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Recently, Pickering emulsions stabilized by edible particles have attracted significant attention from the scientific community and food industry owing to their surfactant-free character. However, those edible particles are mostly used for stabilizing oil-in-water emulsions, whereas those for water-in-oil emulsions are very limited. In this article, stable water-in-oil Pickering emulsions were prepared through dispersing phytosterol particles in oil phase, and the effects of antisolvent treatment, the type of oil, particle concentration, and water fraction on the stability, type, and morphology of these emulsions were investigated. In addition, the release profile of salt as a model aqueous compound from these emulsions has also been studied. Results showed that due to its higher water content, the antisolvent pretreatment of phytosterol in the ethanol/water system facilitated the dispersion of dried phytosterol particles into oil phase as microcrystals. Water-in-oil Pickering emulsions with droplet sizes of 80-100 μm were fabricated at phytosterol concentrations of 1.5-3% w/v and water fractions of 0.2-0.6. The dissolved phytosterol molecules in oil phase could help in emulsion stabilization through interfacial crystallization during emulsification, evidenced by polar microscopic observations. Moreover, the salt release from phytosterol-stabilized Pickering emulsions showed a temperature-dependent profile which could have potential application in a controlled-release system. The current study provided important information for fabrication of stable water-in-oil emulsion using natural particles.

Background Methylglyoxal, a reactive carbonyl compound widely present in thermally processed foods, is produced from sugar degradation and lipid oxidation. Methylglyoxal can yield various aroma compounds by reacting with amino acids and act as a precursor to generate other toxins, including advanced glycation end products, acrylamide and 4(5)-methylimidazole. Scope and approach: This review highlights the formation and the transformation of methylglyoxal, its benefits and its deleterious effects as well as the interaction with dietary ingredients and scavenging reagents. Moreover, the role of amino acids and phenolic compounds in methylglyoxal mitigation in foods and the possible consequences of the intake of the derived adducts was discussed. Key findings and conclusions: The formation and the transformation of methylglyoxal simultaneously occur during food processing. Amino acids and phenolic compounds can efficiently scavenge methylglyoxal, thereby forming numerous adducts, due to their highly nucleophilic reactivity with methylglyoxal. The absorption, metabolism and toxicology of dietary methylglyoxal–phenolic adducts remain largely unknown and require further investigation before applying polyphenols to control methylglyoxal in foods. The selective addition of amino acids may provide a satisfactory strategy to control methylglyoxal in foods, but their effects on food quality and the toxicity of derived adducts should be deeply investigated.

Our previous research showed that thioacetal and Schiff base formed between 5-hydroxymethylfurfural (HMF) and cysteine or lysine considerably decreased the cytotoxicity of HMF. In this study, two adol condensation adducts, named 2β-amino-3α-hydroxy-3-(5-(hydroxymethyl)furan-2-yl)propanoic acid (HGA) and 2α-amino-3β-hydroxy-3-(5-(hydroxymethyl)furan-2-yl)propanoic acid (HGB), were prepared from the reaction products of glycine and HMF, and their cytotoxicities were investigated in Caco-2 cells. Compared with HMF, HGA and HGB displayed lower cytotoxicities against Caco-2 cells with IC50 values of 36.50 and 43.47 mM, respectively, versus 16.11 mM (HMF). In contrast to our findings in thioacetal and Schiff base products, HGA and HGB underwent a very high metabolism rate (99%) in Caco-2 cells. HGA and HGB may degrade to other products instead of HMF since no extracellular or intracellular HMF was detected.

Acrolein (ACR), glyoxal (GO), methylglyoxal (MGO), hydroxymethylfurfural (HMF), and malondialdehyde (MDA) are toxic contaminants for humans. This work aimed to investigate whether intake of proteins can mitigate their toxicity. Simulated gastrointestinal digestion of proteins from pork, chicken, milk powder and soy protein isolate eliminated amount of ACR, GO, MGO, HMF, and MDA. Among six amino acids, cysteine showed highest capacity for elimination of these toxic compounds through the formation of adducts; it reached the highest elimination capacity for GO, MGO, ACR, MDA, and HMF in 40 min at pH 2.0, and 20 min at pH 7.0. The formed adducts between cysteine and GO, MGO, or ACR showed much lower toxicity against Caco-2 cells. Incubation of the cells with 8 mM GO and MGO for 48 h decreased the cell viability to 16.1%, 16.9% respectively; while incubation of the same concentration of their adducts still kept the cell viability at 82.2% and 81.6% respectively. Cysteine showed much higher detoxifying capacity for ACR than GO and MGO, which can lower the toxicity of ACR toward Caco-2 cells by 80 times.

