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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. -
Pharmacokinetic Interactions Between Herbal Medicines and Drugs: Their Mechanisms and Clinical Relevance
life Review Pharmacokinetic Interactions between Herbal Medicines and Drugs: Their Mechanisms and Clinical Relevance Laura Rombolà 1 , Damiana Scuteri 1,2 , Straface Marilisa 1, Chizuko Watanabe 3, Luigi Antonio Morrone 1, Giacinto Bagetta 1,2,* and Maria Tiziana Corasaniti 4 1 Preclinical and Translational Pharmacology, Department of Pharmacy, Health and Nutritional Sciences, Section of Preclinical and Translational Pharmacology, University of Calabria, 87036 Rende, Italy; [email protected] (L.R.); [email protected] (D.S.); [email protected] (S.M.); [email protected] (L.A.M.) 2 Pharmacotechnology Documentation and Transfer Unit, Preclinical and Translational Pharmacology, Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036 Rende, Italy 3 Department of Physiology and Anatomy, Tohoku Pharmaceutical University, 981-8558 Sendai, Japan; [email protected] 4 School of Hospital Pharmacy, University “Magna Graecia” of Catanzaro and Department of Health Sciences, University “Magna Graecia” of Catanzaro, 88100 Catanzaro, Italy; [email protected] * Correspondence: [email protected]; Tel.: +39-0984-493462 Received: 28 May 2020; Accepted: 30 June 2020; Published: 4 July 2020 Abstract: The therapeutic efficacy of a drug or its unexpected unwanted side effects may depend on the concurrent use of a medicinal plant. In particular, constituents in the medicinal plant extracts may influence drug bioavailability, metabolism and half-life, leading to drug toxicity or failure to obtain a therapeutic response. This narrative review focuses on clinical studies improving knowledge on the ability of selected herbal medicines to influence the pharmacokinetics of co-administered drugs. Moreover, in vitro studies are useful to anticipate potential herbal medicine-drug interactions. -
1 Termite Feeding Deterrent from Japanese Larch Wood K. Chen A, W
Termite feeding deterrent from Japanese larch wood K. Chen a, W. Ohmurab, S. Doic, M. Aoyamad* a Kunming University of Science and Technology, Kunming, People’s Republic of China b Forestry and Forest Products Research Institute, Tsukuba 305-8687, Japan c Institute of Wood Technology, Akita Prefectural University, Noshiro 016-0876, Japan d Laboratory of Bioresource Science, Department of Applied Chemistry, Kitami Institute of Technology, Kitami 090-8507, Japan Abstract Extraction of flavonoids from Japanese larch (Larix leptolepis) wood with water was carried out to prepare a termite feeding deterrent. A two-stage procedure for the extraction was adopted. The first extraction step was performed at ambient temperature (22C) and the second at elevated temperatures ranging 50-100C. The first step mainly gave a mixture of polysaccharides together with small amount of flavonoids. At the *Corresponding author. I will move to new laboratory (kitami Institute of Technology) in January, 2004. I can not, at present, supply my facsimile number and e-mail address. They will be available at the time of proof-reading. 1 second step, the yield of extract and its chemical composition were greatly affected by the temperature. The yield of solubilised carbohydrates steadily increased with a rise in the temperature, while the overall yield of flavonoids reached its optimum at 70C. An additional increase in the temperature resulted in a decrease in the yield. Model experiments using dihydroflavonols confirmed the occurrence of oxidative dehydrogenation and/or intramolecular rearrangement during the hydrothermal treatment at higher temperatures. The crude water extracts showed strong feeding deterrent activities against the subterranean termite, Coptotermes formosanus, in a choice paper disc assay. -
