DOCSLIB.ORG

Thesis Submitted for the Degree of Doctor of Philosophy

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Thesis Submitted for the Degree of Doctor of Philosophy University of Bath PHD Phytochemistry of hydroxycoumarins from Manihot esculenta Euphorbiaceae (cassava) Alhalaseh, Lidia Award date: 2017 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: 07. Oct. 2021 Phytochemistry of hydroxycoumarins from Manihot esculenta Euphorbiaceae (Cassava) Lidia Kamal Jameel Alhalaseh A thesis submitted for the degree of Doctor of Philosophy University of Bath Department of Pharmacy and Pharmacology August 2017 COPYRIGHT Attention is drawn to the fact that copyright of this thesis rests with its author. A copy of this thesis has been supplied on condition that anyone who consults it is understood to recognise that its copyright rests with its author and they must not copy it or use material from it except as permitted by law or with the consent of the author. This thesis may be made available for consultation within the University Library and may be photocopied or lent to other libraries for the purposes of consultation. Signed on behalf of the Faculty of Science. Signed: ……………………………… Date: …………………….. 1 Abstract This is an interdisciplinary research project on cassava (Manihot esculenta Crantz, Euphorbiaceae) ultimately working towards producing cassava roots which are long-lasting, free of post-harvest physiological deterioration (PPD). It aims to contribute to ensuring food security. In cassava, scopoletin and its -glycoside scopolin are considered phytoanticipants, not phytoalexins, due to their increasing accumulation during the PPD process compared to their barely detectable levels in fresh roots. Starting with a focussed literature review on the potential of cassava, contrasted with its limitations on harvesting due to PPD, and biosynthesis along the phenylpropanoid pathway of key hydroxycoumarins, e.g. scopoletin and esculetin, the associated gaps in our current knowledge have been set out. Whether scopoletin is biosynthesized de novo from L-phenylalanine in response to stress, or whether stress prompts its release from the corresponding glycoside is unknown. Therefore, assessing hydroxycoumarin biosynthesis and quantifying their accumulation patterns have been undertaken in wild-type and transgenic plants in order to elucidate the divergence in scopoletin biosynthetic pathways. The identification of key genes on each pathway leading to scopoletin in cassava, and then exploring their functional identities using the model plant A. thaliana and genetically engineered E. coli, where the genes were isolated, cloned, and expressed, were also undertaken. Transgenic A. thaliana lines with no activity of the key enzymes on the proposed pathway, namely F6ʹH1, CCoAOMT, and EOMT, were developed. Competition feeding experiments using stable isotopically labelled potential biosynthetic intermediates showed the incorporation of labelled ferulate into scopoletin in transgenic A.t-F6´H1 and M.e-F6´H. This confirmed the activity of other hydroxylase enzymes rather than F6´H1 in the ortho-hydroxylation steps. The hydroxycoumarins of interest were isolated, characterized, and quantified in the wild type and mutant lines using chromatographic and spectroscopic techniques, mainly NMR, HR-MS, and LC- MS. Taken together, a significant contribution to knowledge about hydroxycoumarin biosynthesis has been made. 2 This Thesis is dedicated to my late father 3 Acknowledgements I express my deepest gratitude to my main supervisor Dr Ian S. Blagbrough for giving me the chance to explore freely during the 3-labworking years, and for his tireless efforts in proofreading my dissertation during writing-up. Also, for his guidance, persistent assistance, and support especially in family-related issues. I also thank my co-supervisors Dr John R. Beeching and Dr Michael G. Rowan without their valuable constructive suggestions, constant support and guidance over the course of my PhD the completion of this project would not have been achievable. Dr Shaun B. Reeksting has my gratefulness for his assistance with the LC- MS spectroscopic experiments, and for being