| Revision as of 15:55, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 442512532 of page Vicine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 15:44, 11 March 2024 edit Marbletan (talk | contribs)Extended confirmed users5,453 editsmNo edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 427415928 |
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| verifiedrevid = 470630004 |
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|ImageFile=vicine.png |
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| ImageFile=vicin.svg |
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|ImageSize=200px |
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| ImageSize=200px |
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|IUPACName= <small>2,6-diamino-5-oxy]-1H- pyrimidin-4-one</small> |
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| IUPACName = 2,6-Diamino-5-(β-{{small|D}}-glucopyranosyloxy)pyrimidin-4(1''H'')-one |
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|OtherNames= |
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| SystematicName = 2,6-Diamino-5-<nowiki/>{oxy}pyrimidin-4(1''H'')-one |
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|Section1= {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 82575 |
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| ChemSpiderID = 82575 |
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| InChI = 1/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1 |
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| InChI = 1/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KGNGTSCIQCLKEH-SYCVNHKBSA-N |
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| StdInChIKey = KGNGTSCIQCLKEH-SYCVNHKBSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 152-93-2 --> |
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| CASNo=152-93-2 |
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| PubChem=91446 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O=C2\N=C(\N)NC(=C2/O1O((O)(O)1O)CO)/N |
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| UNII = COL14PJW3X |
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| PubChem=135413566 |
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| SMILES = O=C2\N=C(\N)NC(=C2/O1O((O)(O)1O)CO)/N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=10|H=16|N=4|O=7 |
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| Formula = C<sub>10</sub>H<sub>16</sub>N<sub>4</sub>O<sub>7</sub> |
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| MolarMass = 304.25 g/mol |
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'''Vicine''' is an ] ] found mainly in ]s, which are also called broad beans (''])''.<ref>{{Cite journal|vauthors=Lattanzio V, Bianco VV, Crivelli G, Miccolis V |date=May 1983 |title=Variability of Amino Acids, Protein, Vicine and Convicine in ''Vicia faba'' (L) Cultivars |journal=Journal of Food Science|volume=48|issue=3|pages=992–993|doi=10.1111/j.1365-2621.1983.tb14950.x}}</ref> Vicine is toxic in individuals who have a ]. It causes ], called favism. The formation of vicine in ''Vicia faba'' has been studied, but this natural formation has not yet been found.<ref name=":0">{{cite book|title=Toxic constituents of plant foodstuffs |last1=Mager |first1=J. |last2=Razin |first2=A. |last3=Herschko |first3=A. |publisher=Springer |orig-year=1969 |editor-last=Liener|editor-first=I. |pages=293–312|chapter=10. Favism |chapter-url=https://www.google.com.au/books/HsHi-_5QWdcC?&pg=PA293 |isbn= 9780323147378 |year=2012}}</ref><ref>{{cite journal |last1=Khazaei |first1=Hamid |title=Eliminating vicine and convicine, the main anti-nutritional factors restricting faba bean usage |journal=Trends in Food Science & Technology |date=September 2019 |volume=91 |pages=549–556 |doi=10.1016/j.tifs.2019.07.051 |doi-access=free }}</ref> |
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== History == |
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Vicine was initially isolated in 1870 from the seeds of ''Vicia sativa'' by a method of ] with sulfuric acid and subsequent ] with mercury sulfate (HgSO<sub>4</sub>). Later vicine was also found in other ''Vicia'' species, namely ''Vicia faba'', beet juice and peas. The chemical structure of the compound was built gradually. First the glycosidic nature of the compound was recognized in 1896. The same year the ] of vicine, ], was isolated. In the beginning of the 20th century the ] structure was recognized. Despite these initial successes, the correct formula of vicine was determined only in 1953 and it is 2,4-diamino-6-oxypyrimidine-5-(β-<small>D</small>-glucopyranoside).<ref name=":0" /> |
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== Metabolism == |
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Vicine is an inactive compound in the body. When vicine enters the body through food, it is hydrolysed by the intestinal microflora to a highly reactive ] generating compound, the aglycone ].<ref name=":0" /> Upon ], the glucose part of the molecule is split off and that results in the reduced divicine. Divicine is then taken up in the blood through the ].<ref>{{cite journal|vauthors=Baker MA, Bosia A, Pescarmona G, Turrini F, Arese P |title=Mechanism of action of divicine in a cell-free system and in glucose-6-phosphate dehydrogenase-deficient red cells |journal=Toxicologic Pathology |volume=12 |issue=4 |pages=331–6 |date=June 1984 |pmid=6099911 |doi=10.1177/019262338401200405 |s2cid=26038580}}</ref><ref name=":1">{{cite journal|vauthors=Luzzatto L, Arese P |title=Favism and Glucose-6-Phosphate Dehydrogenase Deficiency |journal=The New England Journal of Medicine |volume=378 |issue=1 |pages=60–71 |date=January 2018 |pmid=29298156 |doi=10.1056/NEJMra1708111}}</ref> |
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== Adverse effects == |
