Menadione (BioDeep_00000002279)

 

Secondary id: BioDeep_00000268087

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene

化学式: C11H8O2 (172.0524268)
中文名称: 甲萘醌, 维生素K3
谱图信息: 最多检出来源 Homo sapiens(blood) 0.09%

分子结构信息

SMILES: CC1=CC(=O)C2=CC=CC=C2C1=O
InChI: InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

描述信息

Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. -- Pubchem; Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin. -- Wikipedia.
B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BA - Vitamin k
D006401 - Hematologic Agents > D003029 - Coagulants > D006490 - Hemostatics
D050299 - Fibrin Modulating Agents > D000933 - Antifibrinolytic Agents
D018977 - Micronutrients > D014815 - Vitamins
Prothrombogenic vitamin (synthetic)
Menadione is a naphthoquinone that is converted into active vitamin K2 in the body.
Menadione is a naphthoquinone that is converted into active vitamin K2 in the body.

同义名列表

62 个代谢物同义名

Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene; 2-methyl-1,4-dihydronaphthalene-1,4-dione; Menadione sodium bisulfite, trihydrate; 2-Methyl-1,4-naphthalenedione; 2-Methyl-1,4-naphthalendione; Vitamin K3 sodium bisulfite; 2-Methyl-1,4-naphthoquinone; Sodium bisulfite, menadione; Bisulfite, menadione sodium; 3-Methyl-1,4-naphthoquinone; Menadione sodiuM bisulfite; 2-Methyl-1,4-naphthochinon; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naftochinon; 2-Methylnaphthoquinone; Bisulfite, menadione; Menadione bisulfite; Kipca-oil soluble; Menaquinone O; Thyloquinone; Menaphthone; Vitamin K 3; Menaphthene; menaquinone; Menaphtone; Kayquinone; Vitamin K3; vitamin K2; Menaphthon; K-Thrombyl; Vitamin K0; menadione; Prokayvit; Kaergona; Kappaxin; Klottone; Panosine; Aquinone; Mitenone; Kappaxan; Menadion; Kolklot; Mitenon; K-Vitan; Vikasol; Kaynone; Kativ-g; Hemodal; Aquakay; Vicasol; Kayklot; Kareon; Karcon; Juva-K; Synkay; Kanone; Kaykot; Koaxin; Kipca; MNQ; Menadione; Menadione



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(1)

PlantCyc(0)

代谢反应

51 个相关的代谢反应过程信息。

Reactome(48)