patient and welcoming despite my fussy comments and endless repetitive analysis. I thank Dr Tim J. Woodman for his assistance with the NMR spectroscopic experiments. Thank you also to Don Perry, Andrew James, and all the technical staff in the Department of Pharmacy and Pharmacology and the Department of Biology and Biochemistry, University of Bath, for helping me to overcome many technical issues. I gratefully thank Mu´tah University, Jordan for granting me this PhD scholarship. Very special thanks to my colleagues in 5W3.20 and 4S1.52 for the friendly working environment and for all the useful scientific discussions we had which contributed considerably to this project. A special thanks to Dr Soad A. Bayoumi and Dr Shi Liu whose previous work got me inspired in cassava. Finally, my deepest thanks to my parents, parents in law, sisters and brother who were always encouraging and supportive. My greatest thanks go to my husband Dr Mohannad J. Al-Zregat for showing faith in me, for his selfless love, and for his moral and financial support. Words will never be enough to express how grateful I am to my daughters Diana and Katia for having the magical tools to draw a smile on my face even in the most difficult and stressful moments I have ever experienced. 4 Abbreviations µg microgram 4CL 4-coumarate CoA ligase 4-MU 4-methylumbelliferone ACMV African Cassava Mosaic Virus aq. aqueous att attachment site bp base pair C3´H p-coumaroyl shikimate/quinate 3´-hydroxylase C4´H cinnamate-4´-hydroxylase CAMBIA Centre for the Application of Molecular Biology to International Agriculture CBM cassava basic medium CCoAOMT caffeoyl CoA 3´-O-methyltransferase cDNA complementary DNA COMT caffeic acid methyltransferase CTAB cetyl trimethyl ammonium bromide Da Dalton DMSO dimethylsulfoxide DNA deoxyribonucleic acid EDTA ethylene diamine tetra acetic acid ESI electrospray ionization F6´H feruloyl CoA 6´-hydroxylase Fw forward GMO genetically modified organisms GST glutathione-S-transferase GT glucosyltransferase GUS β-glucuronidase gene h hour HCT shikimate: quinate hydroxycinnamoyl transferase HPLC high performance liquid chromatography HRMS high resolution mass spectrometry 5 HSQC heteronuclear single quantum coherence Hz Hertz IAA iso-amyl alcohol LB Luria-Bertani medium LB1 left border primer LC-MS liquid chromatography-mass spectrometry LLD lower limit of detection LLQ lower limit of quantification LP left primer M molar m/z mass over charge MCS multiple cloning sites MES 2-(N-morpholino)ethane-sulfonic acid mg milligram MHz mega-Hertz ml millilitre MS mass spectrometry NASC Nottingham Arabidopsis Stock Centre NCBI the National Centre for Biotechnology Information ng nanogram NMR nuclear magnetic resonance ºC degree Celsius OD optical density OMT O-methyl transferase PAL phenylalanine ammonia lyase PCR polymerase chain reaction PPD post-harvest physiological deterioration ppm parts per million PVP poly vinyl pyrrolidone RCF relative centrifugal force RE restriction enzyme Rev reverse Rf retention factor 6 RH relative humidity RNA ribonucleic acid RNAi RNA interference RNase ribonuclease ROS reactive oxygen species RP right primer RT reverse transcriptase SAM S-adenosyl-L-methionine SDS sodium dodecyl sulfate SOC super optimal broth with catabolite repression SOD superoxide dismutase SPE solid phase extraction TAE tris-acetate EDTA TIGER The Institute for Genome Research TLC thin layer chromatography Tris tris(hydroxymethyl)methylamine UDP-glucose uridine diphosphate-glucose UTR untranslated region v/v volume/volume w/v weight/volume w/w weight/weight X-Gal 5-bromo-4-chloro-3-indoyl-β-D-galactoside 7 Contents Abstract 2 Dedication 3 Acknowledgements 4 Abbreviations 5 Chapter 1. General introduction and literature review 10 1.1. Aims and objectives 10 1.2. Cassava 12 1.3. Phenylpropanoids 21 Chapter 2. The roles of hydroxycoumarins in M. esculenta and A. thaliana under normal and abiotic stress conditions 32 2.1. Introduction 32 2.2. Materials 34 2.3. General methods 36 2.4. Results and discussion 41 Chapter 3. Complementation of Arabidopsis thaliana mutants through expressing cassava O-methyltransferase genes 58 3.1. Introduction 58 3.2. Materials 61 3.3. General methods 67 3.4. Results and discussion 84 Chapter 4. Tracing scopoletin biosynthesis in wild type and transgenic M. esculenta and A. thaliana 100 4.1. Introduction 100 4.2. Materials 103 4.3. General methods 103 4.4. Results and discussion 108 8 Chapter 5. Functional expression of cassava O-methyltransferase enzymes in transgenic Escherichia coli 150 5.1. Introduction 150 5.2. Materials 154 5.3. General methods