Flavonoids with meta-hydroxyl groups have been proven to react with methylglyoxal (MGO) and form mono- and di-MGO adducts via nucleophilic addition reactions. Rutin, a rutinoside of quercetin with typical meta-phenol structure, is widely distributed in plant-sourced materials. Interestingly, different from the adducts reported between flavonoids and MGO, new rutin-MGO adducts with dione structures on the moiety of MGO were identified and proven to occur in various foods (0.66-6.58 mg/kg in total) and in vivo (up to 5.01 μg/L in plasma of rats administered with 100 mg/kg bodyweight of rutin). The three adducts discovered were assigned as 6-(1,2-propanedione)-8-(1-acetol)-rutin, 6-(1-acetol)-8-(1,2-propanedione)-rutin, and 6-(1,2-propanedione)-8-(1,2-propanedione)-rutin. Cytotoxicity evaluation in different cell lines indicated that the formation of these rutin-MGO adducts remarkably reduced the toxicity of MGO, which provide further promise for the application of rutin as a scavenger of dicarbonyl compounds by dietary supplement and addition in foods.

In physiological and thermally-processed conditions, alanine and serine efficiently eliminate acrolein to generate two main adducts, 2-(5-formyl-3,6-dihydropyridin-1(2H)-yl) propanoic acid and 2-(5-formyl-3,6-dihydropyridin-1(2H)-yl)-3-hydroxypropanoic acid, with amounts of 81.6 ± 4.24 μg/kg and 23.72 ± 0.40 μg/kg in fried potato crisps, respectively. Adduct formation markedly decreased the cytotoxicity of acrolein against Caco-2, GES-1 and HUVEC cells. The cell viability of them remained approximately100% after incubation with 200 µmolL-1 adducts, while the IC50 values for acrolein in the three cells were 66, 54, and 16 µmolL-1 respectively. The adducts express the protective effects by tremendous reduction of cell apoptosis, reactive oxygen species (ROS) production, and DNA damage.

Quercetin (Que) or quercetin-containing food stuffs are widely incorporated in bakery foods for improving food texture and health effects, and scavenging reactive aldehydes, such as methylglyoxal (MGO) that exhibits various deleterious effects including contribution to neurodegeneration. This study aimed to investigate the cytotoxicity of the adducts formed between quercetin and MGO resulted from the incorporation of quercetin in foods. Two highly-purified adducts (Que-mono-MGO and Que-di-MGO) were found to display higher cytotoxicity than their precursor MGO and quercetin. They elevated apoptosis via upregulation of expression of apoptotic markers, including p-P38, cleaved caspase-9 and -3, and pro-apoptotic Bax. They induced mitochondrial dysfunction via decreasing mitochondrial membrane potential and increasing lactate dehydrogenase release. Moreover, they attenuated levels of p-Akt, Nrf2, NQO-1, and HO-1, proving that they induced neurodegeneration apoptosis through mitochondria-mediated signaling pathways (PI3K-Akt and Nrf2-HO-1/NQO-1). These findings indicated that the safety consequence of MGO after scavenged by polyphenols needs to be concerned.

Water-in-oil (W/O) Pickering emulsions were successfully synthesized by water-dispersible phytosterol (PS) particles formed through simple antisolvent precipitation. The effects of the organic/aqueous ratio on the particle morphology, crystallinity, and contact angle were investigated. Sheet-like PS particles with reduced crystallinity were further used as W/O Pickering emulsion stabilizers. The properties of the formed W/O emulsions could be transformed by changing the oil type, water-phase fraction, or particle contents. Results showed that emulsions with 80% water fraction could be stabilized by 3% particles in the aqueous phase, where dodecane was used as the oil phase. W/O Pickering emulsions stabilized by PS particles showed temperature responsiveness. When dried, PS particles could be well dispersed either in the water or oil phase to stabilize W/O Pickering emulsions. Therefore, this kind of PS particles could not only enrich the family of food-grade Pickering stabilizers, especially the W/O type, but also provide a smart Pickering stabilizer to fabricate environmental-responsive emulsion products.

Acrolein is a highly toxic agent that can be generated exogenously and endogenously. Therefore, a highly specific and sensitive probe for acrolein with potential applications in acrolein detection must be developed. In this research, a novel fluorescent probe named "probe for acrolein detection" (Pr-ACR) was designed and synthesized based on a naphthalimide fluorophore skeleton, and a thiol group (-SH) was introduced into its structure for acrolein recognition. The -SH traps acrolein via Michael addition and the resultant interaction product of the probe inhibits the photoinduced electron transfer process and produce a strong fluorescence at 510 nm. The probe showed high sensitivity and specificity for acrolein. HPLC-MS/MS analysis verified that it can be used to quantify acrolein in foods, such as soda crackers, red wine, and baijiu, with a fluorescence spectrophotometer. After methyl esterification, the methyl esterified probe (mPr-ACR) successfully visualised acrolein in Hela cells under a laser scanning confocal microscope. This finding proved that Pr-ACR and mPr-ACR are potential tools for the detection and visualisation of acrolein from different sources.

