A potential biotechnological process for the sustainable production of vitamin K₁

References

• Russell RM, Suter PM. Vitamin and trace mineral deficiency and excess. In: Kasper D, Fauci A, Hauser S, et al., editors. Harrison’s principles of internal medicine. 19th ed. New York, NY: McGraw-Hill Education; 2015.
   Google Scholar
• Zehnder JL. Drugs used in disorders of coagulation. Basic and clinical pharmacology. 13th ed. New York, NY: McGraw-Hill Education; 2015.
   Google Scholar
• Lissauer T, Clayden G, editors. Illustrated textbook of paediatrics. 4th ed. London, UK: Elsevier Health Sciences; 2011.
   Google Scholar
• Vermeer C. Vitamin K: the effect on health beyond coagulation – an overview. Food Nutr Res. 2012;56:5329.
   Web of Science ®Google Scholar
• Booth SL. Roles for vitamin K beyond coagulation. Annu Rev Nutr. 2009;29:89–110.
   PubMed Web of Science ®Google Scholar
• Ferland G. Vitamin K and the nervous system: an overview of its actions. J Adv Nutr. 2012;3:204–212.
   PubMed Web of Science ®Google Scholar
• Shiraki M, Tsugawa N, Okano T. Recent advances in vitamin K-dependent Gla-containing proteins and vitamin K nutrition. Osteoporos Sarcopenia. 2015;1:22–38.
   Google Scholar
• Willems BAG, Vermeer C, Reutelingsperger CPM, et al. The realm of vitamin K dependent proteins: shifting from coagulation toward calcification. Mol Nutr Food Res. 2014;58:1620–1635.
   PubMed Web of Science ®Google Scholar
• Feskanich D, Weber P, Willett WC, et al. Vitamin K intake and hip fractures in women: a prospective study. Am J Clin Nutr. 1999;69:74–79.
   PubMed Web of Science ®Google Scholar
• Booth SL, Tucker KL, Chen H, et al. Dietary vitamin K intakes are associated with hip fracture but not with bone mineral density in elderly men and women. Am J Clin Nutr. 2000;71:1201–1208.
   Google Scholar
• Yaegashi Y, Onoda T, Tanno K, et al. Association of hip fracture incidence and intake of calcium, magnesium, vitamin D, and vitamin K. Eur J Epidemiol. 2008;23:219–225.
   PubMed Web of Science ®Google Scholar
• Apalset EM, Gjesdal CG, Eide GE, et al. Intake of vitamin K1 and K2 and risk of hip fractures: the Hordaland health study. Bone. 2011;49:990–995.
   PubMed Web of Science ®Google Scholar
• Cheung AM, Tile L, Lee Y, et al. Vitamin K supplementation in postmenopausal women with osteopenia (ECKO Trial): a randomized controlled trial. PLOS Med. 2008;5:e196
   PubMed Web of Science ®Google Scholar
• Knapen MHJ, Drummen NE, Smit E, et al. Three-year low-dose menaquinone-7 supplementation helps decrease bone loss in healthy postmenopausal women. Osteoporos Int. 2013;24:2499–2507.
   PubMed Web of Science ®Google Scholar
• Chan R, Leung J, Woo J. No association between dietary vitamin K intake and fracture risk in Chinese community-dwelling older men and women: a prospective study. Calcif Tissue Int. 2012;90:396–403.
   PubMed Web of Science ®Google Scholar
• Rejnmark L, Vestergaard P, Charles P, et al. No effect of vitamin K1 intake on bone mineral density and fracture risk in perimenopausal women. Osteoporos Int. 2006;17:1122–1132.
   PubMed Web of Science ®Google Scholar
• Kasukawa Y, Miyakoshi N, Ebina T, et al. Effects of risedronate alone or combined with vitamin K2 on serum undercarboxylated osteocalcin and osteocalcin levels in postmenopausal osteoporosis. J Bone Miner Metab. 2014;32:290–297.
   PubMed Web of Science ®Google Scholar
• Palermo A, Tuccinardi D, D’Onofrio L, et al. Vitamin K and osteoporosis: myth or reality? Metab Clin Exp. 2017;70:57–71.
   PubMed Web of Science ®Google Scholar
• Hao G, Zhang B, Gu M, et al. Vitamin K intake and the risk of fractures. Medicine (Baltimore). 2017;96.
   Web of Science ®Google Scholar
• Cockayne S, Adamson J, Lanham-New S, et al. Vitamin K and the prevention of fractures: systematic review and meta-analysis of randomized controlled trials. Arch Intern Med. 2006;166:1256–1261.
   PubMed Web of Science ®Google Scholar
• Fang Y, Hu C, Tao X, et al. Effect of vitamin K on bone mineral density: a meta-analysis of randomized controlled trials. J Bone Miner Metab. 2012;30:60–68.
   PubMed Web of Science ®Google Scholar
• Shea MK, Holden RM. Vitamin K status and vascular calcification: evidence from observational and clinical studies. Adv Nutr Int Rev. 2012;3:158–165.
   PubMed Web of Science ®Google Scholar
• Harshman SG, Shea MK. The role of vitamin K in chronic aging diseases: inflammation, cardiovascular disease, and osteoarthritis. Curr Nutr Rep. 2016;5:90–98.
   PubMedGoogle Scholar
• Shea MK, Cushman M, Booth SL, et al. Associations between vitamin K status and haemostatic and inflammatory biomarkers in community-dwelling adults. The multi-ethnic study of atherosclerosis. Thromb Haemost. 2014;112:438–444.
   PubMed Web of Science ®Google Scholar
• Presse N, Belleville S, Gaudreau P, et al. Vitamin K status and cognitive function in healthy older adults. Neurobiol Aging. 2013;34:2777–2783.
   PubMed Web of Science ®Google Scholar
• Tamadon-Nejad S. Warfarin-induced vitamin K deficiency is associated with cognitive and behavioral perturbations, and alterations in brain sphingolipids in rats [M.S. thesis]. Montreal, Canada: University of Montreal; 2012.
