Epigallocatechin gallate: Difference between revisions

Browse history interactively ← Previous editContent deleted Content addedVisual WikitextInline

Revision as of 12:48, 7 January 2012 edit87.148.176.144 (talk) →EGCG and Sjögren's syndrome: blargh← Previous edit		Latest revision as of 08:38, 11 September 2024 edit undoGTMotor815 (talk \| contribs)33 edits delete advertisement linkTag: references removed
(405 intermediate revisions by more than 100 users not shown)
Line 1:		Line 1:
			{{Short description\|Catechin (polyphenol) in tea}}
	{{redirect\|EGCG\|the software\|Extended GCG}}		{{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=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 ester of ] and ], and is a type of ].

			'''Epigallocatechin gallate''' ('''EGCG'''), also known as '''epigallocatechin-3-gallate''', is the ] of ] and ], and is a type of ].
	EGCG is the most abundant catechin in ] and is a potent antioxidant that may have therapeutic applications in the treatment of many disorders (e.g. cancer). It is found in green - but not black tea because during black tea production, the catechins are converted to theaflavins and thearubigins<ref>Lorenz, M., Urban, J. (January 2009) "Green and Black Tea are Equally Potent Stimuli of NO Production and Vasodilation: New Insights into Tea Ingredients Involved". "Basic Research in Cardiology" "'104" (1): 100-110.</ref>. In a high temperature environment, an epimerization change is more likely to occur; however as exposure to boiling water for 30 straight minutes only leads to a 12.4% reduction in the total amount of EGCG, the amount lost in a brief exposure is insignificant. In fact, even when special conditions were used to create temperatures well-above that of boiling water, the amount lost scaled up only slightly.<ref name="ncbi">{{cite journal\|pmid=18361498 \| doi=10.1021/jf0730338 \| volume=56 \| issue=8 \| title=Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range \| year=2008 \| month=April \| journal=J. Agric. Food Chem. \| pages=2694–701 \| author=Wang R, Zhou W, Jiang X}}</ref>

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

	==~~EGCG~~ ~~and HIV~~==		==Food sources==
	There has been research investigating the benefit of EGCG from green tea in the treatment of ] infection, where EGCG has been shown to reduce plaques related to AIDS-related dementia in the laboratory, as well as block ].<ref>{{cite journal \|author=Williamson MP, McCormick TG, Nance CL, Shearer WT \|title=Epigallocatechin gallate, the main polyphenol in green tea, binds to the T-cell receptor, CD4: Potential for HIV-1 therapy \|journal=The Journal of Allergy and Clinical Immunology \|volume=118 \|issue=6 \|pages=1369–74 \|year=2006 \|month=December \|pmid=17157668 \|doi=10.1016/j.jaci.2006.08.016}}</ref><ref>{{cite journal \|author=Hamza A, Zhan CG \|title=How can (-)-epigallocatechin gallate from green tea prevent HIV-1 infection? Mechanistic insights from computational modeling and the implication for rational design of anti-HIV-1 entry inhibitors \|journal=The Journal of Physical Chemistry. B \|volume=110 \|issue=6 \|pages=2910–7 \|year=2006 \|month=February \|pmid=16471901 \|doi=10.1021/jp0550762}}</ref><ref>{{cite journal \|author=Yamaguchi K, Honda M, Ikigai H, Hara Y, Shimamura T \|title=Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1) \|journal=Antiviral Research \|volume=53 \|issue=1 \|pages=19–34 \|year=2002 \|month=January \|pmid=11684313 \|doi=10.1016/S0166-3542(01)00189-9}}</ref> However, these effects have yet to be confirmed in live human trials, and it does not imply that green tea will cure or block HIV infection, but it may help regulate ] as long as it is not involved in adverse drug reactions. The concentrations of EGCG used in the studies could not be reached by drinking green tea. More study into EGCG and HIV is currently underway.<ref>{{cite journal \|author=Nance CL, Shearer WT \|title=Is green tea good for HIV-1 infection? \|journal=The Journal of Allergy and Clinical Immunology \|volume=112 \|issue=5 \|pages=851–3 \|year=2003 \|month=November \|pmid=14610469 \|doi=10.1016/j.jaci.2003.08.048}}</ref>

