Identification of Plasma and Urinary Metabolites and Catabolites Derived
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Thesis of Potentially Sweet Dihydrochalcone Glycosides
University of Bath PHD The synthesis of potentially sweet dihydrochalcone glycosides. Noble, Christopher Michael Award date: 1974 Awarding institution: University of Bath Link to publication Alternative formats If you require this document in an alternative format, please contact: [email protected] General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Download date: 05. Oct. 2021 THE SYNTHESIS OF POTBTTIALLY SWEET DIHYDROCHALCOITB GLYCOSIDES submitted by CHRISTOPHER MICHAEL NOBLE for the degree of Doctor of Philosophy of the University of Bath. 1974 COPYRIGHT Attention is drawn to the fact that copyright of this thesis rests with its author.This copy of the the sis has been supplied on condition that anyone who con sults it is understood to recognise that its copyright rests with its author and that no quotation from the thesis and no information derived from it may be pub lished without the prior written consent of the author. -
Natural Sources, Pharmacokinetics, Biological Activities and Health Benefits of Hydroxycinnamic Acids and Their Metabolites
nutrients Review Natural Sources, Pharmacokinetics, Biological Activities and Health Benefits of Hydroxycinnamic Acids and Their Metabolites Matej Sova 1,* and Luciano Saso 2 1 Faculty of Pharmacy, University of Ljubljana, Aškerˇceva7, 1000 Ljubljana, Slovenia 2 Department of Physiology and Pharmacology "Vittorio Erspamer", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy; [email protected] * Correspondence: matej.sova@ffa.uni-lj.si; Tel.: +386-1-476-9556 Received: 24 June 2020; Accepted: 22 July 2020; Published: 23 July 2020 Abstract: Hydroxycinnamic acids (HCAs) are important natural phenolic compounds present in high concentrations in fruits, vegetables, cereals, coffee, tea and wine. Many health beneficial effects have been acknowledged in food products rich in HCAs; however, food processing, dietary intake, bioaccessibility and pharmacokinetics have a high impact on HCAs to reach the target tissue in order to exert their biological activities. In particular, metabolism is of high importance since HCAs’ metabolites could either lose the activity or be even more potent compared to the parent compounds. In this review, natural sources and pharmacokinetic properties of HCAs and their esters are presented and discussed. The main focus is on their metabolism along with biological activities and health benefits. Special emphasis is given on specific effects of HCAs’ metabolites in comparison with their parent compounds. Keywords: diet; natural compounds; phenolic acids; hydroxycinnamic acids; metabolites; pharmacokinetic properties; biological activities; health effects 1. Introduction Our diet rich in plant food contains several health-beneficial ingredients. Among such ingredients, polyphenols represent one of the most important natural compounds. Phenolic compounds are members of probably the largest group of plant secondary metabolites and have the main function to protect the plants against ultraviolet radiation or invasion by pathogens [1,2]. -
Flavonoid Glucodiversification with Engineered Sucrose-Active Enzymes Yannick Malbert
Flavonoid glucodiversification with engineered sucrose-active enzymes Yannick Malbert To cite this version: Yannick Malbert. Flavonoid glucodiversification with engineered sucrose-active enzymes. Biotechnol- ogy. INSA de Toulouse, 2014. English. NNT : 2014ISAT0038. tel-01219406 HAL Id: tel-01219406 https://tel.archives-ouvertes.fr/tel-01219406 Submitted on 22 Oct 2015 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Last name: MALBERT First name: Yannick Title: Flavonoid glucodiversification with engineered sucrose-active enzymes Speciality: Ecological, Veterinary, Agronomic Sciences and Bioengineering, Field: Enzymatic and microbial engineering. Year: 