Teris A van Beek

• Faculty Member at Wageningen University & Research

The analysis of catecholamines, such as dopamine, epinephrine and norepinephrine in urine can be used in the diagnosis of certain pathologies, such as hormone-producing tumors. Here, a fast and simple quantitative boronate affinity paper spray tandem mass spectrometric (PS-MS/MS) method is established, which can improve selectivity and reduce ion s...

With the ever-evolving cannabis industry, low-cost and high-throughput analytical methods for cannabinoids are urgently needed. Normally, (potentially) psychoactive cannabinoids, typically represented by Δ9-tetrahydrocannabinol (Δ9-THC), and nonpsychoactive cannabinoids with therapeutic benefits, typically represented by cannabidiol (CBD), are the...

Patulin (PAT) is a mycotoxin, with several acute, chronic, and cellular level toxic effects, produced by various fungi. A limit for PAT in food of has been set by authorities to guarantee food safety. Research on PAT in tea has been very limited although tea is the second largest beverage in the world. In this paper, HPLC−DAD and GC−MS methods for...

Detailed knowledge on natural dyes is important for agronomy and quality control as well as the fastness, stability, and analysis of dyed textiles. Weld (Reseda luteola L.), which is a source of flavone-based yellow dye, is the focus of this study. One aim was to reduce the required amount of dyed textile to ≤50 μg for a successful chromatographic...

Madder, used as a red dye, contains anthraquinones, and some of these can react with DNA possibly causing mutagenic effects. This is especially true for 1,3-dihydroxyanthraquinones with a hydroxymethyl (e.g., lucidin 6, ibericin 10) or methyl group (e.g., rubiadin 9) at C-2. In this research, a new process was developed through which the concentrat...

The control over the amount of psychoactive THC (Δ-9-tetrahydrocannabinol) in commercial cannabidiol (CBD) products has to be strict. A fast and simple semiquantitative Ag(I)-impregnated paper spray mass spectrometric method for differentiating between THC and CBD, which show no difference in standard single-stage or tandem MS, was established. Bec...

Induced phase separation extraction (IPSE) is an efficient sample clean-up technique that can replace liquid-liquid extraction (LLE). The purpose of this study was to miniaturize IPSE by carrying it out in a microfluidic chip. An IPSE chip was designed and evaluated for its ability to separate and purify samples on a microscale. The 5 × 2 cm chip w...

A molecularly imprinted polymeric monolith was synthesized in an aqueous environment in 15 min via UV-irradiation. The imprinted monolith was composed of hydroxyethyl methacrylate as monomer, dimethyl amino ethyl methacrylate as functional monomer, methylene bisacrylamide and piperazine diacrylamide as crosslinkers and human serum albumin as templa...

Introduction: Since a couple of years, low-field (LF) nuclear magnetic resonance (NMR) spectrometers (40-100 MHz) have re-entered the market. They are used for various purposes including analyses of natural products. Similar to high-field instruments (300-1200 MHz), modern LF instruments can measure multiple nuclei and record two-dimensional (2D)...

A simple method to immobilize carbohydrates on a glass surface to obtain a carbohydrate microarray is described. The array was used to study carbohydrate-lectin interactions. The glass surface was modified with aldehyde terminated linker groups of various chain lengths. Coupling of carbohydrates with an amino terminated alkyl spacer to the aldehyde...

This paper reports on the colorimetric properties of natural dyes from madder and weld plants. For both crops, a comparison is made among several individual dye compounds and the total plant extracts. Dyeing properties, colour properties and colour stability have been studied. Insight has been gained into the role of the major dye compounds present...

The main colouring compounds of the dye plant weld (Reseda luteola L.) are the flavones luteolin (lut), lut-7-O-glucoside and lut-7,3ʹ-O-diglucoside. Alum (an aluminium salt)-premordanted wool dyed with weld leads to yellow colours that are of low resistance to light. The photo-stability of lut in aerated methanol–water 8:2 (v/v) solution upon irra...

A high temperature desorption (HTD) direct analysis in real time - high-resolution mass spectrometric (DART-HRMS) method was developed for the rapid analysis of four banned cationic dyes. Rhodamine B is used to dye foods, while malachite green, crystal violet and methylene blue are added to fishponds as antimicrobials. A simple induced phase separa...