	==~~EGCG and Cancer~~==		===Tea===
			It is found in high content in the dried leaves of ] (7380 mg per 100 g), ] (4245 mg per 100 g), and in smaller quantities, ] (936 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>
	There is increasing evidence to show that EGCG – along with other ]s – can be beneficial in treating brain,<ref>{{cite journal \|author=Das A, Banik NL, Ray SK \|title=Flavonoids activated caspases for apoptosis in human glioblastoma T98G and U87MG cells but not in human normal astrocytes \|journal=Cancer \|volume= 116\|issue= 1\|pages= NA\|year=2009 \|month=November \|pmid=19894226 \|doi=10.1002/cncr.24699 \|pmc=3159962}}</ref> prostate,<ref>{{cite journal \|author=Hsieh TC, Wu JM \|title=Targeting CWR22Rv1 prostate cancer cell proliferation and gene expression by combinations of the phytochemicals EGCG, genistein, and quercetin \|journal=Anticancer Research \|volume=29 \|issue=10 \|pages=4025–32 \|year=2009 \|month=October \|pmid=19846946 \|url=http://ar.iiarjournals.org/cgi/pmidlookup?view=long&pmid=19846946}}</ref><ref>{{cite journal \|author=Bettuzzi S, Brausi M, Rizzi F, Peracchia G, Corti A \|title=Chemoprevention of Human Prostate Cancer by Oral Administration of green Tea Catechins in Volunteers with High-Grade Prostate Intraepithelial Neoplasia: A Preliminary Report from a One-Year Proof-of-Principle Study \|journal=American Associaation for Cancer Research \|volume=66 \|pages=1234–1240 \|year=2006 \|month=January \|url=http://cancerres.aacrjournals.org/cgi/reprint/66/2/1234.pdf \|issue=2}}</ref> cervical<ref>{{cite journal \|author=Qiao Y, Cao J, Xie L, Shi X \|title=Cell growth inhibition and gene expression regulation by (-)-epigallocatechin-3-gallate in human cervical cancer cells \|journal=Archives of Pharmacal Research \|volume=32 \|issue=9 \|pages=1309–15 \|year=2009 \|month=September \|pmid=19784588 \|doi=10.1007/s12272-009-1917-3}}</ref> and bladder<ref>{{cite journal \|author=Philips BJ, Coyle CH, Morrisroe SN, Chancellor MB, Yoshimura N \|title=Induction of apoptosis in human bladder cancer cells by green tea catechins \|journal=Biomedical Research \|volume=30 \|issue=4 \|pages=207–15 \|year=2009 \|month=August \|pmid=19729851 \|doi=10.2220/biomedres.30.207}}</ref> cancers. EGCG has been shown to bind and inhibit the anti-apoptotic protein ],<ref>{{cite journal \|author=Leone M, Zhai D, Sareth S, Kitada S, Reed JC, Pellecchia M \|title=Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins \|journal=Cancer Research \|volume=63 \|issue=23 \|pages=8118–21 \|year=2003 \|month=December \|pmid=14678963 \|url=http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=14678963}}</ref> which has been implicated in both cancer cell and normal cell survival.<ref>{{cite journal \|author=Cherbonnel-Lasserre C, Dosanjh MK \|title=Suppression of apoptosis by overexpression of Bcl-2 or Bcl-xL promotes survival and mutagenesis after oxidative damage \|journal=Biochimie \|volume=79 \|issue=9–10 \|pages=613–7 \|year=1997 \|month=October \|pmid=9466700 \|doi=10.1016/S0300-9084(97)82011-1}}</ref>

			===Other===
	==EGCG and Sjögren's syndrome==
			Trace amounts are found in ] skin, ]s, ]s, ]s, ], and ] powder (at 109 mg per 100 g).<ref name=usda/>
	According to the research led at Medical College of Georgia, EGCG may help protect against some autoimmune diseases, including ]. Research results may suggest that EGCG (e.g,. in green tea) can turn on the body’s defense system against TNF-alpha proteins, which are involved in systemic inflammation. Department of Periodontology, US Army Fort Gordon, Fort Gordon, GA, USA Effects of oral consumption of the green tea polyphenol EGCG in a murine model for human Sjogren's syndrome, an autoimmune disease. PMID: 18809413 PMCID: PMC2701648

