Thiamine Modulates Metabolism of the Phenylpropanoid Pathway
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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. -
Secondary Metabolites and Phenylpropanoid Pathway Enzymes
Journal of Photochemistry and Photobiology B: Biology 140 (2014) 332–343 Contents lists available at ScienceDirect Journal of Photochemistry and Photobiology B: Biology journal homepage: www.elsevier.com/locate/jphotobiol Secondary metabolites and phenylpropanoid pathway enzymes as influenced under supplemental ultraviolet-B radiation in Withania somnifera Dunal, an indigenous medicinal plant ⇑ Swabha Takshak, S.B. Agrawal Laboratory of Air Pollution and Global Climate Change, Department of Botany, Banaras Hindu University, Varanasi 221 005, India article info abstract Article history: The present study aims to investigate the effects of supplemental ultraviolet B (3.6 kJ mÀ2 dayÀ1 above Received 28 May 2014 ambient) radiation on secondary metabolites and phenylpropanoid pathway enzymes of Withania Received in revised form 12 August 2014 somnifera under field conditions at 40, 70, and 100 days after transplantation. Secondary metabolites’ Accepted 14 August 2014 (alkaloids, anthocyanins, carotenoids, flavonoids, lignin, phytosterols, saponins, and tannins) concentra- Available online 6 September 2014 tions were analysed at the end of the treatments. Activities of phenylalanine ammonia lyase (PAL), cinnamyl alcohol dehydrogenase (CAD), 4-coumarate-CoA ligase (4CL), chalcone–flavanone isomerase Keywords: (CHI), and dihydroflavonol reductase (DFR) were also determined. In treated plants, secondary metabo- Phenylpropanoid pathway enzymes lite-concentrations generally increased (higher concentrations being recorded in roots compared to Secondary metabolites s-UV-B leaves). Anomalies were recorded for lycopene in roots and phytosterols in leaves (all sampling ages); Withania somnifera b-carotene declined in leaves at third sampling age. s-UV-B-treated plants depicted decrease in withan- olide A content with concomitant increase in withaferin A (two major alkaloids analysed by HPLC) com- pared to their respective controls. -
Utilizing UVPD Fragmentation for Plant Molecules: Phenylpropanoids
Utilizing UVPD Fragmentation for Plant Molecules: Phenylpropanoids Romain Huguet1, Tim Stratton1, Seema Sharma1, Christopher Mullen1, Jesse Canterbury1, and Vlad Zabrouskov1 1Thermo Fisher Scientific, San Jose, California, USA RESULTS A significant difference between the fragmentation approaches arises from the means in which UVPD Laser In addition to early observation of typically higher energy fragmentation channels in the UVPD, an ABSTRACT they initiate fragmentation. In HCD, energy is imparted by the initial injection of the ions into the increase in fragment ions arising from ionization of the aromatic rings or the conjugated double For this work, we used a Nd:YAG (neodymium doped yttrium aluminum garnet) laser. This is an collision cell and collisions with a relatively static gas. A greater voltage offset gives rise to more Purpose: Investigate the potential use of UVPD to provide unique and potentially diagnostic Compound Structure and UV Absorption bond chalconoids was observed (Figure 6). While ionization was largely the result of the ketone or optically pumped laser that typically emits in the infrared range (>1000nm). When operated in a energetic collisions. The energy is internally distributed with bonds breaking to form fragment ions fragmentation information for structure determination of small molecules, specifically alcohol functions present on the compounds, specific absorption of photons generated unique pulsed Q-switching mode, where the laser energy is released in a pulse when reaching a threshold, which may also undergo subsequent fragmentation events generating several generations of phenylpropanoids and chalconoids. fragmentation. Several of these fragment ions were not observed in HCD at any energy level frequency doubling of the pulses can be used to obtain shorter wavelengths. -
Phenolics in Human Health