High-field NMR is an expensive and important quality control technique. In recent years, cheaper and simpler low-field NMR has become available as a new quality control technique. In this study, 60 MHz 1H-NMR was compared with GC-MS and refractometry for the detection of adulteration of essential oils, taking patchouli essential oil as a test case....

The leaves of Pogostemon cablin (Blanco) Benth. (Lamiaceae) are the source of patchouli essential oil, which is – with an annual production of about 1300 tonnes – an important and unique commodity in the fragrance industry. All the literature pertaining to patchouli was critically reviewed with an emphasis on the qualitative and quantitative chemic...

A simplified coupling of surface plasmon resonance (SPR) immuno-biosensing with ambient ionization mass spectrometry (MS) was developed. It combines two orthogonal analysis techniques: the biosensing capability of SPR and the chemical identification power of high resolution MS. As a proof-of-principle, deoxynivalenol (DON), an important mycotoxin,...

A competitive inhibition immunoassay is described for the mycotoxins deoxynivalenol (DON) and ochratoxin A (OTA) in beer using a portable nanostructured imaging surface plasmon resonance (iSPR) biosensor, also referred to as imaging nanoplasmonics. The toxins were directly and covalently immobilized on a 3-dimensional carboxymethylated dextran (CMD...

Comprehensive hyphenated two-dimensional liquid chromatography mass spectrometry (LC×LC-MS) is a very powerful analytical tool achieving high throughput resolution of highly complex natural samples. However, even using this approach there is still the possibility of not resolving some of the analytes of interest. For instance, triacylglycerols (TAG...

Rationale: Recently, several direct and/or ambient mass spectrometry (MS) approaches have been suggested for drugs of abuse imaging in hair. The use of mass spectrometers with insufficient selectivity could result in false-positive measurements due to isobaric interferences. Different mass analyzers have been evaluated regarding their selectivity...

Plants have evolved inducible resistance and tolerance mechanisms against insect herbivores. Resistance mechanisms that affect herbivorous insects directly can be effective against generalist herbivores, but will not deter specialist herbivores from attacking the plant. Tolerance mechanisms and indirect plant resistance are more likely effective st...

Plants evolved strategies to attract pollinators that are essential for reproduction. However, plant defence against herbivores may trade off with pollinator attraction. Here, we investigated the role of inducible plant secondary metabolites in such a trade-off. Our objective was to reveal the mechanisms underlying the effects of induced plant resp...

Forensic hair evidence can be used to obtain retrospective timelines of drug use by the analysis of hair segments. However, this is a laborious and time consuming process and mass spectrometry (MS) imaging techniques, showing great potential for single hair targeted analysis, are less useful due to differences in hair growth rate between individual...

A 6-plex competitive inhibition immunoassay for mycotoxins in barley was developed on a prototype portable nanostructured imaging surface plasmon resonance (iSPR) instrument, also referred to as imaging nanoplasmonics. As a benchmark for the prototype nanoplasmonics instrument, first a double 3-plex assay was developed for the detection of deoxyniv...

External contamination can cause false positive results in forensic hair testing for drugs of abuse and is therefore a major concern when hair evidence is used in court. Current literature about decontamination strategies is mainly focused on external cocaine contamination and no consensus on the best decontamination procedure for hair samples cont...

An on-line high-performance liquid chromatography (HPLC) method for the rapid and selective detection of boronic acids in complex mixtures was developed. After optimization experiments at an HPLC flow rate of 0.40mL/min, the HPLC-separated analytes were mixed post-column with a solution of 75μM alizarin and 0.1% triethylamine in acetonitrile, which...

Oriented immobilization of antibodies using boronic acids presents a strong potential for improving immunoassay performance but is not widely used yet, possibly because of difficulties encountered in its implementation. How to choose the boronic acid structure and how should it be attached to the surface? How to choose an antibody that will bind to...