Load more

Recommended publications
  • Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity
    toxins Article Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity Massimo Picardo 1 , Oscar Núñez 2,3 and Marinella Farré 1,* 1 Department of Environmental Chemistry, IDAEA-CSIC, 08034 Barcelona, Spain; [email protected] 2 Department of Chemical Engineering and Analytical Chemistry, University of Barcelona, 08034 Barcelona, Spain; [email protected] 3 Serra Húnter Professor, Generalitat de Catalunya, 08034 Barcelona, Spain * Correspondence: [email protected] Received: 5 October 2020; Accepted: 26 November 2020; Published: 28 November 2020 Abstract: This study presents the application of a suspect screening approach to screen a wide range of natural toxins, including mycotoxins, bacterial toxins, and plant toxins, in surface waters. The method is based on a generic solid-phase extraction procedure, using three sorbent phases in two cartridges that are connected in series, hence covering a wide range of polarities, followed by liquid chromatography coupled to high-resolution mass spectrometry. The acquisition was performed in the full-scan and data-dependent modes while working under positive and negative ionisation conditions. This method was applied in order to assess the natural toxins in the Ter River water reservoirs, which are used to produce drinking water for Barcelona city (Spain). The study was carried out during a period of seven months, covering the expected prior, during, and post-peak blooming periods of the natural toxins. Fifty-three (53) compounds were tentatively identified, and nine of these were confirmed and quantified. Phytotoxins were identified as the most frequent group of natural toxins in the water, particularly the alkaloids group.
    [Show full text]
  • PHD PHARMACOGNOSY- EMMANUEL K. KUMATIA.Pdf
    ANALGESIC AND ANTI-INFLAMMATORY CONSTITUENTS OF ANNICKIA POLYCARPA STEM AND ROOT BARKS AND CLAUSENA ANISATA ROOT A THESIS SUBMITTED IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN THE DEPARTMENT OF PHARMACOGNOSY FACULTY OF PHARMACY AND PHARMACEUTICAL SCIENCES COLLEGE OF HEALTH SCIENCES BY EMMANUEL KOFI KUMATIA KWAME NKRUMAH UNIVERSITY OF SCIENCE AND TECHNOLOGY (KNUST) KUMASI-GHANA AUGUST, 2016 DECLARATION I declare that this thesis is the product of my own research work. It does not contain any manuscript that was earlier accepted for the award of any other degree in any University nor any published work of anybody except where cited and due acknowledgments made in the text. ……………………………….. ……………………… Emmanuel Kofi Kumatia Date ………………………………… ……………………… Prof. (Mrs.) Rita Akosua Dickson Date (Supervisor) ……………………………...... ……………………… Prof. Kofi Annan Date (Supervisor) ……………………………...... ……………………… Prof. Abraham Yeboah Mensah Date (Head of Department of Pharmacognosy) ii DEDICATIONS This work is especially dedicated to my mother, Madam Veronica Akoto, my wife, Mrs. Anne Boakyewaa Anokye-Kumatia and my children, Evzen Fifii Kumatia and Eliora Nana Akua Kumatia. iii ABSTRACT Clausena anisata and Annickia polycarpa are medicinal plants used to treat various painful and inflammatory disorders among other ailments in traditional medicine. The aim of this study was to investigate the analgesic/antinociceptive and anti-inflammatory activities of the ethanol extracts of C. anisata root (CRE), A. polycarpa stem (ASE) and root barks (AR) in order to provide scientific justification for their use as anti-inflammatory and analgesic agents. Analgesic activity was evaluated using the hot plate and the acetic acid induced writhing assays. The mechanism of antinociception was evaluated by employing pharmacological antagonism assays at the opioid and cholinergic receptors in the hot plate and the writhing assays.
