没食子酸エピガロカテキン

関: epigallocatechin gallate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/16 02:04:22」(JST)

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「EGCG」はこの項目へ転送されています。ソフトウェアについては「Extended GCG」をご覧ください。

没食子酸エピガロカテキン（もっしょくしさんエピガロカテキン、Epigallocatechin gallate、EGCG）はエピガロカテキンと没食子酸のエステルであり、カテキンの一種である。エピガロカテキン 3-ガラートとしても知られている。

EGCGは、植物の中で特に茶に最も豊富に含まれているカテキンである。また強力な抗酸化活性を示し、がんを含む多くの疾患に対して治療効果を有するのではないかと言われている。緑茶に含まれており、紅茶ではEGCGがテアルビジンに変換されているため含まれていない^[要出典]。高温環境では、エピメリ化が起こる可能性が高いが、30秒間沸騰する水に曝されていてもEGCGの全量の12.4%しか減少せず、短い時間での減少は統計的に有意ではなかった。実際に、沸騰水以上の温度の特殊な条件でも、量の減少はわずかにしか増大しなかった^[1]。

EGCGは多くのサプリメントに用いられている。

EGCGとHIV

緑茶中のEGCGが、ヒト免疫不全ウイルス (HIV) 感染の治療において有益であるとの研究がある。EGCGは、実験室においてAIDS関連認知症と関連しているプラークを減少させ、gp120（英語版）の働きを阻害した^[2]^[3]^[4]。

しかしながら、これらの効果はヒトにおける臨床試験では実証されておらず、緑茶がHIV感染を治療あるいは予防することを示してはいない。しかし、副作用と関係がない限りは、ウイルス量（英語版）の制御を助ける可能性がある。これらの研究で使用されているEGCGの濃度は、実際に飲まれる緑茶では到達することが出来ない。EGCGとHIVに関するさらなる研究が進行中である^[5]。

EGCGとがん

その他のフラボノイドと共にEGCGが、脳腫瘍^[6]、前立腺がん^[7]^[8]、子宮頸がん^[9]、膀胱がん^[10]の治療に有益ではないかとする研究結果が増えてきている。EGCGは、がん細胞と正常細胞の生存に共に関与している^[11]抗アポトーシスタンパク質Bcl-xl（英語版）に結合し阻害する^[12]。

EGCGとシェーグレン症候群

米ジョージア医科大学での研究によると、EGCGはシェーグレン症候群を含むある種の自己免疫疾患に対して予防効果があるのではないかとされている^[13]^[14]。研究結果から、（例えば緑茶中の）EGCGは、全身性炎症に関与しているTNF-αタンパク質に対する人体の防御機構を活性化することが示唆された^[15]。

薬物相互作用

南カリフォルニア大学でのマウスモデルを用いた最近の研究で、緑茶および緑茶抽出物（英語版） (green tea extract, GTE) と一般的に関連付けられている多種多様の恩恵と対照的に、EGCGが抗がん剤ボルテゾミブに結合し、顕著にバイオアベイラビリティを低下させ、治療効果を無くしてしまうことが明らかにされた^[16]。この研究を指揮したSchönthal博士は、多発性骨髄腫およびマントル細胞リンパ腫の治療中の患者に対しては、緑茶および緑茶抽出物製品の摂取は強く禁忌とすべきとしている^[16]。

発癌性の可能性

茶ポリフェノールの中、EGCGは化学抗がん剤であるエトポシドおよびドキソルビシンと同様に強力なトポイソメラーゼ阻害剤（英語版）であることが明らかにされている^[17]^[18]^[19]^[20]^[21]。この性質は抗発癌活性に必要であることが考えられるが、一方この活性によってEGCGが発癌性を示す可能性も考えられる。妊娠中のポリフェノール化合物の多量の摂取は新生児白血病のリスクを増大させることが疑われている。バイオフラボノイドサプリメントは、妊娠中の女性に使用してはならない^[22]^[23]^[24]。妊娠中の茶の大量摂取と小児悪性中枢神経 (CNS) 腫瘍のリスクの増大との間に強い相関があることが明らかにされている^[1]^[25]。

