Increasing Hesperetin Bioavailability by Modulating Intestinal Metabolism and Transport
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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. -
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. -
Glycosides in Lemon Fruit
Food Sci. Technol. Int. Tokyo, 4 (1), 48-53, 1998 Characteristics of Antioxidative Flavonoid Glycosides in Lemon Fruit Yoshiaki MIYAKE,1 Kanefumi YAMAMOT0,1 Yasujiro MORIMITSU2 and Toshihiko OSAWA2 * Central Research Laboratory of Pokka Corporation, Ltd., 45-2 Kumanosyo, Shikatsu-cho, Nishikasugai-gun, Aichi 481, Japan 2Department of Applied Biological Sciences, Nagoya University, Nagoya 46401, Japan Received June 12, 1997; Accepted September 27, 1997 We investigated the antioxidative flavonoid glycosides in the peel extract of lemon fruit (Citrus limon). Six flavanon glycosides: eriocitrin, neoeriocitrin, narirutin, naringin, hesperidin, and neohesperidin, and three flavone glycosides: diosmin, 6~-di- C-p-glucosyldiosmin (DGD), and 6- C-p-glucosyldiosmin (GD) were identified by high- performance liquid chromatography (HPLC) analysis. Their antioxidative activity was examined using a linoleic acid autoxidation system. The antioxidative activity of eriocitrin, neoeriocitrin and DGD was stronger than that of the others. Flavonoid glycosides were present primarily in the peel of lemon fruit. There was only a small difference in the content of the flavonoid glycosides of the lemon fruit juice from various sources and varieties. Lemon fruit contained abundant amounts of eriocitrin and hesperidin and also contained narirutin, diosmin, and DGD, but GD, neoeriocitrin, naringin, and neohesperidin were present only in trace amounts. The content of DGD, GD, and eriocitrin was especially abundant in lemons and limes; however, they were scarcely found in other citrus fruits. The content of flavonoid compounds in lemon juice obtained by an in-line extractor at a juice factory was more abundant than that obtained by hand-squeezing. These compounds were found to be stable even under heat treatment conditions (121'C, 15 min) in acidic solution. -
GRAS Notice (GRN) No. 719, Orange Pomace
GRAS Notice (GRN) No. 719 https://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS/NoticeInventory/default.htm SAFETY EVALUATION DOSSIER SUPPORTING A GENERALLY RECOGNIZED AS SAFE (GRAS) CONCLUSION FOR ORANGE POMACE SUBMITTED BY: PepsiCo, Inc. 700 Anderson Hill Road Purchase, NY 10577 SUBMITTED TO: U.S. Food and Drug Administration Center for Food Safety and Applied Nutrition Office of Food Additive Safety HFS-200 5100 Paint Branch Parkway College Park, MD 20740-3835 CONTACT FOR TECHNICAL OR OTHER INFORMATION: Andrey Nikiforov, Ph.D. Toxicology Regulatory Services, Inc. 154 Hansen Road, Suite 201 Charlottesville, VA 22911 July 3, 2017 Table of Contents Part 1. SIGNED STATEMENTS AND CERTIFICATION ...........................................................1 A. Name and Address of Notifier .............................................................................................1 B. Name of GRAS Substance ...................................................................................................1 C. Intended Use and Consumer Exposure ................................................................................1 D. Basis for GRAS Conclusion ................................................................................................2 E. Availability of Information ..................................................................................................3 Part 2. IDENTITY, METHOD OF MANUFACTURE, SPECIFICATIONS, AND PHYSICAL OR TECHNICAL EFFECT.................................................................................................4 -
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. -
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. -
Flavone Synthases from Lonicera Japonica and L. Macranthoides