International Journal of Chemical Engineering and Applications, Vol. 5, No. 5, October 2014 Phenolics in Human Health T. Ozcan, A. Akpinar-Bayizit, L. Yilmaz-Ersan, and B. Delikanli with proteins. The high antioxidant capacity makes Abstract—Recent research focuses on health benefits of polyphenols as an important key factor which is involved in phytochemicals, especially antioxidant and antimicrobial the chemical defense of plants against pathogens and properties of phenolic compounds, which is known to exert predators and in plant-plant interferences [9]. preventive activity against infectious and degenerative diseases, inflammation and allergies via antioxidant, antimicrobial and proteins/enzymes neutralization/modulation mechanisms. Phenolic compounds are reactive metabolites in a wide range of plant-derived foods and mainly divided in four groups: phenolic acids, flavonoids, stilbenes and tannins. They work as terminators of free radicals and chelators of metal ions that are capable of catalyzing lipid oxidation. Therefore, this review examines the functional properties of phenolics. Index Terms—Health, functional, phenolic compounds. I. INTRODUCTION In recent years, fruits and vegetables receive considerable interest depending on type, number, and mode of action of the different components, so called as “phytochemicals”, for their presumed role in the prevention of various chronic diseases including cancers and cardiovascular diseases. Plants are rich sources of functional dietary micronutrients, fibers and phytochemicals, such -
Comparison of Metabolome and Transcriptome of Flavonoid
International Journal of Molecular Sciences Article Comparison of Metabolome and Transcriptome of Flavonoid Biosynthesis Pathway in a Purple-Leaf Tea Germplasm Jinmingzao and a Green-Leaf Tea Germplasm Huangdan reveals Their Relationship with Genetic Mechanisms of Color Formation Xuejin Chen, Pengjie Wang, Yucheng Zheng, Mengya Gu, Xinying Lin, Shuyan Wang, Shan Jin * and Naixing Ye * College of Horticulture, Fujian Agriculture and Forestry University/Key Laboratory of Tea Science in University of Fujian Province, Fuzhou 350002, China; [email protected] (X.C.); [email protected] (P.W.); [email protected] (Y.Z.); [email protected] (M.G.); [email protected] (X.L.); [email protected] (S.W.) * Correspondence: [email protected] (S.J.); [email protected] (N.Y.) Received: 4 May 2020; Accepted: 7 June 2020; Published: 11 June 2020 Abstract: Purple-leaf tea is a phenotype with unique color because of its high anthocyanin content. The special flavor of purple-leaf tea is highly different from that of green-leaf tea, and its main ingredient is also of economic value. To probe the genetic mechanism of the phenotypic characteristics of tea leaf color, we conducted widely targeted metabolic and transcriptomic profiling. The metabolites in the flavonoid biosynthetic pathway of purple- and green-leaf tea were compared, and results showed that phenolic compounds, including phenolic acids, flavonoids, and tannins, accumulated in purple-leaf tea. The high expression of genes related to flavonoid biosynthesis (e.g., PAL and LAR) exhibits the specific expression of biosynthesis and the accumulation of these metabolites. Our result also shows that two CsUFGTs were positively related to the accumulation of anthocyanin. -
Phenolic Profile of Sercial and Tinta Negra Vitis Vinifera L
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Repositório Digital da Universidade da Madeira Food Chemistry 135 (2012) 94–104 Contents lists available at SciVerse ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Phenolic profile of Sercial and Tinta Negra Vitis vinifera L. grape skins by HPLC–DAD–ESI-MSn Novel phenolic compounds in Vitis vinifera L. grape Rosa Perestrelo a,b, Ying Lu b, Sónia A.O. Santos c, Armando J.D. Silvestre c, Carlos P. Neto c, ⇑ José S. Câmara b, Sílvia M. Rocha a, a QOPNA, Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal b CQM/UMa – Centro de Química da Madeira, Centro de Ciências Exactas e da Engenharia da, Universidade da Madeira, Campus Universitário da Penteada, 9000-390 Funchal, Portugal c CICECO, Departamento de Química, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal