(12) Patent Application Publication (10) Pub. No.: US 2015/0140141 A1 Milow Et Al
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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. -
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. -
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. -
Flesh Color Diversity of Sweet Potato: an Overview of the Composition, Functions, Biosynthesis, and Gene Regulation of the Major Pigments
Phyton-International Journal of Experimental Botany Tech Science Press DOI:10.32604/phyton.2020.011979 Review Flesh Color Diversity of Sweet Potato: An Overview of the Composition, Functions, Biosynthesis, and Gene Regulation of the Major Pigments Hanna Amoanimaa-Dede, Chuntao Su, Akwasi Yeboah, Chunhua Chen, Shaoxia Yang, Hongbo Zhu* and Miao Chen* Department of Biotechnology, College of Agricultural Sciences, Guangdong Ocean University, Zhanjiang, 524088, China ÃCorresponding Authors: Hongbo Zhu. Email: [email protected]; Chen Miao. Email: [email protected] Received: 08 June 2020; Accepted: 31 July 2020 Abstract: Sweet potato is a multifunctional root crop and a source of food with many essential nutrients and bioactive compounds. Variations in the flesh color of the diverse sweet potato varieties are attributed to the different phytochemicals and natural pigments they produce. Among them, carotenoids and anthocyanins are the main pigments known for their antioxidant properties which provide a host of health benefits, hence, regarded as a major component of the human diet. In this review, we provide an overview of the major pigments in sweet potato with much emphasis on their biosynthesis, functions, and regulatory control. More- over, current findings on the molecular mechanisms underlying the biosynthesis and accumulation of carotenoids and anthocyanins in sweet potato are discussed. Insights into the composition, biosynthesis, and regulatory control of these major pigments will further advance the biofortification of sweet potato and provide a reference for breeding carotenoid- and anthocyanin-rich varieties. Keywords: Anthocyanin; biosynthesis; carotenoid; flesh color; sweet potato 1 Introduction Sweet potato [Ipomoea batatas (L.) Lam.] is a dicot perennial Convolvulaceae plant cultivated as an annual crop. -
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. -
The Role of Extractives in the Natural Durability of the Heartwood of Dicorynia Guianensis Amsh
The role of extractives in the natural durability of the heartwood of Dicorynia guianensis Amsh: new insights in antioxydant and antifungal properties Jean-Baptiste Say Anouhe, Florence Bobelé Niamké, Milcard Faustin, David Virieux, Jean-Luc Pirat, Augustin Amissa Adima, Seraphin Kati-Coulibaly, Nadine Amusant To cite this version: Jean-Baptiste Say Anouhe, Florence Bobelé Niamké, Milcard Faustin, David Virieux, Jean-Luc Pirat, et al.. The role of extractives in the natural durability of the heartwood of Dicorynia guianensis Amsh: new insights in antioxydant and antifungal properties. Annals of Forest Science, Springer Nature (since 2011)/EDP Science (until 2010), 2018, 75 (1), pp.15. 10.1007/s13595-018-0691-0. hal-01779497 HAL Id: hal-01779497 https://hal.umontpellier.fr/hal-01779497 Submitted on 26 May 2020 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. Copyright Annals of Forest Science (2018) 75: 15 https://doi.org/10.1007/s13595-018-0691-0 ORIGINAL PAPER The role of extractives in the natural durability of the heartwood of Dicorynia guianensis -
Evaluation of Anticancer Activities of Phenolic Compounds In
