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Chemical Compound Review

SureCN571905     2-(3,7-dimethylocta-2,6- dienyl)-3-methyl...

Synonyms: AC1L974N
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Disease relevance of menaquinone


High impact information on menaquinone


Chemical compound and disease context of menaquinone


Biological context of menaquinone

  • The DNA segment responsible for the complementation contained an open reading frame (GenBankTM accession number Z49210Z49210) with 44% sequence identity over 262 amino acids to UbiE, which is required for a C-methyltransferase step in the Q and menaquinone biosynthetic pathways in Escherichia coli [15].
  • Vitamin K2 (menatetrenone) effectively prevents fractures and sustains lumbar bone mineral density in osteoporosis [16].
  • The NSAR is also functionally promiscuous and catalyzes an efficient OSBS reaction; intriguingly, the operon for menaquinone biosynthesis in G. kaustophilus does not encode an OSBS, raising the possibility that the NSAR is a bifunctional enzyme rather than an accidentally promiscuous enzyme [17].
  • We originally reported that vitamin K2 (VK2) analogs, including menaquinone 4 (MK4) but not vitamin K1, effectively induce apoptosis in various types of primary cultured leukemia cells and leukemia cell lines in vitro [18].
  • The G+C content of SOSP1-21T genomic DNA is 53.9%, and MK-9(H2) was the only menaquinone detected [19].

Anatomical context of menaquinone


Associations of menaquinone with other chemical compounds


Gene context of menaquinone

  • The menD gene of Escherichia coli codes for the first enzyme of menaquinone biosynthesis, 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC) synthase [28].
  • In B. subtilis the ubiE homolog is likely to be required for menaquinone biosynthesis and is located within the gerC gene cluster, known to be involved in spore germination and normal vegetative growth [29].
  • Metl appears to be a member of a conserved family of methyltransferases that share homology with, but are distinct from, the UbiE family of methyltransferases involved in ubiquinone and menaquinone biosynthesis [30].
  • A new gene (menF) encoding an isochorismate synthase specifically involved in menaquinone (vitamin K2) biosynthesis has been cloned and sequenced [31].
  • Our previous assumption that entC is responsible for both menaquinone and enterobactin biosynthesis is inconsistent with these mutant studies and has to be revised [32].

