menaquinone (BioDeep_00000858475)
Main id: BioDeep_00000017481
PANOMIX_OTCML-2023 BioNovoGene_Lab2019
代谢物信息卡片
Menatetrenone
化学式: C31H40O2 (444.302814)
中文名称: 维生素 K2, 维生素K2
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
InChI: InChI=1S/C31H40O2/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/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+
描述信息
M - Musculo-skeletal system > M05 - Drugs for treatment of bone diseases > M05B - Drugs affecting bone structure and mineralization
D006401 - Hematologic Agents > D003029 - Coagulants > D006490 - Hemostatics
Menaquinone-4 is a vitamin K, used as a hemostatic agent, and also a adjunctive therapy for the pain of osteoporosis.
同义名列表
5 个代谢物同义名
Menatetrenone; menaquinone; Vitamin K2(MK-4); Menaquinone K4; Menaquinone-4
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:78277
- KEGGdrug: D00100
- PubChem: 5282367
- DrugBank: DB12148
- ChEMBL: CHEMBL259223
- CAS: 11032-49-8
- CAS: 6041-00-5
- CAS: 863-61-6
- medchemexpress: HY-B2156
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-573
分类词条
相关代谢途径
Reactome(14)
- Metabolism
- Metabolism of vitamins and cofactors
- Metabolism of fat-soluble vitamins
- Metabolism of vitamin K
- Metabolism of proteins
- Post-translational protein modification
- Gamma carboxylation, hypusinylation, hydroxylation, and arylsulfatase activation
- Gamma-carboxylation, transport, and amino-terminal cleavage of proteins
- Gamma-carboxylation of protein precursors
- Disease
- Diseases of hemostasis
- Defects of Formation of Fibrin Clot (Clotting Cascade)
- Defective factor IX causes hemophilia B
- Defective gamma-carboxylation of F9
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products.
ACS pharmacology & translational science.
2023 May; 6(5):683-701. doi:
10.1021/acsptsci.2c00194. [PMID: 37200814] - Andreas Meinitzer, Dietmar Enko, Sieglinde Zelzer, Florian Prüller, Nerea Alonso, Eva Fritz-Petrin, Markus Herrmann. Development of a liquid chromatography mass spectrometry method for the determination of vitamin K1, menaquinone-4, menaquinone-7 and vitamin K1-2,3 epoxide in serum of individuals without vitamin K supplements.
Clinical chemistry and laboratory medicine.
2022 06; 60(7):1011-1019. doi:
10.1515/cclm-2022-0192. [PMID: 35427444] - Jessie L Ellis, Xueyan Fu, J Philip Karl, Christopher J Hernandez, Joel B Mason, Russell A DeBose-Boyd, Sarah L Booth. Multiple Dietary Vitamin K Forms Are Converted to Tissue Menaquinone-4 in Mice.
The Journal of nutrition.
2022 04; 152(4):981-993. doi:
10.1093/jn/nxab332. [PMID: 34550377] - Yuning Zhang, Yashpal S Chhonker, Veenu Bala, Alex Hagg, Linda G Snetselaar, Terry L Wahls, Daryl J Murry. Reversed phase UPLC/APCI-MS determination of Vitamin K1 and menaquinone-4 in human plasma: Application to a clinical study.
Journal of pharmaceutical and biomedical analysis.
2020 May; 183(?):113147. doi:
10.1016/j.jpba.2020.113147. [PMID: 32086127] - Dong-Jae Jun, Marc M Schumacher, Seonghwan Hwang, Lisa N Kinch, Nick V Grishin, Russell A DeBose-Boyd. Schnyder corneal dystrophy-associated UBIAD1 is defective in MK-4 synthesis and resists autophagy-mediated degradation.
Journal of lipid research.
2020 05; 61(5):746-757. doi:
10.1194/jlr.ra119000551. [PMID: 32188638] - Jirayu Tanprasertsuk, Guylaine Ferland, Mary Ann Johnson, Leonard W Poon, Tammy M Scott, Aron K Barbey, Kathryn Barger, Xiang-Dong Wang, Elizabeth J Johnson. Concentrations of Circulating Phylloquinone, but Not Cerebral Menaquinone-4, Are Positively Correlated with a Wide Range of Cognitive Measures: Exploratory Findings in Centenarians.