	==~~EGCG~~ ~~and endometriosis~~ ==		== 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>
	Xu et al. found that antiangiogenic effects of EGCG inhibits the growth of blood vessels and thus reduces lesion size in experimental endometriosis (mouse model).<ref>{{DOI\|10.1016/j.fertnstert.2011.07.008}}</ref>

			==Research==
	==Drug Interactions==
			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 recent study using mouse models at the ] showed that, in contrast to the myriad benefits commonly associated with green tea and ] (GTE), EGCG binds with the anti-cancer drug ], significantly reducing its bioavailability and thereby rendering it therapeutically useless.<ref name=neith20090204>{{cite web \| last = Neith \| first = Katie \| title = Green tea blocks benefits of cancer drug, study finds \| url=http://www.usc.edu/uscnews/stories/16226.html \| accessdate = 2009-02-04 }}</ref> Dr. Schönthal, who headed the study, suggests that consumption of green tea and GTE products be strongly contraindicated for patients undergoing treatment for multiple myeloma and mantle cell lymphoma.<ref name=neith20090204/> EGCG has a slight stimulatory effect due to it increasing adrenaline levels.<ref>{{cite web\|url=http://examine.com/supplements/Green+Tea+Catechins/ \|title=Examine.com: Green Tea Catechins}}</ref>{{Verify credibility\|date=September 2011}}Epigallocatechin-3-gallate, may reduce the ] of the drug ] when they are taken together.<ref>Ge J, Tan BX, Chen Y, Yang L, Peng XC, Li HZ, Lin HJ, Zhao Y, Wei M, Cheng K, Li LH, Dong H, Gao F, He JP, Wu Y, Qiu M, Zhao YL, Su JM, Hou JM, Liu JY.,"Interaction of green tea polyphenol epigallocatechin-3-gallate with sunitinib: potential risk of diminished sunitinib bioavailability", J Mol Med (Berl). 2011 Jun;89(6):595-602</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 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>
	==Carcinogenic potential==

