amounts of syringaldehyde, syringic acid, and gallic acid, as well as lesser amounts of vanillin and vanillic acid, were measurable in most samples of whiskey, brandy, and rum but were largely undetectable in gin, vodka, liqueurs, and miscellaneous spirits. 5-(Hydroxymethyl)furfural was the predominant furan in the former three beverages, notably cognac, with 2-furaldehyde the next highest, but these were undetectable in most of the latter beverages. Highest TAS values were given by armagnac, cognac, and bourbon whiskey, all three of which tended toward the highest concentrations of phenols. Negative TAS values were exhibited by rum, vodka, gin, and miscellaneous spirits in line with the low or undetectable phenol concentrations in these beverages. Wood aging is the most likely source of phenols and furans in distilled spirits. Those beverages exposed to this treatment contain significant antioxidant activity, which is between the ranges for white and red wines, with the potential to augment the antiatherosclerotic functions attributable to the ethanol that they contain.     

Headspace GC and sensory analysis characterization of the influence of different milk additives on the flavor release of coffee beverages

Previous investigations of coffee flavor have been confined to the analysis of the aroma substances. These investigations showed that about 30 volatile compounds were substantially responsible for the coffee flavor. The aim of this study was to investigate the influence of different milk additives and one coffee whitener on the release of flavor impact compounds from coffee beverages. For the investigation of these effects an external static headspace technique was developed. With this technique the most potent odorants of the coffee beverage were determined. Analyses were performed by gas chromatography/olfactometry, flame ionization detection, and mass spectrometric detection. In addition, sensory studies of the odor profiles were performed. Milk and vegetable products as additives for coffee beverages affected the release of aroma substances in the brew through their lipid, protein, and carbohydrate components. All beverages with an additive showed reduced, but typical, odor profiles for each additive.     

Rationalizing the formation of damascenone: synthesis and hydrolysis of damascenone precursors and their analogues, in both aglycone and glycoconjugate forms

Storage of megastigma-4,6,7-trien-3,9-diol (5), and megastigma-3,4-dien-7-yn-9-ol (6) in aqueous ethanol solution at pH 3.0 and 3.2 gave exclusively damascenone (1) and damascenone adducts at room temperature. The diol (5) had half-lives for the conversion of 32 and 48 h at pH 3.0 and pH 3.2, respectively. The acetylenic alcohol (6) had half-lives of 40 and 65 h at the same pH levels. In order to study the reactivity of the C-9 hydroxyl function in 5 and in the previously investigated allenic triol 2, two model compounds, megastigma-4,6,7-trien-9-ol (7) and megastigma-6,7-dien-9-ol (8) were synthesized. No 1,3-transposition of oxygen to form analogues of damascenone was observed when 7 and 8 were subjected to mild acidic conditions. Such transposition takes place only with highly conjugated acetylenic precursors such as 6 or tertiary allenic alcohols such as 2. The placement of glucose at C-3 of 5 and at C-9 of 6 gave the glycosides 9 and 10, respectively. The effect of such glucoconjugation was to increase the observed half-lives by a factor of only 1.6-1.7 for the allenic glucoside 9, and by 2.1-2.2 for the acetylenic glucoside 10. These studies indicate that the effect of glycosylation on damascenone formation is probably not important on the time scale of wine making and maturation.     

Fate of damascenone in wine: the role of SO2

Damascenone has been shown to undergo reaction with common wine components. Following the action of acid and heat alone, two bicyclic compounds, 4,9,9-trimethyl-8-methylenebicyclo[3.3.1]non-6-en-2-one (2) and 4,4,9-trimethyl-8-methylenebicyclo[3.3.1] non-6-en-2-one (3), were isolated. However, this conversion takes place only very slowly, if at all, under milder conditions (45 degrees C). When treated with a variety of nucleophiles at pH 3.0 and 5.5, the concentration of damascenone in buffered aqueous ethanol decreased by minor amounts (10-20%) except for cysteine and 2-mercaptoethanol addition at pH 5.5 (approximately 40 and approximately 30%, respectively) and SO2 (>90% at pH 3.0; 100% at pH 5.5). An adduct from this last combination was prepared and shown to be the C9 sulfonic acid derivative of damascenone. A detailed investigation into the effect of SO2 demonstrated that loss of damascenone in model wine was directly related to the concentration of added SO2 but was essentially unaffected by small changes in pH.     

