- Elke A. Trautwein (1)
- Bart A.J. Noordover (1)
- Niels Agerbirk (1)
- C. Chocano (1)
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- Carl Erik Olsen (1)
- C. García (1)
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- Linda Gootjes (1)
- T. Hernandez (1)
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- Harro J. Bouwmeester (2)
- K. Jindo (1)
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- Yuguang Lin (1)
- A. Lommen (1)
- Joop Loon Van (1)
- Claudio Luchinat (1)
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- Doris M. Jacobs (2)
- J. Melgares de Aguilar (1)
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- Alain Mesmaeker de (1)
- Jan Meuldijk (1)
- Caroline Müller (1)
- M.W.F. Nielen (1)
- Ronald P. Mensink (1)
- Carolien P. Ruyter-Spira (2)
- John P.M. Duynhoven Van (1)
- Jean Paul Vincken (2)
- Jogchum Plat (1)
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- A.H. Roos (1)
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- Sara Ruschioni (1)
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- Edoardo Saccenti (1)
- Mark Sanders (2)
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- Claudio Screpanti (2)
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- Leonardo Tenori (1)
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Zeapyranolactone − A novel strigolactone from maize
Charnikhova, Tatsiana V. ; Gaus, Katharina ; Lumbroso, Alexandre ; Sanders, Mark ; Vincken, Jean Paul ; Mesmaeker, Alain De; Ruyter-Spira, Carolien P. ; Screpanti, Claudio ; Bouwmeester, Harro J. - \ 2018
Phytochemistry letters 24 (2018). - ISSN 1874-3900 - p. 172 - 178.
Maize (Zea mays) - NMR - Prep-HPLC–MS - Strigolactones - Zeapyranolactone
The structure of a new strigolactone present in the root exudate and root extract of maize hybrid cv NK Falkone plants was elucidated and characterized as zeapyranolactone: Methyl.(E)-3-((4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)-2-(4,4,5-trimethyl-2-oxo-2,3,4,6,7,7a-hexahydrocyclopenta[b]pyran-7-yl)acrylate. Unlike any other strigolactone published so far, it contains a 4,4-dimethyltetrahydropyran-2-one as A ring. The impact of the elucidation of this structure on the earlier postulated biosynthetic pathway of another maize strigolactone, zealactone, is discussed.
Age and Sex Effects on Plasma Metabolite Association Networks in Healthy Subjects
Vignoli, Alessia ; Tenori, Leonardo ; Luchinat, Claudio ; Saccenti, Edoardo - \ 2018
Journal of Proteome Research 17 (2018)1. - ISSN 1535-3893 - p. 97 - 107.
differential network analysis - metabolism - metabolomics - network inference - NMR
In the era of precision medicine, the analysis of simple information like sex and age can increase the potential to better diagnose and treat conditions that occur more frequently in one of the two sexes, present sex-specific symptoms and outcomes, or are characteristic of a specific age group. We present here a study of the association networks constructed from an array of 22 plasma metabolites measured on a cohort of 844 healthy blood donors. Through differential network analysis we show that specific association networks can be associated with sex and age: Different connectivity patterns were observed, suggesting sex-related variability in several metabolic pathways (branched-chain amino acids, ketone bodies, and propanoate metabolism). Reduction in metabolite hub connectivity was also found to be associated with age in both sex groups. Network analysis was complemented with standard univariate and multivariate statistical analysis that revealed age- and sex-specific metabolic signatures. Our results demonstrate that the characterization of metabolite-metabolite association networks is a promising and powerful tool to investigate the human phenotype at a molecular level.