BioCyc(2)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

40 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

  • Natália Gonçalves Silva, Marco Preto, Vitor Vasconcelos, Ralph Urbatzka. Reduction of neutral lipid reservoirs, bioconversion and untargeted metabolomics reveal distinct roles for vitamin K isoforms on lipid metabolism. Food & function. 2024 Feb; 15(4):2170-2180. doi: 10.1039/d3fo02915h. [PMID: 38312068]
  • Antonio Catalano, Khalil Mitri, Paola Perugini, Giorgia Condrò, Caroline Sands. In vitro and in vivo efficacy of a cosmetic product formulated with new lipid particles for the treatment of aged skin. Journal of cosmetic dermatology. 2023 Dec; 22(12):3329-3339. doi: 10.1111/jocd.16016. [PMID: 37803998]
  • Barbara Anne Fraser, Alexandra Louise Wilkins, Geoffry Nunzio De Iuliis, Diane Rebourcet, Brett Nixon, Robert John Aitken. Development of a model for studying the developmental consequences of oxidative sperm DNA damage by targeting redox-cycling naphthoquinones to the Sertoli cell population. Free radical biology & medicine. 2023 Jun; 206(?):50-62. doi: 10.1016/j.freeradbiomed.2023.06.008. [PMID: 37356777]
  • Youjun Zhang, Silvia Martínez Jaime, Mustafa Bulut, Alexander Graf, Alisdair R Fernie. The conditional mitochondrial protein complexome in Arabidopsis thaliana root and shoot. Plant communications. 2023 Jun; ?(?):100635. doi: 10.1016/j.xplc.2023.100635. [PMID: 37291828]
  • Xingli Huo, Huijun Liu, Shengjie Wang, Shanmei Yin, Zongning Yin. The inhibitory effect and mechanism of small molecules on acetic anhydride-induced BSA acetylation and aggregation. Colloids and surfaces. B, Biointerfaces. 2023 Mar; 225(?):113265. doi: 10.1016/j.colsurfb.2023.113265. [PMID: 36931043]
  • Jenny Beebe, Sophia Josephraj, Chao J Wang, Jacob Danielson, Qingbin Cui, Caoqinglong Huang, Lincoln Barlow, Ryan H Zhang, Taolan Zhang, Harikrishna Nakshatri, Zizheng Dong, Xiaohong Li, Jing-Yuan Liu, Jian-Ting Zhang. Therapeutic Activity of the Lansoprazole Metabolite 5-Hydroxy Lansoprazole Sulfide in Triple-Negative Breast Cancer by Inhibiting the Enoyl Reductase of Fatty Acid Synthase. Journal of medicinal chemistry. 2022 10; 65(20):13681-13691. doi: 10.1021/acs.jmedchem.2c00642. [PMID: 36257066]
  • Xun Yu, Cui Meng, Xiaocheng Tan, Yuwei Su, Zhiping Cao, Tzann-Shun Hwang, Lin Li. RsmA3 modulates RpoS through the RetS-Gac-Rsm signalling pathway in response to H2 O2 stress in the phytopathogen Pseudomonas syringae. Environmental microbiology. 2022 10; 24(10):4755-4770. doi: 10.1111/1462-2920.16132. [PMID: 35837862]
  • Ana Maria Murta Santi, Juliana Martins Ribeiro, João Luís Reis-Cunha, Gabriela de Assis Burle-Caldas, Isabella Fernandes Martins Santos, Paula Alves Silva, Daniela de Melo Resende, Daniella Castanheira Bartholomeu, Santuza Maria Ribeiro Teixeira, Silvane Maria Fonseca Murta. Disruption of multiple copies of the Prostaglandin F2alpha synthase gene affects oxidative stress response and infectivity in Trypanosoma cruzi. PLoS neglected tropical diseases. 2022 10; 16(10):e0010845. doi: 10.1371/journal.pntd.0010845. [PMID: 36260546]
  • Tianmeng Dai, Xin Zhang, Ming Li, Xinyue Tao, Min Jin, Peng Sun, Qicun Zhou, Lefei Jiao. Dietary vitamin K3 activates mitophagy, improves antioxidant capacity, immunity and affects glucose metabolism in Litopenaeus vannamei. Food & function. 2022 Jun; 13(11):6362-6372. doi: 10.1039/d2fo00865c. [PMID: 35612417]
  • Francisco J García-Machado, Ana L García-García, Andrés A Borges, David Jiménez-Arias. Root treatment with a vitamin K3 derivative: a promising alternative to synthetic fungicides against Botrytis cinerea in tomato plants. Pest management science. 2022 Mar; 78(3):974-981. doi: 10.1002/ps.6707. [PMID: 34738317]
  • Tomoko Kuroiwa, Yoshihisa Ohtani, Yoshiaki Obara, Fuminori Terada, Kimika Watanabe, Hitoshi Shirakawa, Michio Komai, Hiroshi Satoh, Shigeru Sato, Toshihiro Ichijo. Effect of vitamin K3 supplementation on immunoglobulin G concentration in colostrum of periparturient Holstein dairy cows. Animal science journal = Nihon chikusan Gakkaiho. 2022 Jan; 93(1):e13706. doi: 10.1111/asj.13706. [PMID: 35266246]
  • Hanako Bai, Hikoji Arai, Kentarou Ikuta, Sho Ishikawa, Yoshihisa Ohtani, Kunihiro Iwashita, Nao Okada, Hitoshi Shirakawa, Michio Komai, Fuminori Terada, Yoshiaki Obara. Effects of dietary vitamin K3 supplementation on vitamin K1 and K2 (menaquinone) dynamics in dairy cows. Animal science journal = Nihon chikusan Gakkaiho. 2022 Jan; 93(1):e13680. doi: 10.1111/asj.13680. [PMID: 35029011]
  • Petar D Petrov, Polina Soluyanova, Sonia Sánchez-Campos, José V Castell, Ramiro Jover. Molecular mechanisms of hepatotoxic cholestasis by clavulanic acid: Role of NRF2 and FXR pathways. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Dec; 158(?):112664. doi: 10.1016/j.fct.2021.112664. [PMID: 34767876]
