DOCSLIB.ORG

Contributions to Betalain Biochemistry

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Contributions to Betalain Biochemistry Contributions to Betalain Biochemistry New structures, condensation reactions, and vacuolar transport Dissertation zur Erlangung des akademischen Grades doctor rerum naturalium (Dr. rer. nat.) vorgelegt der Mathematisch-Naturwissenschaftlich-Technischen Fakultät (mathematisch-naturwissenschaftlicher Bereich) der Martin-Luther-Universität Halle-Wittenberg von Naoko Kobayashi geb. am 21.11.1967 in Toronto Gutachter: 1. Prof. D. Strack 2. Prof. T. Hartmann 3. Prof. T. M. Kutchan Halle (Saale), 20. 11. 2002 urn:nbn:de:gbv:3-000004594 [http://nbn-resolving.de/urn/resolver.pl?urn=nbn%3Ade%3Agbv%3A3-000004594] Danksagung Diese Arbeit wurde im Institut für Pflanzenbiochemie (IPB) in Halle (Saale) in der Abteilung Sekundärstoffwechsel unter der Anleitung von Herrn Prof. Dr. Dieter Strack angefertigt. Ich möchte mich bei Herrn Prof. D. Strack sehr herzlich für die Überlassung des interessanten Themas, die gute Betreuung und das Interesse am Forschritt der Arbeit bedanken. Mein besonderer Dank gilt Herrn Dr. Willibald Schliemann (IPB) für die engagierte Betreuung meiner Arbeit und die vielen wertvollen Diskussionen. Herrn Prof. Dr. Enrico Martinoia und Herrn Dr. Markus Klein, Institut de Botanique, Laboratoire de Physiologie Végétale, Université de Neuchâtel, Neuchâtel (Schweiz), danke ich für die Betreuung der Arbeit zum Vakuolentransport. Mein Dank gilt Herrn Prof. Dr. Nicolaus Amrhein, ETH Zürich (Schweiz), und Herrn Dr. Alfred Baumert (IPB), die mir AIP, ein PAL-Inhibitor, und (S)-4-Thiaprolin zur Verfügung stellten. Herrn Dr. Hartmut Böhm, Deutsches Institut für Ernährungsforschung, Bergholz-Rehbrücke, danke ich für die Überlassung von Hairy-Root-Kulturen der Gelben Rübe. Frau Dr. Inna Kuzovkina, K. A. Timiryasev Institut für Pflanzenphysiologie, Russische Akademie der Wissenschaften, Moskau (Russland), danke ich für die Überlassung von Hairy- Root-Kulturen der Roten Bete. Herrn Dr. Lothar Frese, Bundesanstalt für Züchtungsforschung an Kulturpflanzen, Braunschweig, danke ich für Samen der Gelben Rübe und Herrn Ralf Dehn, Botanischer Garten, Martin-Luther-Universität, Halle, für Blüten und Früchte verschiedener Kakteen. Herrn Dr. Jürgen Schmidt (IPB) danke ich für die LC-MS Analysen. Herrn Dr. Victor Wray, Herrn Dr. Manfred Nimtz und Herrn Dr. Michael Kiess (GBF, Braunschweig) danke ich für die 1H-NMR-, die Zucker- und Aminosäure-Analysen. Bei allen Mitarbeitern der Abteilung Sekundärstoffwechsel bedanke ich mich für die freundliche Arbeitsatmosphäre und die Unterstützung im Labor. Mein besonderer Dank gilt Frau Barbara Kolbe für die Unterstützung und die Toleranz. Ebenso möchte ich mich bei Herrn Dr. Thomas Fester, Herrn Dr. Thomas Vogt und Dr. Bettina Hause für wertvolle Diskussionen bedanken. Frau Christine Kaufmann danke ich für die Unterstützung bei grafischen Arbeiten und Frau Annette Kohlberg für die fotografischen Arbeiten. Den Mitarbeitern der Gärtnerei danke ich für die Anzucht und Pflege meiner Versuchspflanzen. Mein Forschungsaufenthalt in IPB wurde durch die Deutsche Forschungsgemeinschaft (Stelle und Sachmittel) dankenswerker Weise unterstützt. Parts from this thesis has been published and presented in lectures and posters above all in securing the priority. Publications SCHLIEMANN, W., KOBAYASHI, N., STRACK, D. (1999) The decisive step in betaxanthin bio- synthesis is a spontaneous reaction. Plant Physiol. 119, 1217-1232. KOBAYASHI, N., SCHMIDT, J., NIMTZ, M., WRAY, V., SCHLIEMANN, W. (2000) Betalains from Christmas cactus. Phytochemistry 54, 419-426. KOBAYASHI, N., SCHMIDT, J., WRAY, V., SCHLIEMANN, W. (2001) Formation and occurrence of dopamine-derived betacyanins. Phytochemistry 56, 429-436. YAMAMOTO, K., KOBAYASHI, N., YOSHITAMA, K., TERAMOTO, S., KOMAMINE, A. (2001) Isolation and purification of tyrosine hydroxylase from callus cultures of Portulaca grandiflora. Plant Cell Physiol. 