www.nature.com/scientificreports OPEN Flavone synthases from Lonicera japonica and L. macranthoides reveal differential flavone Received: 14 October 2015 Accepted: 09 December 2015 accumulation Published: 12 January 2016 Jie Wu1,2, Xiao-Chen Wang2,3, Yang Liu1,2, Hui Du1, Qing-Yan Shu1, Shang Su1,2, Li-Jin Wang1,2, Shan-Shan Li1 & Liang-Sheng Wang1 Flavones are important secondary metabolites found in many plants. In Lonicera species, flavones contribute both physiological and pharmaceutical properties. However, flavone synthase (FNS), the key enzyme responsible for flavone biosynthesis, has not yet been characterized inLonicera species. In this study, FNSII genes were identified fromLonicera japonica Thunb. and L. macranthoides Hand.- Mazz. In the presence of NADPH, the recombinant cytochrome P450 proteins encoded by LjFNSII-1.1, LjFNSII-2.1, and LmFNSII-1.1 converted eriodictyol, naringenin, and liquiritigenin to the corresponding flavones directly. The different catalytic properties between LjFNSII-2.1 and LjFNSII-1.1 were caused by a single amino acid substitution at position 242 (glutamic acid to lysine). A methionine at position 206 and a leucine at position 381 contributed considerably to the high catalytic activity of LjFNSII-1.1. In addition, LjFNSII-1.1&2.1 and LmFNSII-1.1 also biosynthesize flavones that were further modified by O-glycosylation in transgenic tobacco. The expression levels of the FNSII genes were consistent with flavone accumulation patterns in flower buds. Our findings suggested that the weak catalytic activity of LmFNSII-1.1 and the relatively low expression of LmFNSII-1.1 in flowers might be responsible for the low levels of flavone accumulation in flower buds ofL. -
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. -
Biochemical Characterization of a Flavonoid O-Methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
molecules Article Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production 1, 2, 1 1 1 Hye Lin Park y, Jae Chul Lee y, Kyungha Lee , Jeong Min Lee , Hyo Jeong Nam , Seong Hee Bhoo 1,3, Tae Hoon Lee 2,3, Sang-Won Lee 1,* and Man-Ho Cho 1,3,* 1 Department of Genetic Engineering, Kyung Hee University, Yongin 17104, Korea; [email protected] (H.L.P.); [email protected] (K.L.); [email protected] (J.M.L.); [email protected] (H.J.N.); [email protected] (S.H.B.) 2 Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea; [email protected] (J.C.L.); [email protected] (T.H.L.) 3 Global Center for Pharmaceutical Ingredient Materials, Kyung Hee University, Yongin 17104, Korea * Correspondence: [email protected] (S.-W.L.); [email protected] (M.-H.C.) These authors equally contributed to this work. y Academic Editors: Sławomir Dresler and Barbara Hawrylak-Nowak Received: 3 September 2020; Accepted: 25 September 2020; Published: 28 September 2020 Abstract: Methylation is a common structural modification that can alter and improve the biological activities of natural compounds. O-Methyltransferases (OMTs) catalyze the methylation of a wide array of secondary metabolites, including flavonoids, and are potentially useful tools for the biotechnological production of valuable natural products. An OMT gene (PfOMT3) was isolated from perilla leaves as a putative flavonoid OMT (FOMT). Phylogenetic analysis and sequence comparisons showed that PfOMT3 is a class II OMT. -
Characterization of a Flavonoid 3'/5'/7-O-Methyltransferase
molecules Article Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the In Vitro Cytotoxicity of Its Methylated Products 1,2,3, 1,2,3, 1,2,3 1,2,3 1,2,3 Xiaojuan Liu y, Yue Wang y , Yezhi Chen , Shuting Xu , Qin Gong , Chenning Zhao 1,2,3, Jinping Cao 1,2,3 and Chongde Sun 1,2,3,* 1 College of Agriculture & Biotechnology, Zhejiang University, Zijingang Campus, Hangzhou 310058, China; [email protected] (X.L.); [email protected] (Y.W.); [email protected] (Y.C.); [email protected] (S.X.); [email protected] (Q.G.); [email protected] (C.Z.); [email protected] (J.C.) 2 Zhejiang Provincial Key Laboratory of Horticultural Plant Integrative Biology, Zhejiang University, Zijingang Campus, Hangzhou 310058, China 3 The State Agriculture Ministry Laboratory of Horticultural Plant Growth, Development and Quality Improvement, Zhejiang University, Zijingang Campus, Hangzhou 310058, China * Correspondence: [email protected]; Tel.: +86-0571-8898-2229 These authors contributed equally to this work. y Received: 18 January 2020; Accepted: 12 February 2020; Published: 15 February 2020 Abstract: O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. -
