関: methylmethionine sulfonium chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/02 11:15:46」(JST)

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S-Methylmethionine (SMM) is a derivative of methionine with the chemical formula (CH₃)₂S⁺CH₂CH₂CH(NH₃⁺)CO₂⁻. This cation is an intermediate in many biosynthetic pathways owing to the sulfonium functional group. The natural derivative S-methylmethionine is biosynthesized from L-methionine which is first converted to S-adenosylmethionine. The subsequent conversion, involving replacement of the adenosyl group by a methyl group is catalyzed by the enzyme methionine S-methyltransferase. S-methylmethionine is particularly abundant in plants, being more abundant than methionine.^[2]

S-Methylmethionine is sometimes referred to as vitamin U,^[3] but it is not considered a true vitamin. The term was coined in 1950 by Garnett Cheney for uncharacterized anti-ulcerogenic^[4] factors in raw cabbage juice that may help speed healing of peptic ulcers.

S-Methylmethionine is claimed to have protective effects in the gastrointestinal mucosa and in the liver.^[5]

Biosynthesis and biochemical function

S-Methylmethionine arises via the methylation of methionine by S-adenosyl methionine (SAM). The coproduct is S-adenosyl homocysteine.^[2]

The biological roles of S-methylmethionine are not well understood. Speculated roles include methionine storage, use as a methyl donor, regulation of SAM.^[2] A few plants use S-methylmethionine as a precursor to the osmolyte dimethylsulfoniopropionate (DMSP). Intermediates include dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.^[6]

Beer flavor precursor in barley malt

S-Methylmethionine is found in barley and during the malting process, particularly the curing stage in kilning, heat causes it to break down to form dimethyl sulfide (DMS).^[7]

References

^ ^a ^b ^c ^d Merck Index, 12th ed., 10165 ISBN 0-911910-12-3
^ ^a ^b ^c Bourgis F (1999). "S-methylmethionine plays a major role in phloem sulfur transport and is synthesized by a novel type of methyltransferase". The Plant Cell Online 11 (8): 1485–1498. doi:10.1105/tpc.11.8.1485.
^ National Center for Biomedical Ontology. "Methylmethionine Sulfonium Chloride".
^ Cheney G (September 1950). "Anti-peptic ulcer dietary factor (vitamin "U") in the treatment of peptic ulcer". J Am Diet Assoc 26 (9): 668–72. PMID 15436263.
^ Patel AD, Prajapati NK (2012). "Review on Biochemical Importance of Vitamin-U" (PDF). Journal of Chemical and Pharmaceutical Research 4 (1): 209–215.
^ McNeil SD (1999). "Betaines and related osmoprotectants. Targets for metabolic engineering of stress resistance". Plant Physiology 120 (4): 945–949. doi:10.1104/pp.120.4.945.
^ Hornsey IS (1999). Brewing. Royal Society of Chemistry. p. 47. ISBN 9780854045686.

External links

Vitamin U at the US National Library of Medicine Medical Subject Headings (MeSH)

English Journal

Vitamin U has a protective effect on valproic acid-induced renal damage due to its anti-oxidant, anti-inflammatory, and anti-fibrotic properties.

Gezginci-Oktayoglu S1, Turkyilmaz IB, Ercin M, Yanardag R, Bolkent S.
Protoplasma.Protoplasma.2015 Mar 24. [Epub ahead of print]
The aim of present study was to investigate the effect of vitamin U (vit U, S-methylmethionine) on oxidative stress, inflammation, and fibrosis within the context of valproic acid (VPA)-induced renal damage. In this study, female Sprague Dawley rats were randomly divided into four groups: Group I co
PMID 25802006

Methionine and S-methylmethionine exhibit temporal and spatial accumulation patterns during the Arabidopsis life cycle.

Frank A1, Cohen H, Hoffman D, Amir R.
Amino acids.Amino Acids.2015 Mar;47(3):497-510. doi: 10.1007/s00726-014-1881-1. Epub 2014 Dec 10.
Methionine is a nutritionally essential sulfur-containing amino acid found at low levels in plant tissues. Yet, the factors that regulate its synthesis and accumulation in seeds are not fully known. Recent genetic studies demonstrate that Arabidopsis seeds are able to synthesize methionine de novo t
PMID 25488426

Methionine Biosynthesis is Essential for Infection in the Rice Blast Fungus Magnaporthe oryzae.