    [Show full text]
  • Chemical Profiles and Simultaneous Quantification of Aurantii Fructus By
    molecules Article Chemical Profiles and Simultaneous Quantification of Aurantii fructus by Use of HPLC-Q-TOF-MS Combined with GC-MS and HPLC Methods Yingjie He 1,2,† ID , Zongkai Li 3,†, Wei Wang 2, Suren R. Sooranna 4 ID , Yiting Shi 2, Yun Chen 2, Changqiao Wu 2, Jianguo Zeng 1,2, Qi Tang 1,2,* and Hongqi Xie 1,2,* 1 Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha 410128, China; [email protected] (Y.H.); [email protected] (J.Z.) 2 National and Local Union Engineering Research Center for the Veterinary Herbal Medicine Resources and Initiative, Hunan Agricultural University, Changsha 410128, China; [email protected] (W.W.); [email protected] (Y.S.); [email protected] (Y.C.); [email protected] (C.W.) 3 School of Medicine, Guangxi University of Science and Technology, Liuzhou 565006, China; [email protected] 4 Department of Surgery and Cancer, Chelsea and Westminster Hospital, Imperial College London, London SW10 9NH, UK; [email protected] * Correspondence: [email protected] (Q.T.); [email protected] (H.X.); Fax: +86-0731-8461-5293 (H.X.) † These authors contributed equally to this work. Received: 1 August 2018; Accepted: 29 August 2018; Published: 30 August 2018 Abstract: Aurantii fructus (AF) is a traditional Chinese medicine that has been used to improve gastrointestinal motility disorders for over a thousand years, but there is no exhaustive identification of the basic chemical components and comprehensive quality control of this herb. In this study, high-performance liquid chromatography coupled with quadrupole time of flight mass spectrometry (HPLC-Q-TOF-MS) and gas chromatography coupled mass spectrometry (GC-MS) were employed to identify the basic chemical compounds, and high-performance liquid chromatography (HPLC) was developed to determine the major biochemical markers from AF extract.
    [Show full text]
  • Dr. Duke's Phytochemical and Ethnobotanical Databases Chemicals Found in Ammi Majus
    Dr. Duke's Phytochemical and Ethnobotanical Databases Chemicals found in Ammi majus Activities Count Chemical Plant Part Low PPM High PPM StdDev Refernce Citation 0 5-HYDROXYMARMESIN Plant -- 10 5-METHOXY-PSORALEN Plant -- 0 5-[2-(3- Plant 1000.0 -- METHYLBUTYROXY)-3- HYDROXY-3- METHYLBUTOXY]-PS. 1 5-[2-(ACETOXY)-3- Seed 1000.0 -- HYDROXY-3- METHYLBUTOXY]- PSORALEN 21 8-METHOXY-PSORALEN Plant -- 0 8-[2-(3- Plant 100.0 -- METHYLBUTYROXY)-3- HYDROXY-3- METHYLBUTOXY]-PS. 4 ALLOIMPERATORIN Seed 1.0 -- 0 AMMAJIN Seed -- 0 AMMIDIN Plant -- 0 AMMIFURIN Seed -- 0 AMMIRIN Seed -- 1 AMMOIDIN Plant -- 0 ANGALCIN Plant -- 17 ANGELICIN Plant -- 0 ANGENOMALIN Plant -- 26 BERGAPTEN Seed 400.0 3100.0 0.22232578675103337 -- 4 CALCIUM-OXALATE Seed -- 0 CAMESOL Plant -- 0 CAMPESELOL Plant -- 0 CAMPESENIN Plant -- 0 CAMPESIN Plant -- 1 CELLULOSE Seed 224000.0 1.1650981847855737 -- 0 COUMARINIC-ACID Plant -- 0 DELTOIN Plant -- Activities Count Chemical Plant Part Low PPM High PPM StdDev Refernce Citation 0 DIHYDROOROSELSELONE Plant -- 0 DL-PIPERITONE Seed 1000.0 -- 0 EO(ASS.) Seed 10000.0 -- 0 FAT Seed 129400.0 -0.71629528571714 -- 0 FURANOCHROMONE Plant -- 0 FURANOCOUMARIN Plant -- 9 FUROCOUMARIN Plant -- 0 GLYCOSIDES Seed 10000.0 -1.1706691766863613 -- 2 HERACLENIN Seed 700.0 -- 25 IMPERATORIN Seed 100.0 8000.0 1.111306994003492 -- 8 ISOIMPERATORIN Seed -- 15 ISOPIMPINELLIN Seed -- 3 ISOQUERCETIN Seed -- 11 ISORHAMNETIN Plant -- 1 ISORHAMNETIN-3- Leaf -- GLUCOSIDE 0 ISORHAMNETIN-3- Leaf -- GLUCURONIDE 2 ISORHAMNETIN-3- Leaf -- RUTINOSIDE 0 KAEMPFEROL-7-O-
    [Show full text]