Coptis Japonica</Emphasis>
Plant Cell Reports (1988) 7:1-4 Plant Cell Reports © Springer-Verlag 1988 Alternative final steps in berberine biosynthesis in Coptisjaponica cell cultures E. Galneder 1 M. Rueffer 1, G. Wanner 1, 2, M. Tabata 1, 3, and M. H. Zenk 1 1 Lehrstuhl tar Pharmazeutische Biologie der Universitfit Mfinchen, Karlstrasse 29, D-8000 Mt~nchen 2, Federal Republic of Germany 2 Botanisches Institut der Universitfit Miinchen, Menzinger Strasse 67, D-8000 Manchen 19, Federal Republic of Germany 3 Faculty of Pharmaceutical Sciences, Kyoto University, Kyoto 606, Japan Received October 30, 1987 - Communicated by K. Hahlbrock ABSTRACT oxidase (STOX) reported from our laboratory (Amann et al., 1984) in that the Coptis enzyme dehydrogenated In Coptis japonica cell cultures an alternative path- only (S)-canadine while other tetrahydroprotober- way has been discovered which leads from (S)-tetra- berines were reported to be inactive. In further hydrocolumbamine via (S)-canadine to berberine. The contrast to the STOX enzyme, their enzyme did not two enzymes involved have been partially purified. produce hydrogen peroxide but rather H20 as one of (S)-Tetrahydrocolumbamine is stereospecifically the reaction products. Our analysis of the Coptis transformed into (S)-canadine under formation of the system reported here led to the surprising result methylenedioxy bridge in ring A. This new enzyme was that the terminal two steps in the biosynthesis of named (S)-canad/ne synthase. (S)-Canadine in turn is berberine in 8erberis and Coptis are biochemically stereospecifically dehydrogenated to berberine by an completely different while similar at the cytological oxidase, (S)-canadine oxidase (COX), which was level. -
Guava (Psidium Guajava L.) Leaves: Nutritional Composition, Phytochemical Profile, and Health-Promoting Bioactivities
foods Review Guava (Psidium guajava L.) Leaves: Nutritional Composition, Phytochemical Profile, and Health-Promoting Bioactivities Manoj Kumar 1 , Maharishi Tomar 2, Ryszard Amarowicz 3,* , Vivek Saurabh 4 , M. Sneha Nair 5, Chirag Maheshwari 6, Minnu Sasi 7, Uma Prajapati 4, Muzaffar Hasan 8, Surinder Singh 9, Sushil Changan 10 , Rakesh Kumar Prajapat 11, Mukesh K. Berwal 12 and Varsha Satankar 13 1 Chemical and Biochemical Processing Division, ICAR—Central Institute for Research on Cotton Technology, Mumbai 400019, India; [email protected] 2 ICAR—Indian Grassland and Fodder Research Institute, Jhansi 284003, India; [email protected] 3 Institute of Animal Reproduction and Food Research, Polish Academy of Sciences, Tuwima 10 Str., 10-748 Olsztyn, Poland 4 Division of Food Science and Postharvest Technology, ICAR—Indian Agricultural Research Institute, New Delhi 110012, India; [email protected] (V.S.); [email protected] (U.P.) 5 Department of Nutrition and Dietetics, Faculty of Allied Health Sciences, Manav Rachna International Institute of Research and Studies, Faridabad 121004, Haryana, India; [email protected] 6 Department of Agriculture Energy and Power, ICAR—Central Institute of Agricultural Engineering, Bhopal 462038, India; [email protected] 7 Division of Biochemistry, ICAR—Indian Agricultural Research Institute, New Delhi 110012, India; [email protected] 8 Agro Produce Processing Division, ICAR—Central Institute of Agricultural Engineering, Citation: Kumar, M.; Tomar, M.; Bhopal 462038, India; [email protected] 9 Amarowicz, R.; Saurabh, V.; Nair, Dr. S.S. Bhatnagar University Institute of Chemical Engineering and Technology, Panjab University, Chandigarh 160014, India; [email protected] M.S.; Maheshwari, C.; Sasi, M.; 10 Division of Crop Physiology, Biochemistry and Post-Harvest Technology, ICAR—Central Potato Research Prajapati, U.; Hasan, M.; Singh, S.; Institute, Shimla 171001, India; [email protected] et al. -