Effect of theobromine consumption on serum lipoprotein profiles in apparently healthy humans with low HDL-cholesterol concentrations
Jacobs, Doris M. ; Smolders, Lotte ; Lin, Yuguang ; Roo, Niels de; Trautwein, Elke A. ; Duynhoven, John van; Mensink, Ronald P. ; Plat, Jogchum ; Mihaleva, Velitchka V. - \ 2017
Frontiers in Molecular Biosciences 4 (2017)AUG. - ISSN 2296-889X
HDL - Lipoprotein - NMR - PLS model - Theobromine
Scope: Theobromine is a major active compound in cocoa with allegedly beneficial effect on high-density-lipoprotein-cholesterol (HDL-CH). We have investigated the effect of theobromine (TB) consumption on the concentrations of triglyceride (TG) and cholesterol (CH) in various lipoprotein (LP) subclasses. Methods: In a randomized, double-blind, placebo-controlled, cross-over study, 44 apparently healthy women and men (age: 60 ± 6 years, BMI: 29 ± 3 kg/m2) with low baseline HDL-CH concentrations consumed a drink supplemented with 500 mg/d theobromine for 4 weeks. TG and CH concentrations in 15 LP subclasses were predicted from diffusion-edited 1H NMR spectra of fasting serum. Results: The LP phenotype of the subjects was characterized by low CH concentrations in the large HDL particles and high TG concentrations in large VLDL and chylomicron (CM) particles, which clearly differed from a LP phenotype of subjects with normal HDL-CH. TB only reduced CH concentrations in the LDL particles by 3.64 and 6.79%, but had no effect on TG and CH in any of the HDL, VLDL and CM subclasses. Conclusion: TB was not effective on HDL-CH in subjects with a LP phenotype characterized by low HDL-CH and high TG in VLDL.
Zealactones. Novel natural strigolactones from maize
Charnikhova, Tatsiana V. ; Gaus, Katharina ; Lumbroso, Alexandre ; Sanders, Mark ; Vincken, Jean Paul ; Mesmaeker, Alain de; Ruyter-Spira, Carolien P. ; Screpanti, Claudio ; Bouwmeester, Harro J. - \ 2017
Phytochemistry 137 (2017). - ISSN 0031-9422 - p. 123 - 131.
Maize (Zea mays) - NMR - Prep-HPLC-MS - Seed germination - Striga hermonthica (Orobanchaceae) - Strigolactones - UHPLC-MS-MS - Zealactone
In the root exudate and root extracts of maize hybrid cv NK Falkone seven putative strigolactones were detected using UPLC-TQ-MS-MS. All seven compounds displayed MS-MS-fragmentation common for strigolactones and particularly the presence of a fragment of m/z 97 Da, which may indicate the presence of the so-called D-ring, suggests they are strigolactones. The levels of all these putative strigolactones increased upon phosphate starvation and decreased upon fluridone (carotenoid biosynthesis inhibitor) treatment, both of which are a common response for strigolactones. All seven compounds were subsequently isolated with prep-HPLC-MS. They all exhibited Striga hermonthica seed germination inducing activity just as the synthetic strigolactone analog GR24. The structure of two of the seven compounds was elucidated by NMR spectroscopy as: methyl (2E,. 3E)-4-(3,. 3-dimethyl-5-oxo-2-(prop-1-en-2-yl)tetrahydrofuran-2-yl)-2-(((4-methyl-5-oxo-2,. 5-dihydrofuran-2-yl)oxy)methylene)but-3-enoate (two diastereomers 1a and 1b). Strigolactones (1a/b) are closely related to the methyl ester of carlactonoic acid (MeCLA) and heliolactone. However, they contain a unique 4,4-dimethyltetrahydrofuran-2-one motif as the "A-ring" instead of the classical (di)methylcyclohexene. Because these compounds were isolated from maize (Zea mays) we called them "zealactone 1a and 1b". The implications of this discovery for our view on strigolactones and their biosynthesis are discussed.
Impact of Compost Application during 5 Years on Crop Production, Soil Microbial Activity, Carbon Fraction, and Humification Process
Jindo, K. ; Chocano, C. ; Melgares de Aguilar, J. ; González, D. ; Hernandez, T. ; García, C. - \ 2016
Communications in Soil Science and Plant Analysis 47 (2016)16. - ISSN 0010-3624 - p. 1907 - 1919.