  • Yong He, Fei Xu, Zina Ibrahim, Qinati Feyissa, Jennifer L Reed, Jaroslav G Vostal. Viral reduction of human blood by ultraviolet A-photosensitized vitamin K5. Journal of medical virology. 2021 08; 93(8):5134-5140. doi: 10.1002/jmv.27008. [PMID: 33837954]
  • Ruyu Wang, Qing Hu, Haonan Wang, Guanghao Zhu, Mengge Wang, Qian Zhang, Yishu Zhao, Chunyu Li, Yani Zhang, Guangbo Ge, Hongzhuan Chen, Lili Chen. Identification of Vitamin K3 and its analogues as covalent inhibitors of SARS-CoV-2 3CLpro. International journal of biological macromolecules. 2021 Jul; 183(?):182-192. doi: 10.1016/j.ijbiomac.2021.04.129. [PMID: 33901557]
  • Melania Iara Funk, Melisa Ailén Conde, Graciela Piwien-Pilipuk, Romina María Uranga. Novel antiadipogenic effect of menadione in 3T3-L1 cells. Chemico-biological interactions. 2021 Jul; 343(?):109491. doi: 10.1016/j.cbi.2021.109491. [PMID: 33945810]
  • Sajjad Hassan Askari, Muhammad Arslan Ashraf, Shafaqat Ali, Muhammad Rizwan, Rizwan Rasheed. Menadione sodium bisulfite alleviated chromium effects on wheat by regulating oxidative defense, chromium speciation, and ion homeostasis. Environmental science and pollution research international. 2021 Jul; 28(27):36205-36225. doi: 10.1007/s11356-021-13221-0. [PMID: 33751380]
  • Theng Choon Ooi, Farah Wahida Ibrahim, Shakirah Ahmad, Kok Meng Chan, Lek Mun Leong, Nihayah Mohammad, Ee Ling Siew, Nor Fadilah Rajab. Antimutagenic, Cytoprotective and Antioxidant Properties of Ficus deltoidea Aqueous Extract In Vitro. Molecules (Basel, Switzerland). 2021 May; 26(11):. doi: 10.3390/molecules26113287. [PMID: 34072474]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tanja Jankovic-Karasoulos, Dale McAninch, Clare Dixon, Shalem Y-L Leemaqz, Maxime François, Wayne R Leifert, Dylan McCullough, Carmela Ricciardelli, Claire T Roberts, Tina Bianco-Miotto. The effect of zinc on human trophoblast proliferation and oxidative stress. The Journal of nutritional biochemistry. 2021 04; 90(?):108574. doi: 10.1016/j.jnutbio.2020.108574. [PMID: 33388345]
  • Qinati Feyissa, Fei Xu, Zina Ibrahim, Ying Li, Kevin L Xu, Zihan Guo, Justen Ahmad, Jaroslav G Vostal. Synergistic bactericidal effects of pairs of photosensitizer molecules activated by ultraviolet A light against bacteria in plasma. Transfusion. 2021 02; 61(2):594-602. doi: 10.1111/trf.16180. [PMID: 33219568]
  • Ewelina Bik, Lukasz Mateuszuk, Marta Stojak, Stefan Chlopicki, Malgorzata Baranska, Katarzyna Majzner. Menadione-induced endothelial inflammation detected by Raman spectroscopy. Biochimica et biophysica acta. Molecular cell research. 2021 02; 1868(2):118911. doi: 10.1016/j.bbamcr.2020.118911. [PMID: 33227312]
  • Muhammad Arslan Ashraf, Rizwan Rasheed, Sadia Zafar, Muhammad Iqbal, Zulfiqar Ahmad Saqib. Menadione sodium bisulfite neutralizes chromium phytotoxic effects in okra by regulating cytosolutes, lipid peroxidation, antioxidant system and metal uptake. International journal of phytoremediation. 2021; 23(7):736-746. doi: 10.1080/15226514.2020.1854171. [PMID: 33321045]
  • Jessie L Ellis, J Philip Karl, Angela M Oliverio, Xueyan Fu, Jason W Soares, Benjamin E Wolfe, Christopher J Hernandez, Joel B Mason, Sarah L Booth. Dietary vitamin K is remodeled by gut microbiota and influences community composition. Gut microbes. 2021 Jan; 13(1):1-16. doi: 10.1080/19490976.2021.1887721. [PMID: 33651646]
  • O B Ibitoye, T O Ajiboye. Protocatechuic acid protects against menadione-induced liver damage by up-regulating nuclear erythroid-related factor 2. Drug and chemical toxicology. 2020 Nov; 43(6):567-573. doi: 10.1080/01480545.2018.1523187. [PMID: 30585516]
  • Wencheng Xu, Hongguang Wu, Shuhe Chen, Xiaoqin Wang, Sachiko Tanaka, Kentaro Sugiyama, Haruki Yamada, Toshihiko Hirano. Cytotoxic effects of vitamins K1, K2, and K3 against human T lymphoblastoid leukemia cells through apoptosis induction and cell cycle arrest. Chemical biology & drug design. 2020 10; 96(4):1134-1147. doi: 10.1111/cbdd.13696. [PMID: 32305047]
  • Jae Yun Moon, Da Jeong Kim, Hye Sun Kim. Sulforaphane ameliorates serum starvation-induced muscle atrophy via activation of the Nrf2 pathway in cultured C2C12 cells. Cell biology international. 2020 Sep; 44(9):1831-1839. doi: 10.1002/cbin.11377. [PMID: 32401383]
  • Karzan J Salih, Owen Duncan, Lei Li, Brendan O'Leary, Ricarda Fenske, Josua Trösch, A Harvey Millar. Impact of oxidative stress on the function, abundance, and turnover of the Arabidopsis 80S cytosolic ribosome. The Plant journal : for cell and molecular biology. 2020 07; 103(1):128-139. doi: 10.1111/tpj.14713. [PMID: 32027433]