Isoflavones in soy-based foods consumed in Brazil: levels,distribution, and estimated intake

The isoflavone content and profile in processed soy-based products consumed in Brazil were determined by high-performance liquid chromatography and photodiode array detection of the intact isoflavones (naturally occurring aglycons, malonyl, acetyl, and beta-glycosides derivatives). Total isoflavone content varied significantly among products, from 2 to 100 mg/100 g (wet basis, expressed as aglycons), with the lowest content being found for soy-based enteral/oral diets and the highest found for textured soy proteins. For soy beverages isoflavone content varied from 12 to 83 mg/L. Soy sauce, miso, and tofu had isoflavone contents of 5.7 mg/L, 20 mg/100 g, and 7 mg/100 g, respectively. The beta-glycosides were the predominant form of the isoflavones in the products analyzed, except for miso, shoyu, and "Diet Shake" in which the aglycons were present in the highest proportions. On the basis of these data, the daily intake of isoflavone from soy products was estimated: the highest values were found for infants fed soy-based formulas, from 1.6 to 6.6 mg/kg of body weight.     

Effectiveness of Plant-Derived Sorbents for the Remediation of Low-Energy Intertidal Wetlands Contaminated by Oil Spills

The use of plant-derived sorbent was investigated as a remediation strategy for low-energy intertidal wetlands contaminated by crude oil spills. Effectiveness of plant-derived sorbent as a wicking agent was evaluated in microcosms simulating intertidal wetlands. Microcosms were designed to impose three different oil penetration depths (0.25, 0.5, and 1.0?cm), two different tidal amplitudes (±5 and ±10?cm above oil-contaminated surface), and two different types of sorbents (raw bagasse and hydrophobic-treated bagasse). We observed that the use of plant-derived sorbent was beneficial not only in removing oil but also in preventing further contamination. Oil penetration depth and tidal amplitude both negatively influenced the effectiveness of the sorbent. Effectiveness of the hydrophobic-treated sorbent was always higher than that of untreated one at any given oil penetration depth and tidal amplitude. Effectiveness of hydrophobic-treated sorbent was relatively low compared to that of raw bagasse. The most plausible explanation is that oil wicking mainly occurred during low tide. From a cost-effectiveness point of view, we suggest the use of raw bagasse immediately after an oil spill for remediation of low-energy intertidal wetlands. The observed results imply that this technique has potential to stimulate biodegradation by wicking oil out of contaminated intertidal wetlands subsurface to the aerobic zone where biodegradation can take place.     

Pungent principal of Alpinia galangal (L.) swartz and its applications

The pungent principal of galangal [Alpinia galangal (L.) Swartz] rhizomes was isolated and identified as 1'-acetoxychavicol acetate (galangal acetate). Galangal acetate exhibits a unique pungent sensation, which is less intense than that of capsaicin and without a lingering effect. Applications of galangal acetate were tested in beverages, sweet goods, dressings, and personal care products. In many applications, galangal acetate is preferred to other pungent ingredients. It can be used as an alcohol enhancer or an alcohol replacer in alcohol and alcohol-free beverages. Galangal acetate is not stable in aqueous solutions and undergoes hydrolysis/isomerization reactions. Therefore, galangal acetate was absent in galangal essential oil obtained by steam distillation. However, galangal acetate was found as one of the major volatile components of the galangal rhizomes by headspace GC analysis. The stability of galangal acetate was studied under various conditions.     

Use of epichlorohydrin-treated chitosan resin as an adsorbent to isolate kappa-casein glycomacropeptide from sweet whey

This study was undertaken to develop a method to isolate glycomacropeptide (GMP), a bioactive compound, from sweet whey by using chitosan resins as anion exchangers. Shrimp shells were used to prepare two chitosan (polyglucosamine) resins, one with the primary amine (-NH(2)) (resin A) and the other with the secondary amine (-NH-) (resin B) as the major functional group. These resins were tested as adsorbents for the isolation of GMP from sweet whey, and the results obtained were compared with those obtained with commercial anion exchangers. The most important finding in this experiment was that the GMP binding capacity of resin A was much higher than that of resin B. Resin A may be the anion exchanger to be tested for industrial scale production of GMP. Amino acid analysis of the GMP-depleted whey fraction suggests that this product can replace sweet whey as an ingredient in various food products including infant formulas, bakery products, and beverages.     

