scholarly journals Phytochemistry reflects different evolutionary history in traditional classes versus specialized structural motifs

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Kathryn A. Uckele ◽  
Joshua P. Jahner ◽  
Eric J. Tepe ◽  
Lora A. Richards ◽  
Lee A. Dyer ◽  
...  
Keyword(s):  
Phylogenetic Signal ◽  
Spectroscopic Characterization ◽  
Proton Nuclear Magnetic Resonance ◽  
Sequencing Data ◽  
Secondary Chemistry ◽  
Multivariate Tests ◽  
H Nmr ◽  
Similar Chemical ◽  
Phylogenetic Resolution ◽  
Chemical Profiles

AbstractFoundational hypotheses addressing plant–insect codiversification and plant defense theory typically assume a macroevolutionary pattern whereby closely related plants have similar chemical profiles. However, numerous studies have documented variation in the degree of phytochemical trait lability, raising the possibility that phytochemical evolution is more nuanced than initially assumed. We utilize proton nuclear magnetic resonance (1H NMR) data, chemical classification, and double digest restriction-site associated DNA sequencing (ddRADseq) to resolve evolutionary relationships and characterize the evolution of secondary chemistry in the Neotropical plant clade Radula (Piper; Piperaceae). Sequencing data substantially improved phylogenetic resolution relative to past studies, and spectroscopic characterization revealed the presence of 35 metabolite classes. Metabolite classes displayed phylogenetic signal, whereas the crude 1H NMR spectra featured little evidence of phylogenetic signal in multivariate tests of chemical resonances. Evolutionary correlations were detected in two pairs of compound classes (flavonoids with chalcones; p-alkenyl phenols with kavalactones), where the gain or loss of a class was dependent on the other’s state. Overall, the evolution of secondary chemistry in Radula is characterized by strong phylogenetic signal of traditional compound classes and weak phylogenetic signal of specialized chemical motifs, consistent with both classic evolutionary hypotheses and recent examinations of phytochemical evolution in young lineages.

scholarly journals Evidence for both phylogenetic conservatism and lability in the evolution of secondary chemistry in a tropical angiosperm radiation

2020 ◽  
Author(s):  
Kathryn A. Uckele ◽  
Joshua P. Jahner ◽  
Eric J. Tepe ◽  
Lora A. Richards ◽  
Lee A. Dyer ◽  
...  
Keyword(s):  
Phylogenetic Signal ◽  
Genotyping By Sequencing ◽  
Spectroscopic Characterization ◽  
Proton Nuclear Magnetic Resonance ◽  
Sequencing Data ◽  
Secondary Chemistry ◽  
H Nmr ◽  
Similar Chemical ◽  
Phylogenetic Resolution ◽  
Chemical Profiles

SummaryOver evolutionary timescales, shifts in plant secondary chemistry may be associated with patterns of diversification in associated arthropods. Although foundational hypotheses of plant-insect codiversification and plant defense theory posit closely related plants should have similar chemical profiles, numerous studies have documented variation in the degree of phylogenetic signal, suggesting phytochemical evolution is more nuanced than initially assumed. We utilize proton nuclear magnetic resonance (1H NMR) data, chemical classification, and genotyping-by-sequencing to resolve evolutionary relationships and characterize the evolution of secondary chemistry in the Neotropical plant clade Radula (Piper; Piperaceae). Sequencing data substantially improved phylogenetic resolution relative to past studies, and spectroscopic characterization revealed the presence of 35 metabolite classes. Broad metabolite classes displayed strong phylogenetic signal, whereas the crude 1H NMR spectra featured evolutionary lability in chemical resonances. Evolutionary correlations were detected in two pairs of compound classes (flavonoids with chalcones; p-alkenyl phenols with kavalactones), where the gain or loss of a class was dependent on the other’s state. Overall, the evolution of secondary chemistry in Radula is characterized by strong phylogenetic signal of broad compound classes and concomitant evolutionary lability of specialized chemical motifs, consistent with both classic evolutionary hypotheses and recent examinations of phytochemical evolution in young lineages.

