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Chemical Compound Review

Phylloquinone     3-methyl-2-[(E,7R,11R)- 3,7,11,15...

Synonyms: Vitamin- K1, Vitamin-?K1, CHEMBL1550, SureCN3882, vitamin K1, 11, ...
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Disease relevance of VITAMIN K1


High impact information on VITAMIN K1


Chemical compound and disease context of VITAMIN K1


Biological context of VITAMIN K1

  • Whether these biphasic kinetics reflect unidirectional electron transfer, involving only the PsaA-side phylloquinone or bi-directional electron transfer, involving both the PsaA- and PsaB-side phylloquinones, has been the source of some controversy [12].
  • In an effort to identify amino acid residues near the phylloquinone binding sites, all tryptophans and histidines that are conserved between PsaA and PsaB in the region of the 10th and 11th transmembrane alpha-helices were mutated in Chlamydomonas reinhardtii [13].
  • METHODS: Twenty-two patients with asymptomatic prolongation of prothrombin time were prospectively randomized and treated with 1 mg of phytonadione IV or 1 mg SC [4].
  • OBJECTIVE: The objective of this study was to compare, in younger and older adults, the relative bioavailability of phylloquinone from a vegetable with that of a fortified oil [14].
  • RESULTS: There was an increase and subsequent decrease in measures of bone formation (P = 0.002) and resorption (P = 0.08) after dietary phylloquinone restriction and repletion, respectively [15].

Anatomical context of VITAMIN K1


Associations of VITAMIN K1 with other chemical compounds

  • Recruitment of a foreign quinone into the A1 site of photosystem I. Altered kinetics of electron transfer in phylloquinone biosynthetic pathway mutants studied by time-resolved optical, EPR, and electrometric techniques [20].
  • We estimate the redox potential of plastoquinone-9 in the A(1) site to be more oxidizing than phylloquinone so that electron transfer from Q(-) to F(X) is thermodynamically unfavorable in the menA and menB mutants [20].
  • Targeted inactivation of the menA and menB genes, which code for phytyl transferase and 1,4-dihydroxy-2-naphthoate synthase, respectively, prevented the synthesis of phylloquinone, thereby confirming the participation of these two gene products in the biosynthetic pathway [2].
  • CONCLUSIONS: For patients who are excessively anticoagulated with warfarin, small doses of SC phytonadione may not correct the INR as rapidly or as effectively as when administered IV [4].
  • These results show that undercarboxylated osteocalcin, plasma phylloquinone, and urinary gamma-carboxyglutamic acid excretion appear to be sensitive measures of vitamin K nutritional status because all of these variables were responsive to changes in dietary intake [21].

Gene context of VITAMIN K1

  • The menD(-) and menE(-) strains were generated, and both were found to lack phylloquinone [22].
  • The menD and menE homologs code for 2-succinyl-6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid-CoA synthase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803 [22].
  • The mutated nuclear gene encoded 1,4-dihydroxy-2-naphtoic acid phytyltransferase, an enzyme of phylloquinone biosynthesis, and high-performance liquid chromatography analysis revealed that the abc4 mutant contained no phylloquinone, and only about 3% plastoquinone [23].
  • The directionality of electron transfer in Photosystem I (PS I) is investigated using site-directed mutations in the phylloquinone (QK) and FX binding regions of Synnechocystis sp. PCC 6803 [24].
  • Therefore, the loss of phylloquinone methylation affects photosystem I stability or turnover, and the limitation in functional photosystem I complexes results in overreduction of photosystem II under high light [7].

Analytical, diagnostic and therapeutic context of VITAMIN K1

  • As demonstrated by radioimmunoassay, selective barium salt adsorption, and two coagulation assays which discriminate between precursor- and mature-prothrombin, these cells retained their ability to synthesize precursor prothrombin (preprothrombin) in the absence of exogenous phylloquinone (vitamin K) [25].
  • Sensitive HPLC methods for measuring plasma phylloquinone are now available, and related methods for measuring long-chain menaquinones can be developed [26].
  • CONCLUSION: For patients with supratherapeutic international normalized ratio values, our survey suggests that a substantial number of anticoagulation clinics underutilize oral phytonadione [27].
  • Oral administration of phytonadione has been shown to be an effective alternative to the intravenous route, but these methods have never been compared directly [28].
  • Treatment of excessive anticoagulation with phytonadione (vitamin K): a meta-analysis [29].