  • Xiaoyang Li, Richard A Himes, Lyndsey C Prosser, Charleston F Christie, Emma Watt, Sharon F Edwards, Cameron S Metcalf, Peter J West, Karen S Wilcox, Sherine S L Chan, C James Chou. Discovery of the First Vitamin K Analogue as a Potential Treatment of Pharmacoresistant Seizures. Journal of medicinal chemistry. 2020 06; 63(11):5865-5878. doi: 10.1021/acs.jmedchem.0c00168. [PMID: 32390424]
  • Fei Xu, Qinati Feyissa, Zina Ibrahim, Ying Li, Kevin L Xu, Zihan Guo, Justen Ahmad, Jaroslav G Vostal. Inactivation of bacteria in plasma by photosensitizers benzophenone and vitamins K3, B1 and B6 with UV A light irradiation. Photodiagnosis and photodynamic therapy. 2020 Jun; 30(?):101713. doi: 10.1016/j.pdpdt.2020.101713. [PMID: 32165334]
  • Mohamed-Elamir F Hegazy, Masashi Fukaya, Mona Dawood, Ge Yan, Anette Klinger, Edmond Fleischer, Asmaa W Zaglool, Thomas Efferth. Vitamin K3 thio-derivative: a novel specific apoptotic inducer in the doxorubicin-sensitive and -resistant cancer cells. Investigational new drugs. 2020 06; 38(3):650-661. doi: 10.1007/s10637-019-00810-7. [PMID: 31254176]
  • Ting-Hang Liu, Mohammad A Yaghmour, Miin-Huey Lee, Thomas M Gradziel, Johan H J Leveau, Richard M Bostock. An roGFP2-Based Bacterial Bioreporter for Redox Sensing of Plant Surfaces. Phytopathology. 2020 Feb; 110(2):297-308. doi: 10.1094/phyto-07-19-0237-r. [PMID: 31483224]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Albert Godoy-Hernandez, Daniel J Tate, Duncan G G McMillan. Revealing the Membrane-Bound Catalytic Oxidation of NADH by the Drug Target Type-II NADH Dehydrogenase. Biochemistry. 2019 10; 58(42):4272-4275. doi: 10.1021/acs.biochem.9b00752. [PMID: 31592658]
  • Firoz Anwar, Ruqaiyah Khan, Richa Sachan, Imran Kazmi, Alisha Rawat, Abdullah Sabih, Rajbala Singh, Muhammad Afzal, Aftab Ahmad, Abdulaziz S Al-Orab, F A Al-Abbasi, Prakash Chandra Bhatt, Vikas Kumar. Therapeutic role of calcium and vitamin K3 in chemically induced hepatocarcinogenesis - new tools for cancer treatment. Archives of physiology and biochemistry. 2019 Jul; 125(3):270-275. doi: 10.1080/13813455.2018.1455708. [PMID: 29663832]
  • Yang Yu, Jiao Du, Yabo Wang, Mengyao Zhang, Zhiqiang Huang, Junsong Cai, Anfei Fang, Yuheng Yang, Ling Qing, Chaowei Bi, Jiasen Cheng. Survival factor 1 contributes to the oxidative stress response and is required for full virulence of Sclerotinia sclerotiorum. Molecular plant pathology. 2019 07; 20(7):895-906. doi: 10.1111/mpp.12801. [PMID: 31074170]
  • Daiva Majiene, Jolita Kuseliauskyte, Arturas Stimbirys, Aiste Jekabsone. Comparison of the Effect of Native 1,4-Naphthoquinones Plumbagin, Menadione, and Lawsone on Viability, Redox Status, and Mitochondrial Functions of C6 Glioblastoma Cells. Nutrients. 2019 Jun; 11(6):. doi: 10.3390/nu11061294. [PMID: 31181639]
  • Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chemico-biological interactions. 2019 May; 305(?):12-20. doi: 10.1016/j.cbi.2019.03.026. [PMID: 30926317]
  • Basheer A Balogun, Najeeb O Aliyu, Taofeek O Ajiboye. Menadione perturbs oxidative stress biomarkers and testicular function indices of rats. Journal of biochemical and molecular toxicology. 2019 May; 33(5):e22282. doi: 10.1002/jbt.22282. [PMID: 30536483]
  • Xiaoyuan Ren, Sebastin M Santhosh, Lucia Coppo, Fernando T Ogata, Jun Lu, Arne Holmgren. The combination of ascorbate and menadione causes cancer cell death by oxidative stress and replicative stress. Free radical biology & medicine. 2019 04; 134(?):350-358. doi: 10.1016/j.freeradbiomed.2019.01.037. [PMID: 30703479]
  • Richtier Gonçalves da Cruz, Laurent Beney, Patrick Gervais, Simone Possedente de Lira, Thais Maria Ferreira de Souza Vieira, Sebastien Dupont. Comparison of the antioxidant property of acerola extracts with synthetic antioxidants using an in vivo method with yeasts. Food chemistry. 2019 Mar; 277(?):698-705. doi: 10.1016/j.foodchem.2018.10.099. [PMID: 30502205]
  • Amiti, Ramasamy Tamizhselvi, Venkatraman Manickam. Menadione (vitamin K3) inhibits hydrogen sulfide and substance P via NF-кB pathway in caerulein-induced acute pancreatitis and associated lung injury in mice. Pancreatology : official journal of the International Association of Pancreatology (IAP) ... [et al.]. 2019 Mar; 19(2):266-273. doi: 10.1016/j.pan.2019.01.012. [PMID: 30685119]
  • S Zhang, M Jain, L A Fleites, P A Rayside, D W Gabriel. Identification and Characterization of Menadione and Benzethonium Chloride as Potential Treatments of Pierce's Disease of Grapevines. Phytopathology. 2019 Feb; 109(2):233-239. doi: 10.1094/phyto-07-18-0244-fi. [PMID: 30407880]