   Google Scholar
• Annweiler C, Ferland G, Barberger-Gateau P, et al. Vitamin K antagonists and cognitive impairment: results from a cross-sectional pilot study among geriatric patients. J Gerontol Ser A. 2015;70:97–101.
   PubMed Web of Science ®Google Scholar
• Daines AM, Payne RJ, Humphries ME, et al. The synthesis of naturally occurring vitamin K and vitamin K analogues. Curr Org Chem. 2003;7:1625–1634.
   Web of Science ®Google Scholar
• Berenjian A, Mahanama R, Kavanagh J, et al. Vitamin K series: current status and future prospects. Crit Rev Biotechnol. 2015;35:199–208.
   PubMed Web of Science ®Google Scholar
• Schurgers LJ, Geleijnse JM, Grobbee DE, et al. Nutritional intake of vitamins K1 (phylloquinone) and K2 (menaquinone) in The Netherlands. J Nutr Environ Med. 1999;9:115–122.
   Google Scholar
• Kamao M, Suhara Y, Tsugawa N, et al. Vitamin K content of foods and dietary vitamin K intake in Japanese young women. J Nutr Sci Vitaminol.). 2007;53:464–470.
   PubMed Web of Science ®Google Scholar
• Van Arnum SD. Vitamin K. Kirk-Othmer Encyclopedia of Chemical Technology [Internet]. 4th ed. New York, NY: John Wiley & Sons, Inc.; 2000 [cited 2017 Jul 5]. Available from: http://onlinelibrary.wiley.com.ezproxy1.library.usyd.edu.au/doi/10.1002/0471238961.2209200101181421.a02/abstract.
   Google Scholar
• MacCorquodale DW, Binkley SB, Thayer SA, et al. On the constitution of vitamin K1. J Am Chem Soc. 1939;61:1928–1929.
   Google Scholar
• Fieser LF. Synthesis of vitamin K1. J Am Chem Soc. 1939;61:3467–3475.
   Google Scholar
• McKee RW, Binkley SB, Thayer SA, et al. The isolation of vitamin K2. J Biol Chem. 1939;131:327–344.
   Google Scholar
• Fieser LF, Campbell WP, Fry EM. Synthesis of quinones related to vitamins K1 and K2. J Am Chem Soc. 1939;61:2206–2218.
   Google Scholar
• Jacobsen BK, Dam H. Vitamin K in bacteria. Biochim Biophys Acta. 1960;40:211–216.
   PubMedGoogle Scholar
• Ansbacher S, Fernholz E. Simple compounds with vitamin K activity. J Am Chem Soc. 1939;61:1924–1925.
   Google Scholar
• Fieser LF, Bowen DM, Campbell WP, et al. Quinones having vitamin K activity. J Am Chem Soc. 1939;61:1925–1926.
   Google Scholar
• Almquist HJ, Klose AA. Synthetic and natural antihemorrhagic compounds. J Am Chem Soc. 1939;61:2557–2558.
   Google Scholar
• Macfie JM, Bacharach AL, Chance MRA. A vitamin K analogue in obstructive jaundice. Br Med J. 1939;2:1220.
   PubMedGoogle Scholar
• Anderson ER, Karabin JE, Udesky H, et al. Parenteral administration of a watersoluble compound with vitamin k activity: 4-amino-2-methyl-1-naphthol hydrochloride. Arch Surg. 1940;41:1244–1250.
   Google Scholar
• Combs GF Jr. The vitamins. 4th ed. Saint Louis: Elsevier Science; 2012.
   Google Scholar
• Sadowski JA, Esmon CT, Suttie JW. Vitamin K-dependent carboxylase. Requirements of the rat liver microsomal enzyme system. J Biol Chem. 1976;251:2770–2776.
   PubMed Web of Science ®Google Scholar
• Jones JP, Fausto A, Houser RM, et al. Effect of vitamin K homologues on the conversion of preprothrombin to prothrombin in rat liver microsomes. Biochem Biophys Res Commun. 1976;72:589–597.
   PubMed Web of Science ®Google Scholar
• Buitenhuis HC, Soute BAM, Vermeer C. Comparison of the vitamins K1, K2 and K3 as cofactors for the hepatic vitamin K-dependent carboxylase. Biochim Biophys Acta Gen Subj. 1990;1034:170–175.
   PubMedGoogle Scholar
• Mack DO, Wolfensberger M, Girardot JM, et al. The carboxylation activity of vitamin K analogs with substitutions at position 2, 3, or 5. J Biol Chem. 1979;254:2656–2664.
   PubMed Web of Science ®Google Scholar
• Monks TJ, Hanzlik RP, Cohen GM, et al. Quinone chemistry and toxicity. Toxicol Appl Pharmacol. 1992;112:2–16.
   PubMed Web of Science ®Google Scholar
• Menadione. Merck Index Online [Internet]. London, UK: Royal Society of Chemistry; 2013 [cited 2017 Aug 8]. Available from: https://www.rsc.org/Merck-Index/monograph/m7169/menadione%20derivative%20sodium%20bisulfite?q=authorize.
   Google Scholar
• Menaquinones. Merck Index Online [Internet]. London, UK: Royal Society of Chemistry; 2013 [cited 2017 Aug 8]. Available from: https://www.rsc.org/Merck-Index/monograph/m7171/menaquinones%20derivative%20menaquinone%20?q=authorize.
   Google Scholar
• Phylloquinone. Merck Index Online [Internet]. London, UK: Royal Society of Chemistry; 2013 [cited 2017 Aug 8]. Available from: https://www.rsc.org/Merck-Index/monograph/m8762/phylloquinone?q=authorize.
   Google Scholar
• Sommer P, Kofler M. Physicochemical properties and methods of analysis of phylloquinones, menaquinones, ubiquinones, plastoquinones, menadione, and related compounds. Vitam Horm. 1967;24:349–399.
   Google Scholar
• Pennock JF. Occurrence of vitamins K and related quinones. In: Robert S. Harris IGW, John A. Loraine, G.F. Marrian, and Kenneth V. Thimann, editors. Vitamins and hormones. Cambridge, MA: Academic Press; 1967; p. 307–329.