Analytical, diagnostic and therapeutic context of menaquinone


  1. Respiratory chain is required to maintain oxidized states of the DsbA-DsbB disulfide bond formation system in aerobically growing Escherichia coli cells. Kobayashi, T., Kishigami, S., Sone, M., Inokuchi, H., Mogi, T., Ito, K. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  2. Characterization of the menaquinone reduction site in the diheme cytochrome b membrane anchor of Wolinella succinogenes NiFe-hydrogenase. Gross, R., Pisa, R., Sänger, M., Lancaster, C.R., Simon, J. J. Biol. Chem. (2004) [Pubmed]
  3. 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]
  4. 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]
  5. Identification of a novel gene cluster participating in menaquinone (vitamin K2) biosynthesis. Cloning and sequence determination of the 2-heptaprenyl-1,4-naphthoquinone methyltransferase gene of Bacillus stearothermophilus. Koike-Takeshita, A., Koyama, T., Ogura, K. J. Biol. Chem. (1997) [Pubmed]
  6. The genome sequence of the capnophilic rumen bacterium Mannheimia succiniciproducens. Hong, S.H., Kim, J.S., Lee, S.Y., In, Y.H., Choi, S.S., Rih, J.K., Kim, C.H., Jeong, H., Hur, C.G., Kim, J.J. Nat. Biotechnol. (2004) [Pubmed]
  7. The molecular phylogeny and systematics of the actinomycetes. Embley, T.M., Stackebrandt, E. Annu. Rev. Microbiol. (1994) [Pubmed]
  8. Roles of a conserved arginine residue of DsbB in linking protein disulfide-bond-formation pathway to the respiratory chain of Escherichia coli. Kadokura, H., Bader, M., Tian, H., Bardwell, J.C., Beckwith, J. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  9. Metabolism and energy generation in homoacetogenic clostridia. Hugenholtz, J., Ljungdahl, L.G. FEMS Microbiol. Rev. (1990) [Pubmed]
  10. Differences in protonation of ubiquinone and menaquinone in fumarate reductase from Escherichia coli. Maklashina, E., Hellwig, P., Rothery, R.A., Kotlyar, V., Sher, Y., Weiner, J.H., Cecchini, G. J. Biol. Chem. (2006) [Pubmed]
  11. Menatetrenone inhibits bone resorption partly through inhibition of PGE2 synthesis in vitro. Hara, K., Akiyama, Y., Tajima, T., Shiraki, M. J. Bone Miner. Res. (1993) [Pubmed]
  12. Biosynthesis of bacterial menaquinones: the membrane-associated 1,4-dihydroxy-2-naphthoate octaprenyltransferase of Escherichia coli. Shineberg, B., Young, I.G. Biochemistry (1976) [Pubmed]
  13. Menaquinone biosynthesis: mutants of Escherichia coli K-12 requiring 2-succinylbenzoate. Guest, J.R. J. Bacteriol. (1977) [Pubmed]
  14. Preventive effect of selenium, methionine and antioxidants against encephalomalacia of chicks induced by dilauryl succinate. Yoshida, M., Hoshi, H. J. Nutr. (1977) [Pubmed]
  15. Characterization of the COQ5 gene from Saccharomyces cerevisiae. Evidence for a C-methyltransferase in ubiquinone biosynthesis. Barkovich, R.J., Shtanko, A., Shepherd, J.A., Lee, P.T., Myles, D.C., Tzagoloff, A., Clarke, C.F. J. Biol. Chem. (1997) [Pubmed]
  16. Vitamin K2 (menatetrenone) effectively prevents fractures and sustains lumbar bone mineral density in osteoporosis. Shiraki, M., Shiraki, Y., Aoki, C., Miura, M. J. Bone Miner. Res. (2000) [Pubmed]
  17. Evolution of enzymatic activities in the enolase superfamily: N-succinylamino acid racemase and a new pathway for the irreversible conversion of D- to L-amino acids. Sakai, A., Xiang, D.F., Xu, C., Song, L., Yew, W.S., Raushel, F.M., Gerlt, J.A. Biochemistry (2006) [Pubmed]
  18. Apoptosis/differentiation-inducing effects of vitamin K2 on HL-60 cells: dichotomous nature of vitamin K2 in leukemia cells. Miyazawa, K., Yaguchi, M., Funato, K., Gotoh, A., Kawanishi, Y., Nishizawa, Y., Yuo, A., Ohyashiki, K. Leukemia (2001) [Pubmed]
  19. New lineage of filamentous, spore-forming, gram-positive bacteria from soil. Cavaletti, L., Monciardini, P., Bamonte, R., Schumann, P., Rohde, M., Sosio, M., Donadio, S. Appl. Environ. Microbiol. (2006) [Pubmed]
  20. Restoration of respiratory electron-transport reactions in quinone-depleted particle preparations from Anacystis nidulans. Peschek, G.A. Biochem. J. (1980) [Pubmed]
  21. Vanadium(V) reduction by Shewanella oneidensis MR-1 requires menaquinone and cytochromes from the cytoplasmic and outer membranes. Myers, J.M., Antholine, W.E., Myers, C.R. Appl. Environ. Microbiol. (2004) [Pubmed]
  22. Vitamin K(2) inhibits adipogenesis, osteoclastogenesis, and ODF/RANK ligand expression in murine bone marrow cell cultures. Takeuchi, Y., Suzawa, M., Fukumoto, S., Fujita, T. Bone (2000) [Pubmed]
  23. Anaerobic electron transport in anaerobic flagellum formation in Escherichia coli. Hertz, R., Bar-Tana, J. J. Bacteriol. (1977) [Pubmed]
  24. Role of menaquinone in inactivation and activation of the Bacillus cereus forespore respiratory system. Escamilla, J.E., Barquera, B., Ramírez, R., García-Horsman, A., del Arenal, P. J. Bacteriol. (1988) [Pubmed]
  25. Comparative efficacy of hormone replacement therapy, etidronate, calcitonin, alfacalcidol, and vitamin K in postmenopausal women with osteoporosis: The Yamaguchi Osteoporosis Prevention Study. Ishida, Y., Kawai, S. Am. J. Med. (2004) [Pubmed]
  26. ENDOR and special TRIPLE resonance spectroscopy of photoaccumulated semiquinone electron acceptors in the reaction centers of green sulfur bacteria and heliobacteria. Muhiuddin, I.P., Rigby, S.E., Evans, M.C., Amesz, J., Heathcote, P. Biochemistry (1999) [Pubmed]
  27. Role of the tetraheme cytochrome CymA in anaerobic electron transport in cells of Shewanella putrefaciens MR-1 with normal levels of menaquinone. Myers, J.M., Myers, C.R. J. Bacteriol. (2000) [Pubmed]
  28. Sequence and overexpression of the menD gene from Escherichia coli. Popp, J.L. J. Bacteriol. (1989) [Pubmed]
  29. A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of the Escherichia coli ubiE gene. Lee, P.T., Hsu, A.Y., Ha, H.T., Clarke, C.F. J. Bacteriol. (1997) [Pubmed]
  30. Identification of a novel family of putative methyltransferases that interact with human and Drosophila presenilins. Zhang, S.X., Guo, Y., Boulianne, G.L. Gene (2001) [Pubmed]
  31. A new isochorismate synthase specifically involved in menaquinone (vitamin K2) biosynthesis encoded by the menF gene. Daruwala, R., Kwon, O., Meganathan, R., Hudspeth, M.E. FEMS Microbiol. Lett. (1996) [Pubmed]
  32. The role of isochorismate hydroxymutase genes entC and menF in enterobactin and menaquinone biosynthesis in Escherichia coli. Dahm, C., Müller, R., Schulte, G., Schmidt, K., Leistner, E. Biochim. Biophys. Acta (1998) [Pubmed]
  33. Effect of vitamin K2 on three-dimensional trabecular microarchitecture in ovariectomized rats. Mawatari, T., Miura, H., Higaki, H., Moro-Oka, T., Kurata, K., Murakami, T., Iwamoto, Y. J. Bone Miner. Res. (2000) [Pubmed]
  34. Vitamin K and the prevention of fractures: systematic review and meta-analysis of randomized controlled trials. Cockayne, S., Adamson, J., Lanham-New, S., Shearer, M.J., Gilbody, S., Torgerson, D.J. Arch. Intern. Med. (2006) [Pubmed]
  35. Quantitative and qualitative measurements of K vitamins in human intestinal contents. Conly, J.M., Stein, K. Am. J. Gastroenterol. (1992) [Pubmed]
  36. Effects of vitamin K2 in hemodialysis patients with low serum parathyroid hormone levels. Nakashima, A., Yorioka, N., Doi, S., Masaki, T., Ito, T., Harada, S. Bone (2004) [Pubmed]
  37. Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection. Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., Ozawa, K. J. Chromatogr. (1989) [Pubmed]
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