スペクトルデータ

UVスペクトル

UV-Vis
保持時間	34.5 min (C₁₈ RP, アセトニトリル 80%)
λmax	274, 240 nm（右図）
モル吸光係数 (molar absorptivity)
IR
Major absorption bands	cm⁻¹
NMR
¹H NMR（英語版） (500 MHz, CD₃OD): d : doublet, dd : doublet of doublets, m : multiplet, s : singlet	δ (Chemical shift) :
¹³C NMR（英語版）
その他のNMRデータ
MS
Masses of main fragments	ESI-MS [M+H]+ m/z : 459

脚注

^ ^a ^b Wang R, Zhou W, Jiang X (2008). “Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range”. J. Agric. Food Chem. 56 (8). doi:10.1021/jf0730338. PMID 18361498.
^ Williamson MP, McCormick TG, Nance CL, Shearer WT (December 2006). “Epigallocatechin gallate, the main polyphenol in green tea, binds to the T-cell receptor, CD4: Potential for HIV-1 therapy”. The Journal of Allergy and Clinical Immunology 118 (6): 1369–74. doi:10.1016/j.jaci.2006.08.016. PMID 17157668.
^ Hamza A, Zhan CG (February 2006). “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”. The Journal of Physical Chemistry. B 110 (6): 2910–7. doi:10.1021/jp0550762. PMID 16471901.
^ Yamaguchi K, Honda M, Ikigai H, Hara Y, Shimamura T (January 2002). “Inhibitory effects of (−)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1)”. Antiviral Research 53 (1): 19–34. doi:10.1016/S0166-3542(01)00189-9. PMID 11684313.
^ Nance CL, Shearer WT (November 2003). “Is green tea good for HIV-1 infection?”. The Journal of Allergy and Clinical Immunology 112 (5): 851–3. doi:10.1016/j.jaci.2003.08.048. PMID 14610469.
^ Das A, Banik NL, Ray SK (November 2009). “Flavonoids activated caspases for apoptosis in human glioblastoma T98G and U87MG cells but not in human normal astrocytes”. Cancer 116 (1): NA. doi:10.1002/cncr.24699. PMID 19894226.
^ Hsieh TC, Wu JM (October 2009). “Targeting CWR22Rv1 prostate cancer cell proliferation and gene expression by combinations of the phytochemicals EGCG, genistein and quercetin”. Anticancer Research 29 (10): 4025–32. PMID 19846946.
^ Bettuzzi S, Brausi M, Rizzi F, Peracchia G, Corti A (January 2006). “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”. American Associaation for Cancer Research 66: 1234–1240.
^ Qiao Y, Cao J, Xie L, Shi X (September 2009). “Cell growth inhibition and gene expression regulation by (−)-epigallocatechin-3-gallate in human cervical cancer cells”. Archives of Pharmacal Research 32 (9): 1309–15. doi:10.1007/s12272-009-1917-3. PMID 19784588.
^ Philips BJ, Coyle CH, Morrisroe SN, Chancellor MB, Yoshimura N (August 2009). “Induction of apoptosis in human bladder cancer cells by green tea catechins”. Biomedical Research 30 (4): 207–15. doi:10.2220/biomedres.30.207. PMID 19729851.
^ Cherbonnel-Lasserre C, Dosanjh MK (October 1997). “Suppression of apoptosis by overexpression of Bcl-2 or Bcl-xL promotes survival and mutagenesis after oxidative damage”. Biochimie 79 (9–10): 613–7. doi:10.1016/S0300-9084(97)82011-1. PMID 9466700.
^ Leone M, Zhai D, Sareth S, Kitada S, Reed JC, Pellecchia M (December 2003). “Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins”. Cancer Research 63 (23): 8118–21. PMID 14678963.
^ Hsu S, Dickinson DP, Qin H, Lapp C, Lapp D, Borke J, Walsh DS, Bollag WB, Stöppler H, Yamamoto T, Osaki T, Schuster G (2005). “Inhibition of autoantigen expression by (−)-epigallocatechin-3-gallate (the major constituent of green tea) in normal human cells”. J. Pharmacol. Exp. Ther. 315 (2): 805-811. doi:10.1124/jpet.105.090399. PMID 16046615.