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. -
Chondroprotective Agents
Europaisches Patentamt J European Patent Office © Publication number: 0 633 022 A2 Office europeen des brevets EUROPEAN PATENT APPLICATION © Application number: 94109872.5 © Int. CI.6: A61K 31/365, A61 K 31/70 @ Date of filing: 27.06.94 © Priority: 09.07.93 JP 194182/93 Saitama 350-02 (JP) Inventor: Niimura, Koichi @ Date of publication of application: Rune Warabi 1-718, 11.01.95 Bulletin 95/02 1-17-30, Chuo Warabi-shi, 0 Designated Contracting States: Saitama 335 (JP) CH DE FR GB IT LI SE Inventor: Umekawa, Kiyonori 5-4-309, Mihama © Applicant: KUREHA CHEMICAL INDUSTRY CO., Urayasu-shi, LTD. Chiba 279 (JP) 9-11, Horidome-cho, 1-chome Nihonbashi Chuo-ku © Representative: Minderop, Ralph H. Dr. rer.nat. Tokyo 103 (JP) et al Cohausz & Florack @ Inventor: Watanabe, Koju Patentanwalte 2-5-7, Tsurumai Bergiusstrasse 2 b Sakado-shi, D-30655 Hannover (DE) © Chondroprotective agents. © A chondroprotective agent comprising a flavonoid compound of the general formula (I): (I) CM < CM CM wherein R1 to R9 are, independently, a hydrogen atom, hydroxyl group, or methoxyl group and X is a single bond or a double bond, or a stereoisomer thereof, or a naturally occurring glycoside thereof is disclosed. The 00 00 above compound strongly inhibits proteoglycan depletion from the chondrocyte matrix and exhibits a function to (Q protect cartilage, and thus, is extremely effective for the treatment of arthropathy. Rank Xerox (UK) Business Services (3. 10/3.09/3.3.4) EP 0 633 022 A2 BACKGROUND OF THE INVENTION 1 . Field of the Invention 5 The present invention relates to an agent for protecting cartilage, i.e., a chondroprotective agent, more particularly, a chondroprotective agent containing a flavonoid compound or a stereoisomer thereof, or a naturally occurring glycoside thereof. -
Microgram Journal, Vol 3, Number 2
MICROGRAM Laboratory Operations Division Office Of Science And Drug Abuse Prevention BUREAU OF NARCOTICS & DANGEROUS DRUGS / U.S. DEPARTMENT OF JUSTICE / WASHINGTION, D.C. 20537 Vol.III, No. 2 March-April, 1970 STP (4-Methyl-2,5-dimethoxyamphetamine) hydrochloride was found coating the inside of capsules sent to BNDDfrom Germany. The capsules were clear, hard gelatin, standard shape size No. o. Average weight was 114 milligrams. Each capsule had a white crystalline coating on inner surface of capsule body. Apparently a measu~ed amount of solution had been placedin the cap·sule body, after which it was rotated to spread the solution on the inner surface. The substance contained 8. 7 milli grams STP (DOM)HCl per ca·psule. · These were the first STP capsules of this type seen by our laboratory. A few years ago, capsules were ob tained in the U.S. similarly coated with LSD. STP (Free Base) on laboratory filter paper, also from Germany, was seen for the first time in our laboratory. The STP spots, containing approxi mately 8 miliigrams STP base each, were 5/8 to 3/4 inch in diameter. The paper was 1\ inches square. Phencyclidine (Free Base) was recently analyzed on parsley leaves. Called "Angel DUst, 11 the phencyclidine on two samples of leaves was 2.6% and 3.6%. Approximately thirty pounds of 94% pure powder was also analyzed. (For identification of phencyclidine base, see Microgram, II, 1, p.3 (Jan 1969). IMITATIONSof well-known drug products are examined frequently in our Special Testing and Research Laboratory. Many of these are well made preparations and closely resemble the imitated product. -