article info abstract Article history: This study represents the first phytochemical research of phenolic components of Sercial and Tinta Negra Received 25 November 2011 Vitis vinifera L. The phenolic profiles of Sercial and Tinta Negra V. vinifera L. grape skins (white and red Received in revised form 9 February 2012 varieties, respectively) were established using high performance liquid chromatography–diode array Accepted 17 April 2012 detection–electrospray ionisation tandem mass spectrometry (HPLC–DAD–ESI-MSn), at different ripening Available online 27 April 2012 stages (véraison and maturity). A total of 40 phenolic compounds were identified, which included 3 hydroxybenzoic acids, 8 hydroxycinnamic acids, 4 flavanols, 5 flavanones, 8 flavonols, 4 stilbenes, and Keywords: 8 anthocyanins. -
Wine and Grape Polyphenols — a Chemical Perspective
Wine and grape polyphenols — A chemical perspective Jorge Garrido , Fernanda Borges abstract Phenolic compounds constitute a diverse group of secondary metabolites which are present in both grapes and wine. The phenolic content and composition of grape processed products (wine) are greatly influenced by the technological practice to which grapes are exposed. During the handling and maturation of the grapes several chemical changes may occur with the appearance of new compounds and/or disappearance of others, and con- sequent modification of the characteristic ratios of the total phenolic content as well as of their qualitative and quantitative profile. The non-volatile phenolic qualitative composition of grapes and wines, the biosynthetic relationships between these compounds, and the most relevant chemical changes occurring during processing and storage will be highlighted in this review. 1. Introduction Non-volatile phenolic compounds and derivatives are intrinsic com-ponents of grapes and related products, particularly wine. They constitute a heterogeneous family of chemical compounds with several compo-nents: phenolic acids, flavonoids, tannins, stilbenes, coumarins, lignans and phenylethanol analogs (Linskens & Jackson, 1988; Scalbert, 1993). Phenolic compounds play an important role on the sensorial characteris-tics of both grapes and wine because they are responsible for some of organoleptic properties: aroma, color, flavor, bitterness and astringency (Linskens & Jackson, 1988; Scalbert, 1993). The knowledge of the relationship between the quality of a particu-lar wine and its phenolic composition is, at present, one of the major challenges in Enology research. Anthocyanin fingerprints of varietal wines, for instance, have been proposed as an analytical tool for authen-ticity certification (Kennedy, 2008; Kontoudakis et al., 2011). -
Dietary Supplements Compendium Volume 1
2015 Dietary Supplements Compendium DSC Volume 1 General Notices and Requirements USP–NF General Chapters USP–NF Dietary Supplement Monographs USP–NF Excipient Monographs FCC General Provisions FCC Monographs FCC Identity Standards FCC Appendices Reagents, Indicators, and Solutions Reference Tables DSC217M_DSCVol1_Title_2015-01_V3.indd 1 2/2/15 12:18 PM 2 Notice and Warning Concerning U.S. Patent or Trademark Rights The inclusion in the USP Dietary Supplements Compendium of a monograph on any dietary supplement in respect to which patent or trademark rights may exist shall not be deemed, and is not intended as, a grant of, or authority to exercise, any right or privilege protected by such patent or trademark. All such rights and privileges are vested in the patent or trademark owner, and no other person may exercise the same without express permission, authority, or license secured from such patent or trademark owner. Concerning Use of the USP Dietary Supplements Compendium Attention is called to the fact that USP Dietary Supplements Compendium text is fully copyrighted. Authors and others wishing to use portions of the text should request permission to do so from the Legal Department of the United States Pharmacopeial Convention. Copyright © 2015 The United States Pharmacopeial Convention ISBN: 978-1-936424-41-2 12601 Twinbrook Parkway, Rockville, MD 20852 All rights reserved. DSC Contents iii Contents USP Dietary Supplements Compendium Volume 1 Volume 2 Members . v. Preface . v Mission and Preface . 1 Dietary Supplements Admission Evaluations . 1. General Notices and Requirements . 9 USP Dietary Supplement Verification Program . .205 USP–NF General Chapters . 25 Dietary Supplements Regulatory USP–NF Dietary Supplement Monographs . -