Acute effect of tea, wine, beer, and polyphenols on ecto-alkaline phosphatase activity in human vascular smooth muscle cells

Alkaline phosphatase (ALP) is an ecto-enzyme widely distributed across species. It modulates a series of transmembranar transport systems, has an important role in bone mineralization, and can also be involved in vascular calcification. Polyphenol-rich diets seem to have protective effects on human health, namely, in the prevention of cardiovascular diseases. We aimed to investigate the effects of polyphenols and polyphenol-rich beverages upon membranar alkaline phosphatase (ecto-ALP) activity in intact human vascular smooth muscle cells (AALTR). The ecto-ALP activity was determined at pH 7.8, with p-nitrophenyl phosphate as the substrate, by absorbance spectrophotometry at 410 nm. Cell viability was assessed by the lactate dehydrogenase (LDH) method, and the polyphenol content of beverages was assessed using the Folin-Ciocalteu reagent. All polyphenols tested inhibited ecto-ALP activity, in a concentration-dependent way. Teas, wines, and beers also inhibited ecto-ALP activity, largely according to their polyphenol content. All tested compounds and beverages improved or did not change AALTR cell viability. Stout beer was an exception to the described behavior. Although more studies must be done, the inhibition of AALTR ecto-ALP activity by polyphenolic compounds and polyphenol-containing beverages may contribute to their cardiovascular protective effects.     

Formation of Damascenone under both commercial and model fermentation conditions

The fermentations, at a commercial winery, of six different grape musts encompassing the varieties Riesling, Chardonnay, Sauvignon blanc, Shiraz, Grenache, and Pinot noir were monitored for damascenone concentration. In every case, the concentration of damascenone increased during fermentation from low or undetectable levels to concentrations of several parts per billion. Further increases in damascenone concentration were observed during barrel aging of three of these wines. Two ketones, megastigma-4,6,7-triene-3,9-dione (4) and 3-hydroxymegastigma-4,6,7-trien-9-one (5), were synthesized and subjected to fermentation conditions using two yeasts, AWRI 796, and AWRI 1537. In the case of the former compound, 4, synthesis confirmed the original, tentative assignment of the structure and confirmed 4 as a natural product, isolated from honey. Both compounds, under the action of both yeasts, produced appreciable amounts of damascenone (1), with ketone 5 and AWRI 796 yeast yielding the highest concentration of 1.     

Isolation, identification, and quantification of roasted coffee antibacterial compounds

Coffee brew is a widely consumed beverage with multiple biological activities due both to naturally occurring components and to the hundreds of chemicals that are formed during the roasting process. Roasted coffee extract possesses antibacterial activity against a wide range of microorganisms, including Staphylococcus aureus and Streptococcus mutans, whereas green coffee extract exhibits no such activity. The naturally occurring coffee compounds, such as chlorogenic acids and caffeine, cannot therefore be responsible for the significant antibacterial activity exerted by coffee beverages against both bacteria. The very low minimum inhibitory concentration (MIC) found for standard glyoxal, methylglyoxal, and diacetyl compounds formed during the roasting process points to these alpha-dicarbonyl compounds as the main agents responsible for the antibacterial activity of brewed coffee against Sa. aureus and St. mutans. However, their low concentrations determined in the beverage account for only 50% of its antibacterial activity. The addition of caffeine, which has weak intrinsic antibacterial activity, to a mixture of alpha-dicarbonyl compounds at the concentrations found in coffee demonstrated that caffeine synergistically enhances the antibacterial activity of alpha-dicarbonyl compounds and that glyoxal, methylglyoxal, and diacetyl in the presence of caffeine account for the whole antibacterial activity of roasted coffee.     

Phenolic acids in berries, fruits, and beverages

The contents of soluble and total phenolic acids were analyzed in samples of 29 berries and berry products, 24 fruits and fruit peels, and 12 beverages. Variation of phenolic acids in berries was also studied. Soluble phenolic acids were extracted with methanolic acetic acid, and a tentative quantification was performed by high-performance liquid chromatography (HPLC). The total phenolic acid content was determined by HPLC after alkaline and acid hydrolyses. The content of total phenolic acids as aglycones in the above samples varied from 0 (pear cider) to 103 mg/100 g fresh weight (rowanberry). Besides rowanberry, the best phenolic acid sources among berries were chokeberry (96 mg/100 g), blueberry (85 mg/100 g), sweet rowanberry (75 mg/100 g), and saskatoon berry (59 mg/100 g). Among fruits, the highest contents (28 mg/100 g) were determined in dark plum, cherry, and one apple variety (Valkea Kuulas). Coffee (97 mg/100 g) as well as green and black teas (30-36 mg/100 g) were the best sources among beverages. Caffeic acid dominated in all of these samples except in tea brews. Variation in the phenolic acid contents of the berries was either small or moderate.     