Isolation, Identification and Characterization of Allelochemicals/Natural Products
Isolation, Identification and Characterization of Allelochemicals/Natural Products Isolation, Identification and Characterization of Allelochemicals/Natural Products Editors DIEGO A. SAMPIETRO Instituto de Estudios Vegetales “Dr. A. R. Sampietro” Universidad Nacional de Tucumán, Tucumán Argentina CESAR A. N. CATALAN Instituto de Química Orgánica Universidad Nacional de Tucumán, Tucumán Argentina MARTA A. VATTUONE Instituto de Estudios Vegetales “Dr. A. R. Sampietro” Universidad Nacional de Tucumán, Tucumán Argentina Series Editor S. S. NARWAL Haryana Agricultural University Hisar, India Science Publishers Enfield (NH) Jersey Plymouth Science Publishers www.scipub.net 234 May Street Post Office Box 699 Enfield, New Hampshire 03748 United States of America General enquiries : [email protected] Editorial enquiries : [email protected] Sales enquiries : [email protected] Published by Science Publishers, Enfield, NH, USA An imprint of Edenbridge Ltd., British Channel Islands Printed in India © 2009 reserved ISBN: 978-1-57808-577-4 Library of Congress Cataloging-in-Publication Data Isolation, identification and characterization of allelo- chemicals/natural products/editors, Diego A. Sampietro, Cesar A. N. Catalan, Marta A. Vattuone. p. cm. Includes bibliographical references and index. ISBN 978-1-57808-577-4 (hardcover) 1. Allelochemicals. 2. Natural products. I. Sampietro, Diego A. II. Catalan, Cesar A. N. III. Vattuone, Marta A. QK898.A43I86 2009 571.9’2--dc22 2008048397 All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying or otherwise, without the prior permission of the publisher, in writing. The exception to this is when a reasonable part of the text is quoted for purpose of book review, abstracting etc. -
Phytochem Referenzsubstanzen
High pure reference substances Phytochem Hochreine Standardsubstanzen for research and quality für Forschung und management Referenzsubstanzen Qualitätssicherung Nummer Name Synonym CAS FW Formel Literatur 01.286. ABIETIC ACID Sylvic acid [514-10-3] 302.46 C20H30O2 01.030. L-ABRINE N-a-Methyl-L-tryptophan [526-31-8] 218.26 C12H14N2O2 Merck Index 11,5 01.031. (+)-ABSCISIC ACID [21293-29-8] 264.33 C15H20O4 Merck Index 11,6 01.032. (+/-)-ABSCISIC ACID ABA; Dormin [14375-45-2] 264.33 C15H20O4 Merck Index 11,6 01.002. ABSINTHIN Absinthiin, Absynthin [1362-42-1] 496,64 C30H40O6 Merck Index 12,8 01.033. ACACETIN 5,7-Dihydroxy-4'-methoxyflavone; Linarigenin [480-44-4] 284.28 C16H12O5 Merck Index 11,9 01.287. ACACETIN Apigenin-4´methylester [480-44-4] 284.28 C16H12O5 01.034. ACACETIN-7-NEOHESPERIDOSIDE Fortunellin [20633-93-6] 610.60 C28H32O14 01.035. ACACETIN-7-RUTINOSIDE Linarin [480-36-4] 592.57 C28H32O14 Merck Index 11,5376 01.036. 2-ACETAMIDO-2-DEOXY-1,3,4,6-TETRA-O- a-D-Glucosamine pentaacetate 389.37 C16H23NO10 ACETYL-a-D-GLUCOPYRANOSE 01.037. 2-ACETAMIDO-2-DEOXY-1,3,4,6-TETRA-O- b-D-Glucosamine pentaacetate [7772-79-4] 389.37 C16H23NO10 ACETYL-b-D-GLUCOPYRANOSE> 01.038. 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL- Acetochloro-a-D-glucosamine [3068-34-6] 365.77 C14H20ClNO8 a-D-GLUCOPYRANOSYLCHLORIDE - 1 - High pure reference substances Phytochem Hochreine Standardsubstanzen for research and quality für Forschung und management Referenzsubstanzen Qualitätssicherung Nummer Name Synonym CAS FW Formel Literatur 01.039. -
