Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Epigallocatechin gallate: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 16:11, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470070217 of page Epigallocatechin_gallate for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 08:38, 11 September 2024 edit GTMotor815 (talk | contribs)33 edits delete advertisement linkTag: references removed 
Line 1: Line 1:
{{Short description|Catechin (polyphenol) in tea}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{redirect|EGCG|the software|Extended GCG}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464362896 | verifiedrevid = 470454774
|ImageFile=Epigallocatechin gallate structure.svg | ImageFile=Epigallocatechin gallate structure.svg
|ImageSize= | ImageSize=250
⚫ |PIN=(2''R'',3''R'')-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2''H''-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
| ImageAlt=Structural formula of epigallocatechin gallate
⚫ |IUPACName= 3,4,5-trihydroxybenzoate
|OtherNames=(-)-Epigallocatechin gallate | ImageFile2 = Epigallocatechin gallate 3D spacefill.png
| ImageSize2=240
⚫ |Section1= {{Chembox Identifiers
| ImageAlt2=Space-filling model of the epigallocatechin gallate molecule
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | IUPACName=(2''R'',3''R'')-3′,4′,5,5′,7-Pentahydroxyflavan-3-yl 3,4,5-trihydroxybenzoate
⚫ | SystematicName=(2''R'',3''R'')-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2''H''-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
| OtherNames=(-)-Epigallocatechin gallate <br> (2''R'',3''R'')-3′,4′,5,5′,7-pentahydroxyflavan-3-yl gallate
⚫ |Section1={{Chembox Identifiers
| IUPHAR_ligand = 7002
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 58575 | ChemSpiderID = 58575
| InChI = 1/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1 | InChI = 1/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
Line 19: Line 26:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WMBWREPUVVBILR-WIYYLYMNSA-N | StdInChIKey = WMBWREPUVVBILR-WIYYLYMNSA-N
| CASNo_Ref = {{cascite|changed|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 989-51-5 --> | CASNo=989-51-5
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=65064
| UNII = BQM438CTEL
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C09731
⚫ | PubChem=65064
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4806 | ChEBI = 4806
| SMILES = O=C(O2Cc3c(O2c1cc(O)c(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4 | SMILES = O=C(O2Cc3c(O2c1cc(O)c(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4
| MeSHName=Epigallocatechin+gallate | MeSHName=Epigallocatechin+gallate
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=22|H=18|O=11 | C=22 | H=18 | O=11
| MolarMass = 458.372 g/mol | MolarMass = 458.372 g/mol
⚫ | Appearance=
| ExactMass = 458.084911
| Density=
⚫ | Appearance=''
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| Solubility=soluble (5 g/L){{vague|date=May 2013}}<ref name="chemicalland21.com">{{cite web |title=(-)-Epigallocatechin gallate |website=Chemicalland21.com |url=https://www.sigmaaldrich.com/catalog/product/sigma/e4143?lang=en&region=GB}}</ref>
| BoilingPt=
| Solubility=soluble<ref name="chemicalland21.com">http://chemicalland21.com/lifescience/foco/%28-%29-EPIGALLOCATECHIN%20GALLATE.htm</ref> | SolubleOther=soluble in ethanol, DMSO, dimethyl formamide<ref name="chemicalland21.com"/> at about 20 g/L
| SolubleOther=soluble in ethanol, DMSO, dimethyl formamide<ref name="chemicalland21.com"/> at about 20 g/l <ref>http://www.caymanchem.com/pdfs/70935.pdf</ref>
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''Epigallocatechin gallate''' ('''EGCG'''), also known as '''epigallocatechin-3-gallate''', is the ] of ] and ], and is a type of ].

EGCG – the most abundant catechin in ] – is a ] under ] for its potential to affect human health and disease. EGCG is used in many ]s.

