Occurrence of Vicine and Convicine in Faba Bean and Their Removal by Hydrolysis
Total Page:16
File Type:pdf, Size:1020Kb
Load more
Recommended publications
-
Pro-Oxidizing Metabolic Weapons ☆ ⁎ Etelvino J.H
Comparative Biochemistry and Physiology, Part C 146 (2007) 88–110 www.elsevier.com/locate/cbpc Review The dual face of endogenous α-aminoketones: Pro-oxidizing metabolic weapons ☆ ⁎ Etelvino J.H. Bechara a, , Fernando Dutra b, Vanessa E.S. Cardoso a, Adriano Sartori a, Kelly P.K. Olympio c, Carlos A.A. Penatti d, Avishek Adhikari e, Nilson A. Assunção a a Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes 748, 05508-900, São Paulo, SP, Brazil b Centro de Ciências Biológicas e da Saúde, Universidade Cruzeiro do Sul, São Paulo, SP, Brazil c Faculdade de Saúde Pública, Universidade de São Paulo, São Paulo, SP, Brazil d Department of Physiology, Dartmouth Medical School, Hanover, NH, USA e Department of Biological Sciences, Columbia University, New York, NY, USA Received 31 January 2006; received in revised form 26 June 2006; accepted 6 July 2006 Available online 14 July 2006 Abstract Amino metabolites with potential prooxidant properties, particularly α-aminocarbonyls, are the focus of this review. Among them we emphasize 5-aminolevulinic acid (a heme precursor formed from succinyl–CoA and glycine), aminoacetone (a threonine and glycine metabolite), and hexosamines and hexosimines, formed by Schiff condensation of hexoses with basic amino acid residues of proteins. All these metabolites were shown, in vitro, to undergo enolization and subsequent aerobic oxidation, yielding oxyradicals and highly cyto- and genotoxic α-oxoaldehydes. Their metabolic roles in health and disease are examined here and compared in humans and experimental animals, including rats, quail, and octopus. In the past two decades, we have concentrated on two endogenous α-aminoketones: (i) 5-aminolevulinic acid (ALA), accumulated in acquired (e.g., lead poisoning) and inborn (e.g., intermittent acute porphyria) porphyric disorders, and (ii) aminoacetone (AA), putatively overproduced in diabetes mellitus and cri-du-chat syndrome. -
The Use of Plants in the Traditional Management of Diabetes in Nigeria: Pharmacological and Toxicological Considerations
Journal of Ethnopharmacology 155 (2014) 857–924 Contents lists available at ScienceDirect Journal of Ethnopharmacology journal homepage: www.elsevier.com/locate/jep Review The use of plants in the traditional management of diabetes in Nigeria: Pharmacological and toxicological considerations Udoamaka F. Ezuruike n, Jose M. Prieto 1 Center for Pharmacognosy and Phytotherapy, Department of Pharmaceutical and Biological Chemistry, School of Pharmacy, University College London, 29-39 Brunswick Square, WC1N 1AX London, United Kingdom article info abstract Article history: Ethnopharmacological relevance: The prevalence of diabetes is on a steady increase worldwide and it is Received 15 November 2013 now identified as one of the main threats to human health in the 21st century. In Nigeria, the use of Received in revised form herbal medicine alone or alongside prescription drugs for its management is quite common. We hereby 26 May 2014 carry out a review of medicinal plants traditionally used for diabetes management in Nigeria. Based on Accepted 26 May 2014 the available evidence on the species' pharmacology and safety, we highlight ways in which their Available online 12 June 2014 therapeutic potential can be properly harnessed for possible integration into the country's healthcare Keywords: system. Diabetes Materials and methods: Ethnobotanical information was obtained from a literature search of electronic Nigeria databases such as Google Scholar, Pubmed and Scopus up to 2013 for publications on medicinal plants Ethnopharmacology used in diabetes management, in which the place of use and/or sample collection was identified as Herb–drug interactions Nigeria. ‘Diabetes’ and ‘Nigeria’ were used as keywords for the primary searches; and then ‘Plant name – WHO Traditional Medicine Strategy accepted or synonyms’, ‘Constituents’, ‘Drug interaction’ and/or ‘Toxicity’ for the secondary searches. -
Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics
molecules Article Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics Mohamed A. Farag 1,2,* , Mohamed G. Sharaf El-Din 3, Mohamed A. Selim 1,4 , Asmaa I. Owis 5 , Sameh F. Abouzid 5, Andrea Porzel 6 , Ludger A. Wessjohann 6,* and Asmaa Otify 1 1 Pharmacognosy Department, Faculty of Pharmacy, Cairo University, Cairo 12613, Egypt; [email protected] (M.A.S.); [email protected] (A.O.) 2 Chemistry Department, School of Sciences & Engineering, The American University in Cairo, New Cairo 11835, Egypt 3 Pharmacognosy Department, Faculty of Pharmacy, Port Said University, Port Said 42526, Egypt; [email protected] 4 Pharmacognosy Department, Faculty of Pharmacy, Misr University for Science & Technology (MUST), 6th October City 12566, Egypt 5 Pharmacognosy Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62521, Egypt; [email protected] (A.I.O.); [email protected] (S.F.A.) 6 Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany; [email protected] * Correspondence: [email protected] (M.A.F.); [email protected] (L.A.W.) Abstract: Legume sprouts are a fresh nutritive source of phytochemicals of increasing attention worldwide owing to their many health benefits. Nuclear magnetic resonance (NMR) was utilized for the metabolite fingerprinting of 4 major legume sprouts, belonging to family Fabaceae, to be exploited for quality control purposes. Thirty-two metabolites were identified belonging to different Citation: Farag, M.A.; Sharaf El-Din, classes, i.e., fatty acids, sugars, amino acids, nucleobases, organic acids, sterols, alkaloids, and M.G.; Selim, M.A.; Owis, A.I.; isoflavonoids. -
Substantial Depletion of Vicine, Levodopa, and Tyramine in a Fava Bean Protein-Based Nutritional Product
Hindawi International Journal of Food Science Volume 2021, Article ID 6669544, 10 pages https://doi.org/10.1155/2021/6669544 Research Article Substantial Depletion of Vicine, Levodopa, and Tyramine in a Fava Bean Protein-Based Nutritional Product Paul W. Johns and Steven R. Hertzler Abbott Laboratories, Abbott Nutrition Division, 3300 Stelzer Road, Columbus, OH, USA 43219 Correspondence should be addressed to Paul W. Johns; [email protected] Received 5 November 2020; Revised 1 January 2021; Accepted 16 January 2021; Published 30 January 2021 Academic Editor: Chaowalit Monton Copyright © 2021 Paul W. Johns and Steven R. Hertzler. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. A commercial fava bean protein isolate and a liquid nutritional product formulated with it were tested by validated HPLC methods for the favism-associated pyrimidine glycoside vicine, the dopamine precursor levodopa, and the biogenic amine tyramine. The vicine, levodopa, and tyramine concentrations in the protein isolate—306, 13.3, and <0.5 mg/kg, respectively—when expressed on a protein basis—34, 1.5, and <0.06 mg/100 g protein, respectively—were at least 96% lower than the vicine, levodopa, and tyramine (protein-based) concentrations reported for fava beans (≥900, ~200, and ~4 mg/100 g protein, respectively). This was also true for the vicine (13 mg/kg or 22 mg/100 g protein), levodopa (≤0.17 mg/kg or ≤0.3 mg/100 g protein), and tyramine (0.08 mg/kg or 0.14 mg/100 g protein) concentrations in the nutritional product. -