The Journal of nutrition.
2020 01; 150(1):82-90. doi:
10.1093/jn/nxz200. [PMID: 31504672] - Stephanie G Harshman, M Kyla Shea, Xueyan Fu, Michael A Grusak, Donald Smith, Stefania Lamon-Fava, Athan Kuliopulos, Andrew Greenberg, Sarah L Booth. Atorvastatin Decreases Renal Menaquinone-4 Formation in C57BL/6 Male Mice.
The Journal of nutrition.
2019 03; 149(3):416-421. doi:
10.1093/jn/nxy290. [PMID: 30753659] - She-Ji Weng, Zhong-Jie Xie, Zong-Yi Wu, De-Yi Yan, Jia-Hao Tang, Zi-Jian Shen, Hang Li, Bing-Li Bai, Viraj Boodhun, Xiang Da Eric Dong, Lei Yang. Effects of combined menaquinone-4 and PTH1-34 treatment on osetogenesis and angiogenesis in calvarial defect in osteopenic rats.
Endocrine.
2019 02; 63(2):376-384. doi:
10.1007/s12020-018-1761-7. [PMID: 30244350] - Hang Li, Qiang Zhou, Bing-Li Bai, She-Ji Weng, Zong-Yi Wu, Zhong-Jie Xie, Zhen-Hua Feng, Liang Cheng, Viraj Boodhun, Lei Yang. Effects of combined human parathyroid hormone (1-34) and menaquinone-4 treatment on the interface of hydroxyapatite-coated titanium implants in the femur of osteoporotic rats.
Journal of bone and mineral metabolism.
2018 Nov; 36(6):691-699. doi:
10.1007/s00774-017-0893-9. [PMID: 29280077] - Halima Sultana, Kimika Watanabe, Md Masud Rana, Rie Takashima, Ai Ohashi, Michio Komai, Hitoshi Shirakawa. Effects of Vitamin K₂ on the Expression of Genes Involved in Bile Acid Synthesis and Glucose Homeostasis in Mice with Humanized PXR.
Nutrients.
2018 Jul; 10(8):. doi:
10.3390/nu10080982. [PMID: 30060524] - Nicholas T Au, Tove Ryman, Allan E Rettie, Scarlett E Hopkins, Bert B Boyer, Jynene Black, Jacques Philip, Joseph Yracheta, Alison E Fohner, Morayma Reyes, Timothy A Thornton, Melissa A Austin, Kenneth E Thummel. Dietary Vitamin K and Association with Hepatic Vitamin K Status in a Yup'ik Study Population from Southwestern Alaska.
Molecular nutrition & food research.
2018 02; 62(3):. doi:
10.1002/mnfr.201700746. [PMID: 29094808] - Saiko Ikeda, Fumiaki Hanzawa, Saki Takahashi, Norie Suzuki, Kana Sano, Hiroaki Oda, Tomono Uchida. Tissue Distribution of Menaquinone-7 and the Effect of α-Tocopherol Intake on Menaquinone-7 Concentration in Rats.
Journal of nutritional science and vitaminology.
2018; 64(6):391-398. doi:
10.3177/jnsv.64.391. [PMID: 30606961] - Kristin M McCabe, Sarah L Booth, Xueyan Fu, Emilie Ward, Michael A Adams, Rachel M Holden. Vitamin K Metabolism in a Rat Model of Chronic Kidney Disease.
American journal of nephrology.
2017; 45(1):4-13. doi:
10.1159/000451068. [PMID: 27846632] - Marc M Schumacher, Dong-Jae Jun, Youngah Jo, Joachim Seemann, Russell A DeBose-Boyd. Geranylgeranyl-regulated transport of the prenyltransferase UBIAD1 between membranes of the ER and Golgi.
Journal of lipid research.