EVALUATION OF ANTICANCER ACTIVITIES OF PHENOLIC COMPOUNDS IN BLUEBERRIES AND MUSCADINE GRAPES by WEIGUANG YI (Under the Direction of CASIMIR C. AKOH) ABSTRACT Research has shown that diets rich in phenolic compounds may be associated with lower risk of several chronic diseases including cancer. This study systematically evaluated the bioactivities of phenolic compounds in blueberries and muscadine grapes, and assessed their potential cell growth inhibition and apoptosis induction effects using two colon cancer cell lines (HT-29 and Caco-2), and one liver cancer cell line (HepG2). In addition, the absorption of blueberry anthocyanin extracts was evaluated using Caco-2 human intestinal cell monolayers. Polyphenols in three blueberry cultivars (Briteblue, Tifblue and Powderblue), and four cultivars of muscadine (Carlos, Ison, Noble, and Supreme) were extracted and freeze dried. The extracts were further separated into phenolic acids, tannins, flavonols, and anthocyanins using a HLB cartridge and LH20 column. In both blueberries and muscadine grapes, some individual phenolic acids and flavonoids were identified by HPLC with more than 90% purity in anthocyanin fractions. The dried extracts and fractions were added to the cell culture medium to test for cell growth inhibition and induction of apoptosis. Polyphenols from both blueberries and muscadine grapes had significant inhibitory effects on cancer cell growth. The phenolic acid fraction showed relatively lower bioactivities with 50% inhibition at 0.5-3 µg/mL. The intermediate bioactivities were observed in the flavonol and tannin fractions. The greatest inhibitory effect among all four fractions was from the anthocyanin fractions in the three cell lines. Cell growth was significantly inhibited more than 50% by the anthocyanin fractions at concentrations of 15-300 µg/mL. -
Assembly of a Novel Biosynthetic Pathway for Production of the Plant Flavonoid Fisetin in Escherichia Coli
Downloaded from orbit.dtu.dk on: Oct 06, 2021 Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli Stahlhut, Steen Gustav; Siedler, Solvej; Malla, Sailesh; Harrison, Scott James; Maury, Jerome; Neves, Ana Rute; Förster, Jochen Published in: Metabolic Engineering Link to article, DOI: 10.1016/j.ymben.2015.07.002 Publication date: 2015 Document Version Publisher's PDF, also known as Version of record Link back to DTU Orbit Citation (APA): Stahlhut, S. G., Siedler, S., Malla, S., Harrison, S. J., Maury, J., Neves, A. R., & Förster, J. (2015). Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli. Metabolic Engineering, 31, 84-93. https://doi.org/10.1016/j.ymben.2015.07.002 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 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. Metabolic Engineering 31 (2015) 84–93 Contents lists available at ScienceDirect Metabolic Engineering journal homepage: www.elsevier.com/locate/ymben Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli Steen G. -
Flavonoid Glycosides from Chromolaena Odorata Leaves and Their in Vitro Cytotoxic Activity
January 2011 Note Chem. Pharm. Bull. 59(1) 129—131 (2011) 129 Flavonoid Glycosides from Chromolaena odorata Leaves and Their in Vitro Cytotoxic Activity ,a,b a,c c b c Tran Manh HUNG,* To Dao CUONG, Nguyen Hai DANG, Shu ZHU, Pham Quoc LONG, b a Katsuko KOMATSU, and Byung Sun MIN a College of Pharmacy, Catholic University of Daegu; Gyeongsan 712–702, Korea: b Division of Pharmacognosy, Department of Medicinal Resources, Institute of Natural Medicine, University of Toyama; 2630 Sugitani, Toyama 930–0194, Japan: and c Institute of Natural Product Chemistry, Vietnamese Academic of Science and Technology; 18 Hoang Quoc Viet, Hanoi, Vietnam. Received September 6, 2010; accepted October 8, 2010 Two new flavonoid glycosides, (1, 2), and eleven known compounds, (3—13), were isolated from from a 70% EtOH extract of the leaves of Chromolaena odorata (Asteraceae). Their structures were elucidated by 1D and 2D NMR spectroscopic interpretation as well as by chemical studies. The newly isolated compounds were tested in vitro for their cytotoxic activities against the LLC and HL-60 cancer cell lines. Compound 1 showed cytotoxicity against LLC and HL-60 cancer cell lines with IC50 values of 28.2 and 11.6 mM, respectively. Compound 2 exhib- ited significant cytotoxic activity in the inhibition of HL-60 cancer cell lines with IC50 value of 10.8 mM. Key words Chromolaena odorata; Asteraceae; flavonoid glycoside; cytotoxic 12—16,18,21) Chromolaena odorata (L.) KING et ROBINSON (Eupatorium comparison of spectral data with the literature data. odoratum L., family Asteraceae) is a diffuse, scrambling Compound 1 was obtained as a yellowish powder. -