To make preparative Reversed-Phase High Performance Liquid Chromatography (RP-pHPLC) greener, alternative solvents were considered among others in terms of toxicity, cost, safety, workability, chromatographic selectivity and elution strength. The less toxic solvents ethanol, acetone and ethyl acetate were proposed as possible greener replacements f...

Surface Plasmon Resonance (SPR) optical sensing is a label-free technique for real-time monitoring of biomolecular interactions. Recently, a portable imaging SPR (iSPR) prototype instrument, featuring a nanostructured gold chip, has been developed. In the present work, we investigated the crucial first steps, prior to eventual use of the nanostruct...

In agriforensics, time of administration is often debated when illegal drug residues, like clenbuterol, are found in frequently traded cattle. In this proof-of-concept work, the feasibility to obtain retrospective timeline information from segmented calf tail hair analyses has been studied. First, an ultra-performance liquid chromatography tandem m...

In this contribution we report on results of a micromechanical sensor intended for the detection of allergens and biomarkers, which has been developed within the framework of the Euregio funded project “UniHealth”. This project aims at the development of a cost effective label free biosensor system that is intended for point of care applications co...

Laser-ablation electrospray ionization (LAESI) mass spectrometry imaging (MSI) does not require very flat surfaces, high-precision sample preparation, or the addition of matrix. Because of these features, LAESI-MSI may be the method of choice for spatially-resolved food analysis. In this work, LAESI time-of-flight MSI was investigated for macroscop...

From the rootbark of Tabernaemontana chippii and the stembark of T. dichotoma a novel dimeric indole alkaloid was isolated which was named monogagaine. It was assigned structure 1 on the basis of spectral data. It showed antimicrobial activity against Bacillus subtilis.

Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification....

Rationale: Forensic hair analysis methods are laborious, time-consuming and provide only a rough retrospective estimate of the time of drug intake. Recently, hair imaging methods using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) were reported, but these methods require the application of MALDI matrix and are performed...

Females of the parasitoid wasp Trichogramma turkestanica produce the putative polydeoxypropionates (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4-diene and (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4-dien-1-ol or their enantiomers as sex specific volatiles. The structures were assigned on the basis of GC-MS investigations using synthetic r...

This experiment exposes second-year undergraduate students taking a course in analytical organic chemistry to high-performance liquid chromatography (HPLC) and quantitative analysis using the internal standard method. This is accomplished using the real-world application of natural dyes for textiles. The extracted flavonoids of the plant weld are r...

The antifungal activity of bacteria from the genus Collimonas has been well documented, but the chemistry and gene functions that underlie this phenotype are still poorly understood. Screening of a random plasposon insertion library of Collimonas fungivorans Ter331 for loss-of-function mutants revealed the importance of gene cluster K, which is ann...

Herbivory induces changes in plants that influence the associated insect community. The present study addresses the potential trade-off between plant phytochemical responses to insect herbivory and interactions with pollinators. We used a multidisciplinary approach and have combined field and greenhouse experiments to investigate effects of herbivo...

A better characterization of nanometer-thick organic layers (monolayers) as used for engineering surface properties, biosensing, nanomedicine and smart materials will widen their application. The aim of this study was to develop direct analysis in real time high-resolution mass spectrometry (DART-HRMS) into a new and complementary analytical tool f...

Ginkgolic acids (GAs; anacardic acids; 6-alkylsalicylic acids) are both unwanted constituents in standardized Ginkgo biloba (Ginkgo) extracts and desirable constituents for pharmacological assays. Thus, for the quality control of Ginkgo extracts, the availability of pure GAs is important. In this investigation, inexpensive and easily prepared Fe3O4...

A characteristic of traditional medicinal practices, such as traditional Chinese medicines (TCMs) and Indian ayurveda, is the abundant use of plants as drugs. However, the bottleneck in the use of herbal drugs is the control of their safety, effectiveness, and quality. Good quality control (QC) is necessary to achieve the standards of modern medici...

The purpose of this study was to complete the knowledge on the chemical composition and radical scavenging activity of olive tree wood. Two new monoterpene glycosides, (-)-oleuropeic acid 6'-O-α-D-glucopyranosyl ester (6a) and (-)-perillic acid 1'-O-β-D-primeverosyl ester (8), together with the known compounds (-)-oleuropeic acid (1), (-)-olivil (2...