  • Thomas Nietzel, Marlene Elsässer, Cristina Ruberti, Janina Steinbeck, José Manuel Ugalde, Philippe Fuchs, Stephan Wagner, Lara Ostermann, Anna Moseler, Philipp Lemke, Mark D Fricker, Stefanie J Müller-Schüssele, Bruno M Moerschbacher, Alex Costa, Andreas J Meyer, Markus Schwarzländer. The fluorescent protein sensor roGFP2-Orp1 monitors in vivo H2 O2 and thiol redox integration and elucidates intracellular H2 O2 dynamics during elicitor-induced oxidative burst in Arabidopsis. The New phytologist. 2019 02; 221(3):1649-1664. doi: 10.1111/nph.15550. [PMID: 30347449]
  • Jessie L Ellis, Xueyan Fu, Ala Al Rajabi, Michael A Grusak, Martin J Shearer, Elena N Naumova, Edward Saltzman, Kathryn Barger, Sarah L Booth. Plasma Response to Deuterium-Labeled Vitamin K Intake Varies by TG Response, but Not Age or Vitamin K Status, in Older and Younger Adults. The Journal of nutrition. 2019 01; 149(1):18-25. doi: 10.1093/jn/nxy216. [PMID: 30590596]
  • Maryam Hosseini Ghalehno, Mohammad Mirzaei, Masoud Torkzadeh-Mahani. Double strand DNA-based determination of menadione using a Fe3O4 nanoparticle decorated reduced graphene oxide modified carbon paste electrode. Bioelectrochemistry (Amsterdam, Netherlands). 2018 Dec; 124(?):165-171. doi: 10.1016/j.bioelechem.2018.07.014. [PMID: 30064048]
  • Xiaoqing Cui, Hong Zhao, Zengxi Li. Hexagonal cobalt oxyhydroxide nanoflakes/reduced graphene oxide for hydrogen peroxide detection in biological samples. Analytical and bioanalytical chemistry. 2018 Nov; 410(28):7523-7535. doi: 10.1007/s00216-018-1370-6. [PMID: 30306238]
  • Rizwan Rasheed, Muhammad Arslan Ashraf, Sehrish Kamran, Muhammad Iqbal, Iqbal Hussain. Menadione sodium bisulphite mediated growth, secondary metabolism, nutrient uptake and oxidative defense in okra (Abelmoschus esculentus Moench) under cadmium stress. Journal of hazardous materials. 2018 10; 360(?):604-614. doi: 10.1016/j.jhazmat.2018.08.043. [PMID: 30149347]
  • Bettina Ebert, Dieter Ebert, Katrin Koebsch, Edmund Maser, Michael Kisiela. Carbonyl reductases from Daphnia are regulated by redox cycling compounds. The FEBS journal. 2018 08; 285(15):2869-2887. doi: 10.1111/febs.14578. [PMID: 29893480]
  • Ana V Sánchez-Sánchez, Aránzazu Leal-Tassias, Neus Rodríguez-Sánchez, Marina Piquer-Gil, Patricia Martorell, Salvador Genovés, Carlos Acosta, Deborah Burks, Daniel Ramón, José L Mullor. Use of Medaka Fish as Vertebrate Model to Study the Effect of Cocoa Polyphenols in the Resistance to Oxidative Stress and Life Span Extension. Rejuvenation research. 2018 Aug; 21(4):323-332. doi: 10.1089/rej.2017.1982. [PMID: 28982278]
  • Liwen Feng, Don Antoine Lanfranchi, Leandro Cotos, Elena Cesar-Rodo, Katharina Ehrhardt, Alice-Anne Goetz, Herbert Zimmermann, François Fenaille, Stephanie A Blandin, Elisabeth Davioud-Charvet. Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation. Organic & biomolecular chemistry. 2018 04; 16(15):2647-2665. doi: 10.1039/c8ob00227d. [PMID: 29542786]
  • Donika Ivanova, Zhivko Zhelev, Dessislava Lazarova, Plamen Getsov, Rumiana Bakalova, Ichio Aoki. Vitamins C and K3: A Powerful Redox System for Sensitizing Leukemia Lymphocytes to Everolimus and Barasertib. Anticancer research. 2018 03; 38(3):1407-1414. doi: 10.21873/anticanres.12364. [PMID: 29491065]
  • Kishore Reddy Katikireddy, Tomas L White, Taiga Miyajima, Shivakumar Vasanth, Duna Raoof, Yuming Chen, Marianne O Price, Francis W Price, Ula V Jurkunas. NQO1 downregulation potentiates menadione-induced endothelial-mesenchymal transition during rosette formation in Fuchs endothelial corneal dystrophy. Free radical biology & medicine. 2018 02; 116(?):19-30. doi: 10.1016/j.freeradbiomed.2017.12.036. [PMID: 29294389]
  • Jixian Huang, Ziyuan Lu, Yajuan Xiao, Bolin He, Chengyun Pan, Xuan Zhou, Na Xu, Xiaoli Liu. Inhibition of Siah2 Ubiquitin Ligase by Vitamin K3 Attenuates Chronic Myeloid Leukemia Chemo-Resistance in Hypoxic Microenvironment. Medical science monitor : international medical journal of experimental and clinical research. 2018 Feb; 24(?):727-735. doi: 10.12659/msm.908553. [PMID: 29400343]
  • P Martín Muñoz, L Anel-López, J M Ortiz-Rodríguez, M Álvarez, P de Paz, C Balao da Silva, H Rodríguez Martinez, M C Gil, L Anel, F J Peña, C Ortega Ferrusola. Redox cycling induces spermptosis and necrosis in stallion spermatozoa while the hydroxyl radical (OH•) only induces spermptosis. Reproduction in domestic animals = Zuchthygiene. 2018 Feb; 53(1):54-67. doi: 10.1111/rda.13052. [PMID: 28833663]
  • Fei Xu, Ying Li, Justen Ahmad, Yonggang Wang, Dorothy E Scott, Jaroslav G Vostal. Vitamin K5 is an efficient photosensitizer for ultraviolet A light inactivation of bacteria. FEMS microbiology letters. 2018 02; 365(4):. doi: 10.1093/femsle/fny005. [PMID: 29346538]
