Sources of Flavonoids in the U.S. Diet Using USDA's Updated Database
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Flavonoid-Modifying Capabilities of the Human Gut Microbiome—An in Silico Study
nutrients Article Flavonoid-Modifying Capabilities of the Human Gut Microbiome—An In Silico Study Tobias Goris 1,* , Rafael R. C. Cuadrat 2 and Annett Braune 1 1 Research Group Intestinal Microbiology, Department of Molecular Toxicology, German Institute of Human Nutrition Potsdam-Rehbruecke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany; [email protected] 2 Department of Molecular Epidemiology, German Institute of Human Nutrition Potsdam-Rehbruecke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany; [email protected] * Correspondence: [email protected] Abstract: Flavonoids are a major group of dietary plant polyphenols and have a positive health impact, but their modification and degradation in the human gut is still widely unknown. Due to the rise of metagenome data of the human gut microbiome and the assembly of hundreds of thousands of bacterial metagenome-assembled genomes (MAGs), large-scale screening for potential flavonoid-modifying enzymes of human gut bacteria is now feasible. With sequences of characterized flavonoid-transforming enzymes as queries, the Unified Human Gastrointestinal Protein catalog was analyzed and genes encoding putative flavonoid-modifying enzymes were quantified. The results revealed that flavonoid-modifying enzymes are often encoded in gut bacteria hitherto not considered to modify flavonoids. The enzymes for the physiologically important daidzein-to-equol conversion, well studied in Slackia isoflavoniconvertens, were encoded only to a minor extent in Slackia MAGs, but were more abundant in Adlercreutzia equolifaciens and an uncharacterized Eggerthellaceae species. In addition, enzymes with a sequence identity of about 35% were encoded in highly abundant MAGs of uncultivated Collinsella species, which suggests a hitherto uncharacterized daidzein-to-equol potential in these bacteria. -
RNA-Sequencing Analysis Reveals Betalains Metabolism in the Leaf of Amaranthus Tricolor L
RESEARCH ARTICLE RNA-sequencing analysis reveals betalains metabolism in the leaf of Amaranthus tricolor L. Shengcai Liu1☯, Xueli Zheng1☯, Junfei Pan1, Liyun Peng1, Chunzhen Cheng1, Xiao Wang1, 1 1 1 1,2 1 Chunli Zhao , Zihao Zhang , Yuling Lin , Xu XuHan *, Zhongxiong LaiID * 1 Institute of Horticultural Biotechnology, Fujian Agriculture and Forestry University, Fuzhou, China, 2 Institut de la Recherche Interdisciplinaire de Toulouse, Toulouse, France ☯ These authors contributed equally to this work. * [email protected](ZL); [email protected] (XXH) a1111111111 a1111111111 a1111111111 a1111111111 Abstract a1111111111 Amaranth plants contain large amounts of betalains, including betaxanthins and betacya- nins. Amaranthin is a betacyanin, and its molecular structure and associated metabolic pathway differ from those of betanin in beet plants. The chlorophyll, carotenoid, betalain, and flavonoid contents in amaranth leaves were analyzed. The abundance of betalain, beta- OPEN ACCESS cyanin, and betaxanthin was 2±5-fold higher in the red leaf sectors than in the green leaf Citation: Liu S, Zheng X, Pan J, Peng L, Cheng C, sectors. Moreover, a transcriptome database was constructed for the red and green sectors Wang X, et al. (2019) RNA-sequencing analysis of amaranth leaves harvested from 30-day-old seedlings. 22 unigenes were selected to ana- reveals betalains metabolism in the leaf of Amaranthus tricolor L.. PLoS ONE 14(4): lyze the expression profiles in the two leaf sectors. The RNA-sequencing data indicated that e0216001. https://doi.org/10.1371/journal. many unigenes are involved in betalain metabolic pathways. The potential relationships pone.0216001 between diverse metabolic pathways and betalain metabolism were analyzed. -
Combinatorial Biosynthesis of Non-Bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms Sueharu Horinouchi