scholarly journals Electrochemical and Spectroscopic Characterization of Aluminium(III)-para-methyl-meso-tetraphenylporphyrin Complexes Containing Substituted Salicylates as Axial Ligands

2013 ◽  
Vol 2013 ◽  
pp. 1-10
Author(s):  
Gauri D. Bajju ◽  
Deepmala ◽  
Sunil Kumar Anand ◽  
Sujata Kundan ◽  
Narinder Singh
Keyword(s):  
Spectroscopic Characterization ◽  
Redox Properties ◽  
Proton Nuclear Magnetic Resonance ◽  
Spectroscopic Techniques ◽  
Axial Coordination ◽  
H Nmr ◽  
Axial Ligands ◽  
Reduction Mechanisms ◽  
C Nmr

A series of aluminium(III)-p-methyl-meso-tetraphenylporphyrin (p-CH3TPP-Al(III)) containing axially coordinated salicylate anion [p-CH3TPP-Al-X)], where X = salicylate (SA), 4-chlorosalicylate (4-CSA), 5-chlorosalicylate (5-CSA), 5-flourosalicylate (5-FSA), 4-aminosalicylate (4-ASA), 5-aminosalicylate (5-ASA), 5-nitrosalicylate (5-NSA), and 5-sulfosalicylate (5-SSA), have been synthesized and characterized by various spectroscopic techniques including ultraviolet-visible (UV-vis), infrared (IR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy,13C NMR, and elemental analysis. A detailed study of electrochemistry of all the synthesized compounds has been done to compare their oxidation and reduction mechanisms and to explain the effect of axial coordination on their redox properties.

Effects of Saccharomyces Cerevisiae Strains on Chemical Profiles of Cabernet Sauvignon Wines: Based on the Combined Results of 1H NMR, HS-SPME/GC-MS and HPLC-DAD-ESI-MS/MS

2018 ◽  
Vol 18 (2) ◽  
pp. 115-131
Author(s):  
Liang Heng-Yu ◽  
Su Ning ◽  
Guo Kun ◽  
Wang Yuan ◽  
Yang De-Yu
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Principal Component ◽  
Grape Juice ◽  
Pilot Scale ◽  
Ethyl Esters ◽  
Cabernet Sauvignon ◽  
Esi Ms ◽  
H Nmr ◽  
Chemical Profiles ◽  
Indigenous Yeasts

Five Saccharomyces cerevisiae strains (Chinese indigenous yeasts SC5, WC5, SC8, CC17 and commercial starter F15) were inoculated into Cabernet sauvignon grape must and fermented at pilot scale. For the first time, combination of 1H NMR, HS-SPME/GC-MS and HPLC-DAD-ESI-MS/MS metabonomic profiling techniques was performed to analyze the global chemical fingerprints of sampled wines at the end of alcoholic and malolactic fermentation respectively, then 13 non-volatile flavor compounds, 52 volatile organic aromas and 43 polyphenolic molecules were identified and determined correspondently. All principal component analysis (PCA) of two fermentation stages based on the analytical results of 1H NMR, HS-SPME/GC-MS and HPLC-DAD-ESI-MS/MS divided these strains into three clusters: (1) SC5 and SC8, (2) WC5 and F15 and (3) CC17. The wine fermented by indigenous yeast, CC17, showed a very unique chemical profile, such as low pH and high color intensity, reduced amino acids (including proline) and the lowest total higher alcohols levels, most of the fixed acids, glycerol, ethyl esters and anthocyanins concentrations. The statistical results indicate that CC17 strain possesses very special anabolism and catabolism abilities on such substances in grape juice and has potentiality to produce characteristic wines with high qualities.