Chapter 11: Adverse Effects of Naturally Occurring Nonnutritive Substances
chapter eleven Adverse effects of naturally occurring nonnutritive substances H. van Genderen 11.1Introduction 11.2Endogenous toxins of plant origin 11.2.1Nonnutritive natural food components of important toxicological relevance 11.2.1.1α-Aminopropionic acid derivatives 11.2.1.2Agaritine 11.2.1.3Biogenic amines 11.2.1.4Cyanogenic glycosides ©1997 CRC Press LLC 11.2.1.5Glucosinolates 11.2.1.6Glycoalkaloids 11.2.1.7Pyrimidine glycosides 11.3Toxic contaminants of microbial origin 11.3.1Mycotoxins 11.3.1.1Ergot alkaloids 11.3.1.2Aflatoxins 11.3.1.3Ochratoxins 11.3.1.4Trichothecenes 11.3.2Toxins originating from marine algae or plankton 11.3.3Bacterial toxins 11.4Antinutritional plant proteins 11.5Summary Reference and reading list 11.1 Introduction By far the majority of the non-nutritive components are harmless. However, a number of naturally occurring substances have been identified that induce adverse effects. These originate mainly from plants and microorganisms. In this chapter, such substances occurring in common foods are discussed. Cases of adverse effects following the intake of unusual foods, particularly in tropical regions, are not included. Their occurrence is too incidental. The following categories are discussed: – (low-molecular) endogenous toxins of plant origin; ©1997 CRC Press LLC –toxic contaminants of microbial origin; –plant proteins that interfere with the digestion of the absorption of nutrients. 11.2Endogenous toxins of plant origin Low-molecular endogenous toxins of plant origin are products from the so-called second- ary metabolism in plants. In phytochemistry, a distinction is made between primary and secondary metabolism. Primary metabolism includes processes involved in energy me- tabolism such as photosynthesis, growth, and reproduction. -
Copyrighted Material
Index Abhexon, 501, 565 bitter, 636 reactions, 564, 565 dimethylarsinoyl, 415 Abietadiene, 505, 506 oxocarboxylic, 550 Abietic acid, 189 phenolic, 551 Absinthin, 634 reactions, 555 Acacetin, 695 sugar, 212 Acacipetalin, 775, 776 Acidulants, 872 Acenaphthene, 919 Aconitic acid, 546 Acenaphthylene, 919 Acorin, 635 Acephate, 1010 Acrolein, 82 Aceric acid, 213, 214, 259 reactions, 180, 181, 193, 527, 538 Acesulfame K, 865, 866, 870 Acromelic acids, 829 Acetaldehyde, 72, 527 Acrylamide, 899, 900 reactions, 295, 538, 540 content in foods, 900 Acetals, 537, 541 reactions, 901, 902 reactions, 538 Acrylic acid, 1034 Acetic acid, 542, 850 Acrylonitrile, 1039 reactions, 296, 297, 543 Actin, 47 Acetoacetic acid, 551 Actinin, 47 Acetoin, 522, 536 Acylchloropropanediols, 910 reactions, 522 Acyloins, 536 Acetol, see hydroxyacetone Acylsphingosines, see ceramides Acetone, 533 Additives, 847 reactions, 540 Adenine, 396, 397 Acetophenone, 535 Adenosine diphosphate, see ADP Acetylcholine, 399 monophosphate, see AMP Acetylcysteines, see mercapturates triphosphate, see ATP Acetylfuran, 286 Adenylic acid, see AMP Acetylgalactosamine, 53, 58 Adermine, see vitamin B6 Acetylglucosamine, 58 Adhesives, 889 Acetylhistidines, 20 Adhyperflorin, 712 Acetyllactaminic acid, see acetylneuraminic acid Adipic acid, 544 Acetyllysine, 18 ADP, 18, 874 Acetylmuramic acid, 217 Adrastin, 951 Acetylneuraminic acid, 53, 58, 217 COPYRIGHTEDAdrenaline, MATERIALsee epinephrine Acetylpyridine, 590 Adriatoxin, 838 Acetylpyrroline, 18, 501 Advanced glycation end products, 319–23 Acetylpyrroline, reactions, 599 lipoxidation end products, 319 Acetyltetrahydropyridine, 18 Aflatoxicol, 946 Acetyltetrahydropyridine, reactions, 600 Aflatoxins, 942, 945–8 Acids as preservatives, 848 Aflatrem, 961 lipoamino, 129 Afzelechins, 648 aldonic, 212 Agar, 269 alicyclic, 551 Agaric acid, see agaricinic acid aromatic, 551 Agaricinic acid, 835, 865 bile, 140 Agaricone, 705 The Chemistry of Food, First Edition. -