J. Antibiot. 61(12): 709–728, 2008 THE JOURNAL OF REVIEW ARTICLE ANTIBIOTICS Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms Sueharu Horinouchi Received: August 1, 2008 / Accepted: October 14, 2008 © Japan Antibiotics Research Association Abstract One of the approaches of combinatorial biosynthesis is combining genes from different organisms and designing a new set of gene clusters to produce bioactive compounds, leading to diversification of both chemical and natural product libraries. This makes efficient use of the potential of the host organisms, especially when microorganisms are used. An Escherichia coli system, in which artificial biosynthetic pathways for production of plant-specific medicinal polyketides, such as flavonoids, stilbenoids, isoflavonoids, and curcuminoids, are assembled, has been designed and expressed. Starting with amino acids tyrosine and phenylalanine as substrates, this system yields naringenin, resveratrol, genistein, and curcumin, for example, all of which are beneficial to human health because of their wide variety of biological activities. Supplementation of unnatural carboxylic acids to the recombinant E. coli cells carrying the artificial pathways by precursor-directed biosynthesis results in production of unnatural compounds. Addition of decorating or modification enzymes to the artificial pathway leads to production of natural and unnatural flavonols, flavones, and methylated resveratrols. This microbial system is promising for construction of larger libraries by employing other polyketide synthases and decorating enzymes of various origins. In addition, the concept of building and expressing artificial biosynthetic pathways for production of non-bacterial and unnatural compounds in microorganisms should be successfully applied to production of not only plant-specific polyketides but also many other useful compound classes. -
Flavonoids and Flavan-3-Ol from Aerial Part of Agrimonia Pilosa LEDEB
Journal of Multidisciplinary Engineering Science and Technology (JMEST) ISSN: 2458-9403 Vol. 4 Issue 10, October - 2017 Flavonoids and flavan-3-ol from aerial part of Agrimonia pilosa LEDEB. Hoang Le Tuan Anh Nguyen Van Linh Mientrung Institute for Scientific Research Military Institute of Traditional Medicine Vietnam Academy of Science and Technology 442 Kim Giang, Hoang Mai, Hanoi, Vietnam 321 Huynh Thuc Khang, Hue City [email protected] [email protected] Abstract—Using various chromatography mesh, Merck) or RP-18 resins (30-50 µm, Fujisilisa methods, three flavonoids, quercetin-3-O- Chemical Ltd.). Thin layer chromatography (TLC) was rutinoside (1), quercetin-3-O-β-D- performed using pre-coated silica gel 60 F254 (0.25 galactopyranoside (2), quercetin (3), and a flavan- mm, Merck) and RP-18 F254S plates (0.25 mm, Merck). 3-ol, catechin (4) were isolated from methanol Spots were visualized under UV radiation (254 and extract of Agrimonia pilosa. Their structures were 365 nm) and sprayed with aqueous solution of H2SO4 elucidated by 1D- and 2D-NMR spectroscopic (10%), heating with a heat gun. analyses and comparison with those reported in B. Plant materials the literature. Compound 2 was reported from A. pilosa for the first time. The aerial parts of A. pilosa were collected at Trung Khanh, Cao Bang province, Vietnam in August 2013. Keywords—Agrimonia pilosa; flavonoid; Its scientific name was identified by Dr. Pham Thanh quercetin-3-O-β-D-galactopyranoside; quercetin Huyen, Institute of Ecology and Biological Resources, derivatives. VAST. A voucher specimen (6695A) is deposited at I. INTRODUCTION the Herbarium of Military Institute of Traditional Medicine. -
Plant Phenolics: Bioavailability As a Key Determinant of Their Potential Health-Promoting Applications
antioxidants Review Plant Phenolics: Bioavailability as a Key Determinant of Their Potential Health-Promoting Applications Patricia Cosme , Ana B. Rodríguez, Javier Espino * and María Garrido * Neuroimmunophysiology and Chrononutrition Research Group, Department of Physiology, Faculty of Science, University of Extremadura, 06006 Badajoz, Spain; [email protected] (P.C.); [email protected] (A.B.R.) * Correspondence: [email protected] (J.E.); [email protected] (M.G.); Tel.: +34-92-428-9796 (J.E. & M.G.) Received: 22 October 2020; Accepted: 7 December 2020; Published: 12 December 2020 Abstract: Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom that can be categorized as flavonoids and non-flavonoids. Interest in phenolic compounds has dramatically increased during the last decade due to their biological effects and promising therapeutic applications. In this review, we discuss the importance of phenolic compounds’ bioavailability to accomplish their physiological functions, and highlight main factors affecting such parameter throughout metabolism of phenolics, from absorption to excretion. Besides, we give an updated overview of the health benefits of phenolic compounds, which are mainly linked to both their direct (e.g., free-radical scavenging ability) and indirect (e.g., by stimulating activity of antioxidant enzymes) antioxidant properties. Such antioxidant actions reportedly help them to prevent chronic and oxidative stress-related disorders such as cancer, cardiovascular and neurodegenerative diseases, among others. Last, we comment on development of cutting-edge delivery systems intended to improve bioavailability and enhance stability of phenolic compounds in the human body. Keywords: antioxidant activity; bioavailability; flavonoids; health benefits; phenolic compounds 1. Introduction Phenolic compounds are secondary metabolites widely spread throughout the plant kingdom with around 8000 different phenolic structures [1]. -