2016 07; 57(7):1286-99. doi:
10.1194/jlr.m068759. [PMID: 27121042] - Yuji Ikari, Sho Torii, Atsushi Shioi, Toshio Okano. Impact of menaquinone-4 supplementation on coronary artery calcification and arterial stiffness: an open label single arm study.
Nutrition journal.
2016 05; 15(1):53. doi:
10.1186/s12937-016-0175-8. [PMID: 27175730] - Kotaro Shikano, Kaichi Kaneko, Mai Kawazoe, Makoto Kaburaki, Tomoko Hasunuma, Shinichi Kawai. Efficacy of Vitamin K2 for Glucocorticoid-induced Osteoporosis in Patients with Systemic Autoimmune Diseases.
Internal medicine (Tokyo, Japan).
2016; 55(15):1997-2003. doi:
10.2169/internalmedicine.55.6230. [PMID: 27477405] - Sha Liu, Wang Guo, Xue Han, Wendi Dai, Zongli Diao, Wenhu Liu. Role of UBIAD1 in Intracellular Cholesterol Metabolism and Vascular Cell Calcification.
PloS one.
2016; 11(2):e0149639. doi:
10.1371/journal.pone.0149639. [PMID: 26890002] - Katarzyna Wyskida, Agnieszka Żak-Gołąb, Krzysztof Łabuzek, Dariusz Suchy, Rafał Ficek, Kornel Pośpiech, Magdalena Olszanecka-Glinianowicz, Bogusław Okopień, Andrzej Więcek, Jerzy Chudek. Daily intake and serum concentration of menaquinone-4 (MK-4) in haemodialysis patients with chronic kidney disease.
Clinical biochemistry.
2015 Dec; 48(18):1246-51. doi:
10.1016/j.clinbiochem.2015.08.011. [PMID: 26282719] - Keita Hirai, Yuto Yamada, Hideki Hayashi, Masaki Tanaka, Kohei Izumiya, Masayuki Suzuki, Misa Yoshizawa, Hideaki Moriwaki, Takehide Akimoto, Daiki Tsuji, Kazuyuki Inoue, Kunihiko Itoh. Plasma vitamin K concentrations depend on CYP4F2 polymorphism and influence on anticoagulation in Japanese patients with warfarin therapy.
Thrombosis research.
2015 May; 135(5):861-6. doi:
10.1016/j.thromres.2015.02.019. [PMID: 25747538] - Eriko Nakamura, Mami Aoki, Fumiko Watanabe, Ayako Kamimura. Low-dose menaquinone-4 improves γ-carboxylation of osteocalcin in young males: a non-placebo-controlled dose-response study.
Nutrition journal.
2014 Aug; 13(?):85. doi:
10.1186/1475-2891-13-85. [PMID: 25163392] - Sherry M Farley, Scott W Leonard, Jan F Stevens, Maret G Traber. Deuterium-labeled phylloquinone fed to α-tocopherol-injected rats demonstrates sensitivity of low phylloquinone-containing tissues to menaquinone-4 depletion.
Molecular nutrition & food research.
2014 Aug; 58(8):1610-9. doi:
10.1002/mnfr.201300659. [PMID: 25044667] - Fumiaki Hanzawa, Eri Sakuma, Saki Nomura, Tomono Uchida, Hiroaki Oda, Saiko Ikeda. Excess α-tocopherol decreases extrahepatic phylloquinone in phylloquinone-fed rats but not menaquinone-4 in menaquinone-4-fed rats.
Molecular nutrition & food research.
2014 Aug; 58(8):1601-9. doi:
10.1002/mnfr.201300710. [PMID: 24737747] - Jun Iwamoto. Vitamin K₂ therapy for postmenopausal osteoporosis.
Nutrients.
2014 May; 6(5):1971-80. doi:
10.3390/nu6051971. [PMID: 24841104] - Alessandra Gentili, Arturo Cafolla, Tecla Gasperi, Simona Bellante, Fulvia Caretti, Roberta Curini, Virginia Pérez Fernández. Rapid, high performance method for the determination of vitamin K(1), menaquinone-4 and vitamin K(1) 2,3-epoxide in human serum and plasma using liquid chromatography-hybrid quadrupole linear ion trap mass spectrometry.