Degradation of Vicine, Convicine and Their Aglycones During Fermentation of Faba Bean Flour
www.nature.com/scientificreports OPEN Degradation of vicine, convicine and their aglycones during fermentation of faba bean flour Received: 07 March 2016 Carlo Giuseppe Rizzello1, Ilario Losito2,3, Laura Facchini2, Kati Katina4, Accepted: 08 August 2016 Francesco Palmisano2,3, Marco Gobbetti1 & Rossana Coda4 Published: 31 August 2016 In spite of its positive repercussions on nutrition and environment, faba bean still remains an underutilized crop due to the presence of some undesired compounds. The pyrimidine glycosides vicine and convicine are precursors of the aglycones divicine and isouramil, the main factors of favism, a genetic condition which may lead to severe hemolysis after faba bean ingestion. The reduction of vicine and convicine has been targeted in several studies but little is known about their degradation. In this study, the hydrolysis kinetics of vicine and convicine and their derivatives during fermentation with L. plantarum DPPMAB24W was investigated. In particular, a specific HPLC method coupled to ESI-MS and MS/MS analysis, including the evaluation procedure of the results, was set up as the analytical approach to monitor the compounds. The degradation of the pyrimidine glycosides in the fermented flour was complete after 48 h of incubation and the aglycone derivatives could not be detected in any of the samples. The toxicity of the fermented faba bean was established through ex-vivo assays on human blood, confirming the experimental findings. Results indicate that mild and cost effective bioprocessing techniques can be applied to detoxify faba bean also for industrial applications. Faba bean (Vicia faba L.) is a leguminous plant belonging to the Fabaceae family, able to grow in different cli- mates1. -
MOLECULAR BASIS of GLUCOSE-6-PHOSPHATE DEHYDROGENASE DEFICIENCY in CAPE COAST, GHANA by Dan Osei Mensah Bonsu, B.Sc. Human Biolo
MOLECULAR BASIS OF GLUCOSE-6-PHOSPHATE DEHYDROGENASE DEFICIENCY IN CAPE COAST, GHANA by Dan Osei Mensah Bonsu, B.Sc. Human Biology (Hons) A thesis submitted to the Department of Biochemistry and Biotechnology, Kwame Nkrumah University of Science and Technology, Kumasi in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE Department of Biochemistry and Biotechnology College of Science February, 2013 MOLECULAR BASIS OF GLUCOSE-6-PHOSPHATE DEHYDROGENASE DEFICIENCY IN CAPE COAST, GHANA February, 2013 DECLARATION I hereby declare that except for references to other people’s work, which have been duly acknowledged, this thesis is the result of my own research. Neither all nor parts of this thesis have been presented for another degree elsewhere. DAN OSEI MENSAH BONSU (M.Sc. CANDIDATE) SIGNATURE DATE DR. FAREED K. N. ARTHUR (SUPERVISOR) SIGNATURE DATE DR. PETER TWUMASI (SUPERVISOR) SIGNATURE DATE PROF. (MRS) IBOK ODURO (HEAD OF DEPARTMENT) SIGNATURE DATE i ABSTRACT Glucose-6-phosphate dehydrogenase (G6PD) is a cytoplasmic enzyme that is essential for a cell’s capacity to withstand oxidant stress. G6PD-deficiency is the commonest enzymopathy of humans with a worldwide distribution. The geographical correlation of its distribution with the historical endemicity of malaria suggests that the defect has risen in frequency through natural selection by malaria. This study was carried out to ascertain the molecular basis of G6PD-deficiency in Cape Coast in the Central Region of Ghana. Two hundred (200) unrelated persons (82 males and 118 females), all visiting the Out Patients Department (OPD) of the Central Regional Hospital, Cape Coast, were screened for G6PD-deficiency using the methaemoglobin reduction test. -