==Food sources==

===Tea===
It is found in high content in the dried leaves of ] (7380&nbsp;mg per 100 g), ] (4245&nbsp;mg per 100 g), and in smaller quantities, ] (936&nbsp;mg per 100 g).<ref name="usda">{{cite report|url=http://www.ars.usda.gov/SP2UserFiles/Place/12354500/Data/Flav/Flav_R03.pdf|title=USDA Database for the Flavonoid Content of Selected Foods, Release 3|last1=Bhagwat|first1=Seema|last2=Haytowitz|first2=David B.|date=September 2011|publisher=Agricultural Research Service, U.S. Department of Agriculture|pages=2, 98–103|last3=Holden|first3=Joanne M.|access-date=18 May 2015}}</ref> During black tea production, the catechins are mostly converted to ]s and ]s via ]s.{{which|date=May 2015}}<ref>{{cite journal |first1=Mario |last1=Lorenz |first2=Janka |last2=Urban |first3=Ulrich |last3=Engelhardt |first4=Gert |last4=Baumann |first5=Karl |last5=Stangl |first6=Verena |last6=Stangl |date=January 2009 |pmid=19101751 |title=Green and Black Tea are Equally Potent Stimuli of NO Production and Vasodilation: New Insights into Tea Ingredients Involved |journal=Basic Research in Cardiology |volume=104 |issue=1 |pages=100–10 |doi=10.1007/s00395-008-0759-3 |s2cid=20844066 }}</ref>

===Other===
Trace amounts are found in ] skin, ]s, ]s, ]s, ], and ] powder (at 109&nbsp;mg per 100 g).<ref name=usda/>

== Bioavailability ==
When taken orally, EGCG has poor absorption even at daily intake equivalent to 8–16 cups of green tea, an amount causing ] such as ] or ].<ref name="SherryEtAl03">{{cite journal |journal=Clinical Cancer Research |date=15 August 2003 |volume=9 |issue=9 |pages=3312–19 |title=Pharmacokinetics and safety of green tea polyphenols after multiple-dose administration of epigallocatechin gallate and polyphenon E in healthy individuals |first1=H-H. Sherry |last1=Chow |first2=Yan |last2=Cai |first3=Iman A. |last3=Hakim |first4=James A. |last4=Crowell |first5=Farah |last5=Shahi |first6=Chris A. |last6=Brooks |first7=Robert T. |last7=Dorr |first8=Yukihiko |last8=Hara |first9=David S. |last9=Alberts |pmid=12960117 |url=http://clincancerres.aacrjournals.org/content/9/9/3312.long}}</ref> After consumption, EGCG blood levels peak within 1.7 hours.<ref name="lee"/> The absorbed ] is ~5 hours,<ref name="lee"/> but with majority of unchanged EGCG excreted into ] over 0 to 8 hours.<ref name="lee">{{cite journal |journal=Cancer Epidemiology, Biomarkers & Prevention |date=October 2002 |volume=11 |issue=10 Pt 1 |pages=1025–32 |title=Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability |first1=Mao-Jung |last1=Lee |first2=Pius |last2=Maliakal |first3=Laishun |last3=Chen |first4=Xiaofeng |last4=Meng |first5=Flordeliza Y. |last5=Bondoc |first6=Saileta |last6=Prabhu |first7=George |last7=Lambert |first8=Sandra |last8=Mohr |first9=Chung S. |last9=Yang |pmid=12376503 |url=http://cebp.aacrjournals.org/content/11/10/1025.long}}</ref> Methylated metabolites appear to have longer half-lives and occur at 8–25 times the plasma levels of unmetabolized EGCG.<ref name="ManachEtAlReview05">{{cite journal|last1=Manach|first1=C|last2=Williamson|first2=G|last3=Morand|first3=C|last4=Scalbert|first4=A|last5=Rémésy|first5=C|title=Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies.|journal=The American Journal of Clinical Nutrition|date=January 2005|volume=81|issue=1 Suppl|pages=230S–242S|pmid=15640486|url=http://ajcn.nutrition.org/content/81/1/230S.long|doi=10.1093/ajcn/81.1.230S|doi-access=free}}</ref>