Journal of chromatography. A.
2014 Apr; 1338(?):102-10. doi:
10.1016/j.chroma.2014.02.065. [PMID: 24630057] - Yan Jiang, Zhen-Lin Zhang, Zhong-Lan Zhang, Han-Min Zhu, Yi-Yong Wu, Qun Cheng, Feng-Li Wu, Xiao-Ping Xing, Jian-Li Liu, Wei Yu, Xun-Wu Meng. Menatetrenone versus alfacalcidol in the treatment of Chinese postmenopausal women with osteoporosis: a multicenter, randomized, double-blinded, double-dummy, positive drug-controlled clinical trial.
Clinical interventions in aging.
2014; 9(?):121-7. doi:
10.2147/cia.s54107. [PMID: 24426779] - Fumiaki Hanzawa, Saki Nomura, Eri Sakuma, Tomono Uchida, Saiko Ikeda. Dietary sesame seed and its lignan, sesamin, increase tocopherol and phylloquinone concentrations in male rats.
The Journal of nutrition.
2013 Jul; 143(7):1067-73. doi:
10.3945/jn.113.176636. [PMID: 23700348] - Kouji Suzuki, Shigeyoshi Tsuji, Yaeko Fukushima, Takanobu Nakase, Masayuki Hamada, Tetsuya Tomita, Hideki Yoshikawa. Clinical results of alendronate monotherapy and combined therapy with menatetrenone (VitK₂) in postmenopausal RA patients.
Modern rheumatology.
2013 May; 23(3):450-5. doi:
10.1007/s10165-012-0678-x. [PMID: 22692649] - Kristin M McCabe, Sarah L Booth, Xueyan Fu, Navid Shobeiri, Judith J Pang, Michael A Adams, Rachel M Holden. Dietary vitamin K and therapeutic warfarin alter the susceptibility to vascular calcification in experimental chronic kidney disease.
Kidney international.
2013 May; 83(5):835-44. doi:
10.1038/ki.2012.477. [PMID: 23344475] - Michael L Nickerson, Allen D Bosley, Jayne S Weiss, Brittany N Kostiha, Yoshihisa Hirota, Wolfgang Brandt, Dominic Esposito, Shigeru Kinoshita, Ludger Wessjohann, Scott G Morham, Thorkell Andresson, Howard S Kruth, Toshio Okano, Michael Dean. The UBIAD1 prenyltransferase links menaquinone-4 [corrected] synthesis to cholesterol metabolic enzymes.
Human mutation.
2013 Feb; 34(2):317-29. doi:
10.1002/humu.22230. [PMID: 23169578] - Hideki Hayashi. [Personalized drug therapy-directed clinical pharmacology research based on genetic polymorphisms and pharmacokinetics analysis].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2013; 133(10):1079-85. doi:
10.1248/yakushi.13-00178. [PMID: 24088351] - Toshiro Sato, Leon J Schurgers, Kazuhiro Uenishi. Comparison of menaquinone-4 and menaquinone-7 bioavailability in healthy women.
Nutrition journal.
2012 Nov; 11(?):93. doi:
10.1186/1475-2891-11-93. [PMID: 23140417] - Peter F Schnatz, Kimberly A Marakovits, David M O'Sullivan, Kelly Ethun, Thomas B Clarkson, Susan E Appt. Response to an adequate dietary intake of vitamin D3 modulates the effect of estrogen therapy on bone density.
Journal of women's health (2002).
2012 Aug; 21(8):858-64. doi:
10.1089/jwh.2011.3244. [PMID: 22691032] - Sherry M Farley, Scott W Leonard, Edwin M Labut, Hannah F Raines, David J Card, Dominic J Harrington, Debbie J Mustacich, Maret G Traber. Vitamin E decreases extra-hepatic menaquinone-4 concentrations in rats fed menadione or phylloquinone.
Molecular nutrition & food research.