   Google Scholar
• Whatley FR, Allen MB, Arnon DI. Photosynthesis by isolated chloroplasts. VII. Vitamin K and riboflavin phosphate as cofactors of cyclic photophosphorylation. Biochim Biophys Acta. 1959;32:32–46.
   PubMedGoogle Scholar
• Ben-Shem A, Frolow F, Nelson N. Crystal structure of plant photosystem I. Nature. 2003;426:630–635.
   PubMed Web of Science ®Google Scholar
• Collins MD, Jones D. Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implication. Microbiol Rev. 1981;45:316.
   PubMedGoogle Scholar
• Nowicka B, Kruk J. Occurrence, biosynthesis and function of isoprenoid quinones. Biochim Biophys Acta. 2010;1797:1587–1605.
   PubMed Web of Science ®Google Scholar
• Ulrich EL, Girvin ME, Cramer WA, et al. Location and mobility of ubiquinones of different chain lengths in artificial membrane vesicles. Biochemistry (Mosc.). 1985;24:2501–2508.
   Google Scholar
• Roche Y, Peretti P, Bernard S. Influence of the chain length of ubiquinones on their interaction with DPPC in mixed monolayers. Biochim Biophys Acta Biomembr. 2006;1758:468–478.
   PubMed Web of Science ®Google Scholar
• Thor H, Smith MT, Hartzell P, et al. The metabolism of menadione (2-methyl-1,4-naphthoquinone) by isolated hepatocytes. A study of the implications of oxidative stress in intact cells. J Biol Chem. 1982;257:12419–12425.
   PubMed Web of Science ®Google Scholar
• Rossi L, Moore GA, Orrenius S, et al. Quinone toxicity in hepatocytes without oxidative stress. Arch Biochem Biophys. 1986;251:25–35.
   PubMed Web of Science ®Google Scholar
• O’Brien PJ. Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact. 1991;80:1–41.
   PubMed Web of Science ®Google Scholar
• Ross D, Thor H, Orrenius S, et al. Interaction of menadione (2-methyl-1,4-naphthoquinone) with glutathione. Chem Biol Interact. 1985;55:177–184.
   PubMed Web of Science ®Google Scholar
• Mirabelli F, Salis A, Perotti M, et al. Alterations of surface morphology caused by the metabolism of menadione in mammalian cells are associated with the oxidation of critical sulfhydryl groups in cytoskeletal proteins. Biochem Pharmacol. 1988;37:3423–3427.
   PubMed Web of Science ®Google Scholar
• Brown PC, Dulik DM, Jones TW. The toxicity of menadione (2-methyl-1,4-naphthoquinone) and two thioether conjugates studied with isolated renal epithelial cells. Arch Biochem Biophys. 1991;285:187–196.
   PubMed Web of Science ®Google Scholar
• Center for Food Safety and Applied Nutrition. Food Additives and Ingredients – Food Additive Status List [Internet]. Silver Spring, MD: US Federal Drug Administration; [cited 2017 Apr 8]. Available from: http://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm091048.htm#ftnM.
   Google Scholar
• USA Drug Agency Bans Menadione. New York Times [Internet]. 1963 Mar 30;8.
   Google Scholar
• Henrik Dam – Nobel Lecture: The discovery of vitamin K, its biological functions and therapeutical application [Internet]. Nobel Media AB; 2014 [cited 2018 May 15]. Available from: http://www.nobelprize.org/nobel_prizes/medicine/laureates/1943/dam-lecture.html.
   Google Scholar
• Esmon CT, Sadowski JA, Suttie JW. A new carboxylation reaction. The vitamin K-dependent incorporation of H-14-CO3- into prothrombin. J Biol Chem. 1975;250:4744–4748.
   PubMed Web of Science ®Google Scholar
• Friedman PA, Shia M. Some characteristics of a vitamin K-dependent carboxylating system from rat liver microsomes. Biochem Biophys Res Commun. 1976;70:647–654.
   PubMed Web of Science ®Google Scholar
• Nelsestuen GL, Suttie JW. Mode of action of vitamin K. Calcium binding properties of bovine prothrombin. Biochemistry (Mosc.). 1972;11:4961–4964.
   Google Scholar
• Hauschka PV, Lian JB, Gallop PM. Direct identification of the calcium-binding amino acid, gamma-carboxyglutamate, in mineralized tissue. Proc Natl Acad Sci. 1975;72:3925–3929.
   PubMed Web of Science ®Google Scholar
• Ratcliffe JV, Furie B, Furie BC. The importance of specific gamma-carboxyglutamic acid residues in prothrombin. Evaluation by site-specific mutagenesis. J Biol Chem. 1993;268:24339–24345.
   PubMed Web of Science ®Google Scholar
• Sakai T, Lund-Hansen T, Thim L, et al. The gamma-carboxyglutamic acid domain of human factor VIIa is essential for its interaction with cell surface tissue factor. J Biol Chem. 1990;265:1890–1894.
   PubMed Web of Science ®Google Scholar
• Nelsestuen GL, Broderius M, Martin G. Role of gamma-carboxyglutamic acid. Cation specificity of prothrombin and factor X-phospholipid binding. J Biol Chem. 1976;251:6886–6893.
   PubMed Web of Science ®Google Scholar
• Rawala-Sheikh R, Ahmad SS, Monroe DM, et al. Role of gamma-carboxyglutamic acid residues in the binding of factor IXa to platelets and in factor-X activation. Blood. 1992;79:398–405.
   PubMed Web of Science ®Google Scholar
• Zhang L, Jhingan A, Castellino FJ. Role of individual gamma-carboxyglutamic acid residues of activated human protein C in defining its in vitro anticoagulant activity. Blood. 1992;80:942–952.
   PubMed Web of Science ®Google Scholar
• Sugo T, Dahlbäck B, Holmgren A, et al. Calcium binding of bovine protein S. Effect of thrombin cleavage and removal of the gamma-carboxyglutamic acid-containing region. J Biol Chem. 1986;261:5116–5120.
   PubMed Web of Science ®Google Scholar
• Hauschka PV, Wians FH. Osteocalcin-hydroxyapatite interaction in the extracellular organic matrix of bone. Anat Rec. 1989;224:180–188.