A glass liquid-liquid extraction (LLE) microchip with three parallel 3.5cm long and 100μm wide interconnecting channels was optimized in terms of more environmentally friendly (greener) solvents and extraction efficiency. In addition, the optimized chip was successfully hyphenated with nano-liquid chromatography with ultraviolet and mass spectromet...

Ingestion of products containing Chinese star anise (Illicium verum) fruits contaminated or adulterated with Japanese star anise (Illicium anisatum) fruits can cause poisoning due to the neurotoxin anisatin that is present in Japanese star anise. Thus a rapid, simple and unambiguous distinction between the morphologically similar Chinese star anise...

Plants respond to insect herbivores with changes in physical and chemical traits, both locally and systemically, in leaves and flowers. Such phenotypic changes may influence the behaviour of every community member that interacts with the plant. Here, we address effects of plant responses to eggs and subsequent herbivory by caterpillars on plant‐med...

Detailed molecular analysis by Direct Analysis in Real Time High Resolution Mass Spectrometry (DART-HRMS) of ester and amide-terminated monolayers is demonstrated. The structural information obtained allowed monitoring of the progress of a 4-step surface modification.

An investigation to optimize the extraction yield and the radical scavenging activity from the agricultural by-product olive tree wood (Olea europaea L., cultivar Picual) using six different extraction protocols was carried out. Four olive wood samples from different geographical origin, and harvesting time have been used for comparison purposes. A...

Catechol (1,2-diphenols) derivatives are often used as dispersant anchors for Fe3O4 nanoparticles because of the high affinity of catechols for the nanoparticles (see Figure, J. Phys. Chem. 2011, 115,682–691). This “grafting to” approach implies that Fe3O4 nanoparticles could be applied to selectively adsorb some phytochemicals with carboxyl or ort...

A new method for the selective and sensitive detection of boronic acids on thin-layer chromatography plates is described. The plate is briefly dipped in an alizarin solution, allowed to dry in ambient air, and observed under 366 nm light. Alizarin emits a bright yellow fluorescence only in the presence of a boronic acid.

A 3-phase liquid-liquid extraction (LLE) chip was hyphenated with nano-HPLC/ESI-MS (Fig.). Thus the purification, separation and MS detection of alkaloids was accomplished on-line. The system is solvent-efficient with a nanoLC flow rate of 200 nL/min, and chip flow rate of 500 nL/min, sample-efficient (50-330 nL sample volume) and time-efficient (s...

Cu-free "click" chemistry is explored on silicon nitride (Si(3)N(4)) surfaces as an effective way for oriented immobilization of biomolecules. An ω-unsaturated ester was grafted onto Si(3)N(4) using UV irradiation. Hydrolysis followed by carbodiimide-mediated activation yielded surface-bound active succinimidyl and pentafluorophenyl ester groups. T...

After ingestion, products containing Chinese star anise (Illicium verum) contaminated or adulterated with Japanese star anise (Illicium anisatum) or other Illicium species, can cause epilepsy, hallucinations, and nausea due to the rare neurotoxic sesquiterpene dilactone anisatin that is present in Japanese star anise. Thus a rapid, simple and unamb...

An on-line HPLC (high performance liquid chromatography) method for the rapid screening of individual antioxidants in mixtures was developed using crocin as a substrate (i.e. oxidation probe) and 2,2'-azobis(2-amidinopropane dihydrochloride (AAPH)) in phosphate buffer (pH 7.5) as a radical generator. The polyene structure of crocin and AAPH-derived...

In an earlier screening of Lithuanian plants, horehound (Marrubium vulgare) showed good antioxidant activity and as this species is used in herbal teas and cough pastilles it was selected for further investigation. Some fractions of the aerial parts were strong scavengers of the model free radicals DPPH and ABTS+. Activity in the β-carotene bleachi...

Alkaloid-containing plants are an intrinsic part of the regular Western diet. The present paper summarizes the occurrence of alkaloids in the food chain, their mode of action and possible adverse effects including a safety assessment. Pyrrolizidine alkaloids are a reason for concern because of their bioactivation to reactive alkylating intermediate...

