関: See also Vitamin K

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/04 13:36:06」(JST)

wiki en

Phylloquinone, also Vitamin K₁, is a polycyclic aromatic ketone, based on 2-methyl-1,4-naphthoquinone, with a 3-phytyl substituent.

It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants, particularly leaves, since it functions as an electron acceptor during photosynthesis, forming part of the electron transport chain of Photosystem I.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[1]

Terminology

It is often called vitamin K,^[2] phytomenadione or phytonadione. Sometimes a distinction is made with phylloquinone considered natural and phytonadione considered synthetic.^[3]

A stereoisomer of phylloquinone is called vitamin k₁ (note the difference in capitalization).

Biochemistry

Phylloquinone is an electron acceptor during photosynthesis, forming part of the electron transport chain of Photosystem I.

Its best-known function in animals is as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX, and X by the liver. It is also required for the formation of anticoagulant factors protein C and S. It is commonly used to treat warfarin toxicity, and as an antidote for coumatetralyl.

Vitamin K is required for bone protein formation.^[4]

External links

References

^ "WHO Model List of Essential Medicines: 18th list" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
^ Haroon Y, Shearer MJ, Rahim S, Gunn WG, McEnery G, Barkhan P (June 1982). "The content of phylloquinone (vitamin K1) in human milk, cows' milk, and infant formula foods determined by high-performance liquid chromatography". J. Nutr. 112 (6): 1105–17. PMID 7086539.
^ "Vitamin K". Retrieved 2009-03-18.
^ "Vitamin K: Phylloquinone". TrackMyStack. Retrieved 23 August 2015.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ビタミンKの概要 overview of vitamin k
2. ワルファリン関連出血または高用量INRのマネージメント management of warfarin associated bleeding or supratherapeutic inr
3. Vitamin K and the synthesis and function of gamma-carboxyglutamic acid
4. 健康な新生児のルーチンのマネージメントの概要 overview of the routine management of the healthy newborn infant
5. Anticoagulant rodenticide poisoning: Management

English Journal

Assessment of Vitamin and Carotenoid Concentrations of Emerging Food Products: Edible Microgreens.

Xiao Z, Lester GE, Luo Y, Wang Q.SourceDepartment of Nutrition and Food Science, University of Maryland , College Park, Maryland 20742, United States.
Journal of agricultural and food chemistry.J Agric Food Chem.2012 Jul 30. [Epub ahead of print]
Microgreens (seedlings of edible vegetables and herbs) have gained popularity as a new culinary trend over the past few years. Although small in size, microgreens can provide surprisingly intense flavors, vivid colors, and crisp textures and can be served as an edible garnish or a new salad ingredi
PMID 22812633

Phylloquinone (vitamin K(1) ) biosynthesis in plants: two peroxisomal thioesterases of lactobacillales origin hydrolyze 1,4-dihydroxy-2-naphthoyl-coa.

Widhalm JR, Ducluzeau AL, Buller NE, Elowsky CG, Olsen LJ, Basset GJ.SourceCenter for Plant Science Innovation, University of Nebraska-Lincoln, Lincoln, NE 68588, USA Department of Molecular, Cellular, and Developmental Biology, University of Michigan, Ann Arbor, MI 48109, USA.
The Plant journal : for cell and molecular biology.Plant J.2012 Jul;71(2):205-15. doi: 10.1111/j.1365-313X.2012.04972.x. Epub 2012 Jun 19.
It is not known how plants cleave the thioester bond of 1,4-dihydroxy-2-naphthoyl-CoA (DHNA-CoA), a necessary step to form the naphthoquinone ring of phylloquinone (vitamin K(1) ). In fact, only recently has the hydrolysis of DHNA-CoA been demonstrated to be enzyme driven in vivo, and the cognate th
PMID 22372525

Japanese Journal

Selective chemiluminescence method for monitoring of vitamin K homologues in rheumatoid arthritis patients.

Ahmed Sameh,Kishikawa Naoya,Ohyama Kaname,Imazato Takahiro,Ueki Yukitaka,Kuroda Naotaka
Talanta 85(1), 230-236, 2011-07-15
… Therefore, this study aimed to develop a new highly sensitive and selective chemiluminescence (CL) method designated to quantify vitamin K homologues in plasma of RA patients including phylloquinone (PK, vitamin K(1)), menaquinone-4 (MK-4, vitamin K(2)) and menaquinone-7 (MK-7, vitamin K(2)). …
NAID 80021812489

化学的アプローチによるビタミンKの生理作用の解析と生理活性物質への応用

須原義智,和田昭盛,中川公恵,鎌尾まや,津川尚子,岡野登志夫
ビタミン 85(5・6), 271-279, 2011-06-25
… It has two major homologues, the plant-derived vitamin K_1 (phylloquinone: PK)and the bacterium-derived vitamin K_2 (menaquinone-n: MK-n). …
NAID 110008686087

Related Pictures

Molecular Structure Of Vitamin K1 (phylloquinone) Stock Illustration - Illustration of Phylloquinone | Wild Juggling Solaray K-1 Phylloquinone - 100 Tablets - eVitamins.com Molecule Phylloquinone Vitamin K1 Stock Photo - Image: 28176380 Warfarin Stock Photos, Images, & Pictures | Shutterstock Vitamin K1 Powder (Phylloquinone), CAS#: 84-80-0, Vitamin K1 Supplier - Foodchem Vitamin K (phytomenadione/phylloquinone) – Family GP Phylloquinone Meaning - YouTube

