関: glutathione disulfide、oxidized glutathione

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/22 22:24:41」(JST)

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Glutathione disulfide (GSSG) is a disulfide derived from two glutathione molecules.^[1]

In living cells, glutathione disulfide is reduced into two molecules of glutathione with reducing equivalents from the coenzyme NADPH. This reaction is catalyzed by the enzyme glutathione reductase.^[2] Antioxidant enzymes, such as glutathione peroxidases and peroxiredoxins, generate glutathione disulfide during the reduction of peroxides such as hydrogen peroxide (H₂O₂) and organic hydroperoxides (ROOH):^[3]

2 GSH + ROOH → GSSG + ROH + H₂O

Other enzymes, such as glutaredoxins, generate glutathione disulfide through thiol-disulfide exchange with protein disulfide bonds or other low molecular mass compounds, such as coenzyme A disulfide or dehydroascorbic acid.^[4]

2 GSH + R-S-S-R → GSSG + 2 RSH

NeuromodulatorEdit

GSSG, along with glutathione and S-nitrosoglutathione (GSNO), have been found to bind to the glutamate recognition site of the NMDA and AMPA receptors (via their γ-glutamyl moieties), and may be endogenous neuromodulators.^[5]^[6] At millimolar concentrations, they may also modulate the redox state of the NMDA receptor complex.^[6]

ReferencesEdit

^ Meister A, Anderson M (1983). "Glutathione". Annu Rev Biochem 52: 711–60. doi:10.1146/annurev.bi.52.070183.003431. PMID 6137189.
^ Deneke SM, Fanburg BL (October 1989). "Regulation of cellular glutathione". Am. J. Physiol. 257 (4 Pt 1): L163–73. PMID 2572174.
^ Meister A (1988). "Glutathione metabolism and its selective modification" (PDF). J Biol Chem 263 (33): 17205–8. PMID 3053703.
^ Holmgren A, Johansson C, Berndt C, Lönn ME, Hudemann C, Lillig CH (December 2005). "Thiol redox control via thioredoxin and glutaredoxin systems". Biochem. Soc. Trans. 33 (Pt 6): 1375–7. doi:10.1042/BST20051375. PMID 16246122.
^ Steullet, P.; Neijt, H.C.; Cuénod, M.; Do, K.Q. (2006). "Synaptic plasticity impairment and hypofunction of NMDA receptors induced by glutathione deficit: Relevance to schizophrenia". Neuroscience 137 (3): 807–819. doi:10.1016/j.neuroscience.2005.10.014. ISSN 0306-4522.
^ ^a ^b Varga, V.; Jenei, Zs.; Janáky, R.; Saransaari, P.; Oja, S. S. (1997). Neurochemical Research 22 (9): 1165–1171. doi:10.1023/A:1027377605054. ISSN 0364-3190. Missing or empty |title= (help)

UpToDate Contents

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English Journal

Changes in chemical composition and antioxidative properties of rye ginger cakes during their shelf-life.

Zieliński H, Del Castillo MD, Przygodzka M, Ciesarova Z, Kukurova K, Zielińska D.SourceDivision of Food Science, Institute of Animal Reproduction and Food Research of Polish Academy of Sciences, Tuwima 10, P.O. Box 55, 10-718 Olsztyn 5, Poland. Electronic address: haziel@pan.olsztyn.pl.
Food chemistry.Food Chem.2012 Dec 15;135(4):2965-73. doi: 10.1016/j.foodchem.2012.07.009. Epub 2012 Jul 14.
Changes in chemical composition and antioxidative properties of rye ginger cakes during their shelf-life were investigated in this study. In particular, the changes in antioxidants content, antioxidative and reducing capacity, and Maillard reaction development in rye ginger cakes after long-term sto
PMID 22980898

Alcohol depletes coenzyme-Q(10) associated with increased TNF-alpha secretion to induce cytotoxicity in HepG2 cells.

Vidyashankar S, Nandakumar KS, Patki PS.SourceCell Biology and Biochemistry, Research and Development, The Himalaya Drug Company, Makali, Bangalore 562 123, India.
Toxicology.Toxicology.2012 Dec 8;302(1):34-9. Epub 2012 Jul 24.
Alcohol consumption has been implicated to cause severe hepatic steatosis which is mediated by alcohol dehydrogenase (ADH) activity and CYP(450) 2E1 expression. In this context, the effect of ethanol was studied for its influence on lipogenesis in HepG2 cell which is deficient of ADH and does not ex
PMID 22841563

Japanese Journal

Metabolomics changes in a rat model of obstructive jaundice: mapping to metabolism of amino acids, carbohydrates and lipids as well as oxidative stress

Journal of Clinical Biochemistry and Nutrition 57(1), 50-59, 2015
NAID 130005085269

Metabolomics changes in a rat model of obstructive jaundice: mapping to metabolism of amino acids, carbohydrates and lipids as well as oxidative stress

Journal of Clinical Biochemistry and Nutrition advpub(0), 2015
NAID 130005074644

A Comparison of Growth, Immunity and Oxidative Status of Broilers that Differ in Hatching Weight at Early Age

The Journal of Poultry Science 52(2), 137-144, 2015
NAID 130005066310

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★リンクテーブル★

リンク元	「グルタチオンジスルフィド」「glutathione disulfide」
関連記事	「GSS」「GS」

「グルタチオンジスルフィド」

Glutathione disulfide
Names
	IUPAC name (2S)-2-amino-5-[[(2R)-3-[(2R)-2-[[(4S)-4-amino-5-hydroxy-5-oxopentanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl-1- (carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Identifiers
CAS Number	27025-41-8
Abbreviations	GSSG
ChEMBL	ChEMBL1372
ChemSpider	58835
IUPHAR/BPS	6835
Jmol interactive 3D	Image
PubChem	65359; 11215652
	InChI InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 Key: YPZRWBKMTBYPTK-BJDJZHNGSA-N ; InChI=1/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 Key: YPZRWBKMTBYPTK-BJDJZHNGBD ;
	SMILES C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N ;
Properties
Chemical formula	C20H32N6O12S2
Molar mass	612.631 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: glutathione disulfide, GSSG
同: 酸化型グルタチオン、オキシグルタチオン oxiglutatione
商: ビーエスエスプラス
関: グルタチオン

[show details]

っていうか、オキシグルタチオンなんていう名称は正しくない気がする。ただのGSSGじゃん。どういう使い分けがされているの？

酸化型グルタチオン : 約 3,990 件
グルタチオンジスルフィド : 約 902 件
オキシグルタチオン : 約 1,210 件

酸化型グルタチオン。
グルタチオン(GSH)の酸化型(GSSG)である。酸化型グルタチオン、あるいはグルタチオンジスルフィドと呼ばれる。眼内に投与されたオキシグルタチオンは組織に取り込まれグルタチオン還元酵素によりグルタチオンとなり、組織のH2O2の除去などをおこなう。眼内灌流液にオキシグルタチオンを添加することで、角膜保護作用、血液房水柵破壊抑制作用、水晶体透明性維持作用、網膜機能維持作用の効果が期待できる。