Natural Products (Secondary Metabolites)
Biochemistry & Molecular Biology of Plants, B. Buchanan, W. Gruissem, R. Jones, Eds. © 2000, American Society of Plant Physiologists CHAPTER 24 Natural Products (Secondary Metabolites) Rodney Croteau Toni M. Kutchan Norman G. Lewis CHAPTER OUTLINE Introduction Introduction Natural products have primary ecological functions. 24.1 Terpenoids 24.2 Synthesis of IPP Plants produce a vast and diverse assortment of organic compounds, 24.3 Prenyltransferase and terpene the great majority of which do not appear to participate directly in synthase reactions growth and development. These substances, traditionally referred to 24.4 Modification of terpenoid as secondary metabolites, often are differentially distributed among skeletons limited taxonomic groups within the plant kingdom. Their functions, 24.5 Toward transgenic terpenoid many of which remain unknown, are being elucidated with increas- production ing frequency. The primary metabolites, in contrast, such as phyto- 24.6 Alkaloids sterols, acyl lipids, nucleotides, amino acids, and organic acids, are 24.7 Alkaloid biosynthesis found in all plants and perform metabolic roles that are essential 24.8 Biotechnological application and usually evident. of alkaloid biosynthesis Although noted for the complexity of their chemical structures research and biosynthetic pathways, natural products have been widely per- 24.9 Phenylpropanoid and ceived as biologically insignificant and have historically received lit- phenylpropanoid-acetate tle attention from most plant biologists. Organic chemists, however, pathway metabolites have long been interested in these novel phytochemicals and have 24.10 Phenylpropanoid and investigated their chemical properties extensively since the 1850s. phenylpropanoid-acetate Studies of natural products stimulated development of the separa- biosynthesis tion techniques, spectroscopic approaches to structure elucidation, and synthetic methodologies that now constitute the foundation of 24.11 Biosynthesis of lignans, lignins, contemporary organic chemistry. -
Metabolism of Nonesterified and Esterified Hydroxycinnamic Acids In
Article pubs.acs.org/JAFC Metabolism of Nonesterified and Esterified Hydroxycinnamic Acids in Red Wines by Brettanomyces bruxellensis † ‡ § § † Lauren M. Schopp, Jungmin Lee, James P. Osborne, Stuart C. Chescheir, and Charles G. Edwards*, † School of Food Science, Washington State University, Pullman, Washington 99164−6376, United States ‡ USDA−ARS−HCRU worksite, Parma, Idaho 83660, United States § Department of Food Science and Technology, Oregon State University, Corvallis, Oregon 97331, United States ABSTRACT: While Brettanomyces can metabolize nonesterified hydroxycinnamic acids found in grape musts/wines (caffeic, p- coumaric, and ferulic acids), it was not known whether this yeast could utilize the corresponding tartaric acid esters (caftaric, p- coutaric, and fertaric acids, respectively). Red wines from Washington and Oregon were inoculated with B. bruxellensis, while hydroxycinnamic acids were monitored by HPLC. Besides consuming p-coumaric and ferulic acids, strains I1a, B1b, and E1 isolated from Washington wines metabolized 40−50% of caffeic acid, a finding in contrast to strains obtained from California wines. Higher molar recoveries of 4-ethylphenol and 4-ethylguaiacol synthesized from p-coumaric and ferulic acids, respectively, were observed in Washington Cabernet Sauvignon and Syrah but not Merlot. This finding suggested that Brettanomyces either (a) utilized vinylphenols formed during processing of some wines or (b) metabolized other unidentified phenolic precursors. None of the strains of Brettanomyces studied metabolized caftaric or p-coutaric acids present in wines from Washington or Oregon. KEYWORDS: Brettanomyces, hydroxycinnamic acids, phenolic acids, cinnamates, volatile phenols ■ INTRODUCTION pool of precursors available for conversion to volatile phenols. 21 Brettanomyces has been regarded by some as the most severe In fact, Nikfardjam et al. -