Figure S1. Heat Map of R (Pearson's Correlation Coefficient)
Figure S1. Heat map of r (Pearson’s correlation coefficient) value among different samples including replicates. The color represented the r value. Figure S2. Distributions of accumulation profiles of lipids, nucleotides, and vitamins detected by widely-targeted UPLC-MC during four fruit developmental stages. The colors indicate the proportional content of each identified metabolites as determined by the average peak response area with R scale normalization. PS1, 2, 3, and 4 represents fruit samples collected at 27, 84, 125, 165 Days After Anthesis (DAA), respectively. Three independent replicates were performed for each stages. Figure S3. Differential metabolites of PS2 vs PS1 group in flavonoid biosynthesis pathway. Figure S4. Differential metabolites of PS2 vs PS1 group in phenylpropanoid biosynthesis pathway. Figure S5. Differential metabolites of PS3 vs PS2 group in flavonoid biosynthesis pathway. Figure S6. Differential metabolites of PS3 vs PS2 group in phenylpropanoid biosynthesis pathway. Figure S7. Differential metabolites of PS4 vs PS3 group in biosynthesis of phenylpropanoids pathway. Figure S8. Differential metabolites of PS2 vs PS1 group in flavonoid biosynthesis pathway and phenylpropanoid biosynthesis pathway combined with RNA-seq results. Table S1. A total of 462 detected metabolites in this study and their peak response areas along the developmental stages of apple fruit. mix0 mix0 mix0 Index Compounds Class PS1a PS1b PS1c PS2a PS2b PS2c PS3a PS3b PS3c PS4a PS4b PS4c ID 1 2 3 Alcohols and 5.25E 7.57E 5.27E 4.24E 5.20E -
Pharmacological Activities and Biologically Active Compounds Of
Research Signpost 37/661 (2), Fort P.O., Trivandrum-695 023, Kerala, India Phytochemistry: Advances in Research, 2006: 87-103 ISBN: 81-308-0034-9 Editor: Filippo Imperato Pharmacological activities and biologically active compounds 4 of Bulgarian medicinal plants Stephanie Ivancheva, Milena Nikolova and Reneta Tsvetkova Department of Applied Botany, Institute of Botany, Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria Abstract Bulgarian medicinal plants, which have been studied during the last years, are reviewed. The review includes the following families: Amaryllidaceae, Asteraceae, Berberidaceae, Boraginaceae, Fabaceae, Geraniaceae, Lamiaceae, Oleaceae, Onagraceae, Scrophulariaceae, Solanaceae, Ranunculaceae, Rosaceae, Rutaceae, Valerianaceae, Zygophyllaceae. Main pharmacological properties are antiviral, antimicrobial, antioxidative, anti-inflammatory, antiseptic, spasmolytic, sedative and hypotensive. Correspondence/Reprint request: Dr. Stephanie Ivancheva, Department of Applied Botany, Institute of Botany Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria. E-mail: [email protected] 88 Stephanie Ivancheva et al. Introduction Bulgaria is situated in the Balkan peninsula, South-East Europe, between 22˚ 21’ 40” and 28˚ 36’ 35” E longitude, and 41˚ 14’ 05” and 44˚ 12’ 45” N latitude, occupies the area of 110 912 km2 with elevations ranging from 0 to 2925 m and has corresponding subalpine, Mediterranean and continental climates. The relief of the country is quite diverse ranging from plains to low hills and high mountains. The climate is moderate continental to modified continental, but in southern regions reflects rather a strong Mediterranean influence. As a result of this climatic conditions the Bulgarian flora is remarkable for its diversity (3500 plant species including 600 known medicinal plants) [1]. Bulgarian Flora has become very famous for the treatment of Parkinson disease with Atropa belladonna L.