  • Jj--T) Plant Tissue [3] and Correlations of Virulence with Ability Me to Produce Toxin in Vitro [4]
    Phytochemistry. Vol. 27. No.3. pp. 767 771. 1988. {)()J I 9422/RR UOO +0.00 Printed in Greal Britain. Pergamon Journals LId. , INHIBITION OF TRICHOTHECENE TOXIN BIOSYNTHESIS BY NATURALLY OCCURRING SHIKIMATE AROMATICS A. E. DESJARDINS, R. D. PLAITNER and G. F. SPENCER Northern Regional Research Center. Agricultural Research Service. U.S. Department of Agriculture. 1815 North University Street. Peoria, Ulinois 61604, U.S.A. (Revised received 18 August 1987) Key Word Index-Umbelliferae; Leguminosae; furanocoumarins; flavonoids; Fusaria; trichothecene toxins. Abstract-Certain naturally occurring flavonoids and furanocoumarins are inhibitors of trichothecene toxin biosynthesis. These compounds block T-2 biosynthesis in liquid cultures of Fusarium sporotrichioides NRRL 3299 at concentrations substantially less than required to block fungal growth. Inhibited cultures accumulate variable amounts of trichodiene. the hydrocarbon precursor of the trichothecenes. These inhibitors appear to block the trichothecene biosynthetic pathway after formation of trichodiene and before formation of highly oxygenated trichothecenes. Exposure to these widely occurring plant shikimate aromatics may inhibit trichothecene production during plant pathogenesis. INTRODUCTION Plants produce a great diversity ofsecondary metabolites as normal constituents and as phytoalexins induced by fungal infection. Many of these compounds have been shown to inhibit fungal growth in vitro and have been postulated to similarly restrict fungal growth in plant tissues [1]. Although most research on phytoalexiris and related compounds has concerned their direct fungi­ toxicity. some plant metabolites have also shown indirect ,.. 2 toxin R '" OCOCH1CH (Meh effects such as inactivation of fungal hydrolytic enzymes Neosolaniol R '" OH [2]. Diacetoxyscirpenol R '" H Plant pathogenic species of Fusarium produce a wide variety of phytotoxic secondary metabolites including trichothecene toxins.
    [Show full text]
  • 1 Alkaloid Drugs
    1 Alkaloid Drugs Most plant alkaloids are derivatives of tertiary amines, while others contain primary, secondary or quarternary nitrogen. The basicity of individual alkaloids varies consider- ably, depending on which of the four types is represented. The pK, values (dissociation constants) lie in the range of 10-12 for very weak bases (e.g. purines), of 7-10 for weak bases (e.g. Cinchona alkaloids) and of 3-7 for medium-strength bases (e.g. Opium alkaloids). 1.1 Preparation of Extracts Alkaloid drugs with medium to high alkaloid contents (31%) Powdered drug (Lg) is mixed thoroughly with Iml 10Yo ammonia solution or 10% General method, Na,CO, solution and then extracted for lOmin with 5ml methanol under reflux. The extraction filtrate is then concentrated according to the total alltaloids of the specific drug, so that method A 100p1 contains 50-100pg total alkaloids (see drug list, section 1.4). Rarmalae semen: Powdered drug (Ig) is extracted with lOml methanol for 30min Exception under reflux. The filtrate is diluted 1:10 with methanol and 20pl is used for TLC. Strychni semen: Powdered seeds (Ig) are defatted with 20 rnl n-hexane for 30min under reflux. The defatted seeds are then extracted with lOml methanol for lOmin under reflux. A total of 30yl of the filtrate is used for TL.C. Colchici semen: Powdered seeds (1 g) are defatted with 20 ml n-hexane for 30 min under reflux. The defiitted seeds are then extracted for 15 min with 10ml chloroform. After this, 0.4ml 10% NH, is added to the mixture, shaken vigorously and allowed to stand for about 30min before fillration.