Formation of a seed germination promoter from carbohydrates and amino acids

The ability of plant-derived smoke to act as a germination cue in many species has led to widespread interest in this aspect of seed biology. Recently, 3-methyl-2H-furo[2,3-c]pyran-2-one was identified as the main germination cue from smoke. Here, we report on the formation of this compound from reactions of sugars with amino acids. Heating proteins or amino acids with sugars at 180 degrees C for 30 min produces water soluble extracts that promote germination. High-performance liquid chromatography indicated that the active compound(s) derived from these reactions coeluted with the active fraction from a smoke solution. Gas chromatography-mass spectroscopy showed that the active constituent is identical to the germination cue from plant-derived smoke. The results presented in this paper provide evidence for the formation of the major germination cue found in smoke from ubiquitously occurring organic compounds.     

Development of an Orange‐Flavored Barley β‐Glucan Beverage

Barley β‐glucan concentrate shows great potential as a functional food ingredient, but few product applications exist. The objectives of this study were to formulate a functional beverage utilizing barley β‐glucan concentrate, and to make a sensory evaluation of beverage quality in comparison to pectin beverages and to assess shelf stability over 12 weeks. Three beverage treatments containing 0.3, 0.5, and 0.7% (w/w) barley β‐glucan were developed in triplicate. Trained panelists found peely‐ and fruity‐orange aroma and sweetness intensity to be similar (P > 0.05) for all beverages tested. Beverage sourness intensity differed among beverages (P ≤ 0.05). Panelists evaluated beverages containing 0.3% hydrocolloid as similar (P > 0.05), whereas beverages with 0.5 and 0.7% β‐glucan were more viscous (P ≤ 0.05) than those with pectin at these levels. Acceptability of beverages was similar according to the consumer panel. Shelf stability studies showed no microbial growth and stable pH for all beverages over 12 weeks. Colorimeter values for most beverages decreased (P ≤ 0.05) during the first week of storage, mostly stabilizing thereafter. With an increase in concentration, β‐glucan beverages became lighter in color (P ≤ 0.05) and cloudier, but these attributes for pectin beverages were not affected (P > 0.05). β‐Glucan beverages exhibited cloud loss during the first three weeks of storage. β‐Glucan can therefore be successfully utilized in the production of a functional beverage acceptable to consumers.     

Challenges for research on polyphenols from foods in Alzheimer's disease: bioavailability, metabolism, and cellular and molecular mechanisms

Polyphenols are the most abundant antioxidants in diet. Indeed, fruits, vegetables, beverages (tea, wine, juices), plants, and some herbs are loaded with powerful antioxidant polyphenols. Despite their wide distribution, research on human health benefits truly began in the mid-1990s (Scalbert, A.; Johnson, I. T.; Saltmarsh, M. Am. J. Clin. Nutr. 2005, 81, S15S-217S). Phenolic compounds have been receiving increasing interest from consumers and manufacturers because numerous epidemiological studies have suggested associations between consumption of polyphenol-rich foods or beverages and the prevention of certain chronic diseases such as cancers and cardiovascular diseases (Manach, C.; Mazur, A.; Scalbert, A. Curr. Opin. Lipidol. 2005, 16, 77-84; Duthie, S. J. Mol. Nutr. Food Res. 2007, 51, 665-674). Furthermore, in the past 10 years, research on the neuroprotective effects of dietary polyphenols has developed considerably. These compounds are able to protect neuronal cells in various in vivo and in vitro models through different intracellular targets (Ramassamy, C. Eur. J. Pharmacol. 2006, 545, 51-64). However, it is not at all clear whether these compounds reach the brain in sufficient concentrations and in a biologically active form to exert beneficial effects. On the other hand, it has become clear that the mechanisms of action of these polyphenols go beyond their antioxidant activity and the attenuation of oxidative stress. Therefore, there is a need for more research on their intracellular and molecular targets as special pathways underlying distinct polyphenol-induced neuroprotection. The focus of this review is aimed at presenting the role of some polyphenols from fruits, vegetables, and beverages in neuroprotection and particularly in Alzheimer's disease and the research challenges in this area.     

