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A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
Naturally occurring amino acid
Ergothioneine
Names
Preferred IUPAC name
(2 S H
Other names
L
Identifiers
CAS Number
3D model (JSmol )
Interactive image
ChEBI
ChemSpider
ECHA InfoCard 100.007.131
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13 )14)4-6-5-10-9(15 )11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1 Y
Key: SSISHJJTAXXQAX-ZETCQYMHSA-N Y
InChI=1/C9H15N3O2S/c1-12(2,3)7(8(13 )14)4-6-5-10-9(15 )11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
Key: SSISHJJTAXXQAX-ZETCQYMHBA
C[N+](C )(C )C(CC1=CNC(=S)N1)C(=O)[O-]
S=C1N\C(=C/N1)C[C@@H](C([O-])=O)[N+](C )(C )C
Properties
Chemical formula
C 9 H 15 N 3 O 2 S
Molar mass
229.30 g/mol
Appearance
white solid
Melting point
275 to 277 °C (527 to 531 °F; 548 to 550 K )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine , containing a sulfur atom on the imidazole ring.[1] actinomycetota , cyanobacteria , and certain fungi .[2] [3] Charles Tanret in 1909 and named after the ergot fungus from which it was first purified,[4] [5] [6]
In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes , bone marrow , liver, kidney, seminal fluid , and eyes.[7] in vivo physiological role in humans is unknown.[7] dietary supplement .[8]
Metabolism and sources [ edit ]
Ergothioneine has been found in bacteria, plants, and animals, sometimes at millimolar levels.[9] liver , kidney , black beans , kidney bean , and oat bran , with the highest levels in bolete and oyster mushrooms .[9] [10] erythrocytes , eye lens , semen ,[6] skin .[11]
Although many species contain ergothioneine, only a few make it; the others absorb it from their diet or, in the case of plants, from their environment.[12] Actinomycetota , such as Mycobacterium smegmatis Neurospora crassa [2]
The metabolic pathway to produce ergothioneine starts with the methylation of histidine to produce histidine betaine (hercynine). The sulfur atom is then incorporated from cysteine.[9] [13] Mycobacterium smegmatis [14] Neurospora crassa [15] Schizosaccharomyces pombe [16]
Other species of bacteria, such as Bacillus subtilis Escherichia coli Proteus vulgaris Streptococcus Saccharomycotina cannot make ergothioneine.[17] [18]
Structure [ edit ]
Ergothioneine is a thiourea derivative of the betaine of histidine and contains a sulfur atom bonded to the 2-position of the imidazole ring.[19] glutathione towards alkylating agents like maleimides . It also resists oxidation by air.[9] disulfide form in acidic solutions.[20]
Ergothioneine derivatives [ edit ]
Various derivatives of ergothioneine have been reported in the literature, such as S [21] or selenium -containing selenoneine .[22]
Preliminary research [ edit ]
Although potential effects of ergothioneine are under preliminary research, its physiological role in vivo has not been determined.[1] [7]
Safe intake levels [ edit ]
The Panel on Dietetic Products for the European Food Safety Authority reported safe daily limits of 2.82 mg/kg of body weight for infants, 3.39 mg/kg for small children, and 1.31 mg/kg for adults, including pregnant and breastfeeding women.[8]
See also [ edit ]
References [ edit ]
^ Pfeiffer C, Bauer T, Surek B, Schömig E, Gründemann D (2011). "Cyanobacteria produce high levels of ergothioneine". Food Chemistry . 129 (4 ): 1766–1769. doi :10.1016/j.foodchem.2011.06.047 .
^ Tanret, C. (1909). "Sur une base nouvelle retirée du seigle ergoté : l'ergothioneine" . Comptes rendus hebdomadaires des séances de l'Académie des sciences (in French). 149 : 222-224.
^ Barger, G. ; Erwins, A.J. (1911). "The constitution of ergothioneine : a betaine related to histidine" . Journal of the Chemical Society, Transactions . 99 doi :10.1039/CT9119902336 .
^ a b Mann T, Leone E (January 1953). "Studies on the metabolism of semen. VIII. Ergothioneine as a normal constituent of boar seminal plasma; purification and crystallization; site of formation and function" . The Biochemical Journal . 53 1 ): 140–8. doi :10.1042/bj0530140 . PMC 1198115 PMID 13032046 .
^ a b c Cheah, Irwin K.; Halliwell, Barry (2021-01-26). "Ergothioneine, recent developments" . Redox Biology . 42 doi :10.1016/j.redox.2021.101868 . ISSN 2213-2317 . PMC 8113028 PMID 33558182 .
^ a b Turck D, Bresson JL, Burlingame B, Dean T, Fairweather-Tait S, Heinonen M, et al. (November 2017). "Statement on the safety of synthetic l-ergothioneine as a novel food - supplementary dietary exposure and safety assessment for infants and young children, pregnant and breastfeeding women" . EFSA Journal . 15 11 ): e05060. doi :10.2903/j.efsa.2017.5060 PMC 7010164 PMID 32625352 .
^ a b c d Ey J, Schömig E, Taubert D (August 2007). "Dietary sources and antioxidant effects of ergothioneine". Journal of Agricultural and Food Chemistry . 55 16 ): 6466–74. doi :10.1021/jf071328f . PMID 17616140 .