Ep 2858641 B1
(19) TZZ __T (11) EP 2 858 641 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 31/352 (2006.01) A61K 31/35 (2006.01) 06.09.2017 Bulletin 2017/36 A61P 17/00 (2006.01) A61Q 1/06 (2006.01) A61Q 1/14 (2006.01) A61K 8/49 (2006.01) (2006.01) (2006.01) (21) Application number: 13800034.4 A61K 8/60 A61Q 17/04 A61Q 19/08 (2006.01) A61K 8/86 (2006.01) A61Q 19/10 (2006.01) A61K 8/97 (2017.01) (22) Date of filing: 06.06.2013 A61K 8/99 (2017.01) A61Q 19/00 (2006.01) (86) International application number: PCT/US2013/044464 (87) International publication number: WO 2013/184884 (12.12.2013 Gazette 2013/50) (54) IMPROVED METHODS FOR BOTANICAL AND/OR ALGAE EXTRACTION VERBESSERTES VERFAHREN FÜR PFLANZEN- UND/ODER ALGENEXTRAKTION PROCÉDÉS AMÉLIORÉS POUR L’EXTRACTION DE VÉGÉTAUX ET/OU D’ALGUES (84) Designated Contracting States: • JUDD, Christopher AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Riverhead, NY 11901 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • RICHTER, Nicole Jeannine PL PT RO RS SE SI SK SM TR Port Jefferson, NY 11777 (US) (30) Priority: 06.06.2012 US 201261656221 P (74) Representative: Herzog, Fiesser & Partner Patentanwälte PartG mbB (43) Date of publication of application: Isartorplatz 1 15.04.2015 Bulletin 2015/16 80331 München (DE) (73) Proprietors: (56) References cited: • BASF Corporation WO-A1-2011/140655 KR-B1- 100 741 644 Florham Park, NJ 07932 (US) US-A1- 2006 078 633 US-A1- 2006 099 690 • BASF Beauty Care Solutions France SAS US-A1- 2011 190 175 69007 Lyon (FR) • MINUTH, T. -
05 Chapter 1.Pdf
5 CHAPTER I INTRODUCTION GENERAL PATHWAYS OF MICROBIAL DEGRADATION OF AROMATIC COMPOUNDS A number of microorganisms can perform various types of reactions (Fonken and Johnson, 1972; Beukers et al., 1972) such as oxidation, reduction, hydrolysis, esterification, phosphorylation etc. These enzymatic reactions enable the microorganism to either synthesize or degrade complex organic compounds with ease. Such studies have become important from both fundamental and applied considerations. The microorganisms which are frequently used are fungi or bacteria. A great deal of work has been done on the microbiological transformation of steroids (Charney and Herzog, 1967) and a number of transformations have actually been exploited for commercial applications (Briggs and Brotherton, 1970). To cite an example, cortisone (l) an adrenocorticoid hormone which was effective against rheumatoid arthritis, a grave crippling disease was prepared by a sequence of chemical reaction from bile acids involving 32 steps (Peterson, 1963; Briggs and Brotherton, 1970). The formidable step was the introduction of an oxygen function (Carbonyl group) in the position 11 of the steroidal nucleus. With the combined chemical and microbial methods, the sequence of steps was reduced to only 12. Amongst steroids, the compounds studied are hormones of androstane Biit ocidt and pregnane series, estrogens, bile acids, cardenolides and bufadienolides. Studies have also been carried out on the microbial transformation of terpenes (Ciegler, 1969; Abbott and Cledhill, 1971), carbohydrates (Vezinae et al., 1968) and alkaloids (lizuka and Naito, 1967; Vining, 1969). Besides these compounds the microbial transforma tion studies were also reported on antibiotics (Sebek and Perlman, 1971; Sebek, 1974), herbicides (Kaufman and Kearney, 1976) and pesticides (Bollag, 1974) etc.