42, 969-975. Lectures KOBAYASHI, N., SCHLIEMANN, W., STRACK, D. Betaxanthin biosynthesis in the hairy root culture of Beta vulgaris L. subsp. vulgaris ‘Golden Beet’ (Garden Beet Group) Laboratoire de Physiologie végétale, Université de Neuchâtel (Switzerland), May 14, 1998 SCHLIEMANN, W., KOBAYASHI, N., STEINER, U., STRACK, D. Spontaneous reactions in betalain biosynthesis 4th Dutch-German Workshop on Regulation of Secondary Metabolism, Bad Herrenalb, September 27-29,1998 KOBAYASHI, N., SCHLIEMANN, W., STRACK, D. Betaxanthin formation in plants and hairy root cultures of Beta vulgaris L. Chiba University, Faculty of Pharmaceutical Sciences, Laboratory of Molecular Biology and Biotechnology, Research Center of Medicinal Resources, Chiba (Japan), December 18, 1998 KOBAYASHI, N., SCHMIDT, J., NIMTZ, M., WRAY, V., SCHLIEMANN, W. Betalains from Christmas cactus (Schlumbergera x buckleyi) XXth International Conference on Polyphenols, Freising-Weihenstephan, September 11-15, 2000 Posters SCHLIEMANN, W., KOBAYASHI, N., STEINER, U., STRACK, D. Non-enzymic steps in betalain biosynthesis Botanical Congress, Bremen, August 30 - September 6, 1998 KOBAYASHI, N., SCHLIEMANN, W., STRACK, D. Is the last step in betalain biosynthesis an enzymic or a spontaneous process? 4th Dutch-German Workshop on Regulation of Secondary Metabolism, Bad Herrenalb, September 27-29,1998 SCHLIEMANN, W., KOBAYASHI, N., STEINER, U. S., VOGT, T., STRACK, D. Enzymic and molecular analysis of betalain biosynthesis 75th Annual Meeting of the American Society of Plant Physiologists, Baltimore, MD, USA, July 24-28,1999 KOBAYASHI, N., SCHMIDT, J., SCHLIEMANN, W. Metabolic formation and occurrence of dopamine-derived betacyanins Symposium „Secondary plant products. Botany - Natural Product Chemistry - Technology“. Vereinigung für Angewandte Botanik und Sektion Pflanzliche Naturstoffe der Deutschen Botanischen Gesellschaft, Universität Jena, September 30 - October 2, 1999 KOBAYASHI, N., SCHMIDT, J., STRACK, D., SCHLIEMANN, W. A new biosynthetic pathway leading to dopamine-derived betacyanins DECHEMA-Symposium „Aktuelle Entwicklungen in der Naturstofforschung“, 12. Irseer Naturstofftage der DECHEMA e.V., Irsee, February 23-25, 2000 KOBAYASHI, N., SCHMIDT, J., NIMTZ, M., WRAY, V., SCHLIEMANN, W. Betalains from Schlumbergera x buckleyi Meeting „Biosynthesis and Accumulation of Secondary Products“, Martin-Luther- University Halle-Wittenberg, Halle (Saale), September 24-27, 2000 SCHLIEMANN, W., KOBAYASHI, N., STEINER, U.S., VOGT, T., STRACK, D. Advances in betalain biosynthesis of higher plants Meeting „Biosynthesis and Accumulation of Secondary Products“, Martin-Luther- University Halle-Wittenberg, Halle (Saale), September 24-27, 2000 Content Content 1 Introduction…………………………………………………………………………..1 1.1 Plant pigments……………………………………………………………………….1 1.2 Betalains……………………………………………………………………………..3 1.3 Aim of the study……………………………………………………………………..6 2 Materials………………………………………………………………………………8 2.1 Plants………………………………………………………………………………….8 2.1.1 Beets…………………………………...………………………………………….8 2.1.2 Cactaceae…………………………………………………………………………8 2.1.3 Plants……………………………..…………………………………………….…9 2.2 Cell cultures…………………………………………………………………………..9 2.2.1 Hairy root cultures of beets………………….…………………………….……...9 2.2.2 Other cell cultures……………………………………………………………….10 2.3 Chemicals……………………………………………………………………………11 2.4 Equipments…………………………………………………………………………..11 3 Methods………………………………………………………………………………12 3.1 Isolation and purification of betalains……………………………………………….12 3.1.1 Isolation and purification of dopamine-derived betacyanins……………...…….12 3.1.2 Isolation and purification of betalains from Christmas cactus..…...