2012 Jun; 56(6):912-22. doi:
10.1002/mnfr.201100751. [PMID: 22707266] - Ala Al Rajabi, Sarah L Booth, James W Peterson, Sang Woon Choi, John W Suttie, M Kyla Shea, Benchun Miao, Michael A Grusak, Xueyan Fu. Deuterium-labeled phylloquinone has tissue-specific conversion to menaquinone-4 among Fischer 344 male rats.
The Journal of nutrition.
2012 May; 142(5):841-5. doi:
10.3945/jn.111.155804. [PMID: 22437559] - Pornpimol Rianthavorn, Kantima Pisutikul, Tawatchai Deekajorndech, Supatporn Tepmongkol, Kanya Suphapeetiporn. Prevention of bone loss in children receiving long-term glucocorticoids with calcium and alfacalcidol or menatetrenone.
Journal of pediatric endocrinology & metabolism : JPEM.
2012; 25(3-4):307-12. doi:
10.1515/jpem-2011-0441. [PMID: 22768661] - Asagi Ito, Hitoshi Shirakawa, Naofumi Takumi, Yoshihiko Minegishi, Ai Ohashi, Zakir H Howlader, Yusuke Ohsaki, Toshiro Sato, Tomoko Goto, Michio Komai. Menaquinone-4 enhances testosterone production in rats and testis-derived tumor cells.
Lipids in health and disease.
2011 Sep; 10(?):158. doi:
10.1186/1476-511x-10-158. [PMID: 21914161] - Thawee Songpatanasilp, La-or Chailurkit, Suwannee Chantprasertyothin, Boonsong Ongphiphadhanakul, Nimit Taechakraichana. Effect of GGCX gene polymorphism on the responses of serum undercarboxylated osteocalcin and bone turnover markers after treatment with vitamin K2 (menatetrenone) among postmenopausal Thai women.
Journal of bone and mineral metabolism.
2011 Sep; 29(5):606-14. doi:
10.1007/s00774-011-0263-y. [PMID: 21344298] - I H Baek, W Kang, H Y Yun, S S Lee, K I Kwon. Modelling the atypical absorption of menatetrenone and the metabolism to its epoxide: effect of VKORC1 polymorphism.
Journal of clinical pharmacy and therapeutics.
2011 Jun; 36(3):390-8. doi:
10.1111/j.1365-2710.2010.01183.x. [PMID: 21545618] - Natsuko Sogabe, Rieko Maruyama, Otto Baba, Takayuki Hosoi, Masae Goseki-Sone. Effects of long-term vitamin K(1) (phylloquinone) or vitamin K(2) (menaquinone-4) supplementation on body composition and serum parameters in rats.
Bone.
2011 May; 48(5):1036-42. doi:
10.1016/j.bone.2011.01.020. [PMID: 21295170] - T Terachi, Y Inoue, N Ashihara, M Kobayashi, K Ando, T Matsui. Plasma vitamin K concentration in horses supplemented with several vitamin K homologs.
Journal of animal science.
2011 Apr; 89(4):1056-61. doi:
10.2527/jas.2009-2759. [PMID: 21169510] - Gilbert R Kaats, Harry G Preuss, Harry A Croft, Samuel C Keith, Patti L Keith. A comparative effectiveness study of bone density changes in women over 40 following three bone health plans containing variations of the same novel plant-sourced calcium.
International journal of medical sciences.
2011 Mar; 8(3):180-91. doi:
10.7150/ijms.8.180. [PMID: 21448303] - Mariko Ochiai, Ayumu Nakashima, Norihisa Takasugi, Kei Kiribayashi, Toru Kawai, Koji Usui, Kenichiro Shigemoto, Naoki Hamaguchi, Nobuoki Kohno, Noriaki Yorioka. Vitamin K₂ alters bone metabolism markers in hemodialysis patients with a low serum parathyroid hormone level.
Nephron. Clinical practice.
2011; 117(1):c15-9. doi:
10.1159/000319642. [PMID: 20689320] - Kimie Nakagawa, Yoshihisa Hirota, Natsumi Sawada, Naohito Yuge, Masato Watanabe, Yuri Uchino, Naoko Okuda, Yuka Shimomura, Yoshitomo Suhara, Toshio Okano. Identification of UBIAD1 as a novel human menaquinone-4 biosynthetic enzyme.