  • 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]
  • Letícia Batista Azevedo Rangel, Daniel de Siqueira, Olívia do Rosário Soares, Higor Scardini Santana, Emílio de Castro Miguel, Maura da Cunha, Andre Lacerda de Abreu Oliveira, Diego França Pedrosa, Ludmilla Carvalho Rangel Resgala, Helder Azevedo Rangel Neto, Neuza Felix Gomes-Rochette, Sérgio Ragi Eis, Jones Bernardes Graceli, Ian Victor Silva. Vitamin K Supplementation Modulates Bone Metabolism and Ultra-Structure of Ovariectomized Mice. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 51(1):356-374. doi: 10.1159/000495234. [PMID: 30453296]
  • Luciana Bohl, Solange Guizzardi, Valeria Rodríguez, Lucila Hinrichsen, Viviana Rozados, David Cremonezzi, Nori Tolosa de Talamoni, Gabriela Picotto. Combined calcitriol and menadione reduces experimental murine triple negative breast tumor. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Oct; 94(?):21-26. doi: 10.1016/j.biopha.2017.07.058. [PMID: 28750356]
  • Luciana Moine, Gabriela Díaz de Barboza, Adriana Pérez, Mercedes Benedetto, Nori Tolosa de Talamoni. Glutamine protects intestinal calcium absorption against oxidative stress and apoptosis. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2017 10; 212(?):64-71. doi: 10.1016/j.cbpa.2017.07.006. [PMID: 28732794]
  • Teng-Fei Yuan, Shao-Ting Wang, Yan Li. Quantification of menadione from plasma and urine by a novel cysteamine-derivatization based UPLC-MS/MS method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1063(?):107-111. doi: 10.1016/j.jchromb.2017.08.026. [PMID: 28858751]
  • Maya Kamao, Yoshihisa Hirota, Yoshitomo Suhara, Naoko Tsugawa, Kimie Nakagawa, Toshio Okano, Hiroshi Hasegawa. Determination of Menadione by Liquid Chromatography-Tandem Mass Spectrometry Using Pseudo Multiple Reaction Monitoring. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2017; 33(7):863-867. doi: 10.2116/analsci.33.863. [PMID: 28690267]
  • Murugesan Suganthi, Kuppanagounder P Elango. Synthesis, characterization and serum albumin binding studies of vitamin K3 derivatives. Journal of photochemistry and photobiology. B, Biology. 2017 Jan; 166(?):126-135. doi: 10.1016/j.jphotobiol.2016.11.016. [PMID: 27898366]
  • Nicholas O Thomas, Kate P Shay, Amanda R Kelley, Judy A Butler, Tory M Hagen. Glutathione maintenance mitigates age-related susceptibility to redox cycling agents. Redox biology. 2016 12; 10(?):45-52. doi: 10.1016/j.redox.2016.09.010. [PMID: 27687220]
  • Mantas Šilkūnas, Rita Saulė, Danutė Batiuškaitė, Gintautas Saulis. The Electroporation as a Tool for Studying the Role of Plasma Membrane in the Mechanism of Cytotoxicity of Bisphosphonates and Menadione. The Journal of membrane biology. 2016 10; 249(5):611-621. doi: 10.1007/s00232-016-9895-0. [PMID: 27044359]
  • Estefanía Carrillo-Perdomo, David Jiménez-Arias, Ángel Aller, Andrés A Borges. Menadione Sodium Bisulphite (MSB) enhances the resistance response of tomato, leading to repel mollusc pests. Pest management science. 2016 May; 72(5):950-60. doi: 10.1002/ps.4074. [PMID: 26155989]
  • Maryam Siah, Mohammad Hosein Farzaei, Mohammad Reza Ashrafi-Kooshk, Hadi Adibi, Seyed Shahriar Arab, Mohammad Reza Rashidi, Reza Khodarahmi. Inhibition of guinea pig aldehyde oxidase activity by different flavonoid compounds: An in vitro study. Bioorganic chemistry. 2016 Feb; 64(?):74-84. doi: 10.1016/j.bioorg.2015.12.004. [PMID: 26722818]
  • Ana Crespo-Sempere, Cristina Selma-Lázaro, Jeffrey D Palumbo, Luis González-Candelas, Pedro V Martínez-Culebras. Effect of oxidant stressors and phenolic antioxidants on the ochratoxigenic fungus Aspergillus carbonarius. Journal of the science of food and agriculture. 2016 Jan; 96(1):169-77. doi: 10.1002/jsfa.7077. [PMID: 25644738]
  • Yulia A Sidorova, Maria L Perepechaeva, Elena N Pivovarova, Arkady L Markel, Vyacheslav V Lyakhovich, Alevtina Y Grishanova. Menadione Suppresses Benzo(α)pyrene-Induced Activation of Cytochromes P450 1A: Insights into a Possible Molecular Mechanism. PloS one. 2016; 11(5):e0155135. doi: 10.1371/journal.pone.0155135. [PMID: 27167070]
  • Kavindra Kumar Kesari, Jukka Luukkonen, Jukka Juutilainen, Jonne Naarala. Genomic instability induced by 50Hz magnetic fields is a dynamically evolving process not blocked by antioxidant treatment. Mutation research. Genetic toxicology and environmental mutagenesis. 2015 Dec; 794(?):46-51. doi: 10.1016/j.mrgentox.2015.10.004. [PMID: 26653983]
  • Marco Zaccaria, Matteo Ludovici, Simona Marianna Sanzani, Antonio Ippolito, Riccardo Aiese Cigliano, Walter Sanseverino, Marzia Scarpari, Valeria Scala, Corrado Fanelli, Massimo Reverberi. Menadione-Induced Oxidative Stress Re-Shapes the Oxylipin Profile of Aspergillus flavus and Its Lifestyle. Toxins. 2015 Oct; 7(10):4315-29. doi: 10.3390/toxins7104315. [PMID: 26512693]