…………….12 3.1.3 Isolation of miraxanthin V (dopamine-betaxanthin) and betalamic acid………..12 3.1.4 Partial synthesis of (R)-Phe-betaxanthin and vulgaxanthin I [(S)-Gln-betaxanthin]……………………………………………………………13 3.2 Accumulation and occurrence of betalains……………..………………………...…13 3.2.1 Short-term dopamine feeding experiment…………………………………...…..13 3.2.2 Identification and quantification of dopamine-derived betacyanins by co-injection analyses………………………………..………………………..14 3.2.3 Betacyanin compositions during flower development and in different flower organs of Christmas cactus…………………………….………………………...14 3.2.4 Betacyanin compositions in fruits and flowers from different species of Cactaceae………..……………………………………………………………15 3.3 Feeding experiments………………………………………………………………...15 3.3.1 Feeding of amino acids and amines to hairy root cultures of yellow beet and seedlings of fodder beet…………………………………………………………15 Content 3.3.2 Feeding of (S)-Phe, (R)-Phe and (S)/(R)-Phe to different cultures and fodder beet seedlings…………………………..……………………………15 3.3.3 Uptake kinetics of (S)-Phe, (R)-Phe and (S)/(R)-Phe by hairy root cultures of yellow beet………………………………………………………………………16 3.3.4 Feeding of amino acids and (NH4)2SO4 to hairy root culture of yellow beet……………………………………………………………………16 3.3.5 Feeding of 2-aminoindan 2-phosphonic acid (AIP) to hairy root cultures of yellow beet and seedlings of fodder beet………………………………………..17 3.3.6 Feeding of betalamic acid to broad bean and pea seedlings…………………….17 3.4 Extraction of betalains………………………………………………………………17 3.5 Preparation of protein extracts and assays for the condensation of betalamic acid with amino acids…………………………………………………………………….17 3.6 Uptake of betaxanthins to red beet vacuoles………………...………………………18 3.6.1 Preparation of protoplasts and vacuoles from red beet hypocotyls…….…...……18 3.6.2 Marker enzymes………………………………………………………………….19 3.6.3 Transport studies……………...………………………………………………….20 3.6.4 Preparation of mini-protoplasts and uptake experiments………………………...20 3.7 High performance liquid chromatography (HPLC)………………………………….21 3.8
Load more

Recommended publications
  • Metabolomics Reveals the Molecular Mechanisms of Copper Induced
    Article Cite This: Environ. Sci. Technol. 2018, 52, 7092−7100 pubs.acs.org/est Metabolomics Reveals the Molecular Mechanisms of Copper Induced Cucumber Leaf (Cucumis sativus) Senescence † ‡ § ∥ ∥ ∥ Lijuan Zhao, Yuxiong Huang, , Kelly Paglia, Arpana Vaniya, Benjamin Wancewicz, ‡ § and Arturo A. Keller*, , † Key Laboratory of Pollution Control and Resource Reuse, School of Environment, Nanjing University, Nanjing, Jiangsu 210023, China ‡ Bren School of Environmental Science & Management, University of California, Santa Barbara, California 93106-5131, United States § University of California, Center for Environmental Implications of Nanotechnology, Santa Barbara, California 93106, United States ∥ UC Davis Genome Center-Metabolomics, University of California Davis, 451 Health Sciences Drive, Davis, California 95616, United States *S Supporting Information ABSTRACT: Excess copper may disturb plant photosynthesis and induce leaf senescence. The underlying toxicity mechanism is not well understood. Here, 3-week-old cucumber plants were foliar exposed to different copper concentrations (10, 100, and 500 mg/L) for a final dose of 0.21, 2.1, and 10 mg/plant, using CuSO4 as the Cu ion source for 7 days, three times per day. Metabolomics quantified 149 primary and 79 secondary metabolites. A number of intermediates of the tricarboxylic acid (TCA) cycle were significantly down-regulated 1.4−2.4 fold, indicating a perturbed carbohy- drate metabolism. Ascorbate and aldarate metabolism and shikimate- phenylpropanoid biosynthesis (antioxidant and defense related pathways) were perturbed by excess copper. These metabolic responses occur even at the lowest copper dose considered although no phenotype changes were observed at this dose. High copper dose resulted in a 2-fold increase in phytol, a degradation product of chlorophyll.