==Research==
Well-studied in ], EGCG has various ] in laboratory studies.<ref name=Furst>{{cite journal |last1=Fürst |first1=Robert |last2=Zündorf |first2=Ilse |date=May 2014 |title=Plant-derived anti-inflammatory compounds: hopes and disappointments regarding the translation of preclinical knowledge into clinical progress |journal=Mediators of Inflammation |volume=2014 |page=146832 |id=146832 |doi=10.1155/2014/146832 |pmid=24987194 |pmc=4060065 |doi-access=free }}</ref><ref name="GranjaFrias2017">{{cite journal|last1=Granja|first1=Andreia|last2=Frias|first2=Iúri|last3=Neves|first3=Ana Rute|last4=Pinheiro|first4=Marina|last5=Reis|first5=Salette|title=Therapeutic Potential of Epigallocatechin Gallate Nanodelivery Systems|journal=BioMed Research International|volume=2017|year=2017|pages=1–15|issn=2314-6133|doi=10.1155/2017/5813793|pmid=28791306|pmc=5534279|doi-access=free }}</ref><ref name="WuWang2012">{{cite journal|last1=Wu|first1=Dayong|last2=Wang|first2=Junpeng|last3=Pae|first3=Munkyong|last4=Meydani|first4=Simin Nikbin|title=Green tea EGCG, T cells, and T cell-mediated autoimmune diseases|journal=Molecular Aspects of Medicine|volume=33|issue=1|year=2012|pages=107–18|issn=0098-2997|doi=10.1016/j.mam.2011.10.001|pmid=22020144}}</ref><ref name="RiegseckerWiczynski2013">{{cite journal|last1=Riegsecker|first1=Sharayah|last2=Wiczynski|first2=Dustin|last3=Kaplan|first3=Mariana J.|last4=Ahmed|first4=Salahuddin|title=Potential benefits of green tea polyphenol EGCG in the prevention and treatment of vascular inflammation in rheumatoid arthritis|journal=Life Sciences|volume=93|issue=8|year=2013|pages=307–12|pmid=23871988|pmc=3768132|doi=10.1016/j.lfs.2013.07.006}}</ref>

A 2011 analysis by the ] found that a ] could not be shown for a link between tea catechins and the maintenance of normal blood LDL-cholesterol concentration.<ref name="efsa">{{cite journal |author=EFSA NDA Panel (EFSA Panel on Dietetic Products, Nutrition and Allergies) |journal=EFSA Journal |volume=9 |issue=4 |year=2011 |title=Scientific Opinion on the substantiation of health claims related to Camellia sinensis (L.) Kuntze (tea), including catechins in green tea, and improvement of endothelium-dependent vasodilation (ID 1106, 1310), maintenance of normal blood pressure |doi=10.2903/j.efsa.2011.2055 |page=2055|doi-access=free }}</ref> A 2016 review found that high daily doses (107 to 856&nbsp;mg/day) taken by human subjects over four to 14 weeks produced a small reduction of ].<ref name="LDL">{{cite journal|last1=Momose Y|display-authors=etal|title=Systematic review of green tea epigallocatechin gallate in reducing low-density lipoprotein cholesterol levels of humans.|journal=Int J Food Sci Nutr|volume=67|issue=6|year=2016|pages=606–13|pmid=27324590|doi=10.1080/09637486.2016.1196655|s2cid=39704366}}</ref>