			==Potential toxicity==
	EGCG was, among other ], found to be a strong ], similar to some chemotherapeutic anticancer drugs, for example, ] and ].
	<ref name="Neukam-2008">{{Cite journal \| last1 = Neukam \| first1 = K. \| last2 = Pastor \| first2 = N. \| last3 = Cortés \| first3 = F. \| title = Tea flavanols inhibit cell growth and DNA topoisomerase II activity and induce endoreduplication in cultured Chinese hamster cells \| journal = Mutat Res \| volume = 654 \| issue = 1 \| pages = 8–12 \| month = Jun \| year = 2008 \| doi = 10.1016/j.mrgentox.2008.03.013 \| pmid = 18541453 }}</ref>
	<ref name="Berger-2001">{{Cite journal \| last1 = Berger \| first1 = SJ. \| last2 = Gupta \| first2 = S. \| last3 = Belfi \| first3 = CA. \| last4 = Gosky \| first4 = DM. \| last5 = Mukhtar \| first5 = H. \| title = Green tea constituent (-)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells \| journal = Biochem Biophys Res Commun \| volume = 288 \| issue = 1 \| pages = 101–5 \| month = Oct \| year = 2001 \| doi = 10.1006/bbrc.2001.5736 \| pmid = 11594758 }}</ref>
	<ref name="Suzuki-2001">{{Cite journal \| last1 = Suzuki \| first1 = K. \| last2 = Yahara \| first2 = S. \| last3 = Hashimoto \| first3 = F. \| last4 = Uyeda \| first4 = M. \| title = Inhibitory activities of (-)-epigallocatechin-3-O-gallate against topoisomerases I and II \| journal = Biol Pharm Bull \| volume = 24 \| issue = 9 \| pages = 1088–90 \| month = Sep \| year = 2001 \| doi = 10.1248/bpb.24.1088\| pmid = 11558576 }}</ref>
	<ref name="Bandele-2008">{{Cite journal \| last1 = Bandele \| first1 = OJ. \| last2 = Osheroff \| first2 = N. \| title = (-)-Epigallocatechin gallate, a major constituent of green tea, poisons human type II topoisomerases \| journal = Chem Res Toxicol \| volume = 21 \| issue = 4 \| pages = 936–43 \| month = Apr \| year = 2008 \| doi = 10.1021/tx700434v \| pmid = 18293940 \| pmc = 2893035 }}</ref><ref name="Bandele-2007">{{Cite journal \| last1 = Bandele \| first1 = OJ. \| last2 = Osheroff \| first2 = N. \| title = Bioflavonoids as poisons of human topoisomerase II alpha and II beta \| journal = Biochemistry \| volume = 46 \| issue = 20 \| pages = 6097–108 \| month = May \| year = 2007 \| doi = 10.1021/bi7000664 \| pmid = 17458941 \| pmc = 2893030 }}</ref>
	This property might be responsible for observed anticarcinogenic effects; however, there is also a carcinogenic potential. High intake of polyphenolic compounds during pregnancy is suspected to increase risk of neonatal leukemia. Bioflavonoid supplements should not be used by pregnant women.<ref name="Paolini-2003">{{Cite journal \| last1 = Paolini \| first1 = M. \| last2 = Sapone \| first2 = A. \| last3 = Valgimigli \| first3 = L. \| title = Avoidance of bioflavonoid supplements during pregnancy: a pathway to infant leukemia? \| journal = Mutat Res \| volume = 527 \| issue = 1–2 \| pages = 99–101 \| month = Jun \| year = 2003 \| doi = 10.1016/S0027-5107(03)00057-5\| pmid = 12787918 }}</ref><ref name="Strick-2000">{{Cite journal \| last1 = Strick \| first1 = R. \| last2 = Strissel \| first2 = PL. \| last3 = Borgers \| first3 = S. \| last4 = Smith \| first4 = SL. \| last5 = Rowley \| first5 = JD. \| title = Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia \| journal = Proc Natl Acad Sci U S A \| volume = 97 \| issue = 9 \| pages = 4790–5 \| month = Apr \| year = 2000 \| doi = 10.1073/pnas.070061297 \| pmid = 10758153 \| pmc = 18311 }}</ref><ref name="Ross-2000">{{Cite journal \| last1 = Ross \| first1 = JA. \| title = Dietary flavonoids and the MLL gene: A pathway to infant leukemia? \| journal = Proc Natl Acad Sci U S A \| volume = 97 \| issue = 9 \| pages = 4411–3 \| month = Apr \| year = 2000 \| doi = 10.1073/pnas.97.9.4411\| pmid = 10781030 \| pmc = 34309 }}</ref> Maternal consumption of ] or coffee during pregnancy may elevate the risk of childhood malignant central nervous system (CNS) tumours through unknown mechanisms.<ref name="Plichart-2008">{{Cite journal \| last1 = Plichart \| first1 = M. \| last2 = Menegaux \| first2 = F. \| last3 = Lacour \| first3 = B. \| last4 = Hartmann \| first4 = O. \| last5 = Frappaz \| first5 = D. \| last6 = Doz \| first6 = F. \| last7 = Bertozzi \| first7 = AI. \| last8 = Defaschelles \| first8 = AS. \| last9 = Pierre-Kahn \| first9 = A. \| title = Parental smoking, maternal alcohol, coffee and tea consumption during pregnancy and childhood malignant central nervous system tumours: the ESCALE study (SFCE) \| journal = Eur J Cancer Prev \| volume = 17 \| issue = 4 \| pages = 376–83 \| month = Aug \| year = 2008 \| doi = 10.1097/CEJ.0b013e3282f75e6f \| pmid = 18562965 \| pmc = 2746823 }}</ref>

			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 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>
	==Spectral data==
	]
	{\| border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"