    [Show full text]
  • What Pigments Are in Plants?
    BUILD YOUR FUTURE! ANYANG BEST COMPLETE MACHINERY ENGINEERING CO.,LTD WHAT PIGMENTS ARE IN PLANTS? Pigments Pigments are chemical compounds responsible for color in a range of living substances and in the inorganic world. Pigments absorb some of the light they receive, and so reflect only certain wavelengths of visible light. This makes them appear "colorful.” Cave paintings by early man show the early use of pigments, in a limited range from straw color to reddish brown and black. These colors occurred naturally in charcoals, and in mineral oxides such as chalk and ochre. The WebExhibit on Pigments has more information on these early painting palettes. Many early artists used natural pigments, but nowadays they have been replaced by cheaper and less toxic synthetic pigments. Biological Pigments Pigments are responsible for many of the beautiful colors we see in the plant world. Dyes have often been made from both animal sources and plant extracts . Some of the pigments found in animals have also recently been found in plants. Website: www.bestextractionmachine.com Email: [email protected] Tel: +86 372 5965148 Fax: +86 372 5951936 Mobile: ++86 8937276399 BUILD YOUR FUTURE! ANYANG BEST COMPLETE MACHINERY ENGINEERING CO.,LTD Major Plant Pigments White Bird Of Paradise Tree Bilirubin is responsible for the yellow color seen in jaundice sufferers and bruises, and is created when hemoglobin (the pigment that makes blood red) is broken down. Recently this pigment has also been found in plants, specifically in the orange fuzz on seeds of the white Bird of Paradise tree. The bilirubin in plants doesn’t come from breaking down hemoglobin.
    [Show full text]
  • Natural Colour Book
    THE COLOUR BOOK Sensient Food Colors Europe INDEX NATURAL COLOURS AND COLOURING FOODS INDEX 46 Lycopene 4 We Brighten Your World 47 Antho Blends – Pink Shade 6 Naturally Different 48 Red Cabbage 8 The Colour of Innovation 49 Beetroot – with reduced bluish tone 10 Natural Colours, Colouring Foods 50 Beetroot 11 Cardea™, Pure-S™ 51 Black Carrot 12 YELLOW 52 Grape 14 Colourful Impulses 53 Enocianin 15 Carthamus 54 Red Blends 16 Curcumin 56 VIOLET & BLUE 17 Riboflavin 59 Violet Blends 18 Lutein 61 Spirulina 19 Carrot 62 GREEN 20 Natural Carotene 65 Green Blends 22 Beta-Carotene 66 Copper-Chlorophyllin 24 Annatto 67 Copper-Chlorophyll 25 Yellow/ Orange Blends 68 Chlorophyll/-in 26 ORANGE 69 Spinach 29 Natural Carotene 70 BROWN 30 Paprika Extract 73 Burnt Sugar 32 Carrot 74 Apple 33 Apocarotenal 75 Caramel 34 Carminic Acid 76 BLACK & WHITE 35 Beta-Carotene 79 Vegetable Carbon 36 RED 80 Titanium Dioxide 39 Antho Blends – Strawberry Shade 81 Natural White 40 Aronia 41 Elderberry 83 Regulatory Information 42 Black Carrot 84 Disclaimer 43 Hibiscus 85 Contact Address 44 Carmine 3 INDEX NATURAL COLOURS AND COLOURING FOODS WE BRIGHTEN YOUR WORLD Sensient is as colourful as the world around us. Whatever you are looking for, across the whole spectrum of colour use, we can deliver colouring solutions to best meet your needs in your market. Operating in the global market place for over 100 years Sensient both promises and delivers proven international experience, expertise and capabilities in product development, supply chain management, manufacture, quality management and application excellence of innovative colours for food and beverages.