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  2. Recruitment of a foreign quinone into the A(1) site of photosystem I. I. Genetic and physiological characterization of phylloquinone biosynthetic pathway mutants in Synechocystis sp. pcc 6803. Johnson, T.W., Shen, G., Zybailov, B., Kolling, D., Reategui, R., Beauparlant, S., Vassiliev, I.R., Bryant, D.A., Jones, A.D., Golbeck, J.H., Chitnis, P.R. J. Biol. Chem. (2000) [Pubmed]
  3. A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes. Gross, J., Cho, W.K., Lezhneva, L., Falk, J., Krupinska, K., Shinozaki, K., Seki, M., Herrmann, R.G., Meurer, J. J. Biol. Chem. (2006) [Pubmed]
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  5. The incidence of recurrent venous thromboembolism after treatment with vitamin K antagonists in relation to time since first event: a meta-analysis. van Dongen, C.J., Vink, R., Hutten, B.A., Büller, H.R., Prins, M.H. Arch. Intern. Med. (2003) [Pubmed]
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  7. Deficiency in Phylloquinone (Vitamin K1) Methylation Affects Prenyl Quinone Distribution, Photosystem I Abundance, and Anthocyanin Accumulation in the Arabidopsis AtmenG Mutant. Lohmann, A., Sch??ttler, M.A., Br??h??lin, C., Kessler, F., Bock, R., Cahoon, E.B., D??rmann, P. J. Biol. Chem. (2006) [Pubmed]
  8. Recruitment of a foreign quinone into the A1 site of photosystem I. In vivo replacement of plastoquinone-9 by media-supplemented naphthoquinones in phylloquinone biosynthetic pathway mutants of Synechocystis sp. PCC 6803. Johnson, T.W., Zybailov, B., Jones, A.D., Bittl, R., Zech, S., Stehlik, D., Golbeck, J.H., Chitnis, P.R. J. Biol. Chem. (2001) [Pubmed]
  9. Factor V deficiency and its reversal with gluten restriction. In a patient with celiac disease. Shanahan, F., Aburajab, A., Goodacre, R., Blajchman, M.A. Arch. Intern. Med. (1983) [Pubmed]
  10. Bioavailability of phylloquinone from an intravenous lipid emulsion. Camilo, M.E., Jatoi, A., O'Brien, M., Davidson, K., Sokoll, L., Sadowski, J.A., Mason, J.B. Am. J. Clin. Nutr. (1998) [Pubmed]
  11. Preventive effects of phylloquinone on hemorrhagic death induced by butylated hydroxytoluene in male rats. Takahashi, O., Hiraga, K. J. Nutr. (1979) [Pubmed]
  12. Biochemical and biophysical characterization of photosystem I from phytoene desaturase and zeta-carotene desaturase deletion mutants of Synechocystis Sp. PCC 6803: evidence for PsaA- and PsaB-side electron transport in cyanobacteria. Bautista, J.A., Rappaport, F., Guergova-Kuras, M., Cohen, R.O., Golbeck, J.H., Wang, J.Y., Béal, D., Diner, B.A. J. Biol. Chem. (2005) [Pubmed]
  13. Mutations in both sides of the photosystem I reaction center identify the phylloquinone observed by electron paramagnetic resonance spectroscopy. Boudreaux, B., MacMillan, F., Teutloff, C., Agalarov, R., Gu, F., Grimaldi, S., Bittl, R., Brettel, K., Redding, K. J. Biol. Chem. (2001) [Pubmed]
  14. Response of vitamin K status to different intakes and sources of phylloquinone-rich foods: comparison of younger and older adults. Booth, S.L., O'Brien-Morse, M.E., Dallal, G.E., Davidson, K.W., Gundberg, C.M. Am. J. Clin. Nutr. (1999) [Pubmed]
  15. Effects of a hydrogenated form of vitamin K on bone formation and resorption. Booth, S.L., Lichtenstein, A.H., O'Brien-Morse, M., McKeown, N.M., Wood, R.J., Saltzman, E., Gundberg, C.M. Am. J. Clin. Nutr. (2001) [Pubmed]
