Distinctive Patterns of Flavonoid Biosynthesis in Roots and Nodules of Datisca Glomerata and Medicago Spp
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Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: a Review
molecules Review Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: A Review Hanghang Lou 1,†, Lifei Hu 2,†, Hongyun Lu 1, Tianyu Wei 1 and Qihe Chen 1,* 1 Department of Food Science and Nutrition, Zhejiang University, Hangzhou 310058, China; [email protected] (H.L.); [email protected] (H.L.); [email protected] (T.W.) 2 Hubei Key Lab of Quality and Safety of Traditional Chinese Medicine & Health Food, Huangshi 435100, China; [email protected] * Correspondence: [email protected]; Tel.: +86-0571-8698-4316 † These authors are equally to this manuscript. Abstract: Flavonoids belong to a class of plant secondary metabolites that have a polyphenol structure. Flavonoids show extensive biological activity, such as antioxidative, anti-inflammatory, anti-mutagenic, anti-cancer, and antibacterial properties, so they are widely used in the food, phar- maceutical, and nutraceutical industries. However, traditional sources of flavonoids are no longer sufficient to meet current demands. In recent years, with the clarification of the biosynthetic pathway of flavonoids and the development of synthetic biology, it has become possible to use synthetic metabolic engineering methods with microorganisms as hosts to produce flavonoids. This article mainly reviews the biosynthetic pathways of flavonoids and the development of microbial expression systems for the production of flavonoids in order to provide a useful reference for further research on synthetic metabolic engineering of flavonoids. Meanwhile, the application of co-culture systems in the biosynthesis of flavonoids is emphasized in this review. Citation: Lou, H.; Hu, L.; Lu, H.; Wei, Keywords: flavonoids; metabolic engineering; co-culture system; biosynthesis; microbial cell factories T.; Chen, Q. -
Interpreting Sources and Endocrine Active Components of Trace Organic Contaminant Mixtures in Minnesota Lakes
INTERPRETING SOURCES AND ENDOCRINE ACTIVE COMPONENTS OF TRACE ORGANIC CONTAMINANT MIXTURES IN MINNESOTA LAKES by Meaghan E. Guyader © Copyright by Meaghan E. Guyader, 2018 All Rights Reserved A thesis submitted to the Faculty and the Board of Trustees of the Colorado School of Mines in partial fulfillment of the requirements for the degree of Doctor of Philosophy (Civil and Environmental Engineering). Golden, Colorado Date _____________________________ Signed: _____________________________ Meaghan E. Guyader Signed: _____________________________ Dr. Christopher P. Higgins Thesis Advisor Golden, Colorado Date _____________________________ Signed: _____________________________ Dr. Terri S. Hogue Professor and Department Head Department of Civil and Environmental Engineering ii ABSTRACT On-site wastewater treatment systems (OWTSs) are a suspected source of widespread trace organic contaminant (TOrC) occurrence in Minnesota lakes. TOrCs are a diverse set of synthetic and natural chemicals regularly used as cleaning agents, personal care products, medicinal substances, herbicides and pesticides, and foods or flavorings. Wastewater streams are known to concentrate TOrC discharges to the environment, particularly accumulating these chemicals at outfalls from centralized wastewater treatment plants. Fish inhabiting these effluent dominated environments are also known to display intersex qualities. Concurrent evidence of this phenomenon, known as endocrine disruption, in Minnesota lake fish drives hypotheses that OWTSs, the primary form of wastewater treatment in shoreline residences, may contribute to TOrC occurrence and the endocrine activity in these water bodies. The causative agents specific to fish in this region remain poorly understood. The objective of this dissertation was to investigate OWTSs as sources of TOrCs in Minnesota lakes, and TOrCs as potential causative agents for endocrine disruption in resident fish. -
The Metabolites of the Dietary Flavonoid Quercetin Possess Potent Antithrombotic Activity, and Interact with Aspirin to Enhance Antiplatelet Effects