2014 Number of pages: 257 Flavonoid glycosides are natural plant secondary metabolites exhibiting many physicochemical and biological properties. Glycosylation usually improves flavonoid solubility but access to flavonoid glycosides is limited by their low production levels in plants. In this thesis work, the focus was placed on the development of new glucodiversification routes of natural flavonoids by taking advantage of protein engineering. Two biochemically and structurally characterized recombinant transglucosylases, the amylosucrase from Neisseria polysaccharea and the α-(1→2) branching sucrase, a truncated form of the dextransucrase from L. Mesenteroides NRRL B-1299, were selected to attempt glucosylation of different flavonoids, synthesize new α-glucoside derivatives with original patterns of glucosylation and hopefully improved their water-solubility. -
Dose-Dependent Increase in Unconjugated Cinnamic Acid Concentration in Plasma Following Acute Consumption of Polyphenol Rich Curry in the Polyspice Study
nutrients Article Dose-Dependent Increase in Unconjugated Cinnamic Acid Concentration in Plasma Following Acute Consumption of Polyphenol Rich Curry in the Polyspice Study Sumanto Haldar 1,† ID , Sze Han Lee 2,† ID , Jun Jie Tan 2, Siok Ching Chia 1, Christiani Jeyakumar Henry 1,3,* ID and Eric Chun Yong Chan 1,2,* 1 Clinical Nutrition Research Centre, Agency for Science, Technology and Research, Singapore Institute for Clinical Sciences, Singapore 117599, Singapore; [email protected] (S.H.); [email protected] (S.C.C.) 2 Department of Pharmacy, National University of Singapore, Singapore 117543, Singapore; [email protected] (S.H.L.); [email protected] (J.J.T.) 3 Department of Biochemistry, National University of Singapore, Singapore 117596, Singapore * Correspondence: [email protected] (C.J.H.); [email protected] (E.C.Y.C.); Tel.: +65-6407-0793 (C.J.H.); +65-6516-6137 (E.C.Y.C.) † Contributed equally to this work. Received: 25 June 2018; Accepted: 18 July 2018; Published: 20 July 2018 Abstract: Spices that are rich in polyphenols are metabolized to a convergent group of phenolic/aromatic acids. We conducted a dose-exposure nutrikinetic study to investigate associations between mixed spices intake and plasma concentrations of selected, unconjugated phenolic/aromatic acids. In a randomized crossover study, 17 Chinese males consumed a curry meal containing 0 g, 6 g, and 12 g of mixed spices. Postprandial blood was drawn up to 7 h at regular intervals and plasma phenolic/aromatic acids were quantified via liquid chromatography tandem mass spectrometry (LC-MS/MS). -
Journal of Pharmaceutical and Biomedical Analysis 83 (2013) 108–121
Journal of Pharmaceutical and Biomedical Analysis 83 (2013) 108–121 Contents lists available at SciVerse ScienceDirect Journal of Pharmaceutical and Biomedical Analysis jou rnal homepage: www.elsevier.com/locate/jpba The profiling and identification of the absorbed constituents and metabolites of Paeoniae Radix Rubra decoction in rat plasma and urine by the n HPLC–DAD–ESI-IT-TOF-MS technique: A novel strategy for the systematic screening and identification of absorbed constituents and metabolites from traditional Chinese medicines 1 1 Jing Liang , Feng Xu , Ya-Zhou Zhang, Shuai Huang, Xin-Yu Zang, Xin Zhao, Lei Zhang, ∗ Ming-Ying Shang, Dong-Hui Yang, Xuan Wang, Shao-Qing Cai State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, No. 38 Xueyuan Road, Beijing 100191, China a r t i c l e i n f o a b s t r a c t Article history: Paeoniae Radix Rubra (PRR, the dried roots of Paeonia lactiflora) is a commonly used traditional Chinese Received 23 January 2013 medicine (TCM). A clear understanding of the absorption and metabolism of TCMs is very important Received in revised form 13 April 2013 in their rational clinical use and pharmacological research. To find more of the absorbed constituents Accepted 16 April 2013 and metabolites of TCMs, a novel strategy was proposed. This strategy was characterized by the fol- Available online 9 May 2013 lowing: the establishment and utilization of the databases of parent compounds, known metabolites and characteristic neutral losses; the comparison of base peak chromatograms and ClogPs; and the use Keywords: n of the HPLC–DAD–ESI-IT-TOF-MS technique. -