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Adverse effects almost solely occur in humans that suffer from ]. This deficiency causes a shortage of ] in ] and glutathione is needed for the neutralization of ROS (]) created by the strongly ] ].<ref name=":1" /> ] is a common genetic condition, with a global prevalence of approximately 4.9%, affecting over 400 million individuals worldwide.<ref name=":1" /><ref>{{Cite journal |last1=Khazaei |first1=Hamid |last2=Purves |first2=Randy W. |last3=Hughes |first3=Jessa |last4=Link |first4=Wolfgang |last5=O'Sullivan |first5=Donal M. |last6=Schulman |first6=Alan H. |last7=Björnsdotter |first7=Emilie |last8=Geu-Flores |first8=Fernando |last9=Nadzieja |first9=Marcin |last10=Andersen |first10=Stig U. |last11=Stougaard |first11=Jens |last12=Vandenberg |first12=Albert |last13=Stoddard |first13=Frederick L. |date=2019-09-01 |title=Eliminating vicine and convicine, the main anti-nutritional factors restricting faba bean usage |journal=Trends in Food Science & Technology |volume=91 |pages=549–556 |doi=10.1016/j.tifs.2019.07.051 |issn=0924-2244|doi-access=free }}</ref> It is important to recognize that ] can still be life-threatening if not promptly diagnosed and managed. Effective management often includes interventions as blood transfusions, but with appropriate care, full recovery from favism without lasting complications is the expected outcome.<ref>{{Cite journal |last1=Reading |first1=N. Scott |last2=Sirdah |first2=Mahmoud M. |last3=Shubair |first3=Mohammad E. |author3-link=Mohammed Shabir |last4=Nelson |first4=Benjamin E. |last5=Al-Kahlout |first5=Mustafa S. |last6=Al-Tayeb |first6=Jamal M. |last7=Aboud |first7=Lina N. |last8=Shaban |first8=Maysaa Abu |last9=Luzzatto |first9=Lucio |last10=Prchal |first10=Josef T. |date=2016-09-01 |title=Favism, the commonest form of severe hemolytic anemia in Palestinian children, varies in severity with three different variants of G6PD deficiency within the same community |url=https://www.sciencedirect.com/science/article/pii/S1079979616300821 |journal=Blood Cells, Molecules and Diseases |volume=60 |pages=58–64 |doi=10.1016/j.bcmd.2016.07.001 |pmid=27519946 |issn=1079-9796}}</ref> |
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=== Indications === |
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Persons with G6PD deficiency are asymptomatic. An attack of acute haemolytic anaemia can appear out of nowhere and can be very severe and life-threatening. Indications of such a sudden attack of favism are dark urine, ], ], abdominal pain and in most cases fever.<ref name=":1" /> |
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== Toxicity == |
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The β-glycosidic bond between glucose and the ] at C5 on the pyrimidine ring are hydrolysed to yield the ] of vicine, divicine (2,6-diamino-4,5-dihydroxypyrimidine).<ref>{{cite journal|vauthors=Rizzello CG, Losito I, Facchini L, Katina K, Palmisano F, Gobbetti M, Coda R |title=Degradation of vicine, convicine and their aglycones during fermentation of faba bean flour |journal=Scientific Reports |volume=6 |issue=1 |pages=32452 |date=August 2016 |pmid=27578427 |pmc=5006014 |doi=10.1038/srep32452 |bibcode=2016NatSR...632452R}}</ref> These aglycones have a strong oxidising capacity for ].<ref>{{cite journal|vauthors=Mager J, Glaser G, Razin A, Izak G, Bien S, Noam M |title=Metabolic effects of pyrimidines derived from fava bean glycosides on human erythrocytes deficient in glucose-6-phosphate dehydrogenase |journal=Biochemical and Biophysical Research Communications |volume=20 |issue=2 |pages=235–40 |date=July 1965 |pmid=5850686 |doi=10.1016/0006-291x(65)90352-9}}</ref> In healthy individuals, this is not a problem, as glutathione can be reduced quickly enough to regenerate it. In individuals with a deficiency for ] (G6PD) however, this results in ].<ref>{{cite journal|vauthors=Pulkkinen M, Zhou X, Lampi AM, Piironen V |title=Determination and stability of divicine and isouramil produced by enzymatic hydrolysis of vicine and convicine of faba bean |journal=Food Chemistry |volume=212 |pages=10–9 |date=December 2016 |pmid=27374500 |doi=10.1016/j.foodchem.2016.05.077}}</ref> |
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== Effects on animals == |
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A 10 g vicine /kg diet in laying hens led to reduced feed intake, egg weight, haemoglobin levels and fertility and increased liver weights, liver glutathione levels and plasma lipid levels. A diet with comparable levels of vicine per kg in pigs showed only small effects on protein and energy digestibility.<ref>{{Cite journal|vauthors=Jezierny D, Mosenthin R, Bauer E |date=May 2010 |title=The use of grain legumes as a protein source in pig nutrition: A review |journal=Animal Feed Science and Technology |volume=157|issue=3–4|pages=111–128|doi=10.1016/j.anifeedsci.2010.03.001}}</ref> |
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In another study, laying and broiler hens were fed grains that were soaked for different periods of time, which partly or totally removed vicine. Hens that had had grains with vicine still in them showed a significant decrease in corpuscular haemoglobin, while the others did not.<ref>{{cite journal|vauthors=Farran MT, Darwish AH, Uwayjan MG, Sleiman FT, Ashkarian VM |title=Vicine and convicine in common vetch (Vicia sativa) seeds enhance beta-cyanoalanine toxicity in male broiler chicks |journal=International Journal of Toxicology |volume=21 |issue=3 |pages=201–9 |date=June 2002 |pmid=12055021 |doi=10.1080/10915810290096333 |s2cid=21101425}}</ref> |
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An in vivo study in rats showed that oral administration of vicine resulted in only small reductions in glutathione concentrations and no mortality. ] administration however, led to a rapid decrease in glutathione followed by death because of ].<ref>{{cite journal|vauthors=Arbid MS, Koriem KM, Asaad GF, Megahed HA |title=Effect of the antibiotic neomycin on the toxicity of the glycoside vicine in rats |journal=Journal of Toxicology |volume=2013 |pages=913128 |date=2013 |pmid=23840205 |pmc=3694484 |doi=10.1155/2013/913128 |doi-access=free}}</ref> |
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== References == |
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{{reflist|30em}} |
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==External links== |
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*{{Commons category-inline}} |
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{{Glycosides}} |
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