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Vitamin K


DATA No : VVK0001 INFORMANT : Tetsuya Nakamura

NAME : 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione / 2-methyl-3-phytyl-1,4-naphthoquinone

COMMON NAME: vitamin K1 / 3-phytylmenadione / phytomenadione / phylloquinone
SYMBOL: VK1
FORMULA: C31H46O2 MOL.WT (average) : 450.696


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BIOLOGICAL ACTIVITY
Involvement of vitamin K-dependent clotting factors in coagulation. The vitamin K-dependent proteins ( ellipses) circulate as inactive forms of serine proteases until converted to their active (subscript a) forms. These conversions occur in stages where an active protease, a substrate, and a protein cofactor (triangles) from a Ca2+-mediated association with a phospholipid surface. The protein cofactors V and VII are activated by thrombin (IIa) to achieve their full activity. The clotting system is traditionally divided into two pathways: the extrinsic pathway which involves a tissue factor (TO) in addition to blood components, and an intrinsic pathway, which involves components present in the blood. Protein C is activated by Ida in the presence of an endothelial cell protein called thrombomodulin (TM). Protein C is not a procoagulant but rather functions in a complex with protein S to inactivate Va and VIIIa
[Table 0007] (Ref. 0006).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:Yellow viscous oil (Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:n20D=1.5263(Ref. 0010)

OPTICAL ROTATION:[a]25D=-28deg(Ref. 0001)Optical rotation
[Table 0001] (Ref. 0010)

DENSITY:

SOLUBILITY:Insol in water. Sparingly sol in methanol; sol in ethanol, acetone, benzene, petr ether, hexane, dioxane, chloroform, ether, other fat solvents and in vegetable oils(Ref. 0001)
SPECTRAL DATA
UV SPECTRA: Uv max (petr ether) 242, 248, 260, 269, 325 nm (E1%1cm396, 419, 383, 387, 68) (Ref. 0001). Uv max (ethanol) 243, 248, 262, 270, 330 nm (Ref. 0002).
[Spectrum 0001] (Ref. 0010)Em at 248 nm (EtOH) =18,900 (Ref. 0002/0006).

IR SPECTRA: (liquid) : 6.05m (CO), 6.21, 6.28m (aromatic nucleus) (Ref. 0008)
[Spectrum 0002] (Ref. 0010)
[Table 0002] (Ref. 0010)

NMR SPECTRA: at 60 MHz in CDCl3, i nternal standard Si(CH3)4: multiplet at 453-486 Hz (4 aromatic H), triplet at 302 Hz (J=7 Hz) (olefinic H at C2. , doublet at 201 Hz ) (J=7 Hz) (CH2.-1), singlet at 130 Hz (CH3-2), signal at 107 Hz (trans-methyl group at C3. .(Ref. 0008)
[Spectrum 0003] (Ref. 0010) Proton magnetic resonance data
[Table 0003] (Ref. 0010>

MASS SPECTRA:
[Spectrum 0004] (Ref. 0005)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
The content of vitamin K1 (phylloquinone) was determined in 27 species of green vegetables by HPLC and correlation between Vitamin K1 content and chlorophyll content was investigated. The ratio of vitamin K1 to chlorophyll was about 9 mmol/mol. VK1 content (mg/100g fresh wt.): Parsley (0.73), Perilla (Leaves) (0.65), Ashitaba (Leaves) (0.59), Watercress (0.39), Toumyao (Chinese vegetable) (0.38), Mitsuba (Leaf stalk and leaves) (0.37)
[Table 0004] (Ref. 0007)
Vitamin K contents in human liver
[Table 0005] (Ref. 0022)
CHEMICAL SYNTHESIS
To a dichloromethane solution (20ml) of 2-methyl-1,4-naphthoquinone (172mg, 1.0mmol) BF3.Et2O (3.0mmol) was added under N2 at -78 degC. After that phytyltrimethyltin was (532mg, 1.2mmol) was added, and the temperature of the resulting solution was gradually elevated within 1h. Then, ether and aqueous saturated NaCl solution were added to the reaction mixture. The organic layer and the combined ether extract were dried over anhydrous magnesium sulfate. Subsequent oxidation with excess silver oxide gave crude vitamin K1 after solvent was evaporated in vacuo. The resulting crude product was purified by preparative TLC on silica gel; affording vitamin K1(176mg) (Ref. 0009)
[Table 0006] (Ref. 0008).
METABOLISM
The synthesis of prothrombin in Chinese hamster ovary cells stably transfected with the prothrombin c DNA by immunofluorescent staining. Uncarboxylated proprothrombin undergoes complete g- carboxylation in the endoplasmic reticulum and that g- carboxylation precedes propeptide cleavage during prothrombin biosynthesis (Ref. 0011).
GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Anonym. (1989) Vitamin K1 in The Merck Index , 11th edition (Budavari, S., O'Neil, M. J., Smith, A., and Heckelman, P.E., eds), pp1580, Merck & Co., Inc., Rahway, N. J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0002]
AUTHOR:Dunphy,P.J., and Brodie,A.F.
TITLE:The structure and function of quinones in respiratory metabolism.
JOURNAL:Methods in Enzymology
VOL:18 PAGE : 407 -461 (1971)
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[0005]
AUTHOR:Di Mari, S. J., Supple, J. H., and Rapoport, H.
TITLE:Mass spectra of naphthoquinones. Vitamin K1(20) PubMed ID:5910960
JOURNAL:J Am Chem Soc.
VOL:88 PAGE : 1226-1232 (1966)
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[0006]
AUTHOR:Suttie,W.J. (1991) Vitamin K, in Handbook of Vitamins (2nd ed., Machlin,L.J., ed) , pp145-194, Marcel Dekker, Inc., New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0007]
AUTHOR:Kodaka,K., Ujiie,T.,Ueno,T., and Saito,M.
TITLE:Contents of Vitamin K1 and Chlorophyll in Green Vegetables.
JOURNAL:J Jpn Soc Nutr Food Sci
VOL:39 PAGE : 124 -126 (1986)
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[0008]
AUTHOR:Mayer,H., and Isler,O .
TITLE:Synthesis of Vitamin K.
JOURNAL:Methods in Enzymology
VOL:18 PAGE : 491 -547 (1971)
[TOP]

[0009]
AUTHOR:Naruta,Y., and Maruyama,K.
TITLE:Regio- and sterocontrolled polyprenylation of quinones. A new synthetic method of vitamin K series.
JOURNAL:Chemistry Lett
VOL: PAGE : 881 -884 (1979)
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[0010]
AUTHOR:Sommer,P., and Kofler,M.
TITLE:Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867
JOURNAL:Vitamins and Hormones
VOL:24 PAGE : 349 -399 (1966)
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[0011]
AUTHOR:Bristol, J. A., Ratcliffe, J. V., Roth, D. A., Jacobs, M. A., Furie, B. C., and Furie, B.
TITLE:Biosynthesis of prothrombin: intracellular localization of the vitamin K-dependent carboxylase and the sites of gamma-carboxylation PubMed ID:8839851
JOURNAL:Blood.
VOL:88 PAGE : 2585-2593 (1996)
[TOP]

[0022]
AUTHOR:Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K.
TITLE:Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953
JOURNAL:J Chromatogr.
VOL:489 PAGE : 291-301 (1989)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.