Saint-Macary ME1, Barbisan C2, Gagey MJ1, Frelin O1, Beffa R2, Lebrun MH1, Droux M1.
PloS one.PLoS One.2015 Apr 9;10(4):e0111108. doi: 10.1371/journal.pone.0111108. eCollection 2015.
Methionine is a sulfur amino acid standing at the crossroads of several biosynthetic pathways. In fungi, the last step of methionine biosynthesis is catalyzed by a cobalamine-independent methionine synthase (Met6, EC 2.1.1.14). In the present work, we studied the role of Met6 in the infection proces
PMID 25856162

Japanese Journal

Carcinoma Infection and Immune Systems of Ehrlich Ascites Carcinoma-Bearing Mice Treated with Structurally Similar Sulfonium Compounds

NAKAJIMA Kenji,NAKAJIMA Yoshiki
Bioscience, biotechnology, and biochemistry 75(4), 808-811, 2011-04-23
… The effects of intraperitoneal administration of dimethylsulfonioacetate (DMSA), dimethlsulfoniopropionate (DMSP), and methylmethionine (MeMet) solutions (10 mM each) on the body weights and the hematological parameters (red and white blood cells) of Ehrlich ascites carcinoma (EAC)-bearing mice were examined for up to 10 d. …
NAID 10028272068

胃粘膜傷害における胃・十二指腸ムチンの量的・質的変動に対するメチルメチオニンスルホニウムクロライド(MMSC)後投与の効果

伊東祐子,岡田諭起,三枝陽一,岩井知久,市川尊文,五艘行信,池澤智明,石原和彦
潰瘍 = Ulcer research 35(2), 126-131, 2008-12-25
NAID 10025371302

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リンク元	「メチルメチオニン」
拡張検索	「methylmethionine sulfonium chloride」「methylmethionine sulfonium」

「メチルメチオニン」

S-Methylmethionine^[1]
Names
	IUPAC name (3-Amino-3-carboxy-propyl)-dimethyl-sulfonium
	Other names S-Methyl-L-methionine; Vitamin U
Identifiers
CAS Number	4727-40-6
ChEBI	CHEBI:17728
ChemSpider	128519
	InChI InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1 Key: YDBYJHTYSHBBAU-YFKPBYRVSA-O ; InChI=1/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1 Key: YDBYJHTYSHBBAU-YJIVXYNWBY ;
Jmol interactive 3D	Image
KEGG	C03172
PubChem	145692
	SMILES C[S+](C)CC[C@@H](C(=O)O)N ;
Properties
Chemical formula	C6H15NO2S+
Molar mass	164.247 g/mol
Melting point	139 °C (282 °F; 412 K) (bromide salt, decomposes); 134 °C (273 °F) (chloride salt, decomposes)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (Median dose)	2760 mg/kg (iv, mice, chloride salt)
	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: methylmethionine、methylmethionine sulfonium chloride
関: 塩化メチルメチオニンスルホニウムクロライド、メチルメチオニンスルホニウムクロリド

「methylmethionine sulfonium chloride」

　　[★]

塩化メチルメチオニンスルホニウムクロライド、メチルメチオニンスルホニウムクロリド

関: methylmethionine

「methylmethionine sulfonium」

　　[★] メチルメチオニンスルホニウム

[Merck-1] Merck Index, 12th ed., 10165 ISBN 0-911910-12-3

[Bourgis-2] Bourgis F (1999). "S-methylmethionine plays a major role in phloem sulfur transport and is synthesized by a novel type of methyltransferase". The Plant Cell Online 11 (8): 1485–1498. doi:10.1105/tpc.11.8.1485.

[ontology-3] National Center for Biomedical Ontology. "Methylmethionine Sulfonium Chloride".

[pmid15436263-4] Cheney G (September 1950). "Anti-peptic ulcer dietary factor (vitamin "U") in the treatment of peptic ulcer". J Am Diet Assoc 26 (9): 668–72. PMID 15436263.

[Patel_Prajapati_2012-5] Patel AD, Prajapati NK (2012). "Review on Biochemical Importance of Vitamin-U" (PDF). Journal of Chemical and Pharmaceutical Research 4 (1): 209–215.

[6] McNeil SD (1999). "Betaines and related osmoprotectants. Targets for metabolic engineering of stress resistance". Plant Physiology 120 (4): 945–949. doi:10.1104/pp.120.4.945.

[7] Hornsey IS (1999). Brewing. Royal Society of Chemistry. p. 47. ISBN 9780854045686.

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methylmethionine