
Alphons G J VoragenWageningen University & Research | WUR · Department of Food Sciences and Agrotechnology
Alphons G J Voragen
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Pectin, a complex dietary fiber, constitutes a key structural component of the cell walls of numerous edible plant products. It is resistant to digestion by human enzymes and undergoes depolymerization and saccharification in the gastrointestinal tract through the action of carbohydrate-active enzymes (CAZymes) produced by gut microbiota. This enzy...
The human gastrointestinal microbiota, densely populated with a diverse array of microorganisms primarily from the bacterial phyla Bacteroidota, Bacillota, and Actinomycetota, is crucial for maintaining health and physiological functions. Dietary fibers, particularly pectin, significantly influence the composition and metabolic activity of the gut...
In an attempt to develop a process of enzymatic peeling of mandarin segments suitable for use on an industrial scale, the cell wall fraction of the segment membrane of Satsuma mandarin fruits was extracted to obtain a chelating agent-soluble pectin fraction (ChSS), a dilute sodium hydroxide-soluble pectin fraction (DASS), a 1M sodium hydroxide-solu...
Enzymes from a balanced human gut flora are promising tools to design prebiotic oligosaccharides. In this study, we investigated the action of enzymes from fecal bacteria on the complex polysaccharide konjac glucomannan (KGM). The oligosaccharides produced were compared to oligosaccharides from KGM digests with fungal endo-β-(1,4)-glucanase (EG) or...
The characterization of oligosaccharides in the feces of breast-fed babies is a valuable tool for monitoring the gastrointestinal fate of human milk oligosaccharides (HMOs). In the present study we monitored fecal oligosaccharide profiles together with the HMO-profiles of the respective breast milks up to six months postpartum, by means of capillar...
So far, little is known on the fate of oligosaccharides in the colon of breast- and formula-fed babies. Using capillary electrophoresis with laser induced fluorescence detector coupled to a mass spectrometer (CE-LIF-MS(n)), we studied the fecal oligosaccharide profiles of 27 two-month-old breast-, formula- and mixed-fed preterm babies. The interpre...
The complex formation between β-lactoglobulin and pectins of varying overall charge and local charge density were investigated. Isothermal titration calorimetry experiments were carried out to determine the enthalpic contribution to the complex formation at pH 4.25 and various ionic strengths. Complex formation was found to be an exothermic process...
Recently, various branched arabino-oligosaccharides as present in a sugar beet arabinan digest were characterized using NMR. Although HPAEC often has been the method of choice to monitor the enzymatic degradation reactions of polysaccharides, it was shown that HPAEC was incapable to separate all known linear and branched arabino-oligosaccharides pr...
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
A method was developed to make xylogalacturonans (XGAs) with different degrees of xyloslyation from gum tragacanth (XGA-25, XGA-29, XGA-35 and XGA-47), using alkali treatment at 4°C and acid treatment at 100°C. Ester linkages as well as fucose and arabinose substituents could selectively be removed by this procedure. Galactosyl- and xylosyl-linkage...
Sugar beet arabinan consists of an alpha-(1,5)-linked backbone of L-arabinosyl residues, which can be either single or double substituted with alpha-(1,2)- and/or alpha-(1,3)-linked L-arabinosyl residues. Neutral branched arabino-oligosaccharides were isolated from sugar beet arabinan by enzymatic degradation with mixtures of pure and well-defined...
Cell wall materials derived from leaves and hypocotyls of Arabidopsis mutant and wild type plants have been incubated with a mixture of pure and well-defined pectinases, hemicellulases, and cellulases. The resulting oligosaccharides have been subjected to MALDI-TOF MS and CE-LIF analysis. MALDI-TOF MS analysis provided a fast overview of all oligos...
Mixtures of the complex human milk oligosaccharides (HMOs) are difficult to analyze and gastrointestinal bioconversion products of HMOs may complicate analysis even more. Their analysis, therefore, requires the combination of a sensitive and high-resolution separation technique with a mass identification tool. This study introduces for the first ti...
The analysis and quantification of (galacto)oligosaccharides from food matrices demands both a reproducible extraction method as well as a sensitive and accurate analytical method. Three typical matrices, namely, infant formula, fruit juice, and a maltodextrin-rich preparation, to which a commercial galactooligosaccharide mixture was added in a pro...
Okra pectin obtained by hot buffer extraction (HBSS) consists of an unusual pectic rhamnogalacturonan I structure in which acetyl groups and alpha galactose residues are substituted on rhamnose residues within the backbone. The okra Chelating agent Soluble Solids (CHSS) pectin consists of slightly different structures since relatively more homogala...