			Taken as a capsule or tablet 338 ] per day of EGCG is considered safe, whereas 704 mg per day is safe if consumed as a tea beverage.<ref name="pmid29580974" /> 100 ] of green tea contains about 70.2 mg of EGCG (about 165 mg per cup).<ref name="efsa2018"/>
	! {{chembox header}} \| ]
	\|-
	\|<!-- {{RetentionTime\|4.473}} --> ]
	\| 34.5 min (C<sub>18</sub> RP, Acetonitrile 80%)
	\|-
	\| ]
	\| 274 and 240 ] (see picture)
	\|-
	\| ]
	\|
	\|-

			==Regulation==
	! {{chembox header}} \| ]
			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/>
	\|-
	\| Major absorption bands
	\| cm<sup>−1</sup>
	\|-

			== See also ==
	! {{chembox header}} \| ]
			* ]
	\|-
	\| ]
	<br>(500 MHz, CD3OD):
	<br>d : doublet, dd : doublet of doublets,
	<br>m : multiplet, s : singlet
	\|] :<br>
	<!-- Link to image of spectrum -->
	\|-
	\| ] <!-- Link to image of spectrum -->
	\|-
	\| Other NMR data <!-- Insert special data e.g. <sup>19</sup>F chem. shifts, omit if not used -->
	\|-
	! {{chembox header}} \| ]
	\|-
	\| Masses of <br>main fragments
	\| ESI-MS + m/z : 459<!-- Give list of major fragments -->
	\|-
	\|}

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

	== References ==		== References ==
	{{Reflist\|3}}		{{Reflist\|2}}

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

	]		]
	]		]
	]		]
	]		]

	]
	]
	]
	]
	]
	]
	]
	]
	]

Latest revision as of 08:38, 11 September 2024

Catechin (polyphenol) in tea "EGCG" redirects here. For the software, see Extended GCG.

Epigallocatechin gallate
Names


IUPAC name (2R,3R)-3′,4′,5,5′,7-Pentahydroxyflavan-3-yl 3,4,5-trihydroxybenzoate
Systematic IUPAC name (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Other names (-)-Epigallocatechin gallate (2R,3R)-3′,4′,5,5′,7-pentahydroxyflavan-3-yl gallate
Identifiers
CAS Number	989-51-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4806
ChEMBL	ChEMBL297453
ChemSpider	58575
ECHA InfoCard	100.111.017
IUPHAR/BPS	7002
KEGG	C09731
MeSH	Epigallocatechin+gallate
PubChem CID	65064
UNII	BQM438CTEL
CompTox Dashboard (EPA)	DTXSID1029889
InChI InChI=1S/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/s1Key: WMBWREPUVVBILR-WIYYLYMNSA-N 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/s1Key: WMBWREPUVVBILR-WIYYLYMNBM
SMILES O=C(O2Cc3c(O2c1cc(O)c(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4
Properties
Chemical formula	C₂₂H₁₈O₁₁
Molar mass	458.372 g/mol
Solubility in water	soluble (5 g/L)
Solubility	soluble in ethanol, DMSO, dimethyl formamide at about 20 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Epigallocatechin gallate (EGCG), also known as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.

EGCG – the most abundant catechin in tea – is a polyphenol under basic research for its potential to affect human health and disease. EGCG is used in many dietary supplements.

Food sources

Tea

It is found in high content in the dried leaves of green tea (7380 mg per 100 g), white tea (4245 mg per 100 g), and in smaller quantities, black tea (936 mg per 100 g). During black tea production, the catechins are mostly converted to theaflavins and thearubigins via polyphenol oxidases.

Other

Trace amounts are found in apple skin, plums, onions, hazelnuts, pecans, and carob powder (at 109 mg per 100 g).

Bioavailability

When taken orally, EGCG has poor absorption even at daily intake equivalent to 8–16 cups of green tea, an amount causing adverse effects such as nausea or heartburn. After consumption, EGCG blood levels peak within 1.7 hours. The absorbed plasma half-life is ~5 hours, but with majority of unchanged EGCG excreted into urine over 0 to 8 hours. Methylated metabolites appear to have longer half-lives and occur at 8–25 times the plasma levels of unmetabolized EGCG.

Research

Well-studied in basic research, EGCG has various biological effects in laboratory studies.