Intereferents in Condensed Tannins Quantification by the Vanillin Assay
INTEREFERENTS IN CONDENSED TANNINS QUANTIFICATION BY THE VANILLIN ASSAY IOANNA MAVRIKOU Dissertação para obtenção do Grau de Mestre em Vinifera EuroMaster – European Master of Sciences of Viticulture and Oenology Orientador: Professor Jorge Ricardo da Silva Júri: Presidente: Olga Laureano, Investigadora Coordenadora, UTL/ISA Vogais: - Antonio Morata, Professor, Universidad Politecnica de Madrid - Jorge Ricardo da Silva, Professor, UTL/ISA Lisboa, 2012 Acknowledgments First and foremost, I would like to thank the Vinifera EuroMaster consortium for giving me the opportunity to participate in the M.Sc. of Viticulture and Enology. Moreover, I would like to express my appreciation to the leading universities and the professors from all around the world for sharing their scientific knowledge and experiences with us and improving day by day the program through mobility. Furthermore, I would like to thank the ISA/UTL University of Lisbon and the personnel working in the laboratory of Enology for providing me with tools, help and a great working environment during the experimental period of this thesis. Special acknowledge to my Professor Jorge Ricardo Da Silva for tutoring me throughout my experiment, but also for the chance to think freely and go deeper to the field of phenols. Last but most important, I would like to extend my special thanks to my family and friends for being a true support and inspiration in every doubt and decision. 1 UTL/ISA University of Lisbon “Vinifera Euromaster” European Master of Science in Viticulture&Oenology Ioanna Mavrikou: Inteferents in condensed tannins quantification with vanillin assay MSc Thesis: 67 pages Key Words: Proanthocyanidins; Interference substances; Phenols; Vanillin assay Abstract Different methods have been established in order to perform accurately the quantification of the condensed tannins in various plant products and beverages. -
Fractionation of Orange Peel Phenols in Ultrafiltered Molasses and Mass Balance Studies of Their Antioxidant Levels
7586 J. Agric. Food Chem. 2004, 52, 7586−7592 Fractionation of Orange Peel Phenols in Ultrafiltered Molasses and Mass Balance Studies of Their Antioxidant Levels JOHN A. MANTHEY† Citrus and Subtropical Products Laboratory, Southern Atlantic Area, Agricultural Research Service, U.S. Department of Agriculture, 600 Avenue S N.W., Winter Haven, Florida 33881 Orange peel molasses, a byproduct of juice production, contains high concentrations of phenols, including numerous flavanone and flavone glycosides, polymethoxylated flavones, hydroxycinnamates, and other miscellaneous phenolic glycosides and amines. Extensive fractionation of these phenols was achieved by adsorption, ion exchange, and size exclusion chromatography. Size exclusion chromatography effectively separated the different classes of flavonoids in ultrafiltered molasses, including the polymethoxylated flavones, flavanone-O-trisaccharides, flavanone- and flavone-O- disaccharides, and, finally, flavone-C-glycosides. Mass spectral analysis of the early-eluting flavonoid fractions off the size exclusion column revealed a broad collection of minor-occurring flavone glycosides, which included, in part, glycosides of limocitrin, limocitrol, and chrysoeriol. Most hydroxycinnamates in the molasses were recovered by ion exchange chromatography, which also facilitated the recovery of fractions containing many other miscellaneous phenols. Total antioxidant levels and total phenolic contents were measured for the separate categories of phenols in the molasses. Inhibition of the superoxide anion reduction of nitroblue tetrazolium showed that a significant amount of the total antioxidant activity in orange peel molasses was attributable to minor-occurring flavones. The miscellaneous phenolic-containing fractions, in which a large portion of the total phenolic content in molasses occurred, also constituted a major portion of the total antioxidants in ultrafiltered molasses. -
And Season-Dependent Pattern of Flavonol Glycosides In