Interactions of proteins with phenolic compounds occur in food products containing vegetable sources, such as cocoa, cereals, or yogurts containing fruit. Such interactions can modify protein digestion and protein industrial properties. Noncovalent interactions between globular proteins (proteins important in industry) and procyanidins (phenolic co...
The proliferation and apoptosis of metastatic melanoma cells are often abnormal. We have evaluated the action of a pectic rhamnogalacturonan obtained by hot buffer extraction of okra pods (okra RG-I) on melanoma cell growth and survival in vitro. We added okra RG-I containing an almost pure RG-I carrying very short galactan side chains to 2D (on ti...
Separation and characterization of complex mixtures of oligosaccharides is quite difficult and, depending on elution conditions, structural information is often lost. Therefore, the use of a porous-graphitized-carbon (PGC)-HPLC-ELSD-MS(n)-method as analytical tool for the analysis of oligosaccharides derived from plant cell wall polysaccharides has...
The formation of complexes between proteins and polysaccharides is of great importance for many food systems like foams, emulsions, acidified milk drinks, and so on. The complex formation between beta-lactoglobulin (beta-lg) and pectins with a well-defined physicochemical fine structure has been studied to elucidate the influence of overall charge...
The overall objective of the works performed within PROTECH (Nutritional enhancement of probiotics and prebiotics: Technology aspects on microbial viability, stability, functionality and on prebiotic function, QLK1-CT- 2000-30042) is to address and overcome specific scientific and technological hurdles that impact on the performance of functional f...
This fourvolume set is the most extensive coverage of the very rapidly growing and very important field of glycoscience that is currently available. The books of this set include both strict carbohydrates (monosaccharides, oligosaccharides, polysaccharides) and carbohydrate� containing substances (glycoproteins, glycosphingolipids, proteoglycans)....
A mixture of single side chains from white cabbage pectin were obtained by anion exchange chromatography after applying mild chemical conditions promoting beta-elimination. These pectin fragments were characterized by their molecular weight distribution, sugar composition, 13C-NMR, and MALDI-TOF-MS analysis. These analyses revealed that the large o...
The complex formation between β-lactoglobulin (β-lg) and pectin is studied using pectins with different physicochemical characteristics. Pectin allows for the control of both the overall charge by degree of methyl-esterification as well as local charge density by the degree of blockiness. Varying local charge density, at equal overall charge is a p...
Pectin or pectic substances are collective names for a group of closely associated polysaccharides present in plant cell walls
where they contribute to complex physiological processes like cell growth and cell differentiation and so determine the integrity
and rigidity of plant tissue. They also play an important role in the defence mechanisms agai...
The application of capillary electrophoresis with laser-induced fluorescence detection (CE-LIF) as a tool for the characterization of complex carbohydrate structures was investigated for konjac glucomannan (KGM) oligosaccharide mixtures and the monitoring of their structural changes during 72 h of in vitro fermentation with human gut flora. Differe...
Lignan macromolecule from flaxseed hulls is composed of secoisolariciresinol diglucoside (SDG) and herbacetin diglucoside (HDG) moieties ester-linked by 3-hydroxy-3-methylglutaric acid (HMGA), and of p-coumaric acid glucoside (CouAG) and ferulic acid glucoside (FeAG) moieties ester-linked directly to SDG. The linker molecule HMGA was found to accou...
The okra plant, Abelmoschus esculentus (L.) Moench, a native plant from Africa, is now cultivated in many other areas such as Asia, Africa, Middle East, and the southern states of the USA. Okra pods are used as vegetables and as traditional medicines. Sequential extraction showed that the Hot Buffer Soluble Solids (HBSS) extract of okra consists of...
The latest volume in the successful Special Publication Series captures the most recent research findings in the field of food hydrocolloids. The impressive list of contributions from international experts includes topics such as: * Hydrocolloids as dietary fibre * The role of hydrocolloids in controlling the microstructure of foods * The character...
Enzyme-resistant pectin or modified hairy regions were subjected to size exclusion (HPSEC) and weak anion exchange (WAX) chromatography. Fractions collected after separation were tested for the presence of different pectic epitopes using the monoclonal antibodies LM2, LM5, LM6, and JIM7. Separation by HPSEC showed that based on molecular weight the...
Okra pods are commonly used in Asia as a vegetable, food ingredient, as well as a traditional medicine for many different purposes; for example, as diuretic agent, for treatment of dental diseases and to reduce/prevent gastric irritations. The healthy properties are suggested to originate from the high polysaccharide content of okra pods, resulting...