A 2011 analysis by the European Food Safety Authority found that a cause and effect relationship could not be shown for a link between tea catechins and the maintenance of normal blood LDL-cholesterol concentration. A 2016 review found that high daily doses (107 to 856 mg/day) taken by human subjects over four to 14 weeks produced a small reduction of LDL cholesterol.

Potential toxicity

A 2018 review showed that excessive intake of EGCG may cause liver toxicity. In 2018, the European Food Safety Authority stated that daily intake of 800 mg or more could increase risk of liver damage.

Taken as a capsule or tablet 338 mg per day of EGCG is considered safe, whereas 704 mg per day is safe if consumed as a tea beverage. 100 mL of green tea contains about 70.2 mg of EGCG (about 165 mg per cup).

Regulation

Over 2008 to 2017, the US Food and Drug Administration issued several warning letters to manufacturers of dietary supplements containing EGCG for violations of the Federal Food, Drug, and Cosmetic Act. 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 United States code, while another focused on inadequate quality assurance procedures and labeling violations. The warnings were issued because the products had not been established as safe and effective for their marketed uses and were promoted as "new drugs", without approval as required under the Act.

References

^ "(-)-Epigallocatechin gallate". Chemicalland21.com.
^ Bhagwat, Seema; Haytowitz, David B.; Holden, Joanne M. (September 2011). USDA Database for the Flavonoid Content of Selected Foods, Release 3 (PDF) (Report). Agricultural Research Service, U.S. Department of Agriculture. pp. 2, 98–103. Retrieved 18 May 2015.
Lorenz, Mario; Urban, Janka; Engelhardt, Ulrich; Baumann, Gert; Stangl, Karl; Stangl, Verena (January 2009). "Green and Black Tea are Equally Potent Stimuli of NO Production and Vasodilation: New Insights into Tea Ingredients Involved". Basic Research in Cardiology. 104 (1): 100–10. doi:10.1007/s00395-008-0759-3. PMID 19101751. S2CID 20844066.
Chow, H-H. Sherry; Cai, Yan; Hakim, Iman A.; Crowell, James A.; Shahi, Farah; Brooks, Chris A.; Dorr, Robert T.; Hara, Yukihiko; Alberts, David S. (15 August 2003). "Pharmacokinetics and safety of green tea polyphenols after multiple-dose administration of epigallocatechin gallate and polyphenon E in healthy individuals". Clinical Cancer Research. 9 (9): 3312–19. PMID 12960117.
^ Lee, Mao-Jung; Maliakal, Pius; Chen, Laishun; Meng, Xiaofeng; Bondoc, Flordeliza Y.; Prabhu, Saileta; Lambert, George; Mohr, Sandra; Yang, Chung S. (October 2002). "Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability". Cancer Epidemiology, Biomarkers & Prevention. 11 (10 Pt 1): 1025–32. PMID 12376503.
Manach, C; Williamson, G; Morand, C; Scalbert, A; Rémésy, C (January 2005). "Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies". The American Journal of Clinical Nutrition. 81 (1 Suppl): 230S – 242S. doi:10.1093/ajcn/81.1.230S. PMID 15640486.
Fürst, Robert; Zündorf, Ilse (May 2014). "Plant-derived anti-inflammatory compounds: hopes and disappointments regarding the translation of preclinical knowledge into clinical progress". Mediators of Inflammation. 2014: 146832. doi:10.1155/2014/146832. PMC 4060065. PMID 24987194. 146832.
Granja, Andreia; Frias, Iúri; Neves, Ana Rute; Pinheiro, Marina; Reis, Salette (2017). "Therapeutic Potential of Epigallocatechin Gallate Nanodelivery Systems". BioMed Research International. 2017: 1–15. doi:10.1155/2017/5813793. ISSN 2314-6133. PMC 5534279. PMID 28791306.
Wu, Dayong; Wang, Junpeng; Pae, Munkyong; Meydani, Simin Nikbin (2012). "Green tea EGCG, T cells, and T cell-mediated autoimmune diseases". Molecular Aspects of Medicine. 33 (1): 107–18. doi:10.1016/j.mam.2011.10.001. ISSN 0098-2997. PMID 22020144.
Riegsecker, Sharayah; Wiczynski, Dustin; Kaplan, Mariana J.; Ahmed, Salahuddin (2013). "Potential benefits of green tea polyphenol EGCG in the prevention and treatment of vascular inflammation in rheumatoid arthritis". Life Sciences. 93 (8): 307–12. doi:10.1016/j.lfs.2013.07.006. PMC 3768132. PMID 23871988.
EFSA NDA Panel (EFSA Panel on Dietetic Products, Nutrition and Allergies) (2011). "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". EFSA Journal. 9 (4): 2055. doi:10.2903/j.efsa.2011.2055.
Momose Y; et al. (2016). "Systematic review of green tea epigallocatechin gallate in reducing low-density lipoprotein cholesterol levels of humans". Int J Food Sci Nutr. 67 (6): 606–13. doi:10.1080/09637486.2016.1196655. PMID 27324590. S2CID 39704366.
^ Hu, J; Webster, D; Cao, J; Shao, A (2018). "The safety of green tea and green tea extracts consumption in adults – Results of a systematic review". Regulatory Toxicology and Pharmacology. 95: 412–33. doi:10.1016/j.yrtph.2018.03.019. PMID 29580974.
^ Younes, Maged; Aggett, Peter; Aguilar, Fernando; et al. (18 April 2018). "Scientific opinion on the safety of green tea catechins". EFSA Journal. 16 (4): e05239. doi:10.2903/j.efsa.2018.5239. PMC 7009618. PMID 32625874.
"Sharp Labs Inc: Warning Letter". Inspections, Compliance, Enforcement, and Criminal Investigations. Food and Drug Administration. 9 July 2008. Archived from the original on 23 October 2016. Retrieved 15 September 2015.
"Fleminger Inc.: Warning Letter". Inspections, Compliance, Enforcement, and Criminal Investigations. Food and Drug Administration. 22 February 2010. Archived from the original on 23 October 2016. Retrieved 6 January 2015.
^ "LifeVantage Corporation: Warning Letter". Inspections, Compliance, Enforcement, and Criminal Investigations. Food and Drug Administration. 17 April 2017. Retrieved 30 September 2017.
"N.V.E. Pharmaceuticals, Inc.: Warning Letter". Inspections, Compliance, Enforcement, and Criminal Investigations. Food and Drug Administration. 22 July 2013. Retrieved 30 September 2017.