l -glycine and l -serine are the building blocks of proteins and exhibit various biological activities. This work found that l -glycine and l -serine show low scavenging capacity for methylglyoxal at moderate conditions (pH 7.0, 37 °C). However, they efficiently eliminate methylglyoxal and formaldehyde when the two aldehydes co-exist, via generation of imidazole salt, a compound formed by one molecule of methylglyoxal and formaldehyde, and two molecules of amino acids. The imidazole salts were identified in biscuits and fried potato crisps. Moreover, the formation of imidazole salts greatly decreased the cytotoxicity of their precursors, methylglyoxal and formaldehydes. This finding suggests that glycine and serine can be used to scavenge these two harmful aldehydes both after intake and during food processing.

3-Aminopropanamide (3-APA) is the direct precursor of acrylamide produced in the Maillard reaction between asparagine and reducing sugars. In this research, we found that 3-APA could reduce acrylamide by the formation of adducts between acrylamide and 3-APA via Michael addition. The effects of temperature, heating duration and 3-APA/acrylamide ratio on the reduction of acrylamide were investigated. Addition of 3-APA to acrylamide at a molar ratio of 5:3 at 160 °C for 20 min reduced acrylamide by up to 47.29%. The major adduct was identified as 3,3',3'-nitrilotris, and its cytotoxicity on Caco-2 cells was evaluated to be much lower than acrylamide. The viability of Caco-2 cells retained at 88.31% and 86.43% after incubation with 16 mM 3,3',3'-nitrilotris for 24 and 48 hr, respectively, while those incubated with the same concentration of acrylamide were 23.33% and 19.12%, respectively.; Practical Application: The current study reported 3-APA could reduce acrylamide through the Micheal addition reaction between 3-APA and acrylamide. The adduct showed significantly reduced cytotoxicity compared to acrylamide. The research is critical in evaluation and control of food contaminants. The results brought new insights in the area of food safety, especially in the mechanism researches on formation and mitigation of endogenous contaminants in thermal-processed foods.; © 2018 Institute of Food Technologists®.

The development of high internal phase emulsions (HIPEs) stabilized by food-grade particles (e.g., cellulose nanocrystals, CNCs) has attracted increasing interests in the food colloid field. This paper reports a type of oil-in-water HIPEs using protein (bovine serum albumin, BSA)-covered CNCs as effective stabilizers. The BSA-covered CNCs were simply obtained by mixing aqueous solutions of anionic CNCs with the cationic BSA at pH 3.0. Turbidity and absorption measurements proved the binding of BSA to CNCs. The strong interaction and aggregation of BSA-covered CNCs were verified by atomic force microscopy measurements. Interestingly, the 0.5% (w/v) CNCs covered with a low amount of BSA (0.01%–0.1%, w/v) as the emulsifying agent yielded very stable, gel-like HIPEs (ϕ = 0.8). The stiffness and microstructure of the HIPEs can be modulated either by changing the surface protein coverage at a fixed CNC concentration or by changing the concentration of CNCs with a fixed surface protein coverage (e.g., 80%). The improvement of the stiffness was largely attributed to the enhanced droplet packing effect and interfacial bridging effect. These findings offer a promising opportunity to extend the applications of protein-modified CNCs in the food and pharmaceutical industries.

Epidemiological evidence suggests that whole grain intake is associated with reduced risk of oxidative stress-related chronic disease. It remains unclear that whole grains can improve antioxidant activity in vivo. This study was to investigate the hypolipidemic and antioxidant capability of sorghum, purple rice and rhubarb rice. Our results indicated that sorghum contained the highest total phenolic content, total flavonoid content and total anthocyanin content, and had highest free radical scavenging activity and reducing power than those of the purple rice and rhubarb rice in vitro. Compared with high fat diet group, animals feeding with sorghum had a 24.47% reduction in serum cholesterol, 32.72% reduction in triglyceride, and 27.27% increase in high-density lipoprotein cholesterol, respectively (p

The absorption of a 5-hydroxymethylfurfural (HMF)-cysteine adduct, 1-dicysteinethioacetal-5-hydroxymethylfurfural (DCH), and its effect on antioxidant activity and gut microbiota were investigated. Results indicated that DCH is more easily absorbed in rats than HMF. Serum DCH concentrations were 15-38-fold of HMF concentrations from 30 to 180 min after intragastrical administration at the level of 100 mg/kg of body weight, and 2.7-4.5% of absorbed DCH was converted to HMF. The malondialdehyde content in the plasma, heart, liver, and kidneys significantly increased after drug (100 mg/kg of bw) administration for 1 week, suggesting that HMF and DCH were oxidative-stress-inducing agents, instead of antioxidant agents, in rats. HMF and DCH also modulated gut microbiota. HMF promoted the growth of Lactobacillus, Tyzzerella, Enterobacter, and Streptococcus. DCH increased the ratio of Firmicutes/ Bacteroidetes and promoted the growth of Akkermansia, Shigella, and Escherichia while inhibiting the growth of Lactobacillus.