Carbohydrates occur in food as natural constituents or are added as ingredients. In the last decade a number of novel dietary carbohydrates have been introduced as ingredients for food applications, responding to the growing awareness among consumers of the link between health and diet. One important group is formed by the non-digestible oligosacch...
BACKGROUND: Physicochemical properties and digestibility of proteins can be modified by covalent interactions with oxidized phenolic compounds, i.e., quinones. In order to control these interactions in food products, the covalent interactions between quinones from caffeoylquinic acid (CQA) and amino acid side chains were studied with mass spectrome...
As pectin molecules are too large and heterogeneous to analyze as a whole, the polymer is usually degraded to smaller oligomers, which are often analyzed by high-performance anion exchange chromatography (HPAEC). However, the high salt concentration necessary to elute pectin oligomers by HPAEC is incompatible with online mass detection. To overcome...
IntroductionChemical Structure of PectinsStructural Elements of PectinEnzymesAnalysis of PectinsConcluding RemarksReferences
In flaxseed hulls, lignans are present in an oligomeric structure. Secoisolariciresinol diglucoside (SDG), ester-linked to hydroxy-methyl-glutaric acid (HMGA), forms the backbone of this lignan macromolecule. The hydroxycinnamic acids p-coumaric acid glucoside (CouAG) and ferulic acid glucoside (FeAG) are also part of the lignan macromolecule. Howe...
There is an increasing interest to positively influence the human intestinal microbiota through the diet by the use of prebiotics and/or probiotics. It is anticipated that this will balance the microbial composition in the gastrointestinal tract in favor of health promoting genera such as Bifidobacterium and Lactobacillus. Carbohydrates like non-di...
Starches from cowpea and chickpea seeds were isolated and their properties were compared with those of commercial yellow pea starch. Amylose contents were 25.8%, 27.2%, and 31.2%, and the volume mean diameter of granules, determined in the dry state, were 15.5, 17.9, and 33.8 μm for cowpea, chickpea and yellow pea starches, respectively. All three...
IntroductionArabinoxylans from wheat branArabinoxylans without esterified ferulic acidArabinoxylans with esterified ferulic acidPolysaccharides from beet pulpAlkali extracted pectic polysaccharidesAutoclave extracted pectic polysaccharidesEnzymatic modification of the cross-linked extractsConclusions and future researchReferences
BACKGROUND: The interactions between phenolic compounds and proteins can modify protein properties important in the food industry. To understand the effects of these interactions, the covalent interactions between caffeoylquinic acid (chlorogenic acid, CQA) oxidised by polyphenol oxidase (PPO) at acidic pH 6 (pH 6) and α-lactalbumin, lysozyme and b...
Pectin is of interest both as cell wall component and as food additive. The precise chemical structure of pectin remains under debate, although the structural elements of pectin are rather well described. In order to get more insight in the inter linkage between the various structural elements, apple pectin modified hairy regions were degraded by c...
With the purpose of analysing the molecular size and composition, proteinaceous material was extracted from the insoluble components of a digesta sample obtained from pigs fed a feed consisting of only soybean meal. Gel permeation chromatography indicated that the alkali-extractable fraction of the proteinaceous material from the residue was of rel...
The effect of process conditions used for wheat straw pretreatments on the liquor- and residue-composition was studied. Hereto, the pretreatment conditions were expressed in a ‘combined severity -factor’. The higher the combined severity factor () the more xylan was released from the wheat straw, but the more xylan decomposed and furfural formation...
The affinity of xylan to cellulose is an important aspect of many industrial processes, e.g. production of cellulose, paper making and bio-ethanol production. However, little is known about the adsorption of structurally different xylans to cellulose. Therefore, the adsorption of various xylans to bacterial cellulose (BC) was studied. Also, the rel...
It is more and more realised that pectins are complex mixtures of many different molecules and research is directed towards the fractionation and characterisation of these pectic sub-populations. Since fractionation of pectins generally results in only low amounts of purified material, rapid characterisation methods using low amounts of samples are...
Evidence is presented for the presence of xylogalacturonan (XGA) in Arabidopsis thaliana. This evidence was obtained by extraction of pectin from the seeds, root, stem, young leaves and mature leaves of A. thaliana, followed by treatment of these pectin extracts with xylogalacturonan hydrolase (XGH). Upon enzymatic treatment, XGA oligosaccharides w...
Lignans in flaxseed are known to be part of a macromolecule in which they are connected through the linker-molecule hydroxy-methyl-glutaric acid (HMGA). In this study, the lignan macromolecule was extracted from flaxseed hulls and degraded to its monomeric constituents by complete saponification. Besides secoisolariciresinol diglucoside (SDG), the...