^ Gillespie K, Kodani I, Dickinson DP, Ogbureke KU, Camba AM, Wu M, Looney S, Chu TC, Qin H, Bisch F, Sharawy M, Schuster GS, Hsu SD (2008). “Effects of oral consumption of the green tea polyphenol EGCG in a murine model for human Sjogren's syndrome, an autoimmune disease”. Life Sci. 83 (17-18): 581-588. doi:10.1016/j.lfs.2008.08.011. PMC 2701648. PMID 18809413.
^ Hsu SD, Dickinson DP, Qin H, Borke J, Ogbureke KU, Winger JN, Camba AM, Bollag WB, Stöppler HJ, Sharawy MM, Schuster GS (2007). “Green tea polyphenols reduce autoimmune symptoms in a murine model for human Sjogren's syndrome and protect human salivary acinar cells from TNF-α-induced cytotoxicity”. Autoimmunity 40 (2): 138-147. doi:10.1080/08916930601167343. PMID 17364504.
^ ^a ^b Neith, Katie (2009年2月3日). “Green tea blocks benefits of cancer drug, study finds”. USC News 2011年4月23日閲覧。
^ Neukam, K.; Pastor, N.; Cortés, F. (Jun 2008), “Tea flavanols inhibit cell growth and DNA topoisomerase II activity and induce endoreduplication in cultured Chinese hamster cells”, Mutat Res 654 (1): 8–12, doi:10.1016/j.mrgentox.2008.03.013, PMID 18541453
^ Berger, SJ.; Gupta, S.; Belfi, CA.; Gosky, DM.; Mukhtar, H. (Oct 2001), “Green tea constituent (−)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells”, Biochem Biophys Res Commun 288 (1): 101–5, doi:10.1006/bbrc.2001.5736, PMID 11594758
^ Suzuki, K.; Yahara, S.; Hashimoto, F.; Uyeda, M. (Sep 2001), “Inhibitory activities of (−)-epigallocatechin-3-O-gallate against topoisomerases I and II”, Biol Pharm Bull 24 (9): 1088–90, PMID 11558576
^ Bandele, OJ.; Osheroff, N. (Apr 2008), “(−)-Epigallocatechin gallate, a major constituent of green tea, poisons human type II topoisomerases”, Chem Res Toxicol 21 (4): 936–43, doi:10.1021/tx700434v, PMC 2893035, PMID 18293940
^ Bandele, OJ.; Osheroff, N. (May 2007), “Bioflavonoids as poisons of human topoisomerase IIα and IIβ”, Biochemistry 46 (20): 6097–108, doi:10.1021/bi7000664, PMC 2893030, PMID 17458941
^ Paolini, M.; Sapone, A.; Valgimigli, L. (Jun 2003), “Avoidance of bioflavonoid supplements during pregnancy: a pathway to infant leukemia?”, Mutat Res 527 (1–2): 99–101, PMID 12787918
^ Strick, R.; Strissel, PL.; Borgers, S.; Smith, SL.; Rowley, JD. (Apr 2000), “Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia”, Proc Natl Acad Sci U S A 97 (9): 4790–5, doi:10.1073/pnas.070061297, PMC 18311, PMID 10758153
^ Ross, JA. (Apr 2000), “Dietary flavonoids and the MLL gene: A pathway to infant leukemia?”, Proc. Natl. Acad. Sci. U.S.A. 97 (9): 4411–3, PMC 34309, PMID 10781030
^ Plichart, M.; Menegaux, F.; Lacour, B.; Hartmann, O.; Frappaz, D.; Doz, F.; Bertozzi, AI.; Defaschelles, AS. et al. (Aug 2008), “Parental smoking, maternal alcohol, coffee and tea consumption during pregnancy and childhood malignant central nervous system tumours: the ESCALE study (SFCE)”, Eur J Cancer Prev 17 (4): 376–83, doi:10.1097/CEJ.0b013e3282f75e6f, PMC 2746823, PMID 18562965

外部リンク

エピガロカテキンガレート（EGCG）の体内動態について

wiki en

[Wiki en表示]

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 white tea (4245 mg per 100 g), green tea (7380 mg per 100 g) and, in smaller quantities, black tea.^[3] During black tea production, the catechins are mostly converted to theaflavins and thearubigins.^[4] via polyphenol oxidases.^[which?]