  • Yi-Tsung Lin, Yi-Wei Huang, Shiang-Jiuun Chen, Chia-Wei Chang, Tsuey-Ching Yang. The SmeYZ efflux pump of Stenotrophomonas maltophilia contributes to drug resistance, virulence-related characteristics, and virulence in mice. Antimicrobial agents and chemotherapy. 2015 Jul; 59(7):4067-73. doi: 10.1128/aac.00372-15. [PMID: 25918140]
  • Chitra Bhatia, Stephanie Oerum, James Bray, Kathryn L Kavanagh, Naeem Shafqat, Wyatt Yue, Udo Oppermann. Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships. Chemico-biological interactions. 2015 Jun; 234(?):114-25. doi: 10.1016/j.cbi.2014.12.013. [PMID: 25526675]
  • Oriane Mith, Asma Benhamdi, Teddy Castillo, Muriel Bergé, Colin W MacDiarmid, Janet Steffen, David J Eide, Véronique Perrier, Maeva Subileau, Françoise Gosti, Pierre Berthomieu, Laurence Marquès. The antifungal plant defensin AhPDF1.1b is a beneficial factor involved in adaptive response to zinc overload when it is expressed in yeast cells. MicrobiologyOpen. 2015 Jun; 4(3):409-22. doi: 10.1002/mbo3.248. [PMID: 25755096]
  • Danuta Cembrowska-Lech, Marek Koprowski, Jan Kępczyński. Germination induction of dormant Avena fatua caryopses by KAR(1) and GA(3) involving the control of reactive oxygen species (H2O2 and O2(·-)) and enzymatic antioxidants (superoxide dismutase and catalase) both in the embryo and the aleurone layers. Journal of plant physiology. 2015 Mar; 176(?):169-79. doi: 10.1016/j.jplph.2014.11.010. [PMID: 25618514]
  • Vânia Cristina Desoti, Danielle Lazarin-Bidóia, Fabianne Martins Ribeiro, Solange Cardoso Martins, Jean Henrique da Silva Rodrigues, Tania Ueda-Nakamura, Celso Vataru Nakamura, Valdecir Farias Ximenes, Sueli de Oliveira Silva. The Combination of Vitamin K3 and Vitamin C Has Synergic Activity against Forms of Trypanosoma cruzi through a Redox Imbalance Process. PloS one. 2015; 10(12):e0144033. doi: 10.1371/journal.pone.0144033. [PMID: 26641473]
  • Mustafa Yardimci, Yusuf Sevgiler, Eyyup Rencuzogullari, Mehmet Arslan, Mehmet Buyukleyla, Mehmet Yilmaz. Sex-, tissue-, and exposure duration-dependent effects of imidacloprid modulated by piperonyl butoxide and menadione in rats. Part I: oxidative and neurotoxic potentials. Arhiv za higijenu rada i toksikologiju. 2014 Dec; 65(4):387-98. doi: 10.2478/10004-1254-65-2014-2554. [PMID: 25720026]
  • Maryam Madadkar Haghjou, Louise Colville, Nicholas Smirnoff. The induction of menadione stress tolerance in the marine microalga, Dunaliella viridis, through cold pretreatment and modulation of the ascorbate and glutathione pools. Plant physiology and biochemistry : PPB. 2014 Nov; 84(?):96-104. doi: 10.1016/j.plaphy.2014.08.024. [PMID: 25240268]
  • S Kavitha, T S Chandra. Oxidative stress protection and glutathione metabolism in response to hydrogen peroxide and menadione in riboflavinogenic fungus Ashbya gossypii. Applied biochemistry and biotechnology. 2014 Nov; 174(6):2307-25. doi: 10.1007/s12010-014-1188-4. [PMID: 25178419]
  • Maryam Kamarehei, Razieh Yazdanparast. Modulation of notch signaling pathway to prevent H2O2/menadione-induced SK-N-MC cells death by EUK134. Cellular and molecular neurobiology. 2014 Oct; 34(7):1037-45. doi: 10.1007/s10571-014-0079-0. [PMID: 25005833]
  • Ruijuan Liu, Mengmeng Wang, Li Ding. A novel liquid chromatography-tandem mass spectrometry method for determination of menadione in human plasma after derivatization with 3-mercaptopropionic acid. Talanta. 2014 Oct; 128(?):51-7. doi: 10.1016/j.talanta.2014.04.039. [PMID: 25059129]
  • A Johannisson, A Lundgren, P Humblot, J M Morrell. Naturally and stimulated levels of reactive oxygen species in cooled stallion semen destined for artificial insemination. Animal : an international journal of animal bioscience. 2014 Oct; 8(10):1706-14. doi: 10.1017/s1751731114001499. [PMID: 24916995]
  • Diganta Dey, Ratnamala Ray, Banasri Hazra. Antitubercular and antibacterial activity of quinonoid natural products against multi-drug resistant clinical isolates. Phytotherapy research : PTR. 2014 Jul; 28(7):1014-21. doi: 10.1002/ptr.5090. [PMID: 24318724]
  • Emese D Nagygyörgy, Barbara Kovács, Eva Leiter, Márton Miskei, István Pócsi, László Hornok, Attila L Adám. Toxicity of abiotic stressors to Fusarium species: differences in hydrogen peroxide and fungicide tolerance. Acta microbiologica et immunologica Hungarica. 2014 Jun; 61(2):189-208. doi: 10.1556/amicr.61.2014.2.9. [PMID: 24939687]
  • Dan Li, Elizabeth M Ellis. Aldo-keto reductase 7A5 (AKR7A5) attenuates oxidative stress and reactive aldehyde toxicity in V79-4 cells. Toxicology in vitro : an international journal published in association with BIBRA. 2014 Jun; 28(4):707-14. doi: 10.1016/j.tiv.2014.02.010. [PMID: 24590062]