www.nature.com/scientificreports OPEN Age‑ and season‑dependent pattern of favonol glycosides in Cabernet Sauvignon grapevine leaves Sakina Bouderias1,2, Péter Teszlák1, Gábor Jakab1,2 & László Kőrösi1* Flavonols play key roles in many plant defense mechanisms, consequently they are frequently investigated as stress sensitive factors in relation to several oxidative processes. It is well known that grapevine (Vitis vinifera L.) can synthesize various favonol glycosides in the leaves, however, very little information is available regarding their distribution along the cane at diferent leaf levels. In this work, taking into consideration of leaf position, the main favonol glycosides of a red grapevine cultivar (Cabernet Sauvignon) were profled and quantifed by HPLC–DAD analysis. It was found that amount of four favonol glycosides, namely, quercetin-3-O-galactoside, quercetin-3-O-glucoside, kaempferol-3-O-glucoside and kaempferol-3-O-glucuronide decreased towards the shoot tip. Since leaf age also decreases towards the shoot tip, the obtained results suggest that these compounds continuously formed by leaf aging, resulting in their accumulation in the older leaves. In contrast, quercetin-3-O-glucuronide (predominant form) and quercetin-3-O-rutinoside were not accumulated signifcantly by aging. We also pointed out that grapevine boosted the favonol biosynthesis in September, and favonol profle difered signifcantly in the two seasons. Our results contribute to the better understanding of the role of favonols in the antioxidant defense system of grapevine. Flavonoids are very important secondary metabolites, having various functional roles in diferent physiological and developmental processes in plants1–3. Flavonols as a group of favonoids are mainly accumulated in epidermal cells of plant tissues in response to solar radiation 4, 5, to flter the UV-B light while allowing to pass the photo- synthetically active visible light 6–8. -
Flavonoids and Isoflavonoids Biosynthesis in the Model
plants Review Flavonoids and Isoflavonoids Biosynthesis in the Model Legume Lotus japonicus; Connections to Nitrogen Metabolism and Photorespiration Margarita García-Calderón 1, Carmen M. Pérez-Delgado 1, Peter Palove-Balang 2, Marco Betti 1 and Antonio J. Márquez 1,* 1 Departamento de Bioquímica Vegetal y Biología Molecular, Facultad de Química, Universidad de Sevilla, Calle Profesor García González, 1, 41012-Sevilla, Spain; [email protected] (M.G.-C.); [email protected] (C.M.P.-D.); [email protected] (M.B.) 2 Institute of Biology and Ecology, Faculty of Science, P.J. Šafárik University in Košice, Mánesova 23, SK-04001 Košice, Slovakia; [email protected] * Correspondence: [email protected]; Tel.: +34-954557145 Received: 28 April 2020; Accepted: 18 June 2020; Published: 20 June 2020 Abstract: Phenylpropanoid metabolism represents an important metabolic pathway from which originates a wide number of secondary metabolites derived from phenylalanine or tyrosine, such as flavonoids and isoflavonoids, crucial molecules in plants implicated in a large number of biological processes. Therefore, various types of interconnection exist between different aspects of nitrogen metabolism and the biosynthesis of these compounds. For legumes, flavonoids and isoflavonoids are postulated to play pivotal roles in adaptation to their biological environments, both as defensive compounds (phytoalexins) and as chemical signals in symbiotic nitrogen fixation with rhizobia. In this paper, we summarize the recent progress made in the characterization of flavonoid and isoflavonoid biosynthetic pathways in the model legume Lotus japonicus (Regel) Larsen under different abiotic stress situations, such as drought, the impairment of photorespiration and UV-B irradiation. Emphasis is placed on results obtained using photorespiratory mutants deficient in glutamine synthetase. -
Noncatalytic Chalcone Isomerase-Fold Proteins in Humulus Lupulus Are Auxiliary Components in Prenylated Flavonoid Biosynthesis
Noncatalytic chalcone isomerase-fold proteins in Humulus lupulus are auxiliary components in prenylated flavonoid biosynthesis Zhaonan Bana,b, Hao Qina, Andrew J. Mitchellc, Baoxiu Liua, Fengxia Zhanga, Jing-Ke Wengc,d, Richard A. Dixone,f,1, and Guodong Wanga,1 aState Key Laboratory of Plant Genomics and National Center for Plant Gene Research, Institute of Genetics and Developmental Biology, Chinese Academy of Sciences, 100101 Beijing, China; bUniversity of Chinese Academy of Sciences, 100049 Beijing, China; cWhitehead Institute for Biomedical Research, Cambridge, MA 02142; dDepartment of Biology, Massachusetts Institute of Technology, Cambridge, MA 02139; eBioDiscovery Institute, University of North Texas, Denton, TX 76203; and fDepartment of Biological Sciences, University of North