Liver is the organ most frequently exposed to acrolein, a priority toxic pollutant. In the present study, whether morin can mitigate acrolein-induced cell damage in normal human hepatocyte cell line LO2 was investigated. Morin remarkably inhibited acrolein-induced apoptosis by inhibiting the expression of apoptotic markers, reducing the formation of proinflammatory cytokines, and blocking the ERK/JNK/P38-MAPK signaling pathway. The addition of equimolar morin decreased acrolein-induced cell apoptosis by 52.4%. The expression levels of apoptotic markers, BAX, Cyto-C, AIF, cleaved caspase-3/9, and PARP, decreased by 16%, 14%, 44%, 56%, 23%, and 45%, respectively. The proinflammatory cytokines, such as tumor necrosis factor α, inducible NO synthase, cyclooxygenase-2, interleukin 1β, and IFN-ϒ were reduced by 39%, 55%, 66%, 72%, and 64%, respectively. The phosphorylation level of ERK1/2, JNK, and P38 MAPK decreased by 10%, 47%, and 26%, respectively. The present findings may provide a way to mitigate acrolein-induced hepatic injury.

Summary This work aimed to investigate the reactivity of hydroxymethylfurfural (HMF) with selected amino acids, to identify the produced adducts and to clarify whether or not the adducts release HMF after their digestion under gastric conditions. Results showed that cysteine, glycine and lysine can deplete the added HMF, and their reactivity increased with increasing pH and temperature. Cysteine (25 μmol mL−1) depleted 91.0% of the added HMF (315.3 μg mL−1) at 40 °C in 15 min, lysine did not eliminate HMF until 80 °C, and glycine started to eliminate HMF at 100 °C. Four adducts for cysteine, three adducts for lysine and only one adduct for glycine were identified through HPLC–MS–MS after they reacted with HMF. The adducts formed from the reaction mixture of cysteine, lysine and glycine with HMF only released 1.7%, 2.6% and 10.5% of eliminated HMF, respectively, after their digestion in simulated gastric conditions.

3-Aminopropanamide (3-APA) is the direct precursor of acrylamide produced in the Maillard reaction between asparagine and reducing sugars. In this research, we found that 3-APA could reduce acrylamide by the formation of adducts between acrylamide and 3-APA via Michael addition. The effects of temperature, heating duration and 3-APA/acrylamide ratio on the reduction of acrylamide were investigated. Addition of 3-APA to acrylamide at a molar ratio of 5:3 at 160 °C for 20 min reduced acrylamide by up to 47.29%. The major adduct was identified as 3,3',3'-nitrilotris, and its cytotoxicity on Caco-2 cells was evaluated to be much lower than acrylamide. The viability of Caco-2 cells retained at 88.31% and 86.43% after incubation with 16 mM 3,3',3'-nitrilotris for 24 and 48 hr, respectively, while those incubated with the same concentration of acrylamide were 23.33% and 19.12%, respectively.The current study reported 3-APA could reduce acrylamide through the Micheal addition reaction between 3-APA and acrylamide. The adduct showed significantly reduced cytotoxicity compared to acrylamide. The research is critical in evaluation and control of food contaminants. The results brought new insights in the area of food safety, especially in the mechanism researches on formation and mitigation of endogenous contaminants in thermal-processed foods.

Adducts of 5-hydroxymethylfurfural (HMF)-amino acids are formed during food processing and digestion; the elimination capacity of in vitro intestinal digests of biscuits, instant noodles, and potato crisps for HMF is 652, 727, and 540 μg/g, respectively. However, the safety of these adducts is unknown. In this study, an HMF–cysteine adduct named 1-dicysteinethioacetal-5-hydroxymehtylfurfural (DCH), which was found to be produced in the gastrointestinal tract after HMF intake, was prepared to test its effect toward Caco-2 cells. Compared with HMF, the adduct displayed lower cytotoxicity against Caco-2 cells with an IC50 value of 31.26 mM versus 14.95 mM (HMF). The DCH did not induce cell apoptosis, whereas HMF significantly increased the apoptosis rate after incubation at concentrations of 16, 32, and 48 mM for 72 h. DCH showed an absorption rate considerably lower than that of HMF by Caco-2 cells. Lower absorption of DCH may result in lower toxicity compared with HMF against Caco-2 cells. Intracellular tr...