Nature.
2010 Nov; 468(7320):117-21. doi:
10.1038/nature09464. [PMID: 20953171] - Natalia A Crivello, Sherley L Casseus, James W Peterson, Donald E Smith, Sarah L Booth. Age- and brain region-specific effects of dietary vitamin K on myelin sulfatides.
The Journal of nutritional biochemistry.
2010 Nov; 21(11):1083-8. doi:
10.1016/j.jnutbio.2009.09.005. [PMID: 20092997] - Hitoshi Yoshiji, Ryuichi Noguchi, Masahisa Toyohara, Yasuhide Ikenaka, Mitsuteru Kitade, Kosuke Kaji, Masaharu Yamazaki, Junichi Yamao, Akira Mitoro, Masayoshi Sawai, Motoyuki Yoshida, Masao Fujimoto, Tatsuhiro Tsujimoto, Hideto Kawaratani, Masahito Uemura, Hiroshi Fukui. Combination of vitamin K2 and angiotensin-converting enzyme inhibitor ameliorates cumulative recurrence of hepatocellular carcinoma.
Journal of hepatology.
2009 Aug; 51(2):315-21. doi:
10.1016/j.jhep.2009.04.011. [PMID: 19501932] - Neil Binkley, Judith Harke, Diane Krueger, Jean Engelke, Nellie Vallarta-Ast, Dessa Gemar, Mary Checovich, Richard Chappell, John Suttie. Vitamin K treatment reduces undercarboxylated osteocalcin but does not alter bone turnover, density, or geometry in healthy postmenopausal North American women.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2009 Jun; 24(6):983-91. doi:
10.1359/jbmr.081254. [PMID: 19113922] - Kuniko Hara, Yasuhiro Akiyama. Collagen-related abnormalities, reduction in bone quality, and effects of menatetrenone in rats with a congenital ascorbic acid deficiency.
Journal of bone and mineral metabolism.
2009; 27(3):324-32. doi:
10.1007/s00774-009-0069-3. [PMID: 19333680] - Masataka Shiraki, Akira Itabashi. Short-term menatetrenone therapy increases gamma-carboxylation of osteocalcin with a moderate increase of bone turnover in postmenopausal osteoporosis: a randomized prospective study.
Journal of bone and mineral metabolism.
2009; 27(3):333-40. doi:
10.1007/s00774-008-0034-6. [PMID: 19172219] - Kumiko Ueda, Yuriko Kawaguchi, Seigo Iwakawa. Effect of oxyethylene numbers on the pharmacokinetics of menatetrenone incorporated in oil-in-water lipid emulsions prepared with polyoxyethylene-polyoxypropylene block copolymers and soybean oil in rats.
Biological & pharmaceutical bulletin.
2008 Dec; 31(12):2283-7. doi:
10.1248/bpb.31.2283. [PMID: 19043214] - Kumiko Ueda, Yukiko Asai, Yoshimizu Yoshimura, Seigo Iwakawa. Effect of oil-in-water lipid emulsions prepared with fish oil or soybean oil on the growth of MCF-7 cells and HepG2 cells.
The Journal of pharmacy and pharmacology.
2008 Aug; 60(8):1069-75. doi:
10.1211/jpp.60.8.0013. [PMID: 18644199] - Sarah L Booth, James W Peterson, Donald Smith, M Kyla Shea, John Chamberland, Natalia Crivello. Age and dietary form of vitamin K affect menaquinone-4 concentrations in male Fischer 344 rats.
The Journal of nutrition.
2008 Mar; 138(3):492-6. doi:
10.1093/jn/138.3.492. [PMID: 18287355] - Naoko Tsugawa, Masataka Shiraki, Yoshitomo Suhara, Maya Kamao, Reo Ozaki, Kiyoshi Tanaka, Toshio Okano. Low plasma phylloquinone concentration is associated with high incidence of vertebral fracture in Japanese women.
Journal of bone and mineral metabolism.
