WordNet

the 21st letter of the Roman alphabet (同)u
any of a group of organic substances essential in small quantities to normal metabolism
(chiefly British) of or appropriate to the upper classes especially in language use

PrepTutorEJDIC

uraniumの化学記号
上流の,上流階級にふさわしい / (映画が)児童観覧用の
『ビタミン』,栄養素(身体の喜常な機能を維持するために少量ながら必要な有機化合物)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/05 19:12:42」(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)

UpToDate Contents

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1. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention
2. 水溶性ビタミンの概要 overview of water soluble vitamins
3. ビタミンDの概要 overview of vitamin d
4. ビタミンKの概要 overview of vitamin k
5. ビタミンAの概要 overview of vitamin a

English Journal

Effects of vitamin U (S-methyl methionine sulphonium chloride) on valproic acid induced liver injury in rats.

Sokmen BB, Tunali S, Yanardag R.SourceDepartment of Chemistry, Faculty of Arts and Sciences, Giresun University, 28049 Giresun, Turkey. baharsokmen@yahoo.com
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2012 Oct;50(10):3562-6. doi: 10.1016/j.fct.2012.07.056. Epub 2012 Aug 4.
In this study, we aimed to investigate the effects of vitamin U (Vit U) on valproic acid (VPA)-induced liver damage. Female Sprague Dawley rats were randomly divided into four groups. Group I was intact control animals. Group II was control rats given Vit U (50 mg/kg/day) for fifteen days. Group III
PMID 22889891

Agrobacterium tumefaciens can obtain sulphur from an opine that is synthesized by octopine synthase using S-methylmethionine as a substrate.

Flores-Mireles AL, Eberhard A, Winans SC.SourceDepartment of Microbiology, Cornell University, Ithaca, NY, USA.
Molecular microbiology.Mol Microbiol.2012 Jun;84(5):845-56. doi: 10.1111/j.1365-2958.2012.08061.x. Epub 2012 May 2.
Agrobacterium tumefaciens incites plant tumours that produce nutrients called opines, which are utilized by the bacteria during host colonization. Various opines provide sources of carbon, nitrogen and phosphorous, but virtually nothing was previously known about how A. tumefaciens acquires sulphur
PMID 22486934

Inhibitory Effect of Vitamin U (S-Methylmethionine Sulfonium Chloride) on Differentiation in 3T3-L1 Pre-adipocyte Cell Lines.

Lee NY, Park KY, Min HJ, Song KY, Lim YY, Park J, Kim BJ, Kim MN.SourceArumdaun Nara Skin Clinic, Seoul, Korea.
Annals of dermatology.Ann Dermatol.2012 Feb;24(1):39-44. doi: 10.5021/ad.2012.24.1.39. Epub 2012 Feb 2.
BACKGROUND: S-methylmethionine sulfonium chloride was originally called vitamin U because of its inhibition of ulceration in the digestive system. Vitamin U is ubiquitously expressed in the tissues of flowering plants, and while there have been reports on its hypolipidemic effect, its precise functi
PMID 22363154

Japanese Journal

化学療法下にある末期肝細胞癌患者の亜鉛欠乏

本間和宏,和田安代,榎本真理,小尾俊太郎,若菜宣明,田中越郎
東京農業大学農学集報 58(3), 194-198, 2013-12-16
末期肝細胞癌患者では栄養状態の悪化が多く見られ,これは予後を左右する重要な因子である。化学療法目的で入院した 33名の IV 期肝細胞癌患者で,食事摂取状況と臨床検査データとの関連を調べた。血清中の直接ビリルビン,間接ビリルビン,LDH, AST, ALT, ALP, アルブミン,CRP, AFP さらに入院中の平均食事摂取率,食事摂取量,摂取エネルギー量,摂取食塩相当量,鉄摂取量,亜鉛摂取量,ビ …
NAID 110009658771

IHNに対するアスコルビン酸高濃度投与の有効性はウイルス株や魚体サイズにより影響を受ける

Ishikawa Takanori,Mano Nobuhiro,Minakami Kai [他]
魚病研究 48(4), 113-118, 2013-12
NAID 40019931522

Effect of Supplemental Vitamin E on Antibody Titer in Japanese Black Calves Vaccinated against Bovine Herpesvirus-1

OTOMARU Konosuke,SAITO Shun,ENDO Karura [他]
The journal of veterinary medical science 75(12), 1671-1673, 2013-12
NAID 40019928507

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★リンクテーブル★

「U」

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
Jmol interactive 3D	Image
KEGG	C03172
PubChem	145692
	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 ;
	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).
	verify (what is ?)
	Infobox references

　　[★]

[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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vitamin U