   PubMedGoogle Scholar
• Schurgers LJ, Spronk HMH, Skepper JN, et al. Post-translational modifications regulate matrix Gla protein function: importance for inhibition of vascular smooth muscle cell calcification. J Thromb Haemost. 2007;5:2503–2511.
   PubMed Web of Science ®Google Scholar
• Nakano T, Kawamoto K, Kishino J, et al. Requirement of γ-carboxyglutamic acid residues for the biological activity of Gas6: contribution of endogenous Gas6 to the proliferation of vascular smooth muscle cells. Biochem J. 1997;323:387–392.
   PubMed Web of Science ®Google Scholar
• Hasanbasic I, Rajotte I, Blostein M. The role of γ-carboxylation in the anti-apoptotic function of gas6. J Thromb Haemost. 2005;3:2790–2797.
   PubMed Web of Science ®Google Scholar
• Nelsestuen GL, Shah AM, Harvey SB. Vitamin K-dependent proteins. Vitam Horm. 2000;58:355–389.
   PubMed Web of Science ®Google Scholar
• Shearer MJ. Vitamin K deficiency bleeding (VKDB) in early infancy. Blood Rev. 2009;23:49–59.
   PubMed Web of Science ®Google Scholar
• Sutor AH, von Kries R, Cornelissen EA, et al. Vitamin K deficiency bleeding (VKDB) in infancy. ISTH Pediatric/Perinatal Subcommittee. International Society on Thrombosis and Haemostasis. Thromb Haemost. 1999;81:456–461.
   PubMed Web of Science ®Google Scholar
• Vermeer C. Gamma-carboxyglutamate-containing proteins and the vitamin K-dependent carboxylase. Biochem J. 1990;266:625.
   PubMed Web of Science ®Google Scholar
• Ferland G. The vitamin K-dependent proteins: an update. Nutr Rev. 1998;56:223–230.
   PubMed Web of Science ®Google Scholar
• Petryszak R, Keays M, Tang YA, et al. Expression Atlas update—an integrated database of gene and protein expression in humans, animals and plants. Nucleic Acids Res. 2016;44:D746–D752.
   PubMed Web of Science ®Google Scholar
• Lev M, Milford AF. Vitamin K stimulation of sphingolipid synthesis. Biochem Biophys Res Commun. 1971;45:358–362.
   PubMed Web of Science ®Google Scholar
• Denisova NA, Booth SL. Vitamin K and sphingolipid metabolism: evidence to date. Nutr Rev. 2005;63:111–121.
   PubMed Web of Science ®Google Scholar
• Li J, Lin JC, Wang H, et al. Novel role of vitamin K in preventing oxidative injury to developing oligodendrocytes and neurons. J Neurosci. 2003;23:5816–5826.
   PubMed Web of Science ®Google Scholar
• Ichikawa T, Horie-Inoue K, Ikeda K, et al. Vitamin K2 induces phosphorylation of protein kinase A and expression of novel target genes in osteoblastic cells. J Mol Endocrinol. 2007;39:239–247.
   PubMed Web of Science ®Google Scholar
• Vos M, Esposito G, Edirisinghe JN, et al. Vitamin K2 is a mitochondrial electron carrier that rescues pink1 deficiency. Science. 2012;336:1306–1310.
   PubMed Web of Science ®Google Scholar
• Okano T, Shimomura Y, Yamane M, et al. Conversion of phylloquinone (vitamin K1) into menaquinone-4 (vitamin K2) in mice: two possible routes for menaquinone-4 accumulation in cerebra of mice. J Biol Chem. 2008;283:11270–11279.
   PubMed Web of Science ®Google Scholar
• Nakagawa K, Hirota Y, Sawada N, et al. Identification of UBIAD1 as a novel human menaquinone-4 biosynthetic enzyme. Nature. 2010;468:117–121.
   PubMed Web of Science ®Google Scholar
• Ramotar K, Conly JM, Chubb H, et al. Production of menaquinones by intestinal anaerobes. J Infect Dis. 1984;150:213–218.
   PubMed Web of Science ®Google Scholar
• Fernandez F, Collins MD. Vitamin K composition of anaerobic gut bacteria. FEMS Microbiol Lett. 1987;41:175–180.
   Web of Science ®Google Scholar
• Mathers JC, Fernandez F, Hill MJ, et al. Dietary modification of potential vitamin K supply from enteric bacterial menaquinones in rats. Br J Nutr. 1990;63:639–652.
   PubMed Web of Science ®Google Scholar
• Conly JM, Stein K, Worobetz L, et al. The contribution of vitamin K2 (menaquinones) produced by the intestinal microflora to human nutritional requirements for vitamin K. Am J Gastroenterol. 1994;89:915–923.
   PubMed Web of Science ®Google Scholar
• Ichihashi T, Takagishi Y, Uchida K, et al. Colonic absorption of menaquinone-4 and menaquinone-9 in rats. J Nutr. 1992;122:506–512.
   PubMed Web of Science ®Google Scholar
• Hollander D, Rim E, Pe R. Vitamin K2 colonic and ileal in vivo absorption: bile, fatty acids, and pH effects on transport. Am J Physiol Gastrointest Liver Physiol. 1977;233:G124–G129.
   Google Scholar
• Kindberg C, Suttie J, Uchida K, et al. Menaquinone production and utilization in germ-free rats after inoculation with specific organisms. J Nutr. 1987;117:1032–1035.
   PubMed Web of Science ®Google Scholar
• Conly J, Stein K. Reduction of vitamin K2 concentrations in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med. 1994;17:531–539.
   PubMed Web of Science ®Google Scholar
• Karl JP, Fu X, Wang X, et al. Changes in fecal vitamin K content are associated with the gut microbiota. FASEB J. 2015;29:262.1.
   Web of Science ®Google Scholar
• Suttie JW. The importance of menaquinones in human nutrition. Annu Rev Nutr. 1995;15:399–417.
   PubMed Web of Science ®Google Scholar
• Shearer MJ. Vitamin K in parenteral nutrition. Gastroenterology. 2009;137:S105–S118.