Inhibition of acrylamide formation in food has been extensively reported, but some mitigation methods result in a concomitant increase in hydroxymethylfurfural (HMF), a food contaminant mainly produced through Maillard reaction. Mitigation strategies to reduce HMF are not yet available. This study showed that cysteine alone or in combination with glycine could simultaneously and significantly reduce the content of acrylamide and HMF in asparagine/glucose model as well as in biscuits. Mixing 0.36 g/100 g of cysteine and 0.2 g/100 g (w/w) of glycine into the dough reduced 97.8% and 93.2% of acrylamide and HMF, respectively, in biscuits. Cysteine reduced HMF content possibly by reacting with formed HMF through Michael adduction and Maillard reaction.

Ferulic acid is a natural compound that possesses multiple physiological and pharmaceutical functions. The chemical, physical, and pharmaceutical properties of this phenolic acid can be improved by derivatives with other active compounds. This sentence (Hence, such improvements can widen the applications of ferulic acid in the food, cosmetic, and pharmaceutical industries.) has been deleted. This article reviewed the identification, preparation, and biological activities of feruloyl derivatives of carbohydrates, glycerol and glycerides, amide, fatty alcohol, myo-inositol, and nitric oxide. It also briefly discussed other derivatives. Researchers are encouraged to carry out toxicological, pharmacokinetic, and clinical investigation of potent active feruloyl derivatives and to develop other derivatives. Review Article Pei et al.; ARRB, 5(6): 512-528, 2015; Article no.ARRB.2015.054 513

Ten (10) amino acids (asparagine, aspartic acid, cysteine, glycine, glutamic acid, glutamine, methionine, leucine, tyrosine and lysine) were used to test their effect on elimination of acrylamide, when co-heating of 10 i­mol of acrylamide respectively with 0.1 mmol of amino acids at 160i‚°C for 15 min, acrylamide was eliminated from 7.4% (asparagine) to 94.4% (cysteine) at natural pH, and 11.4% (glutamic acid) to 94.8% (cysteine) at pH 7.0. It was found that cysteine, glysine and lysine showed much higher reactivity with acrylamide than the other seven amino acids. When the molar ratios of amino acid to acrylamide were increased to 60:1 for cysteine and glycine, and 80:1 for lysine, acrylamide in the reaction system was almost eliminated. The elimination efficiencies of the three amino acids for acrylamide were enhanced by addition of glucose. Liquid chromatography/time-of-flight mass spectroscopy showed that cysteine, glycine, and lysine adducted with two molecules of acrylamide, while the other amino acids except for glutamic acid (no adduct compounds were found) just adducted with one mole of acrylamide. This finding may partly explain why cysteine, glycine and lysine showed high capacity to reduce acrylamide content in high-temperature processing food. Key words: Acrylamide, adduct, amino acids.

Four new dimeric naphtho-γ-pyrones, named rubasperone D (1), rubasperone E (2), rubasperone F (3), and its atropisomer rubasperone G (4), together with four known monomeric naphtho-γ-pyrones, TMC 256 A1 (5), rubrofusarin B (6), fonsecin (7), and flavasperone (8), were isolated from the mangrove endophytic fungus Aspergillus tubingensis (GX1-5E) cultivated in solid rice medium. Their structures were elucidated by spectroscopic methods, including IR, 1D- and 2D-NMR, and MS. In the in vitro cytotoxicity assays, 5 displayed inhibitory activities against tumor cell lines of MCF-7, MDA-MB-435, Hep3B, Huh7, SNB19, and U87 MG with IC50 values between 19.92 and 47.98 μM. Compounds 1, 6, and 8 also showed mild cytotoxic activity.

Alterporriol L, a new bianthraquinone derivative, was isolated from a marine fungus Alternaria sp. ZJ9-6B. The cytotoxic activity and anticancer mechanisms of alterporriol L towards breast cancer cells lines were detected using MTT assay, immunofluorescence, and flow cytometry. Simultaneously, the changes in morphological properties of cells were detected before and after treatment with alterporriol L by atomic force microscope (AFM) at a nanometer scale. MTT assay showed that alterporriol L could effectively inhibit the growth and proliferation, and there was a dose-dependent manner of cell death. Moreover, the alterporriol L could induce cancer cell apoptosis or necrosis. Furthermore, the reactive oxygen species, mitochondrial membrane potential, and cytosolic free calcium level were changed after treatment with alterporriol L, suggesting that alterporriol L played vital roles in breast cancer cells through destroying the mitochondrial. And all these alterations are in accord with changes of morphology detected by AFM, which suggested that the AFM is a useful tool to detect the morphological changes of the cancer cells.