Studies on Betalain Phytochemistry by Means of Ion-Pair Countercurrent Chromatography
STUDIES ON BETALAIN PHYTOCHEMISTRY BY MEANS OF ION-PAIR COUNTERCURRENT CHROMATOGRAPHY Von der Fakultät für Lebenswissenschaften der Technischen Universität Carolo-Wilhelmina zu Braunschweig zur Erlangung des Grades einer Doktorin der Naturwissenschaften (Dr. rer. nat.) genehmigte D i s s e r t a t i o n von Thu Tran Thi Minh aus Vietnam 1. Referent: Prof. Dr. Peter Winterhalter 2. Referent: apl. Prof. Dr. Ulrich Engelhardt eingereicht am: 28.02.2018 mündliche Prüfung (Disputation) am: 28.05.2018 Druckjahr 2018 Vorveröffentlichungen der Dissertation Teilergebnisse aus dieser Arbeit wurden mit Genehmigung der Fakultät für Lebenswissenschaften, vertreten durch den Mentor der Arbeit, in folgenden Beiträgen vorab veröffentlicht: Tagungsbeiträge T. Tran, G. Jerz, T.E. Moussa-Ayoub, S.K.EI-Samahy, S. Rohn und P. Winterhalter: Metabolite screening and fractionation of betalains and flavonoids from Opuntia stricta var. dillenii by means of High Performance Countercurrent chromatography (HPCCC) and sequential off-line injection to ESI-MS/MS. (Poster) 44. Deutscher Lebensmittelchemikertag, Karlsruhe (2015). Thu Minh Thi Tran, Tamer E. Moussa-Ayoub, Salah K. El-Samahy, Sascha Rohn, Peter Winterhalter und Gerold Jerz: Metabolite profile of betalains and flavonoids from Opuntia stricta var. dilleni by HPCCC and offline ESI-MS/MS. (Poster) 9. Countercurrent Chromatography Conference, Chicago (2016). Thu Tran Thi Minh, Binh Nguyen, Peter Winterhalter und Gerold Jerz: Recovery of the betacyanin celosianin II and flavonoid glycosides from Atriplex hortensis var. rubra by HPCCC and off-line ESI-MS/MS monitoring. (Poster) 9. Countercurrent Chromatography Conference, Chicago (2016). ACKNOWLEDGEMENT This PhD would not be done without the supports of my mentor, my supervisor and my family. -
LC-MS Resource Guide a Comprehensive Portfolio for Consistent Results in Routine and Advanced LC-MS Applications
LC-MS Resource Guide A Comprehensive Portfolio for Consistent Results in Routine and Advanced LC-MS applications The life science business of Merck KGaA, Darmstadt, Germany operates as MilliporeSigma in the U.S. and Canada. LC-MS Resource Guide Maximize the Performance of Your LC-MS Using Proven Consumables In this guide, we provide a premier selection of proven Supelco® tools and consumables that meet the requirements of scientists who primarily use the LC-MS technique for analysis of drugs, biomolecules separation and analytical assays. • Ascentis® Express Fused-Core® HPLC/ • Supel™-Select SPE Tubes and Well UHPLC Columns improve throughput Plates for sample prep needs and sensitivity, process more samples • SeQuant® ZIC-HILIC™ technique for and get drugs to market faster separation of polar and hydrophilic • BIOshell columns with Fused-Core® compounds technology for faster peptide, protein, • Samplicity® G2 filtration system for glycan, ADC and MAb Separations HPLC samples • Chromolith® HPLC columns with • Clean, low background LiChrosolv® revolutionary monolithic silica solvents and LiChropur® mobile phase technology for fast separation at low additives specifically designed for backpressure and long column life time UHPLC and LC-MS analysis even for Matrix-rich samples • Standards & Certified Reference • Purospher™ STAR columns with Materials for Accurate LC-MS Analyses outstanding batch-to-batch reproducibility and extended pH stability • LC-MS Accessories that maximize performance • Astec® CHIROBIOTIC® chiral stationary phases for -
GRAS Notice (GRN) No.901, Glucosyl Hesperidin