    [Show full text]
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Tuberculosis
    Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Tuberculosis Chemical Activity Count (+)-3-HYDROXY-9-METHOXYPTEROCARPAN 1 (+)-8HYDROXYCALAMENENE 1 (+)-ALLOMATRINE 1 (+)-ALPHA-VINIFERIN 3 (+)-AROMOLINE 1 (+)-CASSYTHICINE 1 (+)-CATECHIN 10 (+)-CATECHIN-7-O-GALLATE 1 (+)-CATECHOL 1 (+)-CEPHARANTHINE 1 (+)-CYANIDANOL-3 1 (+)-EPIPINORESINOL 1 (+)-EUDESMA-4(14),7(11)-DIENE-3-ONE 1 (+)-GALBACIN 2 (+)-GALLOCATECHIN 3 (+)-HERNANDEZINE 1 (+)-ISOCORYDINE 2 (+)-PSEUDOEPHEDRINE 1 (+)-SYRINGARESINOL 1 (+)-SYRINGARESINOL-DI-O-BETA-D-GLUCOSIDE 2 (+)-T-CADINOL 1 (+)-VESTITONE 1 (-)-16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 (-)-3-HYDROXY-9-METHOXYPTEROCARPAN 1 (-)-ACANTHOCARPAN 1 (-)-ALPHA-BISABOLOL 2 (-)-ALPHA-HYDRASTINE 1 Chemical Activity Count (-)-APIOCARPIN 1 (-)-ARGEMONINE 1 (-)-BETONICINE 1 (-)-BISPARTHENOLIDINE 1 (-)-BORNYL-CAFFEATE 2 (-)-BORNYL-FERULATE 2 (-)-BORNYL-P-COUMARATE 2 (-)-CANESCACARPIN 1 (-)-CENTROLOBINE 1 (-)-CLANDESTACARPIN 1 (-)-CRISTACARPIN 1 (-)-DEMETHYLMEDICARPIN 1 (-)-DICENTRINE 1 (-)-DOLICHIN-A 1 (-)-DOLICHIN-B 1 (-)-EPIAFZELECHIN 2 (-)-EPICATECHIN 6 (-)-EPICATECHIN-3-O-GALLATE 2 (-)-EPICATECHIN-GALLATE 1 (-)-EPIGALLOCATECHIN 4 (-)-EPIGALLOCATECHIN-3-O-GALLATE 1 (-)-EPIGALLOCATECHIN-GALLATE 9 (-)-EUDESMIN 1 (-)-GLYCEOCARPIN 1 (-)-GLYCEOFURAN 1 (-)-GLYCEOLLIN-I 1 (-)-GLYCEOLLIN-II 1 2 Chemical Activity Count (-)-GLYCEOLLIN-III 1 (-)-GLYCEOLLIN-IV 1 (-)-GLYCINOL 1 (-)-HYDROXYJASMONIC-ACID 1 (-)-ISOSATIVAN 1 (-)-JASMONIC-ACID 1 (-)-KAUR-16-EN-19-OIC-ACID 1 (-)-MEDICARPIN 1 (-)-VESTITOL 1 (-)-VESTITONE 1
    [Show full text]
  • Division of Pharmaceutical Biology Faculty of Pharmacy University of Helsinki
    Division of Pharmaceutical Biology Faculty of Pharmacy University of Helsinki Plant secondary metabolites in Peucedanum palustre and Angelica archangelica and their plant cell cultures Manu Juho Mikael Eeva ACADEMIC DISSERTATION To be presented with the permission of the Faculty of Pharmacy of the University of Helsinki, for public criticism in Auditorium LS.2 (A109) (Latokartanonkaari 7 – Building B) on May 21th, 2010, at 12 o´clock noon. HELSINKI 2010 Supervisors Prof. Heikki Vuorela Ph. D. (Pharm.) Division of Pharmaceutical Biology Faculty of Pharmacy, University of Helsinki, Finland Prof. Pia Vuorela Ph. D. (Pharm.) Pharmaceutical Sciences Åbo Akademi University, Turku, Finland Prof. Raimo Hiltunen Ph. D. (Pharm.) Division of Pharmaceutical Biology Faculty of Pharmacy, University of Helsinki, Finland Reviewers Prof. Riitta Julkunen-Tiitto Ph. D. Department of Biology University of Eastern Finland, Finland Prof. Juha-Pekka Salminen Ph. D. Department of Chemistry University of Turku, Finland Opponent Prof. Elín Soffía Ólafsdóttir Ph. D. (Pharm.) Faculty of Pharmacetical Sciences School of Health Sciences University of Iceland, Iceland ISBN: 978-952-10-6186-8 (paperback) ISSN 1795-7079 ISBN 978-952-10-6187-5 (PDF) http://ethesis.helsinki.fi/ Yliopistopaino, Helsinki 2010 CONTENTS 1 ACKNOWLEDGEMENTS 5 2 ABSTRACT 7 3 LIST OF ORIGINAL PUBLICATIONS 8 4 ABBREVIATIONS 9 5 INTRODUCTION 10 6 REVIEW OF THE LITERATURE 12 6.1 Botany and distribution of A. archangelica and P. palustre 12 6.2 Ethnobotany of A. archangelica and P. palustre 14 6.3
    [Show full text]
  • Supplementary Materials