Biological Complementary Therapies: a Focus on Botanical Products in Diabetes
In Brief to Practice Research From / Complementary & Integrative Medicine Several botanical and biological products claim to lower blood glucose or decrease complications of diabetes, and some of these are being used by peo- ple with diabetes. Products thought to lower blood glucose include gymnema, fenugreek, bitter melon, ginseng, and nopal. Claims have also been made for aloe, bilberry, and milk thistle, but there is less evidence in support of these. Botanical products thought to decrease diabetes complications include ␥- linolenic acid, ginkgo biloba, and garlic. A vitamin-like substance, ␣-lipoic acid, has been used to treat neuropathic complications. Biological Complementary Therapies: A Focus on Botanical Products in Diabetes No one has thoroughly determined concerns about possible side effects3 how many patients with diabetes use and drug interactions.4 Patients using complementary therapies. A recent complementary therapies have experi- Laura Shane-McWhorter, PharmD, survey of diabetes educators in the enced many serious side effects; in BCPS, FASCP, CDE, BC-ADM western half of the United States1 eval- some cases, they may attribute these uated the most frequently recom- effects to another medication. Because mended and used alternative thera- patients often take medications to pies. These included physical activity, treat their diabetes, concomitant use self-help groups, lifestyle diets, laugh- of complementary therapies may also ter and humor, relaxation therapy, result in toxicity secondary to exag- prayer, imagery/visualization, medita- gerated effects or sub-therapeutic tion, massage, and music therapy. effects of their conventional medica- Although botanical products were tions. included in the survey, they were not Another concern relates to the vari- frequently recommended or used. -
BIOCHEMICAL EFFECT of VICINE and DIVICINE EXTRACTED from FAVA BEANS (VICIA FABA) in RATS Hussein Abd El-Maksoud1, Mohammed A
BENHA VETERINARY MEDICAL JOURNAL (2013) 24: 98-110 BENHA UNIVERSITY FACULTY OF VETERINARY MEDICINE BIOCHEMICAL EFFECT OF VICINE AND DIVICINE EXTRACTED FROM FAVA BEANS (VICIA FABA) IN RATS Hussein Abd El-Maksoud1, Mohammed A. Hussein*2, Anwar Kassem1 1Department of Biochemistry, Faculty of Veterinary Medicine, Benha University, 13736 Moshtohor, Qalioubeya, Egypt. 2Biochemistry Department, Faculty of Pharmacy, October 6th University, October 6th city, Egypt A B S T R A C T Vicine and its aglycone Divicine are two natural phenolics extracted from the tropical plant Fava bean (Vicia faba; broad bean, horse bean). In our study, Divicine was obtained by acid hydrolysis of Vicine. Structural elucidation of the extracted compound Vicine and its aglycon Divicine was proven using elemental analysis, infra-red and mass spectral data. Both the phenolic compounds were tested for their ability to inhibit peroxidation induced by free radicals, named; Fe2+, superoxide, hydrogen peroxide and hydroxyl radicals. In addition, the results were compared with natural and synthetic antioxidants, such as α- tocopherol, ascorbic acid, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA) and trolox. Vicine and Divicine exhibited a strong reducing power, chelating activity on Fe2+, free radical-, hydrogen peroxide- and hydroxyl radical scavenging activities. All the mentioned spectral data and structural conditions explain that, O-deglycosylation of Vicine to give its aglycone, Divicine and increase its ability to inhibit peroxidation and reaction with peroxyl radicals. Key words: Vicine, Divicine, Fava bean, antioxidants proper, free radicals scavenging. (BVMJ 24: 98-110; 2013) 1. INTRODUCTION especially in the developing countries [29] . Faba bean (Vicia faba) (broad bean, horse xidative stress is a widely accepted bean) is an important member of the legume participant in the development and family with highly useful characteristics. -