2008; 26(1):79-85. doi:
10.1007/s00774-007-0790-8. [PMID: 18095068] - Michio Komai, Hitoshi Shirakawa. [Vitamin K metabolism. Menaquinone-4 (MK-4) formation from ingested VK analogues and its potent relation to bone function].
Clinical calcium.
2007 Nov; 17(11):1663-72. doi:
clica071116631672. [PMID: 17982185] - Wonku Kang, Ji-Hoon Jeong, Eunsook Ma, Kwang-il Kwon. Simple and sensitive determination of menatetrenone and its epoxide metabolite in human plasma.
Journal of pharmaceutical and biomedical analysis.
2007 Sep; 44(5):1178-82. doi:
10.1016/j.jpba.2007.04.028. [PMID: 17561362] - Yoshikazu Sakakima, Akemi Hayakawa, Tetsuro Nagasaka, Akimasa Nakao. Prevention of hepatocarcinogenesis with phosphatidylcholine and menaquinone-4: in vitro and in vivo experiments.
Journal of hepatology.
2007 Jul; 47(1):83-92. doi:
10.1016/j.jhep.2007.01.030. [PMID: 17399847] - Sameh Ahmed, Naoya Kishikawa, Kenichiro Nakashima, Naotaka Kuroda. Determination of vitamin K homologues by high-performance liquid chromatography with on-line photoreactor and peroxyoxalate chemiluminescence detection.
Analytica chimica acta.
2007 May; 591(2):148-54. doi:
10.1016/j.aca.2007.03.061. [PMID: 17481401] - Naoyuki Hirata, Noriaki Kanaya, Hitoshi Shimizu, Masanori Watanabe, Akiyoshi Namiki. [Suspicious case of epidural hematoma due to coagulopathy caused by vitamin K deficiency associated with antibiotics].
Masui. The Japanese journal of anesthesiology.
2007 Feb; 56(2):181-5. doi:
NULL. [PMID: 17315736] - Yoshitomo Suhara, Aya Murakami, Kimie Nakagawa, Yukari Mizuguchi, Toshio Okano. Comparative uptake, metabolism, and utilization of menaquinone-4 and phylloquinone in human cultured cell lines.
Bioorganic & medicinal chemistry.
2006 Oct; 14(19):6601-7. doi:
10.1016/j.bmc.2006.06.004. [PMID: 16798001] - Naoko Tsugawa, Masataka Shiraki, Yoshitomo Suhara, Maya Kamao, Kiyoshi Tanaka, Toshio Okano. Vitamin K status of healthy Japanese women: age-related vitamin K requirement for gamma-carboxylation of osteocalcin.
The American journal of clinical nutrition.
2006 Feb; 83(2):380-6. doi:
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The British journal of nutrition.
2006 Feb; 95(2):260-6. doi:
10.1079/bjn20051630. [PMID: 16469140] - Maya Kamao, Yoshitomo Suhara, Naoko Tsugawa, Toshio Okano. Determination of plasma Vitamin K by high-performance liquid chromatography with fluorescence detection using Vitamin K analogs as internal standards.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2005 Feb; 816(1-2):41-8. doi:
10.1016/j.jchromb.2004.11.003. [PMID: 15664332] - Yoshiko Iwasaki-Ishizuka, Hideyuki Yamato, Hisashi Murayama, Ikuko Ezawa, Kiyoshi Kurokawa, Masafumi Fukagawa. Menatetrenone rescues bone loss by improving osteoblast dysfunction in rats immobilized by sciatic neurectomy.
Life sciences.
2005 Feb; 76(15):1721-34. doi:
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Analytical chemistry.
2005 Feb; 77(3):757-63. doi:
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Clinical calcium.
2004 Dec; 14(12):83-8. doi:
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Bone.
2004 Nov; 35(5):1136-43. doi:
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Biochemical and biophysical research communications.
2004 Jul; 319(3):974-9. doi:
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The Journal of pharmacy and pharmacology.
2004 Jul; 56(7):855-9. doi:
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Journal of controlled release : official journal of the Controlled Release Society.
2004 Feb; 95(1):93-100. doi:
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Journal of bone and mineral metabolism.