Cranberries and cranberry products: powerful in vitro, ex vivo, and in vivo sources of antioxidants

Cranberry products and especially cranberry juice (CJ) have been consumed for health reasons primarily due to their effect on urinary tract infections. We investigated the quantity of both free and total (after hydrolysis) phenolic antioxidants in cranberry products using the Folin assay. The order of amount of total polyphenols in cranberry foods on a fresh weight basis was as follows: dried > frozen > sauce > jellied sauce. On a serving size basis for all cranberry products, the order was as follows: frozen > 100% juice > dried > 27% juice > sauce > jellied sauce. High fructose corn syrup (HFCS) is a major source of sugar consumption in the U.S. and contains both glucose and fructose, potential mediators of oxidative stress. We investigated the effect of the consumption of HFCS and ascorbate with CJ antioxidants or without CJ (control) given to 10 normal individuals after an overnight fast. Plasma antioxidant capacity, glucose, triglycerides, and ascorbate were measured 6 times over 7 h after the consumption of a single 240 mL serving of the two different beverages. The control HFCS caused a slight decrease in plasma antioxidant capacity at all time points and thus an oxidative stress in spite of the presence of ascorbate. CJ produced an increase in plasma antioxidant capacity that was significantly greater than control HFCS at all time points. Postprandial triglycerides, due to fructose in the beverages, were mainly responsible for the oxidative stress and were significantly correlated with the oxidative stress as measured by the antioxidant capacity. Cranberries are an excellent source of high quality antioxidants and should be examined in human supplementation studies.     

Protein quality, antigenicity, and antioxidant activity of soy-based foodstuffs

Commercial soy-based foodstuffs, including beverages ( n = 15), cow's milk supplemented with soy isoflavones ( n = 1), snacks ( n = 1), and biscuits ( n = 2), were analyzed to find any link between alterations in protein quality, safety (antigenicity), functionality (antioxidant activity), and food processing. Protein content was analyzed by the Kjeldhal method and available lysine by OPA assay. Chromatographic (RP-HPLC) and electrophoretic (SDS-PAGE) protein profiles were obtained to monitor modifications in the structure of soy allergens. The antigenicity was estimated by immunoblotting against soy total antibodies. Total phenol content was measured by Folin-Ciocalteu, while peroxyl radical scavenging activity of the sample was determined by ORAC FL assay. Protein content did not differ of those declared by the producers. Lysine availability was higher in liquid soy beverages compared to that in other soy foodstuffs studied here. 7S and 11S soy allergens were detected by RP-HPLC and SDS-PAGE, respectively. Both data indicated changes in soy protein patterns due to processing of instant powdered soymilk, soy snacks, and biscuits. Immunoblotting assay showed modifications in the antigenic response of these foodstuffs based on soy, suggesting that their processing had altered the structure of soy allergens. RP-HPLC, SDS-PAGE, and immunoblotting resulted in adequate analytical approaches for detecting changes in protein structure due to processing and adulteration. Protein quality, antigenicity, and antioxidant activity of soy products can be affected as a function of the intensity of the thermal processing.     

Influence of thermally processed carbohydrate/amino acid mixtures on the fermentation by Saccharomyces cerevisiae

The production of alcoholic beverages such as Tequila, Mezcal, whiskey, or beer includes the fermentation of a mash containing Maillard reaction products. Because excessive heating of the mash can lead to complications during the following fermentation step, the impact of Maillard products on the metabolism of Saccharomyces cerevisiae was investigated. For this purpose, fermentation was carried out in a model system in the presence and absence of Maillard reaction products and formation of ethanol served as a marker for the progression of fermentation. We found that increasing amounts of Maillard products reduced the formation of ethanol up to 80%. This effect was dependent on the pH value during the Maillard reaction, reaction time, as well as the carbohydrate and amino acid component used for the generation of Maillard reaction products. Another important factor is the pH value during fermentation: The inhibitory effect of Maillard products was not detectable at a pH of 4 and increased with higher pH-values. These findings might be of relevance for the production of above-mentioned beverages.