Urinary Excretion of Flavonoids Reflects Even Small Changes in the Dietary Intake of Fruits and Vegetables
Cancer Epidemiology, Biomarkers & Prevention 843 Urinary Excretion of Flavonoids Reflects Even Small Changes in the Dietary Intake of Fruits and Vegetables Asgeir Brevik,1 Salka Elbøl Rasmussen,2 Christian A. Drevon,1 and Lene Frost Andersen1 1Institute for Nutrition Research, School of Medicine, University of Oslo, Oslo, Norway and 2Department of Toxicology and Risk Assessment, Danish Institute for Food and Veterinary Research, Søborg, Denmark Abstract Background: Due to the random and systematic mea- Following a 2-week washout and a 1 week run-in pe- surement errors associated with current dietary assess- riod, the regimens were switched between the groups. ment instruments, there is a need to develop more Results: An increased intake of mixed fruits and vegeta- objective methods of measuring the intake of foods of bles from 2 to 5 servings per day significantly enhanced importance to human health. Objective: The purpose urinary excretion of eriodictyol, naringenin, hesperetin, of this study was to test whether urinary excretion of quercetin, kaempferol, isorhamnetin, and tamarixetin. flavonoids could be used to identify subjects who are The citrus flavonoids naringenin and hesperetin meeting Norwegian recommendations for fruit and showed a steep dose-response relationship to dietary vegetable intake (5 servings per day) from individuals intake of fruits and vegetables, whereas the associa- who are consuming the national average amount of tion to eriodictyol, quercetin, kaempferol, isorhamne- fruits and vegetables (2 servings per day). Design: tin, and tamarixetin was more moderate. Conclusion: Twenty-four-hour urine samples were collected in a The present study indicates that urinary excretion of strict crossover controlled feeding study. -
Molecules 2015, 20, 18031-18046; Doi:10.3390/Molecules201018031 OPEN ACCESS
Molecules 2015, 20, 18031-18046; doi:10.3390/molecules201018031 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Plasma Pharmacokinetics of Polyphenols in a Traditional Japanese Medicine, Jumihaidokuto, Which Suppresses Propionibacterium acnes-Induced Dermatitis in Rats Takashi Matsumoto 1,*, Yousuke Matsubara 1, Yasuharu Mizuhara 1, Kyoji Sekiguchi 1, Junichi Koseki 1, Kazuaki Tsuchiya 1, Hiroaki Nishimura 2, Junko Watanabe 1, Atsushi Kaneko 1, Kazuya Maemura 1, Tomohisa Hattori 1 and Yoshio Kase 1 1 Tsumura Research Laboratories, Kampo Scientific Strategies Division, Tsumura & Co., Ibaraki 300-1192, Japan; E-Mails: [email protected] (Y.M.); [email protected] (Y.M.); [email protected] (K.S.); [email protected] (J.K.); [email protected] (K.T.); [email protected] (J.W.); [email protected] (A.K.); [email protected] (K.M.); [email protected] (T.H.); [email protected] (Y.K.) 2 Kampo Formulations Development Center, Production Division, Tsumura & Co., Ibaraki 300-1192, Japan; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +81-29-889-3852; Fax: +81-29-889-3870. Academic Editor: Marcello Iriti Received: 26 August 2015 / Accepted: 27 September 2015 / Published: 30 September 2015 Abstract: Most orally administered polyphenols are metabolized, with very little absorbed as aglycones and/or unchanged forms. Metabolic and pharmacokinetic studies are therefore necessary to understand the pharmacological mechanisms of polyphenols. Jumihaidokuto (JHT), a traditional Japanese medicine, has been used for treatment of skin diseases including inflammatory acne.