  • Jukka Luukkonen, Anu Liimatainen, Jukka Juutilainen, Jonne Naarala. Induction of genomic instability, oxidative processes, and mitochondrial activity by 50Hz magnetic fields in human SH-SY5Y neuroblastoma cells. Mutation research. 2014 Feb; 760(?):33-41. doi: 10.1016/j.mrfmmm.2013.12.002. [PMID: 24374227]
  • Jihang Chen, Hoi Shan Wong, Kam Ming Ko. Ursolic Acid-enriched herba cynomorii extract induces mitochondrial uncoupling and glutathione redox cycling through mitochondrial reactive oxygen species generation: protection against menadione cytotoxicity in h9c2 cells. Molecules (Basel, Switzerland). 2014 Jan; 19(2):1576-91. doi: 10.3390/molecules19021576. [PMID: 24473214]
  • Michael Degen, Bobby Alexander, Muhammad Choudhury, Majid Eshghi, Sensuke Konno. Alternative therapeutic approach to renal-cell carcinoma: induction of apoptosis with combination of vitamin K3 and D-fraction. Journal of endourology. 2013 Dec; 27(12):1499-503. doi: 10.1089/end.2013.0207. [PMID: 24341344]
  • Gemma M Cartwright, Barry Scott. Redox regulation of an AP-1-like transcription factor, YapA, in the fungal symbiont Epichloe festucae. Eukaryotic cell. 2013 Oct; 12(10):1335-48. doi: 10.1128/ec.00129-13. [PMID: 23893078]
  • João P Monteiro, Ana M Silva, Amália S Jurado, Paulo J Oliveira. Rapeseed oil-rich diet alters in vitro menadione and nimesulide hepatic mitochondrial toxicity. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Oct; 60(?):479-87. doi: 10.1016/j.fct.2013.07.073. [PMID: 23933359]
  • Mohamed Saleh Elgawish, Chikako Shimomai, Naoya Kishikawa, Kaname Ohyama, Mitsuhiro Wada, Naotaka Kuroda. Development and validation of the first assay method coupling liquid chromatography with chemiluminescence for the simultaneous determination of menadione and its thioether conjugates in rat plasma. Chemical research in toxicology. 2013 Sep; 26(9):1409-17. doi: 10.1021/tx400253k. [PMID: 23905771]
  • João P Monteiro, André F Martins, Cláudia Nunes, Catarina M Morais, Marlene Lúcio, Salette Reis, Teresa J T Pinheiro, Carlos F G C Geraldes, Paulo J Oliveira, Amália S Jurado. A biophysical approach to menadione membrane interactions: relevance for menadione-induced mitochondria dysfunction and related deleterious/therapeutic effects. Biochimica et biophysica acta. 2013 Aug; 1828(8):1899-908. doi: 10.1016/j.bbamem.2013.04.006. [PMID: 23590997]
  • Maryam Moslehi, Razieh Yazdanparast. SK-N-MC cell death occurs by distinct molecular mechanisms in response to hydrogen peroxide and superoxide anions: involvements of JAK2-STAT3, JNK, and p38 MAP kinases pathways. Cell biochemistry and biophysics. 2013 Jul; 66(3):817-29. doi: 10.1007/s12013-013-9526-7. [PMID: 23417568]
  • Pamela S Tietz Bogert, Bing Q Huang, Sergio A Gradilone, Tetyana V Masyuk, Gary L Moulder, Stephen C Ekker, Nicholas F Larusso. The zebrafish as a model to study polycystic liver disease. Zebrafish. 2013 Jun; 10(2):211-7. doi: 10.1089/zeb.2012.0825. [PMID: 23668934]
  • Seok-Jeong Oh, Hyo-Kyung Han, Keon-Wook Kang, Young-Joo Lee, Moo-Yeol Lee. Menadione serves as a substrate for P-glycoprotein: implication in chemosensitizing activity. Archives of pharmacal research. 2013 Apr; 36(4):509-16. doi: 10.1007/s12272-013-0052-3. [PMID: 23435914]
  • R J Aitken, T B Smith, T Lord, L Kuczera, A J Koppers, N Naumovski, H Connaughton, M A Baker, G N De Iuliis. On methods for the detection of reactive oxygen species generation by human spermatozoa: analysis of the cellular responses to catechol oestrogen, lipid aldehyde, menadione and arachidonic acid. Andrology. 2013 Mar; 1(2):192-205. doi: 10.1111/j.2047-2927.2012.00056.x. [PMID: 23316012]
  • Rafael A de Sá, Frederico A V de Castro, Elis C A Eleutherio, Raquel M de Souza, Joaquim F M da Silva, Marcos D Pereira. Brazilian propolis protects Saccharomyces cerevisiae cells against oxidative stress. Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology]. 2013; 44(3):993-1000. doi: 10.1590/s1517-83822013005000062. [PMID: 24516431]
  • Kyeong-Ah Jung, Mi-Kyoung Kwak. Enhanced 4-hydroxynonenal resistance in KEAP1 silenced human colon cancer cells. Oxidative medicine and cellular longevity. 2013; 2013(?):423965. doi: 10.1155/2013/423965. [PMID: 23766854]
  • Thilo Christopher Fischer, Christian Gosch, Beate Mirbeth, Markus Gselmann, Veronika Thallmair, Karl Stich. Potent and specific bactericidal effect of juglone (5-hydroxy-1,4-naphthoquinone) on the fire blight pathogen Erwinia amylovora. Journal of agricultural and food chemistry. 2012 Dec; 60(49):12074-81. doi: 10.1021/jf303584r. [PMID: 23163769]