  16. Low vitamin K status is associated with osteoarthritis in the hand and knee. Neogi, T., Booth, S.L., Zhang, Y.Q., Jacques, P.F., Terkeltaub, R., Aliabadi, P., Felson, D.T. Arthritis Rheum. (2006) [Pubmed]
  17. The uptake of lipoprotein-borne phylloquinone (vitamin K1) by osteoblasts and osteoblast-like cells: role of heparan sulfate proteoglycans and apolipoprotein E. Newman, P., Bonello, F., Wierzbicki, A.S., Lumb, P., Savidge, G.F., Shearer, M.J. J. Bone Miner. Res. (2002) [Pubmed]
  18. Variations of phylloquinone concentration in human milk at various stages of lactation and in cow's milk at various seasons. Fournier, B., Sann, L., Guillaumont, M., Leclercq, M. Am. J. Clin. Nutr. (1987) [Pubmed]
  19. Comparative distribution, metabolism, and utilization of phylloquinone and menaquinone-9 in rat liver. Reedstrom, C.K., Suttie, J.W. Proc. Soc. Exp. Biol. Med. (1995) [Pubmed]
  20. Recruitment of a foreign quinone into the A1 site of photosystem I. Altered kinetics of electron transfer in phylloquinone biosynthetic pathway mutants studied by time-resolved optical, EPR, and electrometric techniques. Semenov, A.Y., Vassiliev, I.R., van Der Est, A., Mamedov, M.D., Zybailov, B., Shen, G., Stehlik, D., Diner, B.A., Chitnis, P.R., Golbeck, J.H. J. Biol. Chem. (2000) [Pubmed]
  21. Changes in serum osteocalcin, plasma phylloquinone, and urinary gamma-carboxyglutamic acid in response to altered intakes of dietary phylloquinone in human subjects. Sokoll, L.J., Booth, S.L., O'Brien, M.E., Davidson, K.W., Tsaioun, K.I., Sadowski, J.A. Am. J. Clin. Nutr. (1997) [Pubmed]
  22. The menD and menE homologs code for 2-succinyl-6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid-CoA synthase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803. Wade Johnson, T., Naithani, S., Stewart, C., Zybailov, B., Daniel Jones, A., Golbeck, J.H., Chitnis, P.R. Biochim. Biophys. Acta (2003) [Pubmed]
  23. Inactivation and deficiency of core proteins of photosystems I and II caused by genetical phylloquinone and plastoquinone deficiency but retained lamellar structure in a T-DNA mutant of Arabidopsis. Shimada, H., Ohno, R., Shibata, M., Ikegami, I., Onai, K., Ohto, M.A., Takamiya, K. Plant J. (2005) [Pubmed]
  24. Electron transfer in cyanobacterial photosystem I: II. Determination of forward electron transfer rates of site-directed mutants in a putative electron transfer pathway from A0 through A1 to FX. Xu, W., Chitnis, P.R., Valieva, A., van der Est, A., Brettel, K., Guergova-Kuras, M., Pushkar, Y.N., Zech, S.G., Stehlik, D., Shen, G., Zybailov, B., Golbeck, J.H. J. Biol. Chem. (2003) [Pubmed]
  25. Vitamin K-dependent synthesis and modification of precursor prothrombin in cultured H-35 hepatoma cells. Munns, T.W., Johnston, M.F., Liszewski, M.K., Olson, R.E. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
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  28. Comparison of oral vs intravenous phytonadione (vitamin K1) in patients with excessive anticoagulation: a prospective randomized controlled study. Lubetsky, A., Yonath, H., Olchovsky, D., Loebstein, R., Halkin, H., Ezra, D. Arch. Intern. Med. (2003) [Pubmed]
  29. Treatment of excessive anticoagulation with phytonadione (vitamin K): a meta-analysis. Dezee, K.J., Shimeall, W.T., Douglas, K.M., Shumway, N.M., O'malley, P.G. Arch. Intern. Med. (2006) [Pubmed]
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