The metabolites of the dietary flavonoid quercetin possess potent antithrombotic activity, and interact with aspirin to enhance antiplatelet effects Article Published Version Creative Commons: Attribution 4.0 (CC-BY) Open Access Stainer, A. R., Sasikumar, P., Bye, A. P., Unsworth, A. P., Holbrook, L. M., Tindall, M., Lovegrove, J. A. and Gibbins, J. M. (2019) The metabolites of the dietary flavonoid quercetin possess potent antithrombotic activity, and interact with aspirin to enhance antiplatelet effects. TH Open, 3 (3). e244- e258. ISSN 2512-9465 doi: https://doi.org/10.1055/s-0039- 1694028 Available at http://centaur.reading.ac.uk/85495/ It is advisable to refer to the publisher’s version if you intend to cite from the work. See Guidance on citing . To link to this article DOI: http://dx.doi.org/10.1055/s-0039-1694028 Publisher: Thieme All outputs in CentAUR are protected by Intellectual Property Rights law, including copyright law. Copyright and IPR is retained by the creators or other copyright holders. Terms and conditions for use of this material are defined in the End User Agreement . www.reading.ac.uk/centaur CentAUR Central Archive at the University of Reading Reading’s research outputs online Published online: 30.07.2019 THIEME e244 Original Article The Metabolites of the Dietary Flavonoid Quercetin Possess Potent Antithrombotic Activity, and Interact with Aspirin to Enhance Antiplatelet Effects Alexander R. Stainer1 Parvathy Sasikumar1,2 Alexander P. Bye1 Amanda J. Unsworth1,3 Lisa M. Holbrook1,4 Marcus Tindall5 Julie A. Lovegrove6 Jonathan M. Gibbins1 1 Institute for Cardiovascular and Metabolic Research, School of Address for correspondence Jonathan M. -
Combinatorial Biosynthesis of Non-Bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms Sueharu Horinouchi
J. Antibiot. 61(12): 709–728, 2008 THE JOURNAL OF REVIEW ARTICLE ANTIBIOTICS Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms Sueharu Horinouchi Received: August 1, 2008 / Accepted: October 14, 2008 © Japan Antibiotics Research Association Abstract One of the approaches of combinatorial biosynthesis is combining genes from different organisms and designing a new set of gene clusters to produce bioactive compounds, leading to diversification of both chemical and natural product libraries. This makes efficient use of the potential of the host organisms, especially when microorganisms are used. An Escherichia coli system, in which artificial biosynthetic pathways for production of plant-specific medicinal polyketides, such as flavonoids, stilbenoids, isoflavonoids, and curcuminoids, are assembled, has been designed and expressed. Starting with amino acids tyrosine and phenylalanine as substrates, this system yields naringenin, resveratrol, genistein, and curcumin, for example, all of which are beneficial to human health because of their wide variety of biological activities. Supplementation of unnatural carboxylic acids to the recombinant E. coli cells carrying the artificial pathways by precursor-directed biosynthesis results in production of unnatural compounds. Addition of decorating or modification enzymes to the artificial pathway leads to production of natural and unnatural flavonols, flavones, and methylated resveratrols. This microbial system is promising for construction of larger libraries by employing other polyketide synthases and decorating enzymes of various origins. In addition, the concept of building and expressing artificial biosynthetic pathways for production of non-bacterial and unnatural compounds in microorganisms should be successfully applied to production of not only plant-specific polyketides but also many other useful compound classes. -
Development and Optimization of a High Sensitivity LC-MS/MS Method for the Determination of Hesperidin and Naringenin in Rat Plasma: Pharmacokinetic Approach
molecules Article Development and Optimization of a High Sensitivity LC-MS/MS Method for the Determination of Hesperidin and Naringenin in Rat Plasma: Pharmacokinetic Approach Jesús Alfredo Araujo-León 1,* , Rolffy Ortiz-Andrade 2, Rivelino Armando Vera-Sánchez 1, Julio Enrique Oney-Montalvo 1, Tania Isolina Coral-Martínez 1 and Zulema Cantillo-Ciau 3 1 Chromatography Laboratory, Chemistry Faculty, Autonomous University of Yucatan, Mérida 97069, Mexico; [email protected] (R.A.V.-S.); [email protected] (J.E.O.-M.); [email protected] (T.I.C.