    Supplementary materials: Figure S1 T-test plot of the significant difference in variables Table S1 Detail information of commercial oil samples Table S2 Retention time, scan parameters and calibration curve of target compounds Table S3 Observation of metabolites in isoflavonoids biosynthesis pathway Figure S1 T-test plot of the significant difference in variables Table S1 Detail information of commercial oil samples Sample No. Vendor Origin of raw materials Supermarket Specifications CSO1 Lin Long Wuhan, Hubei Carrefour, Wuhan 5L CSO2 Jin Longyu Wuhan, Hubei Supermarket, Wuhan 1.8L CSO3 Fu Linmen Suzhou, Jiangsu RT-MART, Wuhan 1.8L CSO4 Fu Linmen Tianjin Jingkelong Supermarket, Beijing 900mL CSO5 Zhong An Heilongjiang WU MART, Beijing 5L CSO6 Hong Qingting Chongqing Yonghui Superstore, Chongqing 5L CSO7 Ying Mai Zhongshan, Guangdong Supermarket, Chongqing 5L CSO8 Yuan Bao Guangzhou, Guangdong Carrefour, Guangzhou 5L CSO9 Jin Ye Zhenjiang, Jiangsu Supermarket, Hangzhou 1.8L CRO1 Dao Daoquan Nanjing, Jiangsu RT-MART, Wuhan 1.8L CRO2 Ao Xing Xiangyang, Hubei RT-MART, Wuhan 1.8L CRO3 Hengda Xing’an Huhehot, Inner Mongolia Jingkelong Supermarket, Beijing 500mL CRO4 Xian Can Chengdu, Sichuan Supermarket, Chongqing 900mL CRO5 Hong Qingting Chongqing Yonghui Superstores, Chongqing 1L CRO6 Wu Hu Huanggang, Hubei Supermarket, Chongqing 5L CRO7 Dao Mai Shenzhen, Guangdong Supermarket, Guangzhou 2L CRO8 Lao Xiang Shenzhen, Guangdong Carrefour, Guangzhou 900mL CRO9 Fu Linmen Maoming, Guangdong Supermarket, Chongqing 900mL CRO10 Fu Linmen Suzhou, Jiangsu Supermarket, Hangzhou 1.5L CRO11 Chu Laixiang Hangzhou, Zhejiang Supermarket, Hangzhou 1.8L CSO, Commercial soybean oil CRO, Commercial rapeseed oil Table S2 Retention time, scan parameters and calibration curve of target compounds Scan RT Precursor Daughter CE1 Daughter CE2 Tube Calibration curve R2 LOQ Liner range No.
    [Show full text]
  • Chemistry and Health Effects of Furanocoumarins in Grapefruit
    journal of food and drug analysis xxx (2016) 1e13 Available online at www.sciencedirect.com ScienceDirect journal homepage: www.jfda-online.com Review Article Chemistry and health effects of furanocoumarins in grapefruit * Wei-Lun Hung, Joon Hyuk Suh, Yu Wang Citrus Research and Education Center, Department of Food Science and Human Nutrition, University of Florida, Lake Alfred, FL, USA article info abstract Article history: Furanocoumarins are a specific group of secondary metabolites that commonly present in Received 1 September 2016 higher plants, such as citrus plants. The major furanocoumarins found in grapefruits 0 0 Received in revised form (Citrus paradisi) include bergamottin, epoxybergamottin, and 6 ,7 -dihydroxybergamottin. 2 November 2016 During biosynthesis of these furanocoumarins, coumarins undergo biochemical modifi- Accepted 3 November 2016 cations corresponding to a prenylation reaction catalyzed by the cytochrome P450 enzymes Available online xxx with the subsequent formation of furan rings. Because of undesirable interactions with several medications, many studies have developed methods for grapefruit furanocoumarin Keywords: quantification that include high-performance liquid chromatography coupled with UV anticancer activity detector or mass spectrometry. The distribution of furanocoumarins in grapefruits is bergamottin affected by several environmental conditions, such as processing techniques, storage bone health temperature, and packing materials. In the past few years, grapefruit furanocoumarins furanocoumarins have been demonstrated to exhibit several biological activities including antioxidative, grapefruit -inflammatory, and -cancer activities as well as bone health promotion both in vitro and in vivo. Notably, furanocoumarins potently exerted antiproliferative activities against cancer cell growth through modulation of several molecular pathways, such as regulation of the signal transducer and activator of transcription 3, nuclear factor-kB, phosphatidy- linositol-3-kinase/AKT, and mitogen-activated protein kinase expression.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 8,802,892 B2 Bezwada (45) Date of Patent: * Aug