    [Show full text]
  • Sinapate Dehydrodimers and Sinapate-Ferulate Heterodimers In
    J. Agric. Food Chem. 2003, 51, 1427−1434 1427 Sinapate Dehydrodimers and Sinapate−Ferulate Heterodimers in Cereal Dietary Fiber MIRKO BUNZEL,*,† JOHN RALPH,‡,§ HOON KIM,‡,§ FACHUANG LU,‡,§ SALLY A. RALPH,# JANE M. MARITA,‡,§ RONALD D. HATFIELD,‡ AND HANS STEINHART† Institute of Biochemistry and Food Chemistry, Department of Food Chemistry, University of Hamburg, Grindelallee 117, 20146 Hamburg, Germany; U.S. Dairy Forage Research Center, Agricultural Research Service, U.S. Department of Agriculture, Madison, Wisconsin 53706; Department of Forestry, University of WisconsinsMadison, Madison, Wisconsin 53706; and U.S. Forest Products Laboratory, Forest Service, U.S. Department of Agriculture, Madison, Wisconsin 53705 Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 µg/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-O-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.
    [Show full text]
  • Studies on Betalain Phytochemistry by Means of Ion-Pair Countercurrent Chromatography
    STUDIES ON BETALAIN PHYTOCHEMISTRY BY MEANS OF ION-PAIR COUNTERCURRENT CHROMATOGRAPHY Von der Fakultät für Lebenswissenschaften der Technischen Universität Carolo-Wilhelmina zu Braunschweig zur Erlangung des Grades einer Doktorin der Naturwissenschaften (Dr. rer. nat.) genehmigte D i s s e r t a t i o n von Thu Tran Thi Minh aus Vietnam 1. Referent: Prof. Dr. Peter Winterhalter 2. Referent: apl. Prof. Dr. Ulrich Engelhardt eingereicht am: 28.02.2018 mündliche Prüfung (Disputation) am: 28.05.2018 Druckjahr 2018 Vorveröffentlichungen der Dissertation Teilergebnisse aus dieser Arbeit wurden mit Genehmigung der Fakultät für Lebenswissenschaften, vertreten durch den Mentor der Arbeit, in folgenden Beiträgen vorab veröffentlicht: Tagungsbeiträge T. Tran, G. Jerz, T.E. Moussa-Ayoub, S.K.EI-Samahy, S. Rohn und P. Winterhalter: Metabolite screening and fractionation of betalains and flavonoids from Opuntia stricta var. dillenii by means of High Performance Countercurrent chromatography (HPCCC) and sequential off-line injection to ESI-MS/MS. (Poster) 44. Deutscher Lebensmittelchemikertag, Karlsruhe (2015). Thu Minh Thi Tran, Tamer E. Moussa-Ayoub, Salah K. El-Samahy, Sascha Rohn, Peter Winterhalter und Gerold Jerz: Metabolite profile of betalains and flavonoids from Opuntia stricta var. dilleni by HPCCC and offline ESI-MS/MS. (Poster) 9. Countercurrent Chromatography Conference, Chicago (2016). Thu Tran Thi Minh, Binh Nguyen, Peter Winterhalter und Gerold Jerz: Recovery of the betacyanin celosianin II and flavonoid glycosides from Atriplex hortensis var. rubra by HPCCC and off-line ESI-MS/MS monitoring. (Poster) 9. Countercurrent Chromatography Conference, Chicago (2016). ACKNOWLEDGEMENT This PhD would not be done without the supports of my mentor, my supervisor and my family.