^ Kalač P. Edible Mushrooms. Chapter 4 - Health-Stimulating Compounds and Effects. pp 137-153. Academic Press, 2016. ISBN 9780128044551 doi :10.1016/B978-0-12-804455-1.00004-7
^ Markova NG, Karaman-Jurukovska N, Dong KK, Damaghi N, Smiles KA, Yarosh DB (April 2009). "Skin cells and tissue are capable of using L-ergothioneine as an integral component of their antioxidant defense system". Free Radical Biology & Medicine . 46 8 ): 1168–76. doi :10.1016/j.freeradbiomed.2009.01.021 . PMID 19439218 .
^ Audley BS, Tan CH (1968). "The uptake of ergothioneine from the soil into the latex of Hevea brasiliensis". Phytochemistry . 7 11 ): 1999–2000. Bibcode :1968PChem...7.1999A . doi :10.1016/S0031-9422(00 )90759-3 .
^ Melville DB, Ludwig ML, Inamine E, Rachele JR (May 1959). "Transmethylation in the biosynthesis of ergothionelne" . The Journal of Biological Chemistry . 234 (5 ): 1195–8. doi :10.1016/S0021-9258(18 )98157-3 PMID 13654346 . [permanent dead link
^ Seebeck FP (May 2010). "In vitro reconstitution of Mycobacterial ergothioneine biosynthesis". Journal of the American Chemical Society . 132 (19 ): 6632–3. doi :10.1021/ja101721e . PMID 20420449 .
^ Bello MH, Barrera-Perez V, Morin D, Epstein L (February 2012). "The Neurospora crassa mutant NcΔEgt-1 identifies an ergothioneine biosynthetic gene and demonstrates that ergothioneine enhances conidial survival and protects against peroxide toxicity during conidial germination". Fungal Genetics and Biology . 49 2 ): 160–72. doi :10.1016/j.fgb.2011.12.007 . PMID 22209968 .
^ Pluskal T, Ueno M, Yanagida M (2014). "Genetic and metabolomic dissection of the ergothioneine and selenoneine biosynthetic pathway in the fission yeast, S. pombe, and construction of an overproduction system" . PLOS ONE . 9 5 ): e97774. Bibcode :2014PLoSO...997774P . doi :10.1371/journal.pone.0097774 PMC 4020840 PMID 24828577 .
^ Genghof DS (August 1970). "Biosynthesis of ergothioneine and hercynine by fungi and Actinomycetales" . Journal of Bacteriology . 103 (2 ): 475–8. doi :10.1128/JB.103.2.475-478.1970 . PMC 248105 PMID 5432011 .
^ Genghof DS, Inamine E, Kovalenko V, Melville DB (November 1956). "Ergothioneine in microorganisms" . The Journal of Biological Chemistry . 223 (1 ): 9–17. doi :10.1016/S0021-9258(18 )65113-0 PMID 13376573 . [permanent dead link
^ Hartman PE (1990). "[32] Ergothioneine as antioxidant" . Oxygen Radicals in Biological Systems Part B: Oxygen Radicals and Antioxidants . Methods in Enzymology. Vol. 186. pp. 310–8 . doi :10.1016/0076-6879(90 )86124-E . ISBN 978-0-12-182087-9 PMID 2172707 .
^ Heath H, Toennies G (February 1958). "The preparation and properties of ergothioneine disulphide" . The Biochemical Journal . 68 2 ): 204–10. doi :10.1042/bj0680204 . PMC 1200325 PMID 13522601 .
^ Asmus KD, Bensasson RV, Bernier JL, Houssin R, Land EJ (April 1996). "One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C" . The Biochemical Journal . 315 (2 ): 625–9. doi :10.1042/bj3150625 . PMC 1217242 PMID 8615839 .
^ Yamashita Y, Yamashita M (June 2010). "Identification of a novel selenium-containing compound, selenoneine, as the predominant chemical form of organic selenium in the blood of bluefin tuna" . The Journal of Biological Chemistry . 285 (24 ): 18134–8. doi :10.1074/jbc.C110.106377 PMC 2881734 PMID 20388714 .
External links [ edit ]
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Ergothioneine&oldid=1231515846 " C a t e g o r i e s : ● T h i o u r e a s ● A l p h a - A m i n o a c i d s ● I m i d a z o l i n e s H i d d e n c a t e g o r i e s : ● C S 1 F r e n c h - l a n g u a g e s o u r c e s ( fr ) ● A l l a r t i c l e s w i t h d e a d e x t e r n a l l i n k s ● A r t i c l e s w i t h d e a d e x t e r n a l l i n k s f r o m M a r c h 2 0 2 2 ● A r t i c l e s w i t h p e r m a n e n t l y d e a d e x t e r n a l l i n k s ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e c o m p o u n d I D s ● M u l t i p l e c h e m i c a l s i n a n i n f o b o x t h a t n e e d i n d e x i n g ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● A r t i c l e s w i t h c h a n g e d K E G G i d e n t i f i e r ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t
● T h i s p a g e w a s l a s t e d i t e d o n 2 8 J u n e 2 0 2 4 , a t 1 8 : 3 0 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