Synthesis and properties of a benzoxazine monomer containing maleimide and biphenyl groups

2021 ◽  
pp. 095400832199674
Author(s):  
Tao Guo ◽  
Yang Fan ◽  
Chang Bo ◽  
Zhang Qi ◽  
Han Tao ◽  
...  
Keyword(s):  
Weight Loss ◽  
Loss Rate ◽  
Proton Nuclear Magnetic Resonance ◽  
Significant Weight Loss ◽  
Scanning Calorimetry ◽  
Weight Loss Rate ◽  
Reaction Heat ◽  
H Nmr ◽  
Curing Reaction ◽  
Dsc Curves

Benzoxazine resin exhibits excellent properties and is widely used in many fields. Herein, the synthesis of a novel compound, the bis(2,4-dihydro-2 H-3-(4- N-maleimido)phenyl-1,3-benzoxazinyl)biphenyl (BMIPBB), has been reported, which was synthesized by reacting N-(4-aminophenyl)maleimide (APMI), formaldehyde, and 4,4’-dihydroxybiphenyl. 1,3,5-three(4-(maleimido)phenyl)-1,3,5-triazine (TMIPT) was formed as an intermediate during the reaction. The proton nuclear magnetic resonance (1H-NMR) and Fourier transform-infrared (FTIR) spectroscopy experiments were conducted to determine the structure of BMIPBB. BMIPBB was obtained as a reddish-brown solid in 40.1% yield. The thermal properties of BMIPBB were investigated using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) techniques. Analysis of the DSC curves revealed that the broad peak representing the release of curing reaction heat appeared in the temperature range of 140–330°C. The peak temperature was 242.59°C and the heat of the reaction was 393.82 J/g, indicating that the rate of the curing reaction was low and the heat of the reaction was high. Analysis of the TGA results revealed that the weight loss rate was 5% at 110°C. The monomer exhibited a significant weight loss in the range of 320–500°C. The compound lost 50% of its weight at a temperature of 427°C.

scholarly journals Putative imbalanced amino acid metabolism in rainbow trout long term fed a plant-based diet as revealed by 1H-NMR metabolomics

2021 ◽  
Vol 10 ◽  
Author(s):  
Catherine Deborde ◽  
Blandine Madji Hounoum ◽  
Annick Moing ◽  
Mickaël Maucourt ◽  
Daniel Jacob ◽  
...  
Keyword(s):  
Amino Acids ◽  
Rainbow Trout ◽  
Amino Acid ◽  
Amino Acid Content ◽  
Proton Nuclear Magnetic Resonance ◽  
Free Form ◽  
Metabolomic Analysis ◽  
Nmr Metabolomics ◽  
H Nmr

Abstract The long-term effect of a plant (P)-based diet was assessed by proton nuclear magnetic resonance (1H-NMR) metabolomics in rainbow trout fed a marine fish meal (FM)–fish oil (FO) diet (M), a P-based diet and a control commercial-like diet (C) starting with the first feeding. Growth performances were not heavily altered by long-term feeding on the P-based diet. An 1H-NMR metabolomic analysis of the feed revealed significantly different soluble chemical compound profiles between the diets. A set of soluble chemical compounds was found to be specific either to the P-based diet or to the M diet. Pterin, a biomarker of plant feedstuffs, was identified both in the P-based diet and in the plasma of fish fed the P-based diet. 1H-NMR metabolomic analysis on fish plasma and liver and muscle tissues at 6 and 48 h post feeding revealed significantly different profiles between the P-based diet and the M diet, while the C diet showed intermediate results. A higher amino acid content was found in the plasma of fish fed the P-based diet compared with the M diet after 48 h, suggesting either a delayed delivery of the amino acids or a lower amino acid utilisation in the P-based diet. This was associated with an accumulation of essential amino acids and the depletion of glutamine in the muscle, together with an accumulation of choline in the liver. Combined with an anticipated absorption of methionine and lysine supplemented in free form, the present results suggest an imbalanced essential amino acid supply for protein metabolism in the muscle and for specific functions of the liver.

scholarly journals Time–frequency analysis of serum with proton nuclear magnetic resonance for diagnosis of pancreatic cancer

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Asahi Sato ◽  
Toshihiko Masui ◽  
Akitada Yogo ◽  
Takashi Ito ◽  
Keiko Hirakawa ◽  
...  
Keyword(s):  
Pancreatic Cancer ◽  
Carbohydrate Antigen ◽  
Serum Markers ◽  
Proton Nuclear Magnetic Resonance ◽  
Serum Samples ◽  
Time Frequency ◽  
H Nmr ◽  
Free Induction ◽  
Short Time ◽  
Long Term Survivors