Introduction to Food Toxicology
INTRODUCTION TO FOOD TOXICOLOGY Takayuki Shibamoto Department of Environmental Toxicology University of California, Davis Davis, California Leonard F. Bjeldanes Department of Nutritional Sciences University of California, Berkeley Berkeley, California FOOD SCIENCE AND TECHNOLOGY International Series SERIES EDITOR Steve L. Taylor University of Nebraska ADVISORY BOARD John E. Kinsella University of California, Davis Douglas Archer FDA, Washington, D.C. Jesse F. Gregory, LII University of Florida Susan K. Harlander University of Minnesota Daryl B. Lund Rutgers, The State University of New Jersey Barbara O. Schneeman University of California, Davis Robert Macrae University of Hull, United Kingdom A complete list of the books in this series appears at the end of this volume. 2 Contents Foreword Preface CHAPTER I Principles of Toxicology I. Dose—Response II. Safety III. Absorption IV. Translocation V. Storage VI. Excretion CHAPTER 2 Determination of Toxicants in Foods I. Qualitative and Quantitative Analyses of Toxicants in Foods II. Sample Preparations for Determination of Toxicants A. Sampling B. Extraction C. Cleanup D. Chromatography III. Toxicity Testing A. Preliminary Steps for Toxicity Testing B. Acute Toxicity C. Genetic Toxicity D. Metabolism E. Subchronic Toxicity F. Teratogenesis G. Chronic Toxicity CHAPTER 3 Biotransformation I. Conversion of Lipid-Soluble Substances II. Phase I Reactions Ill. Phase II Reactions IV. The Effects of Diet on Biotransformation V. Metabolic Induction 3 VI. CHAPTER 4 Natural Toxins in Animal Foodstuffs I. Toxins Occurring in Animal Liver A. Bile Acids B. Vitamin A II. Toxins Occurring in Marine Animals A. Scombroid Poisoning B. Saxitoxin C. Tetramine D. Pyropheophorbide a E. Tetrodotoxin F. Ciguatoxin CHAPTER 5 Natural Toxins in Plant Foodstuffs I. -
Subject Index*
SUBJECT INDEX* Italicized configurational prefixes (as glycero-) are used as main entries, whereas other italicized prefixes (as scyllo-) are listed under the stem name. A Acetoacetic ester, 240 Absolute configuration, 15 synthesis of DL-mannitol, 250 Acacia species, 685, 510 reactions with sugars, 240 gum arabic, 685 Acetobacter species, Acetaldehyde, see also Ethylidene de- A. acetigenum, 708 rivatives, 235 cellulose synthesis, 708 Acetals, see also Alkylidene derivatives, A. suboxydans, 98, 133, 365 individual aldehydes and ke- action on inositols, 282 tones, individual sugars, and preparation of Anhydro sugars, 1,6-labeled ketoses, 136 acetal type, 227 planteobiose, 501 alkali labile, 390 A. xylinum, 98, 102, 132, 365 definition, 188 cellulose synthesis, 707 preparation, 157, 288 Acetohalogeno sugars, see O-Acetylgly- Acetamide derivatives, 408 cosyl halides; also Acetates and Acetates, see also Acetylation, Es- individual sugars ters, Esterification, Orthoace- Acetolysis, tates and individual compounds, anhydro compounds, 394 139 anhydro sugars, acetal type, 223 ΑΓ-acetyl groups méthylène groups, 232 hydrolysis, 650 polysaccharides, 702 resistance to alkali, 463 Acetone derivatives, see Isopropylidene acetyl migration, 147, 408 Acetylation, see also Acetates, Ortho- acyclic, 139, 142, 144 acetates, and individual com- aldehydo, 139, 142 pounds, 139 anomerization, 141, 483, 495 aminodeoxy sugars, 471 distinction between N- and O-acetyl anomeric ratio, conditions affecting, 140 as analytical procedure, 140 groups, 410 catalysts, 139,