-M.) 2 Pharmacology Laboratory, Chemistry Faculty, Autonomous University of Yucatan, Mérida 97069, Mexico; rolff[email protected] 3 Medicinal Chemistry Laboratory, Chemistry Faculty, Autonomous University of Yucatan, Mérida 97069, Mexico; [email protected] * Correspondence: [email protected]; Tel.: +52-999-922-5708 Academic Editor: Derek J. McPhee Received: 6 August 2020; Accepted: 12 September 2020; Published: 16 September 2020 Abstract: The purpose of this study was to develop, optimize, and fully validate a high-sensitivity methodology using UHPLC-MS/MS to simultaneously quantify hesperidin and naringenin in microsamples (100 µL) of murine plasma after intragastric administration of single pure flavonoids and a mixture. The optimization process allowed for high sensitivity with detection limits of approximately picogram order using an electrospray ionization (ESI) source in negative mode and an experiment based on multiple reaction monitoring (MRM). The validation parameters showed excellent linearity and detection limits, with a precision of less than 8% and a recovery of over 90%. This methodology was applied to compare the pharmacokinetic parameters for the administration of hesperidin and naringenin in individual form or in the form of a mixture. -
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. -
Function-Structural Study of Anti-LDL-Oxidation Effects of Flavonoid Phytochemicals
Journal of Medicinal Plants Research Vol. 6(49), pp. 5895-5904, 25 December, 2012 Available online at http://www.academicjournals.org/JMPR DOI: 10.5897/JMPR12.313 ISSN 1996-0875 ©2012 Academic Journals Full Length Research Paper Function-structural study of anti-LDL-oxidation effects of flavonoid phytochemicals Yiwen Yao 1#, Shuqing Liu 2#, Chunmei Guo 3, Chunyan Zhang 3, Dachang Wu 3, Yixin Ren 2, Hong-Shan Yu 4, Ming-Zhong Sun 3 and Hailong Chen 5* 1Department of Otolaryngology, the First affiliated Hospital of Dalian Medical University, Dalian 116011, China. 2Department of Biochemistry, Dalian Medical University, Dalian 116044, China. 3Department of Biotechnology, Dalian Medical University, Dalian 116044, China. 4School of Bioengineering, Dalian Polytechnic University, Dalian 116034, China. 5Department of Surgery, the First Affiliated Hospital of Dalian Medical University, Dalian 116011, China Accepted 9 March, 2012 As a large group of polyphenolic phytochemicals with excellent anti-oxidation properties, the dietary flavonoid intakes have been shown to be negatively correlated with the incidence of coronary artery disease. Flavonoid compounds potentially inhibit the oxidation of low-density lipoprotein (Ox-LDL) that triggers the generation of a series of oxidation byproducts playing important roles in atherosclerosis development. The diverse inhibitory effects of different flavonoid phytochemicals on Ox-LDL might be closely associated with their intrinsic structures. In current work, we investigated the effects of eight flavonoid phytochemicals in high purity (>95%) with similar core structure on the susceptibility of LDL to Cu 2+ -induced oxidative modification. The results indicated that quercetin, rutin, isoquercitrin, hesperetin, naringenin, hesperidin, naringin and icariin could reduce the Cu 2+ -induced-LDL oxidation by 59.56 ±±±7.03, 46.53 ±±±2.09, 40.52 ±±±4.65, 22.67 ±±±1.68, 20.87 ±±±2.43, 12.34 ±±±2.09, 10.87 ±±±1.68 and 3.53 ±±±3.20%, respectively. -
IN SILICO ANALYSIS of FUNCTIONAL Snps of ALOX12 GENE and IDENTIFICATION of PHARMACOLOGICALLY SIGNIFICANT FLAVONOIDS AS
Tulasidharan Suja Saranya et al. Int. Res. J. Pharm. 2014, 5 (6) INTERNATIONAL RESEARCH JOURNAL OF PHARMACY www.irjponline.com ISSN 2230 – 8407 Research Article IN SILICO ANALYSIS OF FUNCTIONAL SNPs OF ALOX12 GENE AND IDENTIFICATION OF PHARMACOLOGICALLY SIGNIFICANT FLAVONOIDS AS LIPOXYGENASE INHIBITORS Tulasidharan Suja Saranya, K.S. Silvipriya, Manakadan Asha Asokan* Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Viswa Vidyapeetham University, AIMS Health Sciences Campus, Kochi, Kerala, India *Corresponding Author Email: [email protected] Article Received on: 20/04/14 Revised on: 08/05/14 Approved for publication: 22/06/14 DOI: 10.7897/2230-8407.0506103 ABSTRACT Cancer is a disease affecting any part of the body and in comparison with normal cells there is an elevated level of lipoxygenase enzyme in different cancer cells. Thus generation of lipoxygenase enzyme inhibitors have suggested being valuable. Individual variation was identified by the functional effects of Single Nucleotide Polymorphisms (SNPs). 