AbstractAlthough serum markers such as carcinoembryonic antigen (CEA) and carbohydrate antigen (CA19-9) have been widely used in screening for pancreatic cancer (PC), their sensitivity and specificity are unsatisfactory. Recently, a novel tool of analyzing serum using the short-time Fourier transform (STFT) of free induction decays (FIDs) obtained by 1H-NMR has been introduced. We for the first time evaluated the utility of this technology as a diagnostic tool for PC. Serum was obtained from PC patients before starting any treatments. Samples taken from individuals with benign diseases or donors for liver transplantation were obtained as controls. Serum samples from both groups underwent 1H-NMR and STFT of FIDs. STFT data were analyzed by partial least squares discriminant analysis (PLS-DA) to clarify whether differences were apparent between groups. As a result, PLS-DA score plots indicated that STFT of FIDs enabled effective classification of groups with and without PC. Additionally, in a subgroup of PC, long-term survivors (≥ 2 years) could be discriminated from short-term survivors (< 2 years), regardless of pathologic stage or CEA or CA19-9 levels. In conclusion, STFT of FIDs obtained from 1H-NMR have a potential to be a diagnostic and prognostic tool of PC.

Biophysical properties of electrospun chitosan-grafted poly(lactic acid) nanofibrous scaffolds loaded with chondroitin sulfate and silver nanoparticles

2021 ◽  
pp. 088532822110464
Author(s):  
Alexandre F Júnior ◽  
Charlene A Ribeiro ◽  
Maria E Leyva ◽  
Paulo S Marques ◽  
Carlos R J Soares ◽  
...  
Keyword(s):  
Silver Nanoparticles ◽  
Lactic Acid ◽  
Proton Nuclear Magnetic Resonance ◽  
Poly Lactic Acid ◽  
Fibroblast Cells ◽  
Biophysical Properties ◽  
Electrospinning Technique ◽  
Average Pore ◽  
H Nmr ◽  
Substitution Degree

The aim of this work was to study the biophysical properties of the chitosan-grafted poly(lactic acid) (CH-g-PLA) nanofibers loaded with silver nanoparticles (AgNPs) and chondroitin-4-sulfate (C4S). The electrospun CH-g-PLA:AgNP:C4S nanofibers were manufactured using the electrospinning technique. The microstructure of the CH-g-PLA:AgNP:C4S nanofibers was investigated by proton nuclear magnetic resonance (1H-NMR), scanning electron microscopy (SEM), UV-Visible spectroscopy (UV-Vis), X-ray diffraction (XRD), and Fourier transform infrared (ATR-FTIR) spectroscopy. ATR-FTIR and 1H-NMR confirm the CH grafting successfully by PLA with a substitution degree of 33.4%. The SEM measurement results indicated apparently smooth nanofibers having a diameter range of 340 ± 18 nm with porosity of 89 ± 3.08% and an average pore area of 0.27 μm2. UV-Vis and XRD suggest that silver nanoparticles with the size distribution of 30 nm were successfully incorporated into the electrospun nanofibers. The water contact angle of 12.8 ± 2.7° reveals the hydrophilic nature of the CH-g-PLA:AgNP:C4S nanofibers has been improved by C4S. The electrospun CH-g-PLA:AgNP:C4S nanofibers are found to release ions Ag+ at a concentration level capable of rendering an antimicrobial efficacy. Gram-positive bacteria ( S.aureus) were more sensitive to CH-g-PLA:AgNP:C4S than Gram-negative bacteria ( E. coli). The electrospun CH-g-PLA:AgNP:C4S nanofibers exhibited no cytotoxicity to the L-929 fibroblast cells, suggesting cytocompatibility. Fluorescence microscopy demonstrated that C4S promotes the adhesion and proliferation of fibroblast cells onto electrospun CH-g-PLA:AgNP:C4S nanofibers.