GRAS Notice (GRN) No. 901 https://www.fda.gov/food/generally-recognized-safe-gras/gras-notice-inventory ~~~lECTV!~ITJ) DEC 1 2 20,9 OFFICE OF FOOD ADDITI\/c SAFETY tnC Vanguard Regulator~ Services, Inc 1311 Iris Circle Broomfield, CO, 80020, USA Office: + 1-303--464-8636 Mobile: +1-720-989-4590 Email: [email protected] December 15, 2019 Dennis M. Keefe, PhD, Director, Office of Food Additive Safety HFS-200 Food and Drug Administration 5100 Paint Branch Pkwy College Park, MD 20740-3835 Re: GRAS Notice for Glucosyl Hesperidin Dear Dr. Keefe: The attached GRAS Notification is submitted on behalf of the Notifier, Hayashibara Co., ltd. of Okayama, Japan, for Glucosyl Hesperidin (GH). GH is a hesperidin molecule modified by enzymatic addition of a glucose molecule. It is intended for use as a general food ingredient, in food. The document provides a review of the information related to the intended uses, manufacturing and safety of GH. Hayashibara Co., ltd. (Hayashibara) has concluded that GH is generally recognized as safe (GRAS) based on scientific procedures under 21 CFR 170.30(b) and conforms to the proposed rule published in the Federal Register at Vol. 62, No. 74 on April 17, 1997. The publically available data and information upon which a conclusion of GRAS was made has been evaluated by a panel of experts who are qualified by scientific training and experience to assess the safety of GH under the conditions of its intended use in food. A copy of the Expert Panel's letter is attached to this GRAS Notice. -
Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues
International Journal of Molecular Sciences Article Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues Eva Heˇrmánková-Vavˇríková, Alena Kˇrenková, Lucie Petrásková, Christopher Steven Chambers, Jakub Zápal, Marek Kuzma, KateˇrinaValentová * and Vladimír Kˇren Laboratory of Biotransformation, Institute of Microbiology, Czech Academy of Sciences, Vídeˇnská 1083, CZ-142 20 Prague, Czech Republic; [email protected] (E.H.-V.); [email protected] (A.K.); [email protected] (L.P.); [email protected] (C.S.C.); [email protected] (J.Z.); [email protected] (M.K.); [email protected] (V.K.) * Correspondence: [email protected]; Tel.: +420-296-442-509 Academic Editor: Yujiro Hayashi Received: 27 April 2017; Accepted: 13 May 2017; Published: 17 May 2017 Abstract: Isoquercitrin, (IQ, quercetin-3-O-β-D-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-600. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin). The enzymatic procedure gave no products with “hydroxyaromatic” acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. -
Antioxidant and Anti-Inflammatory Activity of Citrus Flavanones Mix
antioxidants Article Antioxidant and Anti-Inflammatory Activity of Citrus Flavanones Mix and Its Stability after In Vitro Simulated Digestion Marcella Denaro †, Antonella Smeriglio *,† and Domenico Trombetta Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Palatucci, 98168 Messina, Italy; [email protected] (M.D.); [email protected] (D.T.) * Correspondence: [email protected]; Tel.: +39-090-676-4039 † Both authors contributed equally. Abstract: Recently, several studies have highlighted the role of Citrus flavanones in counteracting oxidative stress and inflammatory response in bowel diseases. The aim of study was to identify the most promising Citrus flavanones by a preliminary antioxidant and anti-inflammatory screening by in vitro cell-free assays, and then to mix the most powerful ones in equimolar ratio in order to investigate a potential synergistic activity. The obtained flavanones mix (FM) was then subjected to in vitro simulated digestion to evaluate the availability of the parent compounds at the intestinal level. Finally, the anti-inflammatory activity was investigated on a Caco-2 cell-based model stimulated with interleukin (IL)-1β. FM showed stronger antioxidant and anti-inflammatory activity with respect to the single flavanones, demonstrating the occurrence of synergistic activity. The LC-DAD-ESI- MS/MS analysis of gastric and duodenal digested FM (DFM) showed that all compounds remained unchanged at the end of digestion. As proof, a superimposable behavior was observed between FM and DFM in the anti-inflammatory assay carried out on Caco-2 cells. Indeed, it was observed that both FM and DFM decreased the IL-6, IL-8, and nitric oxide (NO) release similarly to the reference Citation: Denaro, M.; Smeriglio, A.; anti-inflammatory drug dexamethasone. -