   PubMed Web of Science ®Google Scholar
• Dietary reference intakes for vitamin A, vitamin K, arsenic, boron, chromium, copper, iodine, iron, manganese, molybdenum, nickel, silicon, vanadium, and zinc. Washington, D.C.: National Academies Press; 2001.
   Google Scholar
• EFSA Panel on Dietetic Products N and A (NDA), Turck D, Bresson J-L, et al. Dietary reference values for vitamin K. EFSA J. 2017;15.
   Web of Science ®Google Scholar
• Schurgers LJ, Vermeer C. Determination of phylloquinone and menaquinones in food. Effect of food matrix on circulating vitamin K concentrations. Pathophysiol Haemostasis Thromb. 2001;30:298–307.
   Google Scholar
• Shearer MJ, Bach A, Kohlmeier M. Chemistry, nutritional sources, tissue distribution and metabolism of vitamin K with special reference to bone health. J Nutr. 1996;126:1181S.
   PubMed Web of Science ®Google Scholar
• Koivu TJ, Piironen VI, Henttonen SK, et al. Determination of phylloquinone in vegetables, fruits, and berries by high-performance liquid chromatography with electrochemical detection. J Agric Food Chem. 1997;45:4644–4649.
   Web of Science ®Google Scholar
• Booth SL, Sadowski JA, Pennington JAT. Phylloquinone (vitamin K1) content of foods in the U.S. food and drug administration’s total diet study. J Agric Food Chem. 1995;43:1574–1579.
   Web of Science ®Google Scholar
• Bolton-Smith C, Price RJG, Fenton ST, et al. Compilation of a provisional UK database for the phylloquinone (vitamin K1) content of foods. Br J Nutr. 2000;83:389–399.
   PubMed Web of Science ®Google Scholar
• Piironen V, Koivu T, Tammisalo O, et al. Determination of phylloquinone in oils, margarines and butter by high-performance liquid chromatography with electrochemical detection. Food Chem. 1997;59:473–480.
   Web of Science ®Google Scholar
• Ferland G, Sadowski JA. Vitamin K1 (phylloquinone) content of edible oils: effects of heating and light exposure. J Agric Food Chem. 1992;40:1869–1873.
   Web of Science ®Google Scholar
• Sumi H. Accumulation of vitamin K (menaquinone-7) in plasma after ingestion of natto and natto Bacilli (B. subtilis natto). Food Sci Technol Res. 1999;5:48–50.
   Google Scholar
• Hojo K, Watanabe R, Mori T, et al. Quantitative measurement of tetrahydromenaquinone-9 in cheese fermented by propionibacteria. J Dairy Sci. 2007;90:4078–4083.
   PubMed Web of Science ®Google Scholar
• Koivu-Tikkanen TJ, Ollilainen V, Piironen VI. Determination of phylloquinone and menaquinones in animal products with fluorescence detection after postcolumn reduction with metallic zinc. J Agric Food Chem. 2000;48:6325–6331.
   PubMed Web of Science ®Google Scholar
• Hirauchi K, Sakano T, Notsumoto S, et al. Measurement of K vitamins in animal tissues by high-performance liquid chromatography with fluorimetric detection. J Chromatogr B Biomed Sci App. 1989;497:131–137.
   Google Scholar
• Elder SJ, Haytowitz DB, Howe J, et al. Vitamin K contents of meat, dairy, and fast food in the U.S. diet. J Agric Food Chem. 2006;54:463–467.
   PubMed Web of Science ®Google Scholar
• Vitamins market – growth, share, opportunities & competitive analysis, 2015–2022 [Internet]. San Jose, CA: Credence Research; 2015 [cited 2017 Jul 28]. Report No.: 57709-12–15. Available from: http://www.credenceresearch.com/report/vitamins-market.
   Google Scholar
• Vitamin ingredients market: production volume to reach 63,512.4 tons by 2025, reports TMR [Internet]. New York, NY: PRNewswire; 2017 [cited 2017 Jul 28]. Available from: http://www.prnewswire.co.uk/news-releases/vitamin-ingredients-market-production-volume-to-reach-635124-tons-by-2025-reports-tmr-616611874.html.
   Google Scholar
• Three things that are influencing growth in the vitamin ingredients market [Internet]. London, UK: Technavio. 2015 [cited 2017 Jul 28]. Available from: https://www.technavio.com/blog/three-things-that-are-influencing-growth-in-the-vitamin-ingredients-market.
   Google Scholar
• IARC. Vitamin K substances. IARC Monogr Carcinog Risks Hum. 2000;76:521.
   Google Scholar
• Coman SM, Parvulescu VI, Wuttke S, et al. Synthesis of vitamin K1 and K1-chromanol by Friedel–Crafts alkylation in heterogeneous catalysis. ChemCatChem. 2010;2:92–97.
   Web of Science ®Google Scholar
• Doebel K, Isler O, inventors; Hoffman-La Roche Inc., assignee. Synthesis of vitamin K1 using boron trifluoride catalysts. United States patent US 2,683,176. 1954 July 6.
   Google Scholar
• Hirschmann R, Miller R, Wendler NL. The synthesis of vitamin K1. J Am Chem Soc. 1954;76:4592–4594.
   Web of Science ®Google Scholar
• Baker BR, Davies TH, McElroy L, et al. The antihemorrhagic activity of sulfonated derivatives of 2-methylnaphthalene. J Am Chem Soc. 1942;64:1096–1101.
   Google Scholar
• Bonrath W, Netscher T. Catalytic processes in vitamins synthesis and production. Appl Catal Gen. 2005;280:55–73.
   Web of Science ®Google Scholar
• Tien J-H, Pang C-Y, Hsu N-H, inventors; Sunny Pharmatec Inc., assignee. Method of making vitamin K1. United States patent application publication US2017/0260117 A1. 2017 Sep 14.
   Google Scholar
• MenaQ7 varieties [Internet]. Oslo, Norway: NattoPharma ASA; 2015 [cited 2017 Nov 6]. Available from: http://menaq7.com/why-menaq7/varieties/.