2004; 22(3):236-40. doi:
10.1007/s00774-003-0473-z. [PMID: 15108065] - Kenji Yamada, Kentaro Inui, Masahiro Iwamoto, Hiroaki Nakamura, Tadao Tsujio, Sadahiko Konishi, Yoichi Ito, Kunio Takaoka, Tatsuya Koike. High serum levels of menatetrenone in male patients with ossification of the posterior longitudinal ligament.
Spine.
2003 Aug; 28(16):1789-93. doi:
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Journal of drug targeting.
2003 May; 11(4):241-6. doi:
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Nutrition (Burbank, Los Angeles County, Calif.).
2003 May; 19(5):446-50. doi:
10.1016/s0899-9007(02)00962-0. [PMID: 12714099] - Toshiya Iketani, Nobuo Kiriike, Murray, B Stein, Kouji Nagao, Toshihiko Nagata, Naomitsu Minamikawa, Atsushi Shidao, Hidehiro Fukuhara. Effect of menatetrenone (vitamin K2) treatment on bone loss in patients with anorexia nervosa.
Psychiatry research.
2003 Mar; 117(3):259-69. doi:
10.1016/s0165-1781(03)00024-6. [PMID: 12686368] - Y Koshihara, K Hoshi, R Okawara, H Ishibashi, S Yamamoto. Vitamin K stimulates osteoblastogenesis and inhibits osteoclastogenesis in human bone marrow cell culture.
The Journal of endocrinology.
2003 Mar; 176(3):339-48. doi:
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Journal of drug targeting.
2003 Jan; 11(1):37-43. doi:
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Nihon yakurigaku zasshi. Folia pharmacologica Japonica.
2002 Dec; 120(6):379-89. doi:
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The Journal of international medical research.
2002 Nov; 30(6):566-75. doi:
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The Journal of pharmacy and pharmacology.
2002 Oct; 54(10):1357-63. doi:
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Metabolism: clinical and experimental.
2002 Oct; 51(10):1230-4. doi:
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Bone.
2002 Jul; 31(1):114-8. doi:
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Bone.
2002 Jun; 30(6):897-900. doi:
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The British journal of nutrition.
2002 Apr; 87(4):307-14. doi:
10.1079/bjnbjn2001519. [PMID: 12064340] - H H W Thijssen, M J Drittij, C Vermeer, E Schoffelen. Menaquinone-4 in breast milk is derived from dietary phylloquinone.
The British journal of nutrition.
2002 Mar; 87(3):219-26. doi:
10.1079/bjnbjn2001505. [PMID: 12064330] - Leon J Schurgers, Cees Vermeer. Differential lipoprotein transport pathways of K-vitamins in healthy subjects.
Biochimica et biophysica acta.
2002 Feb; 1570(1):27-32. doi:
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Japanese journal of pharmacology.
2002 Jan; 88(1):55-61. doi:
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Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA.
2001 Dec; 12(12):996-1000. doi:
10.1007/s001980170007. [PMID: 11846334] - K Kawana, M Takahashi, H Hoshino, K Kushida. Circulating levels of vitamin K1, menaquinone-4, and menaquinone-7 in healthy elderly Japanese women and patients with vertebral fractures and patients with hip fractures.
Endocrine research.
2001 Aug; 27(3):337-43. doi:
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Endocrine journal.
2001 Feb; 48(1):11-8. doi:
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International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
2001 Jan; 71(1):30-5. doi:
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Journal of drug targeting.
2001; 9(5):353-60. doi:
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Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2000 Mar; 15(3):515-21. doi:
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Calcified tissue international.
2000 Feb; 66(2):123-8. doi:
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Journal of bone and mineral metabolism.
2000; 18(2):71-6. doi:
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Nihon yakurigaku zasshi. Folia pharmacologica Japonica.
1999 Nov; 114(5):303-13. doi:
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Biochimica et biophysica acta.
1999 Jan; 1426(1):43-52. doi:
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International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
1999 Jan; 69(1):23-6. doi:
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1999; 17(1):23-9. doi:
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