Enhanced Protection of Biological Membranes During Lipid Peroxidation
International Journal of Molecular Sciences Article Enhanced Protection of Biological Membranes during Lipid Peroxidation: Study of the Interactions between Flavonoid Loaded Mesoporous Silica Nanoparticles and Model Cell Membranes Lucija Mandi´c 1, Anja Sadžak 1 , Vida Strasser 1, Goran Baranovi´c 2, Darija Domazet Jurašin 1 , Maja Dutour Sikiri´c 1 and Suzana Šegota 1,* 1 Ruđer Boškovi´cInstitute, Division of Physical Chemistry, 10000 Zagreb, Croatia; [email protected] (L.M.); [email protected] (A.S.); [email protected] (V.S.); [email protected] (D.D.J.); [email protected] (M.D.S.) 2 Ruđer Boškovi´cInstitute, Division of Organic Chemistry and Biochemistry, 10000 Zagreb, Croatia; [email protected] * Correspondence: [email protected]; Tel.: +385-1-456-1185 Received: 14 April 2019; Accepted: 30 May 2019; Published: 1 June 2019 Abstract: Flavonoids, polyphenols with anti-oxidative activity have high potential as novel therapeutics for neurodegenerative disease, but their applicability is rendered by their poor water solubility and chemical instability under physiological conditions. In this study, this is overcome by delivering flavonoids to model cell membranes (unsaturated DOPC) using prepared and characterized biodegradable mesoporous silica nanoparticles, MSNs. Quercetin, myricetin and myricitrin have been investigated in order to determine the relationship between flavonoid structure and protective activity towards oxidative stress, i.e., lipid peroxidation induced by the addition of hydrogen peroxide and/or Cu2+ ions. Among investigated flavonoids, quercetin showed the most enhanced and prolonged protective anti-oxidative activity. The nanomechanical (Young modulus) measurement of the MSNs treated DOPC membranes during lipid peroxidation confirmed attenuated membrane damage. -
Increasing Hesperetin Bioavailability by Modulating Intestinal Metabolism and Transport
Walter Brand Walter Increasing hesperetin bioavailabiliy by modulating intestinal metabolism and transport and metabolism intestinal by modulating bioavailabiliy hesperetin Increasing Increasing hesperetin bioavailability by modulating intestinal metabolism and transport Walter Brand Boekomslag Walter.indd 1 15-4-2010 8:51:54 Increasing hesperetin bioavailability by modulating intestinal metabolism and transport Walter Brand Thesis committee Thesis supervisors Prof. dr. ir. Ivonne M.C.M. Rietjens Professor of Toxicology Wageningen University Prof. dr. Gary Williamson Professor of Functional Food University of Leeds, UK Prof. dr. Peter J. van Bladeren Professor of Toxico-kinetics and Biotransformation Wageningen University Other members Prof. dr. Martin van den Berg, Institute for Risk Assessment Sciences, Utrecht Dr. Peter C.H. Hollman, RIKILT, Wageningen Prof. dr. Frans G.M. Russel, Radboud University Nijmegen Prof. dr. Renger F. Witkamp, Wageningen University This research was conducted under the auspices of the Graduate School VLAG Increasing hesperetin bioavailability by modulating intestinal metabolism and transport Walter Brand Thesis submitted in fulfilment of the requirements for the degree of doctor at Wageningen University by the authority of Rector Magnificus Prof. dr. M.J. Kroppf, in the presence of the Thesis Committee appointed by the Academic Board to be defended in public on Friday 28 May 2010 at 4 p.m. in the Aula Title: Increasing hesperetin bioavailability by modulating intestinal metabolism and transport 168 pages