   Google Scholar
• Technology & Characteristics of Natto K2™ [Internet]. Shantou, Guangdong: Sungen Bioscience Co. Ltd.; 2016 [cited 2017 Nov 6]. Available from: http://www.sungenbio.com/?page=p560b871c859a7&lang=437&ContentID=15.
   Google Scholar
• Bentley R, Meganathan R. Biosynthesis of vitamin K (menaquinone) in bacteria. Microbiol Rev. 1982;46:241–280.
   PubMedGoogle Scholar
• Seeger JW, Bentley R. Phylloquinone (vitamin K1) biosynthesis in Euglena gracilis strain Z. Phytochemistry. 1991;30:3585–3589.
   Web of Science ®Google Scholar
• Verpoorte R, Heijden R, van der ten Hoopen HJG, et al. Metabolic engineering of plant secondary metabolite pathways for the production of fine chemicals. Biotechnol Lett. 1999;21:467–479.
   Web of Science ®Google Scholar
• Basic Report: 11445, Seaweed, kelp, raw [Internet]. Beltsville, MD: Agricultural Research Service, United States Department of Agriculture; 2017 [cited 2017 Mar 15]. Available from: https://ndb.nal.usda.gov/ndb/foods/show/3158?fgcd=&manu=&lfacet=&format=Abridged&count=&max=35&offset=&sort=&qlookup=seaweed.
   Google Scholar
• Roeck-Holtzhauer YD, Quere I, Claire C. Vitamin analysis of five planktonic microalgae and one macroalga. J Appl Phycol. 1991;3:259–264.
   Web of Science ®Google Scholar
• Demain AL, Adrio JL. Contributions of microorganisms to industrial biology. Mol Biotechnol. 2008;38:41
   PubMed Web of Science ®Google Scholar
• Tuck CO, Pérez E, Horváth IT, et al. Valorization of biomass: deriving more value from waste. Science. 2012;337:695–699.
   PubMed Web of Science ®Google Scholar
• Pfaltzgraff LA, De bruyn M, Cooper EC, et al. Food waste biomass: a resource for high-value chemicals. Green Chem. 2013;15:307.
   Web of Science ®Google Scholar
• Booth SL, Madabushi HT, Davidson KW, et al. Tea and coffee brews are not dietary sources of vitamin K-1 (phylloquinone). J Am Diet Assoc. 1995;95:82–83.
   PubMed Web of Science ®Google Scholar
• Kranert M, Gottschall R, Bruns C, et al. Energy or compost from green waste? – A CO(2) – based assessment. Waste Manag. 2010;30:697–701.
   PubMed Web of Science ®Google Scholar
• Inghels D, Dullaert W, Bloemhof J. A model for improving sustainable green waste recovery. Resour Conserv Recycl. 2016;110:61–73.
   Web of Science ®Google Scholar
• Biffin JR, Regtop HL, Talbot AM. Pasture content and availability of vitamin K in yearlings. Proc Aust Equine Sci Symp. 2008;2:54.
   Google Scholar
• Borowitzka MA. High-value products from microalgae—their development and commercialisation. J Appl Phycol. 2013;25:743–756.
   Web of Science ®Google Scholar
• Spolaore P, Joannis-Cassan C, Duran E, et al. Commercial applications of microalgae. J Biosci Bioeng. 2006;101:87–96.
   PubMed Web of Science ®Google Scholar
• Lee P, Schmidt-Dannert C. Metabolic engineering towards biotechnological production of carotenoids in microorganisms. Appl Microbiol Biotechnol. 2002;60:1–11.
   PubMed Web of Science ®Google Scholar
• Gimpel JA, Henríquez V, Mayfield SP. In metabolic engineering of eukaryotic microalgae: potential and challenges come with great diversity. Front Microbiol. 2015;6:1376.
   PubMed Web of Science ®Google Scholar
• Basset G, Latimer S, Fatihi A, et al. Phylloquinone (vitamin K1): occurrence, biosynthesis and functions. Mini Rev Med Chem. 2016;17(12):1028–1038.
   Web of Science ®Google Scholar
• Brettel K, Sétif P, Mathis P. Flash-induced absorption changes in photosystem I at low temperature: evidence that the electron acceptor A1 is vitamin K1. FEBS Lett. 1986;203:220–224.
   Web of Science ®Google Scholar
• Jordan P, Fromme P, Witt HT, et al. Three-dimensional structure of cyanobacterial photosystem I at 2.5 |[angst]| resolution. Nature. 2001;411:909–917.
   PubMed Web of Science ®Google Scholar
• Singh AK, Bhattacharyya-Pakrasi M, Pakrasi HB. Identification of an atypical membrane protein involved in the formation of protein disulfide bonds in oxygenic photosynthetic organisms. J Biol Chem. 2008;283:15762–15770.
   PubMed Web of Science ®Google Scholar
• Furt F, Oostende C, van Widhalm JR, et al. A bimodular oxidoreductase mediates the specific reduction of phylloquinone (vitamin K1) in chloroplasts. Plant J. 2010;64:38–46.
   PubMed Web of Science ®Google Scholar
• Chitnis PR. PHOTOSYSTEM I: Function and Physiology. Annu Rev Plant Physiol Plant Mol Biol. 2001;52:593–626.
   PubMed Web of Science ®Google Scholar
• Anderson JM, Chow WS, Park Y-I. The grand design of photosynthesis: acclimation of the photosynthetic apparatus to environmental cues. Photosynth Res. 1995;46:129–139.
   PubMed Web of Science ®Google Scholar
• Richmond A. Handbook of microalgal culture: biotechnology and applied phycology. Oxford, UK: Blackwell Science Ltd; 2004.
   Google Scholar
• González JA, Calbó J. Modelled and measured ratio of PAR to global radiation under cloudless skies. Agric For Meteorol. 2002;110:319–325.
   Web of Science ®Google Scholar
• Dubinsky Z, Stambler N. Photoacclimation processes in phytoplankton: mechanisms, consequences, and applications. Aquat Microb Ecol. 2009;56:163–176.
   Web of Science ®Google Scholar
• MacIntyre HL, Kana TM, Anning T, et al. Photoacclimation of photosynthesis irradiance response curves and photosynthetic pigments in microalgae and cyanobacteria1. J Phycol. 2002;38:17–38.