    [Show full text]
  • Survey of Plant Pigments: Molecular and Environmental Determinants of Plant Colors
    ACTA BIOLOGICA CRACOVIENSIA Series Botanica 51/1: 7–16, 2009 SURVEY OF PLANT PIGMENTS: MOLECULAR AND ENVIRONMENTAL DETERMINANTS OF PLANT COLORS EWA MŁODZIŃSKA* Department of Plant Physiology, Wroclaw University, ul. Kanonia 6/8, 50-328 Wrocław, Poland Received January 7, 2009; revision accepted February 20, 2009 It is difficult to estimate the importance of plant pigments in plant biology. Chlorophylls are the most important pigments, as they are required for photosynthesis. Carotenoids are also necessary for their functions in photosyn- thesis. Other plant pigments such as flavonoids play a crucial role in the interaction between plants and animals as visual signals for pollination and seed scattering. Studies related to plant pigmentation are one of the oldest areas of work in plant science. The first publication about carotenoids appeared in the early nineteenth century, and the term "chlorophyll" was first used in 1818 (Davies, 2004). Since then, the biochemical structure of plant pigments has been revealed, as have the biosynthetic pathways for the major pigments that provide a useful variety of colors to blossoms and other plant organs. There is widespread interest in the application of molecular methods to improve our knowledge of gene regulation mechanisms and changes in plant pigment content. Genetic modification has been used to alter pigment production in transgenic plants. This review focuses on flower pigmentation, its bio- chemistry and biology. It presents a general overview of the major plant pigment groups as well as rarer plant dyes and their diversity and function in generating the range of colors observed in plants. Key words: Flower and fruit colors, co-pigmentation, plant dyes, pigment groups.
    [Show full text]
  • Betalains and Phenolics in Red Beetroot (Beta Vulgaris)
    Betalains and Phenolics in Red Beetroot (Beta vulgaris) Peel Extracts: Extraction and Characterisation Tytti Kujala*, Jyrki Loponen and Kalevi Pihlaja Department of Chemistry, Vatselankatu 2, FIN-20014 University of Turku, Finland. Fax: +3582-333 67 00. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 56 c, 343-348 (2001); received January 9/February 12, 2001 Beta vulgaris , Betalains, Phenolics The extraction of red beetroot (Beta vulgaris ) peel betalains and phenolics was compared with two extraction methods and solvents. The content of total phenolics in the extracts was determined according to a modification of the Folin-Ciocalteu method and expressed as gallic acid equivalents (GAE). The profiles of extracts were analysed by high-performance liquid chromatography (HPLC). The compounds of beetroot peel extracted with 80% aqueous methanol were characterised from separated fractions using HPLC- diode array detection (HPLC-DAD) and HPLC- electrospray ionisation-mass spectrometry (HPLC-ESI-MS) tech­ niques. The extraction methods and the choice of solvent affected noticeably the content of individual compounds in the extract. The betalains found in beetroot peel extract were vulgaxanthin I, vulgaxanthin II, indicaxanthin, betanin, prebetanin, isobetanin and neobe- tanin. Also cyclodopa glucoside, /V-formylcyclodopa glucoside, glucoside of dihydroxyindol- carboxylic acid, betalamic acid, L-tryptophan, p-coumaric acid, ferulic acid and traces of un­ identified flavonoids were detected. Introduction acid in their cell walls (Jackman and Smith, 1996). Phenolic compounds are ubiquitous in the plant Except ferulic acid, also other phenolic acids and kingdom and they have been reported to possess phenolic acid conjugates have been reported in many biological effects.