Other

Trace amounts are found in apple skin, plums, onions, hazelnuts, pecans and carob powder (at 109 mg per 100 g).^[3]

Bioavailability

When taken orally, EGCG has poor bioavailability even at such a high amount of daily intake equivalent to 8-16 cups of tea (800 mg), a dose causing mild adverse effects, such as nausea or heartburn.^[5] After consumption, EGCG blood levels peak within 1.7 hours, then are excreted into the urine over 3-15 hours.^[6]

Research on potential therapeutic uses

EGCG has been the subject of a number of basic and clinical research studies investigating its potential use as a therapeutic for a broad range of disorders.^[7]^[8]^[9] As of 2015, however, these effects remain unsubstantiated in humans and there are no approved health claims for EGCG in the United States or Europe.^[8]^[9] The US Food and Drug Administration has issued warning letters against marketers of products claiming that EGCG provides anti-disease effects or overall health benefits.^[10]^[11]

References

^ ^a ^b http://chemicalland21.com/lifescience/foco/%28-%29-EPIGALLOCATECHIN%20GALLATE.htm
^ http://www.caymanchem.com/pdfs/70935.pdf
^ ^a ^b "USDA Database for the Flavonoid Content of Selected Foods, Release 3" (PDF). US Department of Agriculture. 2011. Retrieved 18 May 2015.
^ Lorenz M, Urban J (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. doi:10.1007/s00395-008-0759-3. PMID 19101751.
^ Chow HH, Cai Y, Hakim IA, Crowell JA, Shahi F, Brooks CA, Dorr RT, Hara Y, Alberts DS (2003). "Pharmacokinetics and safety of green tea polyphenols after multiple-dose administration of epigallocatechin gallate and polyphenon E in healthy individuals". Clin Cancer Res 9 (9): 3312–9. PMID 12960117.
^ Lee MJ, Maliakal P, Chen L, Meng X, Bondoc FY, Prabhu S, Lambert G, Mohr S, Yang CS (2002). "Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability". Cancer Epidemiol Biomarkers Prev 11 (10 Pt 1): 1025–32. PMID 12376503.
^ Fürst, R; Zündorf, I (2014). "Plant-derived anti-inflammatory compounds: hopes and disappointments regarding the translation of preclinical knowledge into clinical progress". Mediators Inflamm 2014: 146832. doi:10.1155/2014/146832. PMID 24987194.
^ ^a ^b "Green tea". MedlinePLus, US National Library of Medicine. 9 June 2015. Retrieved 15 September 2015.
^ ^a ^b "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 (ID 1310, 2657), maintenance of normal blood glucose concentrations (ID 1108), maintenance of normal blood LDL cholesterol concentrations (ID 2640), protection of the skin from UV-induced (including photo-oxidative) damage (ID 1110, 1119), protection of DNA from oxidative damage (ID 1120, 1121), protection of lipids from oxidative damage (ID 1275), contribution to normal cognitive function (ID 1117, 2812), “cardiovascular system” (ID 2814), “invigoration of the body” (ID 1274, 3280), decreasing potentially pathogenic gastro-intestinal microorganisms (ID 1118), “immune health” (ID 1273) and “mouth” (ID 2813) pursuant to Article 13(1) of Regulation (EC) No 1924/2006". EFSA Journal (European Food Safety Authority) 9 (4). 2011. doi:10.2903/j.efsa.2011.2055.
^ "Inspections, Compliance, Enforcement, and Criminal Investigations: Warning Letter to Sharp Labs Inc". Food and Drug Administration. 9 July 2008. Retrieved 15 September 2015.
^ "Inspections, Compliance, Enforcement, and Criminal Investigations: Warning Letter to Fleminger Inc". Food and Drug Administration. 22 February 2010. Retrieved 6 January 2015.

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English Journal

Model system-based mechanistic studies of black tea thearubigin formation.

Yassin GH1, Koek JH2, Kuhnert N3.
Food chemistry.Food Chem.2015 Aug 1;180:272-9. doi: 10.1016/j.foodchem.2015.01.108. Epub 2015 Feb 12.
Thearubigins are the most abundant pigments found in black tea, comprising polyphenolic oxidation products, whose composition and chemical nature have remained unresolved until recently. In the course of studying the mechanism of thearubigin formation from green tea flavan-3-ols, a model system, bas
PMID 25766828

Green tea polyphenol epigallocatechin-3-gallate and cranberry proanthocyanidins act in synergy with cathelicidin (LL-37) to reduce the LPS-induced inflammatory response in a three-dimensional co-culture model of gingival epithelial cells and fibroblasts.