Compost - FT-IR - humic acid - NMR - organic farming
Compost amendment is considered as a practical tool to increase the soil organic matter (SOM), which contributes to agricultural sustainability. The objective of the present work was to evaluate the impacts of organic soil management over 5 years on orchard prune production (Prunus salicina), microbial activity, soil carbon (C) fraction, and stabilization degrees of soil humification. Plot experiment was designed with two different soil managements: i) for minimizing anthropogenic disturbances, only mulching of orchard residues derived from prune tree plot area was applied to soil surface (S + V); and ii) the amendment of composted manure was annually practiced in addition to the utilization of orchard residues inside the plot area (S + V + C). After 5 years, the soil with the continuous compost application (S + V + C) showed higher productivity of Prunus salicina (21.4%), greater fruit diameter (7.8%), and heavier fruit weight (22.4%) than the soil without compost application (S + V). Nutrient content in foliar analysis showed no difference between the two treatments (S + V and S + V + C). By contrast, the amended soil by compost (S + V + C) increased the SOM and water-soluble C fraction in parallel with the increase of microbial parameters (microbial biomass C, adenosine triphosphate (ATP), basal respiration, and dehydrogenase). Analyzing soil humic acid character by chemical spectra techniques of Fourier-transform infrared (FT-IR) spectra and 13C nuclear magnetic resonance (13C-NMR), gradual reformation of a more stabilized structure was shown in both soils (S + V and S + V + C), due to the selective biodegradation and humification process after the amendments over 5 years. Especially, in the soil treated with compost application (S + V + C), the increase of functional C groups (aromatic and carboxylic groups), which reinforce the recalcitrant character of soil humified fraction, was clearly observed. The continuous application of composted manure for the duration of 5 years improved the orchard soil fertility as well as productivity. Abbreviations: ATP, adenosine triphosphate; CPMAS, cross-polarization magic angle spinning; EC, electrical conductivity; FT-IR, Fourier-transform infrared; HA, humic acid; HS, humic substance; INTF, iodonitrotetrazolium formazan; K, Potassium; LSD, least significant differences, N, nitrogen; NMR, nuclear magnetic resonance; O, oxygen; OM, organic matter; MBC, microbial biomass C; P, phosphorous; SD, standard deviation; SE, standard error; SOM, soil organic matter; TOC, total organic carbon; WSC, water-soluble C; WS-Ch, water-soluble carbohydrate
Assessment of dietary exposure and effect in humans : The role of NMR
Duynhoven, John P.M. Van; Jacobs, Doris M. - \ 2016
Progress in Nuclear Magnetic Resonance Spectroscopy 96 (2016). - ISSN 0079-6565 - p. 58 - 72.
Dietary effect - Dietary exposure - Metabolite identification - Metabolomics - NMR
In human nutritional science progress has always depended strongly on analytical measurements for establishing relationships between diet and health. This field has undergone significant changes as a result of the development of NMR and mass spectrometry methods for large scale detection, identification and quantification of metabolites in body fluids. This has allowed systematic studies of the metabolic fingerprints that biological processes leave behind, and has become the research field of metabolomics. As a metabolic profiling technique, NMR is at its best when its unbiased nature, linearity and reproducibility are exploited in well-controlled nutritional intervention and cross-sectional population screening studies. Although its sensitivity is less good than that of mass spectrometry, NMR has maintained a strong position in metabolomics through implementation of standardisation protocols, hyphenation with mass spectrometry and chromatographic techniques, accurate quantification and spectral deconvolution approaches, and high-throughput automation. Thus, NMR-based metabolomics has contributed uniquely to new insights into dietary exposure, in particular by unravelling the metabolic fates of phytochemicals and the discovery of dietary intake markers. NMR profiling has also contributed to the understanding of the subtle effects of diet on central metabolism and lipoprotein metabolism. In order to hold its ground in nutritional metabolomics, NMR will need to step up its performance in sensitivity and resolution; the most promising routes forward are the analytical use of dynamic nuclear polarisation and developments in microcoil construction and automated fractionation.
Poly(hydroxy urethane)s based on renewable diglycerol dicarbonate
Velthoven, Juliën L.J. van; Gootjes, Linda ; Es, Daan S. van; Noordover, Bart A.J. ; Meuldijk, Jan - \ 2015
European Polymer Journal 70 (2015). - ISSN 0014-3057 - p. 125 - 135.