★リンクテーブル★

リンク元	「ビタミンK」「フィトナジオン」「phytomenadione」

「ビタミンK」

Phylloquinone
Names
	IUPAC name 2-methyl-3-[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthoquinone
	Other names Vitamin K1; phytomenadione; phytonadione
Identifiers
CAS Number	84-80-0
ChEBI	CHEBI:18067
ChEMBL	ChEMBL1550
ChemSpider	4447652
DrugBank	DB01022
Jmol interactive 3D	Image
PubChem	4812
UNII	A034SE7857
	InChI InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1 Key: MBWXNTAXLNYFJB-NKFFZRIASA-N ; InChI=1/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1 Key: MBWXNTAXLNYFJB-NKFFZRIABL ;
	SMILES CC1=C(C(=O)c2ccccc2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C ;
Properties
Chemical formula	C31H46O2
Molar mass	450.70 g/mol
Pharmacology
ATC code	B02BA01
	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

　　[★]

英: vitamin K, VK
関: ビタミン、(薬剤として存在)フィトナジオン(=ビタミンK1)

図：SPC.360
脂溶性ビタミン
止血薬

種類

ビタミンK₁：phytonadione
ビタミンK₂：menadione
ビタミンK₃：人工合成

生理作用

ビタミンKはγ-glutamyl carboxylase(多分、Ca2+を補酵素として用いる酵素の総称で、γ-carboxyglutamate residueを有する)に必要である。
血液凝固に必要な因子の肝臓における生合成を促進 (SPC.360)

第II因子(プロトロンビン)、第VII因子、第IX因子、第X因子の産生を促進 (SPC.292改)

促進というより、凝固因子のグルタミン酸をγ-カルボキシグルタミン酸(Gla)に変換しないとセリンプロテアーゼとしての酵素活性を発揮できないということ？

プロテインC、プロテインSもビタミンK依存的である。

代謝系を介するので、作用の発現は遅い

血液凝固因子やオステオカルシンの前駆体のプロセッシングに必須であり、補酵素として働く。

bone Gla proteinやmatrix Gla proteinといった骨の石灰化に関与する蛋白質の補酵素として働いており、またビタミンK1(phylloquinone)やビタミンK2は骨粗鬆症の治療薬として臨床試験が進められている(参考1)。

体内産生

腸内細菌によって合成

低栄養or肝障害の存在するとき腸内細菌を死滅させるような広域抗生剤の使用　→　ビタミンK欠乏症

吸収

胆汁により吸収が媒介される

閉塞性黄疸　→　ビタミンK欠乏症

適応

クマリン誘導体による低プロトロンビン血症による出血

==禁忌

臨床関連

ビタミンK欠乏症

特発性乳児ビタミンK欠乏性出血症(乳児ビタミンK欠乏性出血症)

新生児メレナ

閉塞性黄疸、膵臓疾患、小腸疾患(例えばクローン病)、下痢、抗菌薬の長期連用

ビタミンKに依存している血液凝固因子の血中半減期は、以下の通りなので、PTでビタミンK欠乏症のスクリーニングが行われるらしい

半減期(hr)：F II(50-80) > F X(25-60) > F IX](24) >F VII(6)

参考

1. [charged] ビタミンKの概要 - uptodate [1]

「フィトナジオン」

　　[★]

英: phytonadione
同: ビタミンK1 vitamin K1、フィトメナジオン phytomenadione、フィロキノン phylloquinone
商: AquaMEPHYTON, Mephyton; ビタミンＫ１、カチーフN、ビタK1、ヒメロンK1。; (高カロリー輸液)フルカリック、ヘパンED、ネオパレン、エルネオパ; (高カロリー輸液用総合ビタミン剤)ネオラミン・マルチＶ、オーツカＭＶ、ダイメジン・マルチ、ネオラミン・マルチＶ、ビタジェクト; (肝不全用経口栄養剤)アミノレバンEN、オフタルム、ケーワン; (経腸用液)ラコール、ラコールNF、ツインライン、エレンタール、エンシュア・リキッド、ツインラインNF
関: ビタミンK

適応

ビタミンＫ欠乏症の予防及び治療
ビタミンＫ欠乏が推定される出血

併用注意

クマリン系抗凝血薬(ワルファリン)　　←　　添付文書では併用注意だが、資料によっては併用禁忌とある。

「phytomenadione」

　　[★]

フィトメナジオン

関: phylloquinone、phytonadione、vitamin K1

[1] "WHO Model List of Essential Medicines: 18th list" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[pmid7086539-2] Haroon Y, Shearer MJ, Rahim S, Gunn WG, McEnery G, Barkhan P (June 1982). "The content of phylloquinone (vitamin K1) in human milk, cows' milk, and infant formula foods determined by high-performance liquid chromatography". J. Nutr. 112 (6): 1105–17. PMID 7086539.

[urlVitamin_K-3] "Vitamin K". Retrieved 2009-03-18.

[4] "Vitamin K: Phylloquinone". TrackMyStack. Retrieved 23 August 2015.

匿名

検索

案内

案内

phylloquinone