In the past decades, there has been a renewed interest in the use of natural dye plants for textile dyeing, e.g. Reseda luteola (weld). Its main yellow dye constituents are the flavones luteolin-7,3'-O-diglucoside, luteolin-7-O-glucoside and luteolin. The aim of this work was to develop a simple validated industrially usable quantitative method to...

A three-enzyme cascade reaction was successfully realized in a continuous flow microreactor. The first enzyme (Candida antarctica lipase B, also known as Pseudozyma antarctica lipase B) and the third enzyme (horseradish peroxidase) of the cascade process were immobilized in a mild non-contact manner via ssDNA-ssDNA interaction in discrete zones on...

Klicks ohne Cu: Es besteht zunehmendes Interesse an einer reproduzierbaren ortsspezifischen Funktionalisierung von Oberflächen mit Biomolekülen, ohne dabei unerwünschte Gruppen oder Katalysatoren einzuführen, da diese bei späteren Anwendungen stören können. Spannungsvermittelte Alkin-Azid-Klickreaktionen (siehe Bild) könnten diese Anforderungen erf...

Clicks without Cu: There is a growing demand for reproducible site-specific functionalization of surfaces with biomolecules without introduction of unwanted groups or catalysts, as they may interfere with later applications. The title reactions (see picture) could fulfill these requirements, and four recent applications are discussed.

An analytical method for the comparison of the content of chlorophylls and their structurally similar breakdown products in weld is described

Monolithic columns containing ganglioside GM2 and GM3 mimics were prepared for selective removal of serum anti-ganglioside antibodies from patients with acute and chronic immune-mediated neuropathies. ELISA results demonstrated that anti-GM2 IgM antibodies in human sera and a mouse monoclonal anti-GM2 antibody were specifically and selectively adso...

The woody portion of olive tree pruning is a source of natural antioxidants of potential interest for the food industry. This work deals with the isolation and identification of further antioxidants present in an ethyl acetate extract of olive (Olea europaea L.) wood. Thus, a new secoiridoid, oleuropein-3″-methyl ether (1), together with six known...

Wageningse chemici werken aan de ontwikkeling van een minuscule weegschaal op een chip. Mocht hij de verwachtingen waarmaken, dan kan de nanoweegschaal kleine hoeveelheden allergenen in voedsel meten, en misschien ook stoffen in het bloed die in een vroeg stadium auto-immuunziektes verraden.

INTRODUCTION: Because microchips are expensive, it is desirable to have a system that be reused or changed according to one's needs. Typically, biofunctional materials have a shorter active lifetime than the glass substrates. Therefore the goal of this project was to a) provide local and reversible biofunctionalization of glass micro-channels, and...

The sweet, minty-lemony leaves of costmary (Chrysanthemum balsamita) are used for salads and tea, and as flavourings in meats, sausages, cakes and ale. In this study, the extracts isolated from costmary aerial parts were investigated as antioxidants in rapeseed oil and as free radical-scavengers in DPPH and ABTS+ assays. It was found that costmary...

The complete assignment of the 1H-NMR spectrum of the fully saturated tetracyclic sesquiterpene hydrocarbon longicyclene is presented. The assignment was achieved using phase-sensitive double-quantum filtered COSY at 600 MHz, heteronuclear correlation spectroscopy and COLOC spectroscopy. Accurate vicinal 1H-1H coupling constants involving the seven...

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.

Ninety wood-inhabiting fungi were screened for their ability to degrade and detoxify acetone extractives in Scots pine (Pinus sylvestris L.) sapwood under solid-state fermentation conditions. Fungal degradation of resin acids and long-chain fatty acids was investigated by high pressure liquid chromatography with evaporative light scattering detecti...

Affinity chromatography on monolithic supports is a powerful analytical chemical platform because it allows for fast analyses, small sample volumes, strong enrichment of trace biomarkers and applications in microchips. In this review, the recent research using monolithic materials in the field of bioaffinity chromatography (including immunochromato...