    [Show full text]
  • 11. COMPOUNDS INFLUENCING FOOD COLOUR Perception Visual
    11. COMPOUNDS INFLUENCING FOOD COLOUR perception visual colour pigments (colouring matters, colourings) formation primary compounds natural food components natural components of other materials (microorganisms, algae, higher plants), used as additives secondary compounds enzymatic reactions (non-enzymatic browning reaction) chemical reactions synthetic compounds used as additives colour defects natural colours important groups tetrapyrrole colours plants, animals hem colours chlorophyll colours betalain colours plants betacyans betaxanthins flavonoid colours plants anthocyanins anthoxanthins phenolic and quinoid colours plants, animals phenols quinones carotenoid colours plants, animals carotenes xanthophylls TETRAPYRROLE PIGMENTS (TETRAPYRROLES) porphyrin pigments (porphyrins) cyclic hem pigments (hems) chlorophyll pigments (chlorophylls) biline pigments (bilines) linear phycobilins 3 5 7 4 6 2 A B 8 2 3 7 8 1 NH N 9 12 13 17 18 20 10 4 6 9 11 1 A B C 14 16 D 19 19 NH 11 N N N 5 10 N 15 N 18 D C 12 H 16 14 17 15 13 porphyrins bilines hem pigments meat, meat products nomenclature (book 3, tab. 9.1) content (book 3, tab. 9.2, 9.3, 9.4, 9.5) P CH2 N H His93 CH2=CH CH3 N CH2=CH CH3 H C CH=CH 3 2 H C CH=CH N N 3 2 N N Fe (II) Fe (II) N N N N H3C CH3 H3C CH3 CH CH COOH HOOCCH CH HOOCCH2CH2 2 2 2 2 CH CH COOH H2O 2 2 hem (reduced haematin, Fe2+), hemoglobin hematin (Fe3+), myoglobin (P = globin residue,16,8 kDa) protein protein N N O 2 N N myoglobin Fe (II) Fe (II) oxymyoglobin N N N N O O H2O protein N N metmyoglobin Fe (III) N N
    [Show full text]
  • Urfa Pepper) Seed Oil and Evaluation of Its Functional Characteristics
    GRASAS Y ACEITES 71 (4) October–December 2020, e384 ISSN-L: 0017-3495 https://doi.org/10.3989/gya.0915192 Biochemical, compositional, and spectral analyses of İsot (Urfa pepper) seed oil and evaluation of its functional characteristics B. Başyiğita, Ş. Dağhana and M. Karaaslana, * aHarran University, Engineering Faculty, Food Engineering Department, Şanlıurfa, Turkey. *Corresponding author: [email protected] Submitted: 20 September 2019; Accepted: 29 November 2019; Published online: 22 October 2020 SUMMARY: In this study, the physicochemical, functional, and antimicrobial properties of pepper seed oil (PSO) were determined. PSO was subjected to differential scanning calorimeter (DSC), fatty acid composi- tion, carotenoid, capsaicin, and tocopherol analyses. LC-ESI-MS/MS and NMR were used to characterize and quantify phytochemicals. Resveratrol, luteolin, and 4-hydroxycinnamic acid were the principal phenolics in PSO. A high concentration of unsaturated fatty acids (85.3%), especially linoleic acid (73.7%) is present in PSO. Capsaicin, dihydrocapsaicin, α-tocopherol, δ-tocopherol, zeaxanthin, and capsanthin were determined in PSO at concentrations of 762.92, 725.73, 62.40, 643.23, 29.51, 16.83 ppm, respectively. PSO displayed inhibi- tory activity against α-glucosidase rather than α-amylase. The antimicrobial activity of PSO was tested against Escherichia coli, Staphylococcus aureus subsp. aureus, Aspergillus brasiliensis and Candida albicans. The antimi- crobial potential of PSO was expressed as minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and inhibition zone (IZ) diameter. Polyunsaturated fatty acid, capsaicin, carotenoid, tocopherol, resveratrol contents; the antioxidant, α-glucosidase inhibitory and antimicrobial activities of PSO indicated its nutritional value and health promoting nature for the well-being of humans.