Lombardo Bedran TB1, Palomari Spolidorio D2, Grenier D3.
Archives of oral biology.Arch Oral Biol.2015 Jun;60(6):845-53. doi: 10.1016/j.archoralbio.2015.02.021. Epub 2015 Feb 27.
OBJECTIVES: The human antimicrobial peptide cathelicidin (LL-37) possesses anti-inflammatory properties that may contribute to attenuating the inflammatory process associated with chronic periodontitis. Plant polyphenols, including those from cranberry and green tea, have been reported to reduce inf
PMID 25791329

Epigallocatechin-3-gallate pretreatment attenuates doxorubicin-induced cardiotoxicity in rats: A mechanistic study.

Saeed NM1, El-Naga RN2, El-Bakly WM3, Abdel-Rahman HM1, Salah ElDin RA4, El-Demerdash E5.
Biochemical pharmacology.Biochem Pharmacol.2015 Jun 1;95(3):145-55. doi: 10.1016/j.bcp.2015.02.006. Epub 2015 Feb 19.
Doxorubicin (DOX) is a widely used chemotherapeutic agent however its clinical use is limited by cumulative cardiotoxicity. Epigallocatechin-3-gallate (EGCG), a main catechin in green tea, possesses a potent antioxidant, anti-apoptotic and anticancer properties. The current study aimed to investigat
PMID 25701654

Japanese Journal

Health Functions of Compounds Extracted in Cold-water Brewed Green Tea from <i>Camellia Sinensis</i> L.

Japan Agricultural Research Quarterly: JARQ 52(1), 1-6, 2018
NAID 130006338301

Effects of (−)-epigallocatechin-3-gallate on EGFR- or Fusion Gene-driven Lung Cancer Cells

Acta Medica Okayama 71(6), 505-512, 2017-12
NAID 120006370714

カテキン脂肪酸誘導体の抗ウイルス・抗菌活性と化粧品応用 (特集化粧品の新素材と新技術の動向(2))

Fragrance journal : Research & development for cosmetics, toiletries & allied industries = フレグランスジャーナル : 香粧品科学研究開発専門誌 45(4), 53-57, 2017-04
NAID 40021191386

「epigallocatechin gallate」

Epigallocatechin gallate
Names
	IUPAC name [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
	Preferred 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
Identifiers
CAS Number	989-51-5
ChEBI	CHEBI:4806
ChEMBL	ChEMBL297453
ChemSpider	58575
IUPHAR/BPS	7002
Jmol interactive 3D	Image
MeSH	Epigallocatechin+gallate
PubChem	65064
	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/s1 Key: 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/s1 Key: WMBWREPUVVBILR-WIYYLYMNBM ;
	SMILES O=C(O[C@@H]2Cc3c(O[C@@H]2c1cc(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
Appearance
Solubility in water	soluble (33.3-100 g/L)[vague]
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 [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

(−)-没食子酸エピガロカテキン
	IUPAC名 [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
	優先IUPAC名 (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
	別称 (-)-Epigallocatechin gallate
識別情報
CAS登録番号	989-51-5
PubChem	65064
ChemSpider	58575
日化辞番号	J134.058A
MeSH	Epigallocatechin+gallate
ChEMBL	CHEMBL297453
	SMILES O=C(O[C@@H]2Cc3c(O[C@@H]2c1cc(O)c(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4;
	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/s1 ; Key: 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/s1; Key: WMBWREPUVVBILR-WIYYLYMNBM;
特性
化学式	C22H18O11
モル質量	458.37 g mol−1
精密質量	458.084911
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

　　[★]

没食子酸エピガロカテキン

関: EGCG

「没食子酸エピガロカテキン」

　　[★]

英: epigallocatechin gallate、EGCG

「EG」

　　[★] 好酸球性肉芽腫症 eosinophilic granuloma

[ncbi-1] Wang R, Zhou W, Jiang X (2008). “Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range”. J. Agric. Food Chem. 56 (8). doi:10.1021/jf0730338. PMID 18361498.

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