v t e Antioxidants
Food antioxidants	6-Hydroxymelatonin Acetyl-L-carnitine (ALCAR) Alpha-lipoic acid (ALA) Ascorbic acid (vitamin C) Carotenoids (vitamin A) Curcumin Edaravone Polyphenols Glutathione Hydroxytyrosol L-carnitine Ladostigil Melatonin Mofegiline N-Acetylcysteine (NAC) N-Acetylserotonin (NAS) Oleocanthal Oleuropein Rasagiline Resveratrol Selegiline Selenium Tocopherols (vitamin E) Tocotrienols (vitamin E) Tyrosol Ubiquinone (coenzyme Q) Uric acid
Fuel antioxidants	Butylated hydroxyanisole Butylated hydroxytoluene 2,6-Di-tert-butylphenol 1,2-Diaminopropane 2,4-Dimethyl-6-tert-butylphenol Ethylenediamine
Measurements	Folin method ORAC TEAC FRAP

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Capsid inhibitors

Lenacapavir (LEN)

Entry/fusion inhibitors
(Discovery and development)

Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))

Maturation inhibitors

Protease Inhibitors (PI)
(Discovery and development)

1 generation	Amprenavir (APV) Fosamprenavir (FPV) Indinavir (IDV) Lopinavir (LPV) Nelfinavir (NFV) Ritonavir (RTV) Saquinavir (SQV)
2 generation	Atazanavir (ATV)° Darunavir (DRV)° Tipranavir (TPV) TMC-310911

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside and
nucleotide (NRTI)

Non-nucleoside (NNRTI)
(Discovery and development)

1 generation	Efavirenz (EFV) Nevirapine (NVP) Delavirdine (DLV)
2 generation	diarylpyrimidines Dapivirine (DPV) Etravirine (ETR) Rilpivirine (RPV) Doravirine (DOR) Elsulfavirine (ESV)