    [Show full text]
  • Betanin, the Main Pigment of Red Beet
    Betanin, the main pigment of red beet - molecular origin of its exceptionally high free radical scavenging activity Anna Gliszczyńska-Świglo, Henryk Szymusiak, Paulina Malinowska To cite this version: Anna Gliszczyńska-Świglo, Henryk Szymusiak, Paulina Malinowska. Betanin, the main pigment of red beet - molecular origin of its exceptionally high free radical scavenging activity. Food Additives and Contaminants, 2006, 23 (11), pp.1079-1087. 10.1080/02652030600986032. hal-00577387 HAL Id: hal-00577387 https://hal.archives-ouvertes.fr/hal-00577387 Submitted on 17 Mar 2011 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. Food Additives and Contaminants For Peer Review Only Betanin, the main pigment of red beet - molecular origin of its exceptionally high free radical scavenging activity Journal: Food Additives and Contaminants Manuscript ID: TFAC-2005-377.R1 Manuscript Type: Original Research Paper Date Submitted by the 20-Aug-2006 Author: Complete List of Authors: Gliszczyńska-Świgło, Anna; The Poznañ University of Economics, Faculty of Commodity Science
    [Show full text]
  • Transformation of Low Molecular Compounds and Soil Humic Acid by Two Domain Laccase of Streptomyces Puniceus in the Presence of Ferulic and Caffeic Acids
    PLOS ONE RESEARCH ARTICLE Transformation of low molecular compounds and soil humic acid by two domain laccase of Streptomyces puniceus in the presence of ferulic and caffeic acids 1 1 1 1 Liubov I. Trubitsina , Alexander V. LisovID *, Oxana V. Belova , Ivan V. Trubitsin , Vladimir V. Demin2, Andrey I. Konstantinov3, Anna G. Zavarzina2, Alexey A. Leontievsky1 a1111111111 1 G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences (IBPhM RAS), Pushchino, Russia, 2 Faculty of Soil Science, Lomonosov Moscow State University, Moscow, a1111111111 Russia, 3 Faculty of Chemistry, Lomonosov Moscow State University, Moscow, Russia a1111111111 a1111111111 * [email protected] a1111111111 Abstract The two-domain bacterial laccases oxidize substrates at alkaline pH. The role of natural OPEN ACCESS phenolic compounds in the oxidation of substrates by the enzyme is poorly understood. We Citation: Trubitsina LI, Lisov AV, Belova OV, have studied the role of ferulic and caffeic acids in the transformation of low molecular Trubitsin IV, Demin VV, Konstantinov AI, et al. (2020) Transformation of low molecular weight substrates and of soil humic acid (HA) by two-domain laccase of Streptomyces puni- compounds and soil humic acid by two domain ceus (SpSL, previously undescribed). A gene encoding a two-domain laccase was cloned laccase of Streptomyces puniceus in the presence from S. puniceus and over-expressed in Escherichia coli. The recombinant protein was puri- of ferulic and caffeic acids. PLoS ONE 15(9): fied by affinity chromatography to an electrophoretically homogeneous state. The enzyme e0239005. https://doi.org/10.1371/journal. pone.0239005 showed high thermal stability, alkaline pH optimum for the oxidation of phenolic substrates and an acidic pH optimum for the oxidation of K [Fe(CN) ] (potassium ferrocyanide) and Editor: Leonidas Matsakas, Luleå University of 4 6 0 Technology, SWEDEN ABTS (2,2 -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt).
    [Show full text]
  • Promote Optimal Health Antioxidant Benefits Anti-Inflammatory Benefits
    Promote Optimal Health The pigments that give beets their rich colors are called betalains. There are two basic types of betalains: betacyanins and betaxanthins. Betacyanins are pigments are red‐violet in color. Betanin is the best studied of the betacyanins. Betaxanthins are yellowish in color. In light or dark red, crimson, or purple colored beets, betacyanins are the dominant pigments. In yellow beets, betaxanthins predominate, and particularly the betaxanthin called vulgaxanthin. All betalains come from the same original molecule (betalamic acid). The addition of amino acids or amino acid derivatives to betalamic acid is what determines the specific type of pigment that gets produced. The betalain pigments in beets are water‐soluble, and as pigments they are somewhat unusual due to their nitrogen content. Many of the betalains function both as antioxidants and anti‐inflammatory molecules. At the same time, they themselves are also very vulnerable to oxidation (change in structure due to interaction with oxygen). In addition to beets, rhubarb, chard, amaranth, prickly pear cactus, and Nopal cactus are examples of foods that contain betalains. It’s interesting to note that humans appear to vary greatly in their response to dietary betalains. In the United States, only 10‐15% of adults are estimated to be “betalain responders.” A betalain responder is a person who has the capacity to absorb and metabolize enough betalains from beet (and other foods) to gain full antioxidant, anti‐inflammatory, and Phase 2 triggering benefits. (Phase 2 is the second step in our cellular detoxification process). Antioxidant Benefits What’s most striking about beets is not the fact that they are rich in antioxidants; what’s striking is the unusual mix of antioxidants that they contain.
    [Show full text]