Yellow pea starch was fractionated into small and large size granule fractions and then modified with acetic anhydride and vinyl acetate (acetylation after sieving) or first acetylated in the same way and then fractionated into small and large size fractions (acetylation before sieving). Acetylation with different procedures (acetylation before or...
A large number of proteins are glycosylated, either in vivo or as a result of industrial processing. Even though the effect of glycosylation on the aggregation of proteins has been studied extensively in the past, some reports show that the aggregation process is accelerated, whereas others found that the process is inhibited by glycosylation. This...
Bilberries are known to have one of the most complex xyloglucan structures described in the plant kingdom until now. To characterise this structure, xyloglucans were enzymatically degraded and the oligosaccharides obtained were analysed. More than 20 different building blocks were found to make up the xyloglucan polymer. Bilberry xyloglucan was of...
To study the effect of reagent type on the distribution pattern of acetyl groups in acetylated cowpea starch, amylose and amylopectin populations were isolated from the starch granules after modification to a low degree of substitution (DS < 0.1) with acetic anhydride and vinyl acetate, respectively. Slowly reacting reagent vinyl acetate resulted i...
Functionality of pectins as a food ingredient is strongly related to their chemical fine structure. Chemical characteristics of pectins are determined by many different parameters in their manufacture (choice of the raw material and extraction conditions). Pectin companies are thus in need of rapid methods to check the performance of extracted pect...
An experimental design was used to study the effect of pre-drying (to 10, 15 and 20% weight loss) and par-frying conditions
(160, 170 and 180°C) on the crispness of French fries. Par-frying time was adjusted with a software program to obtain equal
moisture content and internal texture for all samples. Crispness was evaluated with a sensory panel. F...
The effect of reagent type on the properties of acetylated starches was studied for yellow pea, cowpea and chickpea starches after modification with acetic anhydride and vinyl acetate. Samples modified with vinyl acetate showed higher swelling volume and peak viscosity than those acetylated with acetic anhydride for the same starch. In addition, th...
4 Volume set: I. Introduction to glycoscience synthesis of carbohydrates. II. Analysis of glycans polysaccharide functional properties. III. Biochemistry of glycoconjugate glycans carbohydrate-mediated interactions. IV. Biochemistry of glycoconjugate glycans carbohydrate-mediated interactions
Various plant polysaccharide derived mono- and oligosaccharides were derivatized with the fluorescent 9-aminopyrene-1,4,6-trisulfonate (APTS) and subjected to capillary electrophoresis (CE) in combination with laser induced fluorescence (LIF) detection. CE-LIF was suitable for mol-based quantification of various APTS-monosaccharides. CE-LIF of APTS...
DDMP saponin can be converted to saponin B by the loss of its DDMP group (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one). The stability of DDMP saponin from pea was investigated under various conditions (temperature, ethanol concentration, pH). DDMP saponin in water was observed to be unstable at acidic and alkaline pHs, and to have an optimal...
The effects of oil content and droplet size distributions of dilute oil-in-water emulsions on release of 4 esters with different hydrophobicities were studied under in vivo, staticheadspace, and artificial throat conditions. The effect of oil content on orthonasal and retronasal perceived intensity of ethyl hexanoate was studied using a sensory pan...
The aggregation behavior as a function of pH was studied for hydrolysates obtained by hydrolysis of soy protein isolate (SPI) and glycinin- and β-conglycinin-rich protein fractions with subtilisin Carlsberg. The substrates were hydrolyzed up to degrees of hydrolysis (DH) of 2.2% and 6.5%. Compared with nonhydrolyzed SPI, a decrease in solubility wa...
Different separation (HPAEC, RP-HPLC, CE) and identification (MALDI-TOF-MS, ESI-MS(n)) techniques were compared to analyse oligosaccharides obtained after incubation of xyloglucan with endo-glucanase. It was possible to analyse xyloglucan oligosaccharides with each technique. Several techniques, including off line (HPAEC-MALDI-TOF-MS) or online (CE...
The fungus Aspergillus niger is an industrial producer of pectin-degrading enzymes. The recent solving of the genomic sequence of A. niger allowed an inventory of the entire genome of the fungus for potential carbohydrate-degrading enzymes. By applying bioinformatics tools, 12 new genes, putatively encoding family 28 glycoside hydrolases, were iden...
The addition of certain substances to foodstuffs was practiced in ancient times, mostly for improving preservation. Salt was added to perishable foodstuffs, such as meat and fish, from prehistoric ages on. Smoke curing can also be considered as the fortuitous addition of constituents to food, as wood smoke contains a number of compounds that are ab...
Laboratory classes are regarded as an important learning activity, but they also have shortcomings: laboratory classes are often an inefficient learning activity for students and often do not sufficiently support students in developing research specific cognitive skills. It is hypothesized that some of such skills can be achieved more effectively w...