   Web of Science ®Google Scholar
• Goss R, Jakob T. Regulation and function of xanthophyll cycle-dependent photoprotection in algae. Photosyn Res. 2010;106:103–122.
   PubMed Web of Science ®Google Scholar
• Davison IR. Environmental effects on algal photosynthesis: temperature. J Phycol. 1991;27:2–8.
   Web of Science ®Google Scholar
• Claquin P, Probert I, Lefebvre S, et al. Effects of temperature on photosynthetic parameters and TEP production in eight species of marine microalgae. Aquat Microb Ecol. 2008;51:1–11.
   Web of Science ®Google Scholar
• Geider RJ, MacIntyre HL, Kana TM. Dynamic model of phytoplankton growth and acclimation: responses of the balanced growth rate and the chlorophyll a: carbon ratio to light, nutrient-limitation and temperature. Mar Ecol Prog Ser. 1997;148:187–200.
   Web of Science ®Google Scholar
• Lürling M, Eshetu F, Faassen EJ, et al. Comparison of cyanobacterial and green algal growth rates at different temperatures. Freshw Biol. 2013;58:552–559.
   Web of Science ®Google Scholar
• Butterwick C, Heaney SI, Talling JF. Diversity in the influence of temperature on the growth rates of freshwater algae, and its ecological relevance. Freshw Biol. 2005;50:291–300.
   Web of Science ®Google Scholar
• Hecky RE, Kilham P. Nutrient limitation of phytoplankton in freshwater and marine environments: a review of recent evidence on the effects of enrichment1. Limnol Oceanogr. 1988;33:796–822.
   Web of Science ®Google Scholar
• Geider RJ, Roche JL. The role of iron in phytoplankton photosynthesis, and the potential for iron-limitation of primary productivity in the sea. Photosynth Res. 1994;39:275–301.
   PubMed Web of Science ®Google Scholar
• Turpin DH. Effects of inorganic N availability on algal photosynthesis and carbon metabolism. J Phycol. 1991;27:14–20.
   Web of Science ®Google Scholar
• Auer MT, Kieser MS, Canale RP. Identification of critical nutrient levels through field verification of models for phosphorus and phytoplankton growth. Can J Fish Aquat Sci. 1986;43:379–388.
   Web of Science ®Google Scholar
• Elser JJ, Marzolf ER, Goldman CR. Phosphorus and nitrogen limitation of phytoplankton growth in the freshwaters of North America: a review and critique of experimental enrichments. Can J Fish Aquat Sci. 1990;47:1468–1477.
   Web of Science ®Google Scholar
• Elser JJ, Bracken MES, Cleland EE, et al. Global analysis of nitrogen and phosphorus limitation of primary producers in freshwater, marine and terrestrial ecosystems. Ecol Letters. 2007;10:1135–1142.
   PubMed Web of Science ®Google Scholar
• Berman-Frank I, Lundgren P, Falkowski P. Nitrogen fixation and photosynthetic oxygen evolution in cyanobacteria. Res Microbiol. 2003;154:157–164.
   PubMed Web of Science ®Google Scholar
• Roberts SC. Production and engineering of terpenoids in plant cell culture. Nat Chem Biol. 2007;3:387–395.
   PubMed Web of Science ®Google Scholar
• Gross J, Meurer J, Bhattacharya D. Evidence of a chimeric genome in the cyanobacterial ancestor of plastids. BMC Evol Biol. 2008;8:117
   PubMed Web of Science ®Google Scholar
• Rohmer M, Knani M, Simonin P, et al. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem J. 1993;295:517–524.
   PubMed Web of Science ®Google Scholar
• Disch A, Schwender J, Müller C, et al. Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC 6714. Biochem J. 1998;333:381–388.
   PubMed Web of Science ®Google Scholar
• Eisenreich W, Bacher A, Arigoni D, et al. Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci. 2004;61:1401–1426.
   PubMed Web of Science ®Google Scholar
• Beck G, Coman D, Herren E, et al. Characterization of the GGPP synthase gene family in Arabidopsis thaliana. Plant Mol Biol. 2013;82:393–416.
   PubMed Web of Science ®Google Scholar
• Keller Y, Bouvier F, d’Harlingue A, et al. Metabolic compartmentation of plastid prenyllipid biosynthesis. Eur J Biochem. 1998;251:413–417.
   PubMedGoogle Scholar
• Meganathan R. Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): A perspective on enzymatic mechanisms. In: Gerald Litwack, Tadhg Begley, editors. Cofactor Biosynth. Cambridge, MA: Academic Press; 2001. p. 173–218.
   Google Scholar
• Johnson TW, Shen G, Zybailov B, et al. 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. J Biol Chem. 2000;275:8523–8530.
   PubMed Web of Science ®Google Scholar
• Gross J, Cho WK, Lezhneva L, et al. A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes. J Biol Chem. 2006;281:17189–17196.
   PubMed Web of Science ®Google Scholar
• Jiang M, Cao Y, Guo Z-F, et al. Menaquinone biosynthesis in Escherichia coli: Identification of 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate as a novel intermediate and re-evaluation of MenD activity. Biochemistry (Mosc.). 2007;46:10979–10989.
   Google Scholar
• Jiang M, Chen X, Guo Z-F, et al. Identification and characterization of (1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase in the menaquinone biosynthesis of Escherichia coli. Biochemistry (Mosc.). 2008;47:3426–3434.
   Google Scholar
• Widhalm JR, Oostende C, van Furt F, et al. A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K1. Proc Natl Acad Sci USA. 2009;106:5599–5603.
   PubMed Web of Science ®Google Scholar
• Fatihi A, Latimer S, Schmollinger S, et al. A dedicated type II NADPH dehydrogenase performs the penultimate step in the biosynthesis of vitamin K1 in synechocystis and arabidopsis. Plant Cell. 2015;27:1730–1741.