Three new bianthraquinone derivatives, alterporriol K (1), L (2) and M (3), along with six known compounds were obtained from extracts of the endophytic fungus Alternaria sp. ZJ9-6B, isolated from the mangrove Aegiceras corniculatum collected in the South China Sea. Their structures were elucidated by one- and two-dimensional NMR spectroscopy, MS data analysis and circular dichroism measurements. Compounds 1, 2 and 3 were first isolated alterporriols with a C-2–C-2′ linkage. The crystallographic data of tetrahydroaltersolanol B (7) was reported for the first time. In the primary bioassays, alterporriol K and L exhibited moderate cytotoxic activity towards MDA-MB-435 and MCF-7 cells with IC50 values ranging from 13.1 to 29.1 µM.

A new isochroman, (3R,4S)-3,4-dihydro-4,5,8-trihydroxy-3-methylisocoumarin (1), and two known compounds were isolated from the marine fungus Phomopsis sp. (No. ZH-111). Their structures were determined by spectroscopic methods, mainly 1D and 2D NMR. Preliminary pharmacological test revealed that compound 1 and exumolide A (3) can accelerate the growth of subintestinal vessel plexus (SIV) branches markedly and compound 2 can inhibit the growth of subintestinal vessel plexus (SIV) branches.

Water-soluble dietary fibers from apple peels and water-insoluble dietary fibers from wheat bran and soybean-seed hull were used to evaluate their binding capacities for four toxic elements (Pb, Hg, Cd, and As), lard, cholesterol, and bile acids. The water-soluble dietary fibers showed a higher binding capacity for three toxic cations, cholesterol, and sodium cholate; and a lower binding capacity for lard, compared to the water-insoluble ones. A mixture of the dietary fibers from all samples - apple peels, wheat bran, and soybean-seed hull - in the ratio 2:4:4 (w/w) significantly increased the binding capacity of water-insoluble dietary fibers for the three toxic cations, cholesterol, and sodium cholate; moreover, the mixture could lower the concentrations of Pb(2+) and Cd(+) in the tested solutions to levels lower than those occurring in rice and vegetables grown in polluted soils. However, all the tested fibers showed a low binding capacity for the toxic anion, AsO(3)(3-).

Sugars and organic acids are important phytochemicals contributing to the nutrition and sensory properties of fruits and berries. Their contents are closely correlated to the genetic background of plants as well as to the environmental conditions during growth. This review focuses on the recent researches on the metabolism of these compounds in fruits and berries in response to the variation of environmental conditions, including temperature, radiation, and water supply. A great deal of investigations indicates that the influence of environmental factors on the composition of fruits/berries depended largely on the genetic background. Moreover, the metabolic regulation in response to environmental changes also varies between different plant developmental stages. Nevertheless, some general trends, like the positive correlation between light intensity and sugar content, were observed in most investigations. In grapes (Vitis vinifera L.), the content of malic acid always decreases as light intensity increases, and as the water supply decreases. PRACTICAL APPLICATIONS: The contents of sugars and organic acids, and especially their relative ratio, are important indicators determining the taste and quality of fruits and fruit products. In this review, we summarized the investigations carried out on the regulation of these sensory contributing primary metabolites in fruits and berries in relation to the variation of environmental conditions. It was indicated that various factors, such as plant genotype, growing period, and interaction between environmental factors, might contribute to the impact of environmental changes on the composition of fruits/berries. The article not only provides comprehensive knowledges in food chemistry and plant physiology but also provide important background knowledge for berry cultivation and breeding, as well as useful guidelines for utilization of fruits and berries in food industry.

Three unique metabolites, namely, phomopsis-H76 A (1), B (2), and C (3), were isolated from the mangrove endophytic fungus Phomopsis sp. (#zsu-H76). Structures were determined by spectroscopic methods, mainly 1D and 2D NMR spectroscopy. Compound 1-3 are all dimers. Compounds 2 and 3 possesses a pyrano[4,3-b]pyran-5(2H)-one ring system that is unprecedented in nature. Primary bioassays showed that 1 accelerated the growth of subintestinal vessel plexus (SIV) branch markedly, whereas 3 showed inhibition of SIV. Compounds 1-3 showed no activity in antibacterial and cytotoxic tests.

This article presents a new route for preparing collagen/hydroxyapatite (Coll/HA) composite. Urease-catalyzed decomposition of urea was used for the first time to prepare Coll/HA. Acting as an automatic pH controller, urea totally eliminated the traditional requirement of an external base additive and facilitated procedures for synthesis as a result. This Coll/HA complex was characterized by Fourier transformed infrared spectroscopy, X-ray diffraction, laser diffraction particle size analyzer, scanning electron microscope (SEM), and transmission electron microscopy. The results indicated that chemical and crystallographic properties of this complex were similar to those of the natural bone and other Coll/HA systems. Laser diffraction particle size measurement and SEM showed that this Coll/HA sample evidenced smaller particle size and narrower particle size distribution than other Coll/HA complex prepared by the traditional co-precipitation method.