Texas, Denton, TX 76203 Contributed by Richard A. Dixon, April 25, 2018 (sent for review February 6, 2018; reviewed by Joerg Bohlmann and Mattheos A. G. Koffas) Xanthohumol (XN) and demethylxanthohumol (DMX) are special- braries have been deposited in the TrichOME database [www. ized prenylated chalconoids with multiple pharmaceutical appli- planttrichome.org (18)], and numerous large RNAseq datasets from cations that accumulate to high levels in the glandular trichomes different hop tissues or cultivars have also been made publically of hops (Humulus lupulus L.). Although all structural enzymes in available. By mining the hops transcriptome data, we and others have the XN pathway have been functionally identified, biochemical functionally identified several key terpenophenolic biosynthetic en- mechanisms underlying highly efficient production of XN have zymes from hop glandular trichomes (1, 18–23); these include car- not been fully resolved. In this study, we characterized two non- boxyl CoA ligase (CCL) genes and two aromatic prenyltransferase catalytic chalcone isomerase (CHI)-like proteins (designated as (PT) genes (HlPT1L and HlPT2) (22, 23). -
Exploring Food Contents in Scientific Literature with Foodmine
Exploring Food Contents in Scientific Literature with FoodMine By Forrest Hooton, Giulia Menichetti and Albert-László Barabási Supplementary Material Section 1: Data Collection Literature mining consisted of three technical steps: search, selection, and information extraction. We began with a general search query, and then applied programmatic filters to the resulting query. After each filter, we inspected the remaining papers to determine if they contained any relevant information. If the paper was selected, we manually extracted information pertaining to compounds reported for garlic and cocoa, and organized it in a central database. We chose PubMed as the search engine for this process, as it represents the largest biomedical database that contains information for over 28 million research papers, and uses open paper indexing with professional review through MeSH terms. Given the recent interest in milk composition determined by experimental research combined with literature investigation, we explored PolySearch2, an online tool to search free-text corpora such as PubMed Central.1,2 We used PolySearch to retrieve information relevant to garlic and cocoa by entering “garlic” and “cocoa” as search terms, respectively. We searched for relevant food metabolites, MeSH compounds, and toxins. PolySearch2 generated 50 results across the three categories for garlic, and 24 results for cocoa. While PolySearch found chemicals associated with garlic and cocoa, our FoodMine process indicates that more information is available. Furthermore, PolySearch -
The Effect of Light Intensity on the Expression of Leucoanthocyanidin
G C A T T A C G G C A T genes Article The Effect of Light Intensity on the Expression of Leucoanthocyanidin Reductase in Grapevine Calluses and Analysis of Its Promoter Activity Jing Cheng 1,2, Keji Yu 1,2,3, Mingyue Zhang 4, Ying Shi 1,2 , Changqing Duan 1,2 and Jun Wang 1,2,* 1 Center for Viticulture and Enology, College of Food Science and Nutritional Engineering, China Agricultural University, Beijing 100083, China; [email protected] (J.C.); [email protected] (K.Y.); [email protected] (Y.S.); [email protected] (C.D.) 2 Key Laboratory of Viticulture and Enology, Ministry of Agriculture and Rural Affairs, Beijing 100083, China 3 Beijing Advanced Innovation Center for Tree Breeding by Molecular Design, Beijing Forestry University, Beijing 100083, China 4 China Meat Research Center, Beijing Academy of Food Sciences, Beijing 100068, China; [email protected] * Correspondence: [email protected]; Tel.: +86-10-62738537 Received: 21 August 2020; Accepted: 29 September 2020; Published: 30 September 2020 Abstract: To investigate the effect of light intensity on flavonoid biosynthesis, grapevine calluses 2 1 2 1 were subjected to high light (HL, 250 µmol m− s− ) and dark (0 µmol m− s− ) in comparison 2 1 to 125 µmol m− s− under controlled conditions (NL). The alteration of flavonoid profiles was determined and was integrated with RNA sequencing (RNA-seq)-based transcriptional changes of the flavonoid pathway genes. Results revealed that dark conditions inhibited flavonoid biosynthesis. Increasing light intensity affected flavonoids differently—the concentrations of flavonols and anthocyanins as well as the expressions of corresponding genes were less affected, whereas flavan-3-ol concentrations were predominantly increased, which caused enhanced trans-flavan-3-ol concentrations.