   PubMed Web of Science ®Google Scholar
• Lohmann A, Schöttler MA, Bréhélin C, et al. Deficiency in phylloquinone (vitamin K1) methylation affects prenyl quinone distribution, photosystem I abundance, and anthocyanin accumulation in the arabidopsis AtmenG mutant. J Biol Chem. 2006;281:40461–40472.
   PubMed Web of Science ®Google Scholar
• Cluis CP, Burja AM, Martin VJJ. Current prospects for the production of coenzyme Q10 in microbes. Trends Biotechnol. 2007;25:514–521.
   PubMed Web of Science ®Google Scholar
• Kim JK, Kim EJ, Jung HY. Vitamin Q10: property, production and application. In: Vandamme EJ, Revuelta JL, editors. Industrial Biotechnology Vitamin, Biopigments, and Antioxidants. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2016. p. 321–365.
   Google Scholar
• Kong MK, Lee PC. Metabolic engineering of menaquinone-8 pathway of Escherichia coli as a microbial platform for vitamin K production. Biotechnol Bioeng. 2011;108:1997–2002.
   PubMed Web of Science ®Google Scholar
• Oliver NJ, Rabinovitch-Deere CA, Carroll AL, et al. Cyanobacterial metabolic engineering for biofuel and chemical production. Curr Opin Chem Biol. 2016;35:43–50.
   PubMed Web of Science ®Google Scholar
• Gomaa MA, Al-Haj L, Abed RM. Metabolic engineering of cyanobacteria and microalgae for enhanced production of biofuels and high-value products. J Appl Microbiol. 2016;121:919–931.
   PubMed Web of Science ®Google Scholar
• Berla BM, Saha R, Immethun CM, et al. Synthetic biology of cyanobacteria: unique challenges and opportunities. Front Microbiol. 2013;4:246.
   PubMed Web of Science ®Google Scholar
• Qin S, Lin H, Jiang P. Advances in genetic engineering of marine algae. Biotechnol Adv 2012;30:1602–1613.
   PubMed Web of Science ®Google Scholar
• León-Bañares R, González-Ballester D, Galván A, et al. Transgenic microalgae as green cell-factories. Trends Biotechnol. 2004;22:45–52.
   PubMed Web of Science ®Google Scholar
• Ni J, Tao F, Wang Y, et al. A photoautotrophic platform for the sustainable production of valuable plant natural products from CO 2. Green Chem. 2016;18:3537–3548.
   Web of Science ®Google Scholar
• Wang Y, Tao F, Ni J, et al. Production of C3 platform chemicals from CO 2 by genetically engineered cyanobacteria. Green Chem. 2015;17:3100–3110.
   Web of Science ®Google Scholar
• Agbor VB, Cicek N, Sparling R, et al. Biomass pretreatment: fundamentals toward application. Biotechnol Adv. 2011;29:675s–685.
   PubMed Web of Science ®Google Scholar
• Günerken E, D’Hondt E, Eppink MHM, et al. Cell disruption for microalgae biorefineries. Biotechnol Adv. 2015;33:243–260.
   PubMed Web of Science ®Google Scholar
• Gutzeit D, Baleanu G, Winterhalter P, et al. Determination of processing effects and of storage stability on vitamin K1 (phylloquinone) in sea buckthorn berries (Hippophaë rhamnoides L. ssp. rhamnoides) and related products. J Food Science. 2007;72:C491–C497.
   PubMed Web of Science ®Google Scholar
• Kurihara K, Takagi Y, inventors; Nisshin Oil Mills Ltd, assignee. Concentration and Purification of Vitamin K1. Japanese patent JPS61249947 (A). 1986 Nov 7.
   Google Scholar
• Kurihara K, Takagi Y, inventors; Nisshin Oil Mills Ltd, assignee. Production of Vitamin K1 Concentrate. Japanese patent JPS62265245 (A). 1987 Nov 18.
   Google Scholar
• Isobe Y, et al., inventors; Honen Corp, assignee. Production of Natural Vitamin K Condensate. Japanese patent JPH05155803 (A). 1993 June 22.
   Google Scholar
• Anastas PT, Warner JC. Green chemistry: theory and practice. Oxford: Oxford University Press; 1998.
   Google Scholar
• Chemat F, Vian MA, Cravotto G. Green extraction of natural products: concept and principles. Int J Mol Sci. 2012;13:8615–8627.
   PubMed Web of Science ®Google Scholar
• Ibañez E, Herrero M, Mendiola JA, et al. Extraction and characterization of bioactive compounds with health benefits from marine resources: macro and micro algae, cyanobacteria, and invertebrates. In: Hayes M, editor. Marine Bioactive Compounds. Boston, MA: Springer US; 2012. p. 55–98.
   Google Scholar
• Kerton FM, Liu Y, Omari KW, et al. Green chemistry and the ocean-based biorefinery. Green Chem. 2013;15:860–871.
   Web of Science ®Google Scholar
• Pennock JF. The biosynthesis of chloroplastidic terpenoid quinones and chromanols. Biochm Soc Trans. 1983;11:504–510.
   PubMed Web of Science ®Google Scholar
• Casani R. Vitamin E-Kirk-Othmer encyclopedia of chemical technology. John Wiley & Sons, Inc.; 2000.
   Google Scholar
• Bruni R, Guerrini A, Scalia S, et al. Rapid techniques for the extraction of vitamin E isomers from Amaranthus caudatus seeds: ultrasonic and supercritical fluid extraction. Phytochem Anal. 2002;13:257–261.
   PubMed Web of Science ®Google Scholar
• Ge Y, Ni Y, Yan H, et al. Optimization of the supercritical fluid extraction of natural vitamin E from wheat germ using response surface methodology. J Food Science. 2002;67:239–243.
   Web of Science ®Google Scholar
• Mendes MF, Pessoa FLP, Uller AMC. An economic evaluation based on an experimental study of the vitamin E concentration present in deodorizer distillate of soybean oil using supercritical CO2. J Supercrit Fluids. 2002;23:257–265.
   Web of Science ®Google Scholar
• Mendiola JA, García-Martínez D, Rupérez FJ, et al. Enrichment of vitamin E from Spirulina platensis microalga by SFE. J Supercrit Fluids. 2008;43:484–489.
   Web of Science ®Google Scholar