In LNV-programma WOT 5 worden door DLO de Wettelijke Onderzoek Taken (WOT) uitgevoerd die betrekking hebben op de visserij. In het KB programma, beschreven in dit rapport, worden middelen bestemd om de deskundigheid te handhaven en kennis te ontwikkelen nodig voor de uitvoering van het WOT programma. Naast het handhaven van deskundigheid, is innova...

For the first time, a microchannel was photochemically patterned with a functional linker. This simple method was developed for the site-specific attachment of DNA via this linker onto silicon oxide surfaces (e.g., fused silica and borosilicate glass), both onto a flat surface and onto the inside of a fused silica microchannel. Sharp boundaries in...

The chemistry, analysis, pharmacology and clinical applications of extracts of the maidenhair tree (G. biloba) are reviewed. This botanically unique tree contains some unusual secondary metabolites, among others a number of highly oxidised terpene trilactones (ginkgolides, bilobalide) which, together with some flavonoids, are considered to be respo...

Phenolic esters like chlorogenic acid play an important role in therapeutic properties of many plant extracts. We aimed to produce phenolic esters in baker's yeast, by expressing tobacco 4CL and globe artichoke HCT. Indeed yeast produced phenolic esters. However, the primary product was identified as N-(E)-p-coumaroyl-3-hydroxyanthranilic acid by N...

An on-line method for the rapid pinpointing of radical scavengers in non-polar mixtures like vegetable oils was developed. To avoid problems with dissolving the sample, normal-phase chromatography on bare silica gel was used with mixtures of hexane and methyl tert-butyl ether as the eluent. The high performance liquid chromatography-separated analy...

A three-phase microchip was developed for the rapid and efficient small-scale purification of alkaloids from plant extracts. As part of the development of such a three-phase microchip, first a two-phase microchip with two channels (3.2 cm and 9.3 cm) was used to study the extraction efficiency of strychnine nitrate and strychnine at various flow ra...

Natural products chemistry has witnessed many new developments in the last 5years like extractions with subcritical water and ionic liquids, LC/HRMS and LC/SPE/cryo-NMR, UHPLC, TLC/MS, MS-based preparative HPLC, comprehensive chromatography (GC×GC, LC×LC), high-throughput screening, introduction of monolithic columns, miniaturisation, and automated...

Hormone and veterinary drug screening and forensics can benefit from the recent developments in desorption electrospray ionisation (DESI) mass spectrometry (MS). In this work the feasibility of DESI application has been studied. Using a linear ion trap or quadrupole time-of-flight (TOF) MS instrument both full-scan and data-dependent collision-indu...

The chemical analysis and quality control of Ginkgo leaves, extracts, phytopharmaceuticals and some herbal supplements is comprehensively reviewed. The review is an update of a similar, earlier review in this journal [T.A. van Beek, J. Chromatogr. A 967 (2002) 21-55]. Since 2001 over 3000 papers on Ginkgo biloba have appeared, and about 400 of them...

The invention relates to oligosaccharide compositions having affinity for proteins and the medical or biotechnological use of such compositions. The invention provides a composition having multivalent binding capacity for a protein comprising at least two oligosaccharide moieties linked to a dendrimer, having multivalent binding capacity for a bact...

Screening for antioxidants requires simple in vitro model systems to investigate antioxidant activity. High resolution screening (HRS), combining a separation technique like HPLC with fast post-column (bio)chemical detection can rapidly pinpoint active compounds in complex mixtures. In this paper both electrochemical and chemistry-based assays are...

An improved comprehensive two-dimensional (LC x LC) HPLC system for the analysis of triacylglycerols was developed. In the first-dimension, a Ag(I)-coated cation exchanger (250 mm x 2.1 mm, 5 microm) was employed with a gradient from 100% MeOH to 6% MeCN in MeOH at 20 microL/min. Using a 10-way valve with two switching loops, 1 min sections of the...

Massetolide A is a cyclic lipopeptide (CLP) antibiotic produced by various Pseudomonas strains from diverse environments. Cloning, sequencing, site-directed mutagenesis, and complementation showed that massetolide A biosynthesis in P. fluorescens SS101 is governed by three nonribosomal peptide synthetase (NRPS) genes, designated massA, massB, and m...