Experimental and Computational Insights into Bis-indolylmethane Derivatives as Potent Antimicrobial Agents Inhibiting 2,2-dialkylglycine Decarboxylase

2021 ◽  
Vol 17 ◽  
Author(s):  
Dnyaneshwar T. Nagre ◽  
Bapu R. Thorat ◽  
Suraj N. Mali ◽  
Mazhar Farooqui ◽  
Brijmohan Agrawal
Keyword(s):  
Antimicrobial Agents ◽  
In Silico Analysis ◽  
Proton Nuclear Magnetic Resonance ◽  
Gas Chromatography Mass Spectrometry ◽  
Amino Acid Residues ◽  
Standard Drug ◽  
H Nmr ◽  
Highly Active ◽  
Dialkylglycine Decarboxylase

Background: A series of bis(indolyl)methanes (3a-3o) have been synthesized using a greener and new approach using the reaction of different substituted aldehydes and indole in the presence of an easily available and biodegradable base such as piperidine in acetic acid at room temperature and characterized with UV (Ultraviolet-visible spectroscopy), Gas chromatography-mass spectrometry (GC-MS), Proton nuclear magnetic resonance (H-NMR), and Fourier transform infrared spectroscopy (FTIR). Methods: All 15 newly synthesized compounds (3a-3o) were subjected to in-vitro anti-microbial activity determination and compared with the known standard drug ciprofloxacin (1-2 µg/mL). Our in-silico analysis on the target protein, pdb id: 1d7u suggested that these analogues would be highly active against bacterial targets and thus, would act as good antimicrobial agents. Results: All 15 newly synthesized compounds (3a-3o) displayed potent activity on various experimental microbial strains (1.0-1.4 µg/mL). Compound, 3k was obtained as the best docked compound against common bacterial target enzyme, (pdb id:1d7u). The standard, Ciprofloxacin, retained the docking score of -111.3 Kcal/mol with similar binding amino acid residues (LYS272 (Pi-cation); ALA A:245 (Pi-sigma); TRP A:138 (Pi-Pi); ALA A:112; and MET A:141 (Pi-alkyl)) as of inbound. Conclusion : We believe that our current study would shed more light on the development of potent bis(indolyl)methanes as antimicrobial agents.

Partition of tert-dodecyl mercaptan in systems containing styrene, polystyrene, and polybutadiene. Its effect on the macromolecular characteristics of high-impact poly styrene

e-Polymers ◽  
2007 ◽  
Vol 7 (1) ◽  
Author(s):  
Natalia Casís ◽  
Carla Vanesa Luciani ◽  
Diana Alejandra Estenoz ◽  
Marisa Martinelli ◽  
Miriam Strumia ◽  
...  
Keyword(s):  
Total Concentration ◽  
Strong Dependence ◽  
Monomer Conversion ◽  
Theoretical Work ◽  
High Impact ◽  
Proton Nuclear Magnetic Resonance ◽  
Molecular Weights ◽  
H Nmr ◽  
Dodecyl Mercaptan ◽  
Good Agreement

AbstractThis work investigates the distribution between phases of tert-dodecyl mercaptan (t-DDM) in systems containing styrene (St), polystyrene (PS), and polybutadiene (PB) with the aim of studying its effect on the molecular macrostructure of High-Impact Polystyrene (HIPS) produced via the bulk process. Experimental work involved the study of several St/PS/PB/t-DDM blends, and of 2 polymerizations of St in presence of PB (with and without t-DDM). Blends were prepared with increasing PS/St ratios to emulate monomer conversions of 7, 9, 11, 13, and 15%, employing 2 base PSs of different molar masses, and several total concentrations of t-DDM. Measurements by Proton Nuclear Magnetic Resonance (1H NMR) indicate that t-DDM is almost evenly distributed between the phases at room temperature. In addition, for samples taken along the 2 investigated polymerizations, monomer conversion, grafting efficiency, and free PS molecular weights were measured. Theoretical work involved first to model the species partitions through the Flory-Huggins theory [1]; and then, to combine such partition model with a polymerization model extended from that by Casís et al. [2]. Theoretical estimations were in good agreement with experimental determinations. Simulations suggest that t-DDM partition coefficients exhibit a weak dependence with temperature, but a strong dependence with its total concentration. Also, the combined partition/polymerization model indicates that the free PS contained in the occlusion regions exhibits lower molecular weights than that in the continuous matrix.

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