Combined formulations

Pharmacokinetic boosters

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)
Transcription inhibitors	Tat antagonists
Translation inhibitors	Trichosanthin
BNAbs	Elipovimab
Other	Abzyme BIT225 Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Fosdevirine Griffithsin Hydroxycarbamide KP-1461 Miltefosine Portmanteau inhibitors Scytovirin Seliciclib Synergistic enhancers Tre recombinase Zinc finger protein transcription factor
Failed agents	Aplaviroc Atevirdine Brecanavir Capravirine Dexelvucitabine Droxinavir Lasinavir Emivirine Lersivirine Lodenosine Loviride Mozenavir Palinavir Telinavir

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

°DHHS recommended initial regimen options. Formerly or rarely used agent.

v t e Flavan-3-ols and their glycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin Robinetinidol
O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A, B, C D Polydine ((+)-catechin 7-O-α-L-arabinoside) Symplocoside (3'-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

Glutamate metabolism and transport modulators

Transporter

EAATsTooltip Excitatory amino acid transporters

vGluTsTooltip Vesicular glutamate transporters

Enzyme

GAHTooltip Glutamine aminohydrolase (glutaminase)	BPTES CB-839 DON
ASTTooltip Aspartate aminotransferase	2-Amino-3-butenoic acid AAOA AMB β-DL-Methylene-aspartate Hydrazinosuccinate
ALTTooltip Alanine aminotransferase	β-Chloro-L-alanine L-Cycloserine Propargylglycine
GDHTooltip Glutamate dehydrogenase	AAOA Bithionol Chloroquine EGCG GTP GW5074 Hexachlorophene Hydroxylamine Palmitoyl-CoA Pyridoxal phosphate
GSTooltip Glutamine synthetase	2-Aminoadipic acid JFD01307SC Methionine sulfoximine Phosphinothricin (glufosinate)
GADTooltip Glutamate decarboxylase	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Metabotropic glutamate receptor modulators • GABA metabolism and transport modulators

Tea (Camellia sinensis)

History

Common
varieties

Black tea	Assam Bohea Ceylon Congou Darjeeling Dianhong Golden Monkey Jin Jun Mei Kangra Keemun Nilgiri Sikkim Tibeti Rize Yingdehong
Oolong tea	Bai Jiguan Ban Tian Yao Baozhong Bu Zhi Chun Da Hong Pao Dong ding Dongfang meiren Fo Shou Gaoshan Huangjin Gui Huang Meigui Jin Xuan Qilan Rougui Ruan zhi Shui Jin Gui Shui Xian Tieluohan Tieguanyin
Green tea	Anji bai cha Aracha Baimao Hou Bancha Biluochun Chun Mee Dafang Genmaicha Lu'an Melon Seed Gunpowder Gyokuro Hōjicha Taiping houkui Huangshan Maofeng Hyson Kabusecha Kamairicha Konacha Kukicha Longjing Matcha Maojian Mecha Mengding Ganlu Sencha Shincha Tamaryokucha
White tea	Bai Mudan Baihao Yinzhen Shoumei
Yellow tea	Junshan Yinzhen Huoshan Huangya
Fermented tea	Pu-erh Doncha Lahpet Kombucha
Blended or flavoured teas	Earl Grey (Lady Grey) Breakfast tea (English, Irish) Jasmine tea Lapsang souchong Masala chai Maghrebi mint tea Prince of Wales Russian Caravan Strobilanthes tonkinensis

General

Culture

Customs	Afternoon/High tea/Evening meal Tea party Tasseography East Asian tea ceremony Chinese Yum cha Japanese Korean Taiwanese Ryukyuan
Areas	Tea garden Teahouse or tearoom Cha chaan teng Chashitsu Mizuya Sukiya-zukuri Roji
By country	American Argentine Azerbaijani Brazilian Chinese Dominican Hong Kong Indian Japanese Mexican Pakistani Russian Senegalese Taiwanese

History

Production and
distribution

By country	Bangladesh Indonesia Kenya Rwanda Sri Lanka United States

Preparation

Health

Tea-based
drinks