Phenolic acids were released from sugarcane bagasse by alkaline hydrolysis at 30 °C for 4 h; The alkaline hydrolysates were ultrafiltrated, the permeates purified with anion exchange resin. The phenolic acids bound by the resin were desorbed by a mixture of water–ethanol–HCl solution (36: 60: 4) after washing the resin with water, ethanol and dilute HCl respectively. The combined eluents were concentrated for crystalization, and the crystals filtered and washed using 1% (v/v) HCl. After this purification process, the purity of products reached 89.7% based on coumaric acid. Results of HPLC/MS, HPLC using standard coumaric acid and ferulic acid showed that the main component of the purified bagasse hydrolysate was p-coumaric acid rather than ferulic acid. The purified products showed the same antioxidant activity, reducing power and free radical scavenging capacity as the standard p-coumaric acid. The technology could be applied on industrial scale. Industrial relevance This research presents a technology to produce coumaric acids from sugarcane bagasse. The first step is to release coumaric acid by alkaline hydrolysis. The second step is to remove the viscous polysaccharides and protein by ultrafiltration. The third step is to purify coumaric acid from the permeate of ultrafiltration by anion chromatography, and the alkaline could be reused to hydrolyze the bagasse. The technology showed potential application on industrial scale.

Great interest and rapid research efforts on acrylamide in foods followed an announcement in April 2002 by the Swedish National Food Authority and the University of Stockholm. Reduction of acrylamide in high-temperature processing foods, including selection of the raw material and variation of processing parameters, etc. were extensive reported. In this research, effect of some agents on acrylamide formation was investigated. A glucose-asparagines reaction model system was used to test the effect of ferulic acid, catechin, CaCl 2 , NaHSO 3 , and l -cysteine on inhibition of acrylamide formation and three efficient inhibitors, NaHSO 3 , CaCl 2 and l -cysteine were screened. The results showed that immersing of the fresh potato chips using different concentration of the agents greatly inhibited acrylamide formation in fried potato crisps, and the efficiency increased as their concentrations increased; among them, l -cysteine is the most efficient agent but CaCl 2 is most potential. Effects of these food additives on the texture of fried potato crisps were also studied. It was found that l -cysteine showed little effect on the texture of the crisps and CaCl 2 is regarded as the suitable choice because of its low price and the acceptable mouth feel of fried crisps treated by CaCl 2 , although it increased the brittleness. Moreover, the application of CaCl 2 in industrial production of fried potato crisps was also studied. In the blanching process (deactivation process of enzymes at 85 °C), a computerized electrical conductivity detector was used to keep the concentration of CaCl 2 at constant and the result showed that immersion of potato slices in CaCl 2 solution at 5 g/L reduced acrylamide formation by more than 85% in fried crisps. Industrial relevance This research presents a technology to inhibit acrylamide formation in fried potato chips by immersion of fresh potato chips with some food additives. The approach suggested that cysteine and calcium chloride significantly decreased the content of acrylamide in fried potato chips and their concentrations could be kept constant by using a conductor as a detector.

Sugarcane bagasse is a large by-product discarded in sugarcane processing factories. In this research, sugarcane bagasse was used to prepare highly valued trans-ferulic acid by alkaline-hydrolysis and purification through combination of activated charcoal adsorption and anion macroporous resin exchange chromatography. The results showed that powdered activated charcoal had much higher adsorption capacity for ferulic acid than that of granular activated charcoal and adsorbed ferulic acid at very low concentration; the adsorbed ferulic acid could be totally washed out by 0.2 mol/l NaOH but only a small part by ethanol or acetic ether. These properties made it possible to remove other substances produced by alkaline-hydrolysis through washing out using hot water and acetic ether before desorbing ferulic acid from active charcoal by NaOH. High purity of ferulic acid was obtained by further treatment of anion macroporous resin exchange chromatography after its washout from the activated charcoal.

Chlorogenic acid (CGA) is a phenolic acid that ubiquitously exists in fruits. This work aims to investigate whether and how CGA influences HMF formation during heating fructose alone, or with an amino acid. The results showed that that CGA increased 5-hydroxymethylfurfural (HMF) formation. At pH 5.5 and 7.0, the addition of 5.0 μmol/ml CGA increased HMF formation by 49.4% and 25.2%, respectively when heating fructose alone, and by 9.0% and 16.7%, respectively when heating fructose with aspartic acid. CGA significantly increased HMF formation by promoting 3-deoxosone formation, and its conversion to HMF by inhibiting HMF elimination, especially in the Maillard reaction system. A comparison of the catalytic capacity of CGA with its six analogous compounds showed that both its di-hydroxyphenyl and carboxyl groups function in increasing HMF formation.