    USOO8802892B2 (12) United States Patent (10) Patent No.: US 8,802,892 B2 BeZWada (45) Date of Patent: * Aug. 12, 2014 (54) FUNCTIONALIZED PHENOLIC (52) U.S. Cl. COMPOUNDS AND POLYMERS CPC ................. C08G 69/44 (2013.01); A61L 27/18 THEREFROM (2013.01); C07D 3II/36 (2013.01); C07C 69/734 (2013.01); C07C 65/24 (2013.01); (71) Applicant: Bezwada Biomedical, LLC, C08G 69/40 (2013.01); A61L 31/04 (2013.01); Hillsborough, NJ (US) C07C 65/21 (2013.01); C07D493/04 (2013.01); A61L 31/10 (2013.01); A23L 1/3002 (72) Inventor: Rao S Bezwada, Hillsborough, NJ (US) (2013.01); A23L 1/30 (2013.01); C07D 31 1/16 (73) Assignee: Bezwada Biomedical, LLC, (2013.01); A61K 2800/522 (2013.01); C07C Hillsborough, NJ (US) 69/732 (2013.01); A61 K8/37 (2013.01); C08G 63/66 (2013.01); C07C2 17/84 (2013.01); (*) Notice: Subject to any disclaimer, the term of this C07C233/25 (2013.01); C07C 69/712 patent is extended or adjusted under 35 (2013.01); A23L I/058 (2013.01); C07C233/18 U.S.C. 154(b) by 0 days. (2013.01); C07C 69/92 (2013.01); C07D 3 II/I2 (2013.01); A61O 19/08 (2013.01); This patent is Subject to a terminal dis C07C 205/37 (2013.01); A61O 19/00 (2013.01) claimer. USPC ............... 562/405:562/490; 562/493: 560/8: Appl. No.: 13/654,068 560/67; 560/70; 560/75; 560/85 (21) (58) Field of Classification Search (22) Filed: Oct. 17, 2012 CPC ........ C07C 15/04; C07C 15/24: CO7C 15/18; C07C 15/58; C07C 43/257; CO7C 43/263; (65) Prior Publication Data C07C 43/267; CO7C 43/275 USPC .............
    [Show full text]
  • Botanical Sources, Chemistry, Analysis, and Biological Activity of Furanocoumarins of Pharmaceutical Interest
    molecules Review Botanical Sources, Chemistry, Analysis, and Biological Activity of Furanocoumarins of Pharmaceutical Interest Renato Bruni 1 , Davide Barreca 2 , Michele Protti 3 , Virginia Brighenti 4, Laura Righetti 1 , Lisa Anceschi 4, Laura Mercolini 3 , Stefania Benvenuti 4, Giuseppe Gattuso 2 and Federica Pellati 4,* 1 Department of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, Italy; [email protected] (R.B.); [email protected] (L.R.) 2 Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale F. Stagno d’Alcontres 31, 98166 Messina, Italy; [email protected] (D.B.); [email protected] (G.G.) 3 Department of Pharmacy and Biotechnology (FaBiT), Alma Mater Studiorum, University of Bologna, Via Belmeloro 6, 40126 Bologna, Italy; [email protected] (M.P.); [email protected] (L.M.) 4 Department of Life Sciences, University of Modena and Reggio Emilia, Via G. Campi 103, 41125 Modena, Italy; [email protected] (V.B.); [email protected] (L.A.); [email protected] (S.B.) * Correspondence: [email protected]; Tel.: +39-059-205-8565 Received: 11 May 2019; Accepted: 6 June 2019; Published: 8 June 2019 Abstract: The aim of this work is to provide a critical review of plant furanocoumarins from different points of view, including their chemistry and biosynthetic pathways to their extraction, analysis, and synthesis, to the main biological activities found for these active compounds, in order to highlight their potential within pharmaceutical science. The limits and the possible improvements needed for research involving these molecules are also highlighted and discussed.
    [Show full text]