Chlorogenic Acid and Its Relationship with Lignin Biosynthesis
UNIVERSIDADE ESTADUAL DE CAMPINAS INSTITUTO DE BIOLOGIA Nathalia Volpi e Silva CHLOROGENIC ACID AND ITS RELATIONSHIP WITH LIGNIN BIOSYNTHESIS ÁCIDO CLOROGÊNICO E SUA RELAÇÃO COM A BIOSSÍNTESE DE LIGNINA CAMPINAS - SP 2019 NATHALIA VOLPI E SILVA CHLOROGENIC ACID AND ITS RELATIONSHIP WITH LIGNIN BIOSYNTHESIS ÁCIDO CLOROGÊNICO E SUA RELAÇÃO COM A BIOSSÍNTESE DE LIGNINA Thesis presented to the Institute of Biology of the University of Campinas in partial fulfillment of the requirements for the degree of Doctor in Genetic and Molecular Biology in the area of Plant Genetics and Breeding. Tese apresentada ao Instituto de Biologia da Universidade Estadual de Campinas como parte dos requisitos exigidos para obtenção do Título de Doutor em Genética e Biologia Molecular, na área de Genética Vegetal e Melhoramento. Supervisor / Orientador: Prof. Dr. Paulo Mazzafera Co-supervisor / Co-Orientador: Prof. Dr. Igor Cesarino ESTE ARQUIVO DIGITAL CORRESPONDE À VERSÃO FINAL DA TESE DEFENDIDA PELA ALUNA NATHALIA VOLPI E SILVA, ORIENTADA PELO PROF. DR. PAULO MAZZAFERA. CAMPINAS - SP 2019 Agência de fomento: FAPESP Agência de fomento: Capes N° Processo: 2014/17831-5, 2016/15834-2 N° Processo: 001 Nº processo:0 Nº processo:0 Campinas, 31de julho de 2019 EXAMINATION COMMITTEE Banca examinadora Dr. Paulo Mazzafera (Supervisor/Orientador) Dr. Paula Macêdo Nobile Dra. Sara Adrian Lopez de Andrade Dr. Douglas Silva Domingues Dr. Michael dos Santos Brito Os membros da Comissão Examinadora acima assinaram a Ata de Defesa, que se encontra no processo de vida acadêmica do aluno. ACKNOWLEDGMENT I would like to thank the São Paulo Research Foundation (Fundação de Amparo à Pesquisa do Estado de São Paulo) Grant (Processo) nº 2014/17831-5, FAPESP and n° 2016/15834-2, FAPESP for the grant/fellowship and all financial support to develop this thesis. -
Capsaicin Formation in P-Fluorophenylalanine Resistant and Normal Cell Cultures of Capsicum Frutescens and Activity of Phenylalanine Ammonia Lyase
Capsaicin formation in p-fluorophenylalanine resistant and normal cell cultures of Capsicum frutescens and activity of phenylalanine ammonia lyase T SUDHAKAR JOHNSON*, R SARADA and G A RAVISHANKARt Plant Cell Biotechnology Department, Central Food Technological Research Institute, Mysore 560013, India *Present address: Dabur Research Foundation, 813, Asaf Ali Road, New Delhi 110002, India t Corresponding author (Fax, 91-821-517233; Email, [email protected]). Callus cultures of Capsicum frutescens capable of producing a maximum of 53 ~g capsaicin/g FW were exposed to various levels of p-fluorophenyialanine (PFP) at 100, 400, 1000 and 2000~M to develop a resistant cell line that over produces capsaicin. After 15 days of culturing on media lacking PFP, cell lines resistant to 100, 400 and 1000~M registered 18%, 34.5% and 45% increase in capsaicin content over normal cell line (cells not exposed to PFP). Capsaicin accumulation was inhibited in 2000 ~M PFP resistant cell line. The profile of phenylalanine ammonia lyase (PAL), the key enzyme in pheny1propanoidpathway in resistant cell cultures was studied and compared with normal cell cultures to understandits role in capsaicin formation. Importantly increased production of capsaicin was obtained using PFP resistant cell lines. The activity profile of PAL had no correlation with capsaicin content in both control and PFP resistant cells. 1. Introduction 2. Materials and methods Capsaicin, a major pungent principle of chilli pepper, is .2.1 Initiation and maintenance of callus derived from phenylpropanoids (Bennet and Kirby 1968). The aromatic moiety of capsaicin is derived from phenyl- Seeds of C. frutescens Mill. IHR 1203 were germinated and alanine and the fatty acid moiety from valine (Leete and maintained in a green house.