Biobased - Diglycerol dicarbonate - Isocyanate-free - NMR - Poly(hydroxy urethane) - Thermal properties
Abstract In this paper, we present a series of amorphous non-isocyanate poly(hydroxy urethane)s (PHU) synthesized from diglycerol dicarbonate in bulk conditions at mild temperatures, without using a catalyst. Diglycerol dicarbonate has been synthesized from diglycerol and dimethyl carbonate and was subsequently reacted with various diamines to form PHUs. These fully bio-based PHUs were amorphous and displayed a broad range of Tg values i.e. from -7 to 66 °C. 1D and 2D NMR techniques were used to determine the ratio between primary and secondary hydroxyl groups formed along the PHU backbone, which was found to be 31:69 for all compositions. The number-average molecular weights were calculated from NMR data and range from 4100 to 9400 g/mol. In FTIR spectra, residual cyclic carbonate groups were observed, which is in agreement with the loss of diamine as detected by NMR. TGA analysis indicated that the polymers are stable up to 200 °C. The polymers synthesized are expected to perform well in e.g. coating applications, given their molecular and thermal properties as well as the abundance of reactive hydroxyl functionalities present along the PHU backbone, which can be used for curing purposes and/or further functionalization.
Taste detection of the non-volatile isothiocyanate moringin results in deterrence to glucosinolate-adapted insect larvae
Müller, Caroline ; Loon, Joop Van; Ruschioni, Sara ; Nicola, Gina Rosalinda De; Olsen, Carl Erik ; Iori, Renato ; Agerbirk, Niels - \ 2015
Phytochemistry 118 (2015). - ISSN 0031-9422 - p. 139 - 148.
Brassicales - Deterrent - Glucosinolate - HPLCMS/MS - Isothiocyanate - Neuron - NMR - Sensory physiology - Specialist herbivores - Stimulant - Taste
Isothiocyanates (ITCs), released from Brassicales plants after hydrolysis of glucosinolates, are known for their negative effects on herbivores but mechanisms have been elusive. The ITCs are initially present in dissolved form at the site of herbivore feeding, but volatile ITCs may subsequently enter the gas phase and all ITCs may react with matrix components. Deterrence to herbivores resulting from topically applied volatile ITCs in artificial feeding assays may hence lead to ambiguous conclusions. In the present study, the non-volatile ITC moringin (4-(α-l-rhamnopyranosyloxy)benzyl ITC) and its glucosinolate precursor glucomoringin were examined for effects on behaviour and taste physiology of specialist insect herbivores of Brassicales. In feeding bioassays, glucomoringin was not deterrent to larvae of Pieris napi (Lepidoptera: Pieridae) and Athalia rosae (Hymenoptera: Tenthredinidae), which are adapted to glucosinolates. Glucomoringin stimulated feeding of larvae of the related Pieris brassicae (Lepidoptera: Pieridae) and also elicited electrophysiological activity from a glucosinolate-sensitive gustatory neuron in the lateral maxillary taste sensilla. In contrast, the ITC moringin was deterrent to P. napi and P. brassicae at high levels and to A. rosae at both high and low levels when topically applied to cabbage leaf discs (either 12, 120 or 1200 nmol moringin per leaf disc of 1 cm diameter). Survival of A. rosae was also significantly reduced when larvae were kept on leaves treated with moringin for several days. Furthermore, moringin elicited electrophysiological activity in a deterrent-sensitive neuron in the medial maxillary taste sensillum of P. brassicae, providing a sensory mechanism for the deterrence and the first known ITC taste response of an insect. In simulated feeding assays, recovery of moringin was high, in accordance with its non-volatile nature. Our results demonstrate taste-mediated deterrence of a non-volatile, natural ITC to glucosinolate-adapted insects.
Application of 1D 1H NMR for fast non-targeted screening and compositional analysis of steroid cocktails and veterinary drug formulations administered to livestock
Lommen, A. ; Schilt, R. ; Weseman, J. ; Roos, A.H. ; Velde, J.W. van; Nielen, M.W.F. - \ 2002
Journal of pharmaceutical and biomedical analysis 28 (2002)1. - ISSN 0731-7085 - p. 87 - 96.
NMR - screening - steroid - anabolic - veterinary drug