==Potential toxicity==

A 2018 review showed that excessive intake of EGCG may cause ].<ref name="pmid29580974">{{cite journal|pmid=29580974|year=2018|last1=Hu|first1=J|title=The safety of green tea and green tea extracts consumption in adults – Results of a systematic review|journal=Regulatory Toxicology and Pharmacology|volume=95|pages=412–33|last2=Webster|first2=D|last3=Cao|first3=J|last4=Shao|first4=A|doi=10.1016/j.yrtph.2018.03.019|doi-access=free}}</ref> In 2018, the ] stated that daily intake of 800&nbsp;mg or more could increase risk of liver damage.<ref name="efsa2018">{{cite journal|title=Scientific opinion on the safety of green tea catechins|journal=EFSA Journal|volume=16|issue=4|doi=10.2903/j.efsa.2018.5239|date=18 April 2018|display-authors=3|last1=Younes|first1=Maged|last2=Aggett|first2=Peter|last3=Aguilar|first3=Fernando|last4=Crebelli|first4=Riccardo|last5=Dusemund|first5=Birgit|last6=Filipič|first6=Metka|last7=Frutos|first7=Maria Jose|last8=Galtier|first8=Pierre|last9=Gott|first9=David|last10=Gundert‐Remy|first10=Ursula|last11=Lambré|first11=Claude|last12=Leblanc|first12=Jean‐Charles|last13=Lillegaard|first13=Inger Therese|last14=Moldeus|first14=Peter|last15=Mortensen|first15=Alicja|last16=Oskarsson|first16=Agneta|last17=Stankovic|first17=Ivan|last18=Waalkens‐Berendsen|first18=Ine|last19=Woutersen|first19=Rudolf Antonius|last20=Andrade|first20=Raul J.|last21=Fortes|first21=Cristina|last22=Mosesso|first22=Pasquale|last23=Restani|first23=Patrizia|last24=Arcella|first24=Davide|last25=Pizzo|first25=Fabiola|last26=Smeraldi|first26=Camilla|last27=Wright|first27=Matthew|pages=e05239|pmid=32625874|pmc=7009618|doi-access=free}}</ref>

Taken as a capsule or tablet 338&nbsp;] per day of EGCG is considered safe, whereas 704&nbsp;mg per day is safe if consumed as a tea beverage.<ref name="pmid29580974" /> 100&nbsp;] of green tea contains about 70.2&nbsp;mg of EGCG (about 165&nbsp;mg per cup).<ref name="efsa2018"/>

==Regulation==
Over 2008 to 2017, the US ] issued several ] to manufacturers of dietary supplements containing EGCG for violations of the ]. Most of these letters informed the companies that their promotional materials promoted EGCG-based dietary supplements in the treatment or prevention of diseases or conditions that cause them to be classified as drugs under the ],<ref>{{cite web |url=http://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2008/ucm200918.htm |archive-url=https://wayback.archive-it.org/7993/20161023103651/http://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2008/ucm200918.htm |url-status=dead |archive-date=23 October 2016 |publisher=Food and Drug Administration |work=Inspections, Compliance, Enforcement, and Criminal Investigations |title=Sharp Labs Inc: Warning Letter |date=9 July 2008 |access-date=15 September 2015 }}</ref><ref>{{cite web |url=http://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2010/ucm202823.htm |archive-url=https://wayback.archive-it.org/7993/20161023102337/http://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2010/ucm202823.htm |url-status=dead |archive-date=23 October 2016 |publisher=Food and Drug Administration |work=Inspections, Compliance, Enforcement, and Criminal Investigations |title=Fleminger Inc.: Warning Letter |date=22 February 2010 |access-date=6 January 2015 }}</ref><ref name="fdawarn2017">{{cite web |url=https://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2017/ucm554234.htm |publisher=Food and Drug Administration |work=Inspections, Compliance, Enforcement, and Criminal Investigations |title=LifeVantage Corporation: Warning Letter |date=17 April 2017|access-date=30 September 2017}}</ref> while another focused on inadequate quality assurance procedures and labeling violations.<ref>{{cite web |url=https://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2013/ucm364258.htm |publisher=Food and Drug Administration |work=Inspections, Compliance, Enforcement, and Criminal Investigations |title=N.V.E. Pharmaceuticals, Inc.: Warning Letter |date=22 July 2013 |access-date=30 September 2017}}</ref> The warnings were issued because the products had not been established as safe and effective for their marketed uses and were promoted as "]", without approval as required under the Act.<ref name=fdawarn2017/>

== See also ==
* ]
* ]
* ]
* ]

== References ==
{{Reflist|2}}

{{Antioxidants}}
{{HIVpharm}}
{{Flavanols}}
{{Estrogen receptor modulators}}
{{Glutamate metabolism and transport modulators}}
{{Teas}}

]
]
]
]