Rhamnogalacturonan II (RG II) can play an important role during processing of berries due to its enzyme resistance and its possible role as a pectic cross-linker. This article describes the presence of RG II in cell walls, in juice and in press cake of bilberries and black currants. RG II was identified and quantified via its diagnostic sugar resid...
Action of xylogalacturonan hydrolase (XGH) towards xylogalacturonan (XGA) present in the alkali saponified “modified hairy regions” from potato and apple pectin was studied.Analysis of enzymatic degradation products from XGA in these complex pectins demonstrated that the degradable xylogalacturonans from both sources have a similar xylose side chai...
Cell wall extracts from a carrot cell culture and tap roots were obtained by sequential extraction with water, EDTA buffer solution and cold sodium hydroxide solution. Arabinogalactan proteins (AGPs) were isolated from the extracts and from the medium of the cell culture and analysed for their molecular weight distribution and carbohydrate composit...
In the present study emulsions were made with various potato protein preparations, which varied in protease inhibitor and patatin content. These emulsions were characterized with respect to average droplet size, plateau surface excess, and the occurrence of droplet aggregation. Droplet aggregation occurred only with potato protein preparations that...
The aim of this research was to use anti-radical power (ARP) to study early lipid oxidation events during frying. The 2,2-diphenyl-1-picrylhydrazyl radical (DPPH¿) test was used to determine the ARP. As oil does not dissolve completely in methanol, which is generally used for the DPPH¿ test, butanol was used instead. Changing the solvent did not in...
The extent of aggregation in whey protein isolate (WPI) hydrolysates induced by Bacillus licheniformis protease was quantified as a function of degree of hydrolysis (DH), temperature and ionic strength. The capacity of the hydrolysates to aggregate added intact protein was also studied. The amount of aggregated material and the size of the aggregat...
The aim of this work is to evaluate the impact of sulfhydryl groups on ovalbumin aggregation and gelation. Ovalbumin was chemically modified to add sulfhydryl groups in various degrees. The rate of aggregation was not affected by the introduction of sulfhydryl groups, and disulfide bond formation was preceded by physical interactions. Hence, disulf...
Unfolding of proteins has often been mentioned as an important factor during the adsorption process at air-water interfaces and in the increase of surface pressure at later stages of the adsorption process. This work focuses on the question whether the folding state of the adsorbed protein depends on the rate of adsorption to the interface, which c...
ABSTRACT Potato and sweet potato starches and derivatives thereof were used to substitute part of the wheat flour in white salted noodle (WSN) manufacture. The quality of the WSN obtained was compared with the quality of WSN made from wheat flour only. When up to 20% of wheat flour was replaced by acetylated potato starch and acetylated sweet potat...
Pectins, complex plant-derived polysaccharides, are novel candidates for biomaterial nanocoatings. Pectic rhamnogalacturonan-I regions (RG-I) can be enzymatically treated to so-called modified hairy regions (MHR). We surveyed the growth and differentiation of murine preosteo-blastic MC3T3-E1 cells on Petri dishes coated with RG-Is from native or ge...
The intermolecular distributions of amide groups within two commercial LMA pectins was studied after removal of the methyl esters followed by fractionation of the different populations by anion exchange chromatography. The populations obtained had almost equal degrees of amidation while the values of the degree of blockiness were not the same, indi...
The major cationic peroxidase in sorghum grain (SPC4) , which is ubiquitously present in all sorghum varieties was purified to apparent homogeneity, and found to be a highly basic protein (pI approximately 11). MS analysis showed that SPC4 consists of two glycoforms with molecular masses of 34,227 and 35,629 Da and it contains a type-b heme. Chemic...
In this study, polysaccharide-producing bacteria were isolated from slimes collected from two Finnish and one Spanish paper mill and the exopolysaccharides (EPSs) produced by 18 isolates were characterised. Most of the isolates, selected on the bases of slimy colony morphology, were members of the family Enterobacteriaceae most frequently belonging...
Thickening and gelling properties of commercial amidated pectins depend on the degree of amidation and methyl-esterification, but also the distribution of these groups is of great importance. Methods have been developed during the last few years to determine the distribution of methyl esters over the pectic backbone. We applied the strategies devel...
Fifty sorghum varieties were screened to determine the effects of germination on levels of starch, α-amylase, β-amylase, phenylalanine ammonia lyase (PAL), peroxidase (POX) and polyphenol oxidase (PPO). Germination decreased starch content, with amylose being more degraded than amylopectin. In germinated grain, α-amylase activity increased several-...