696 SNPs were identified from the ALOX12 gene, out of which 73 were in the coding non-synonymous region, from which 8 were found to be damaging. In silico analysis was performed to determine naturally occurring flavonoids such as isoflavones having the basic 3- phenylchromen-4-one skeleton for the pharmacological activity, like Genistein, Diadzein, Irilone, Orobol and Pseudobaptigenin. O-methylated isoflavones such as Biochanin, Calycosin, Formononetin, Glycitein, Irigenin, 5-O-Methylgenistein, Pratensein, Prunetin, ψ-Tectorigenin, Retusin and Tectorigenine were also used for the study. Other natural products like Aesculetin, a coumarin derivative; flavones such as ajoene and baicalein were also used for the comparative study of these natural compounds along with acteoside and nordihydroguaiaretic acid (antioxidants) and active inhibitors like Diethylcarbamazine, Zileuton and Azelastine as standard for the computational analysis. -
Absorption and Pharmacokinetics of Grapefruit Flavanones in Beagles
Downloaded from British Journal of Nutrition (2007), 98, 86–92 doi: 10.1017/S0007114507707262 q The Authors 2007 https://www.cambridge.org/core Absorption and pharmacokinetics of grapefruit flavanones in beagles Maria de Lourdes Mata-Bilbao1, Cristina Andre´s-Lacueva1, Elena Roura1, Olga Ja´uregui2, Elvira Escribano3, 4 1 Celina Torre and Rosa Maria Lamuela-Ravento´s * . IP address: 1Department of Nutrition and Food Science, CerTA, Faculty of Pharmacy, University of Barcelona, Av. Joan XXIII s/n, Barcelona, Spain 2 Scientific and Technical Services, University of Barcelona, Barcelona, Spain 170.106.35.229 3Biopharmaceutics and Pharmacokinetics Unit, Faculty of Pharmacy, University of Barcelona, Av. Joan XXIII s/n, Barcelona, Spain 4Affinity Pet-care, Barcelona, Spain , on (Received 25 August 2006 – Revised 8 January 2007 – Accepted 24 January 2007) 29 Sep 2021 at 02:36:36 The present study evaluated the pharmacokinetics of three different grapefruit flavanone forms in dog plasma and demonstrated their absorption after an oral intake of a grapefruit extract; pharmacokinetic parameters of these forms were also determined. Ten healthy beagles were adminis- tered 70 mg citrus flavonoids as a grapefruit extract contained in capsules, while two additional dogs were used as controls and given an excipient. The grapefruit flavanone naringin, along with its metabolites naringenin and naringenin glucuronide, was detected in dog plasma. Blood , subject to the Cambridge Core terms of use, available at samples were collected between 0 and 24 h after administration of the extract. Naringin reached its maximun plasma concentration at around 80 min, whereas naringenin and naringenin glucuronide reached their maximun plasma concentrations at around 20 and 30 min, respectively. -
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. -
Nominators Pharmacy Compounding
Fagron North America, IACP, NCPA: Nominators Pharmacy Compounding Advisory Committee review of Chrysin June 23, 2016 Chrysin • Naturally occurring bioflavonoid and polyphenolic compound • Found in passion flower indian trumpet flower, honeycomb, chamomile and oyster mushrooms Chrysin • Bioflavonoids such as chrysin can act as chemical messengers • Necessary in the production of plant pigmentations • Involved in UV filtration • Influence the symbiotic relationships of nitrogen fixation Chrysin • FDA has stated that it is a small molecule, can be characterized easily, and is relatively stable under ordinary storage conditions • Chrysin actually has a molecular size of 254.2375 g/mol • Molecular weight consistent with that of steroid hormones Oral supplement dosing • Because of low bioavailability oral dosing is typically referenced at 400 mg – 3 g Br J Clin Pharmacol. 2001 Feb; 51(2): 143–146. Disposition and metabolism of the flavonoid chrysin in normal volunteers T Walle, Y Otake, J A Brubaker, U K Walle, and P V Halushka Conculsion Even though the systemic availability of chrysin appears to be low, this does not exclude the occurrence of local biological effects of the flavonoid, particularly in the intestine. In summary, this study supports the view that the bioavailability of chrysin, and possibly other flavonoids, in humans is very low, due to extensive presystemic intestinal as well as hepatic glucuronidation… Topical administration feasibility • It has been shown in the study of trans dermal drug delivery systems that one of the main criteria for feasibility of drug delivery through the skin is small molecular size of 500 Daltons or less • Other references states that unionized entities have better absorption.