Different concentrations of ferulic acid were added to film-forming solutions when preparing soy protein isolate-based edible films. The results showed that an optimal concentration of ferulic acid increased the tensile strength, elongation percentage at break and antioxidant activity of films for preservation of fresh lard. The optimal concentration for ferulic acid in film forming solution is 100 mg/100 g. Moreover, the properties of the film were further improved when ferulic acid was oxidized by hydrogen peroxide. A possible mechanism for the role of ferulic acid in the preparation of SPI-based films is that it reacted with amino acids and increased cross-linking of the protein. It is interesting that the absorbance wavelength for ferulic acid-protein (or amino acids) is much longer than ferulic acid or protein (or amino acids) alone. The absorbance shift indicates the formation of a ferulic acid-protein cross-link that may enhance the shelf life of foods by decreasing oxygen permeability.

Feruloylated oligosaccharides (FOs) were prepared by autoclaving corn bran in oxalic acid (0.6%) solution, and their protection effects against oxidative stress in pheochromocytoma cells (PC 12) cells were investigated. The FOs samples, which comprised a mixture of feruloylated mono- and dipentoses with 4.88% bound ferulic acid (FA), as well as xylose, arabinose, galactose, and glucose amounting to 46.43, 40.46, 3.76, and 8.68% of the total sugars, respectively, were prepared by autoclaving the pretreated corn bran in 0.6% oxalic acid and then further separated. Antioxidant activity was tested by 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (DPPH) scavenging and oxygen radical absorbance capacity (ORAC) methods. Oxidative stress was induced by H2O2 in PC 12 neuronal cell culture model. The results showed that FOs exhibited higher antioxidant activity than free ferulic acid, with an IC50 value of 11 versus 128 μM for DPPH and an ORAC value of 4.77 versus 2.62 μmol Trolox/μmol. Tetrazolium blue assay showed that the addition of FOs with an FA concentration >50 μM significantly increased cell viability after treatment with H2O2. Flow cytometry analysis showed that the addition of FOs at concentrations of 800, 200, and 50 μM significantly decreased the apoptosis rate at the sub-G0 phase from 37.5 to 12.7, 16.2, and 20.9% (P < 0.01), respectively. FOs also significantly decreased the malonic dialdehyde content and lactate dehydrogenase (LDH) activity, but increased superoxide dismutase activity in PC 12 cells treated with H2O2 and prevented the damage of cellular membranes by decreasing the release of LDH to the cultures. The addition of FA at 800 μM showed an effect similar to that of FOs at 200 μM. Therefore, the FOs prepared from corn bran are potential functional ingredients for protection against oxidative stress.

A new indene derivative named phomoindene A (1) and four known compounds were isolated from the marine fungus Phomopsis sp. (No. GX7-4A). Their structures were determined by spectroscopic methods, mainly 1D and 2D NMR. Preliminary pharmacological tests revealed that phomoindene A exhibited little cytotoxic activity towards KB, KBv 200, and MCF-7 cell lines.

This research was aimed to investigate why chlorogenic acid, presents at high concentrations in some food raw material, influences acrylamide formation. In the asparagine/glucose Maillard reaction system (pH=6.8), addition of chlorogenic acid significantly increased acrylamide formation and inhibited its elimination. In contrast, the quinone derivative of chlorogenic acid decreased acrylamide formation. Three mechanisms may be involved for increasing acrylamide formation by chlorogenic acid. Firstly, it increased the formation of HMF, which acts as a more efficient precursor than glucose to form acrylamide. Secondly, it decreased activation energy for conversion of 3-aminopropionamide (3-APA) to acrylamide (from 173.2 to 136.6kJ/mol), and enhances deamination from 3-APA. And thirdly, it prevented attack of the produced acrylamide from free radicals by keeping high redox potential during the Maillard reaction.

Antioxidants, including tert-butyl hydroquinone (TBHQ), butylated hydroxy anisole (BHA), butylated hydroxytoluene (BHT), ferulic acid, epigallocatechin gallate (EGCG) and vitamin C (VC), and their corresponding oxidation products, were tested for their influence on elimination of acrylamide and inhibition of acrylamide formation. Our experimental results showed that the antioxidants could neither effectively destruct acrylamide nor inhibit (or even promote) its formation, but their corresponding oxidation products were able to directly destruct acrylamide and its precursor, asparagine, thus inhibit acrylamide formation. Moreover, a positive correlation between the carbonyl value and acrylamide formation was observed in a frying oil–asparagine reaction model system, suggesting that antioxidants can inhibit acrylamide formation by inhibiting oil carbonyl compounds formation.

Three metabolites, named xyloketal J (1), xyloester A (2), and xyloallenolide B (3), together with the known substituted dihydrobenzofuran (4) were isolated from the mangrove endophytic fungus Xylaria sp. (#2508). Structures were determined by spectroscopic methods, mainly 1D and 2D NMR.