Menadiol (menadiol diphosphate) / Alliance - LARVOL DELTA

Biological potential, metabolite profiling and in silico analysis of pomelo (Citrus maxima L.) leaf. (PubMed, J Sci Food Agric) - "This study emphasizes the significance of selecting the most effective extraction methods to maximize the amount and biological activity of pomelo leaf extracts. Compounds number 16 (menadiol dibutyrate), 25 (5-[(4-hydroxypheny) ethenyl]-2-(3-methyl-1-butenyl)-1,3- benzenediol) and 51 (3-hydroxycoumarin) exhibited remarkable in silico activity as bioactive molecules against selected protein receptors, and are recommended for the further drug discovery and development. The findings offer valuable insights for the development of functional foods, nutraceuticals and pharmaceuticals derived from C. maxima L. leaves, highlighting their role in mitigating oxidative stress and preventing chronic diseases. The biological activity can pave the way for innovative applications in health and nutrition sectors."

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Menadiol diacetate mediated subcellular Cd accumulation and nutrients uptake alleviates Cd toxicity and increases growth and yield of summer squash. (PubMed, Int J Phytoremediation) - "In this context, cell wall and vacuole were the key compartments for Cd sequestration. This study highlights MD-priming as a potential strategy to counter Cd toxicity in summer squash plants."

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DsrMKJOP is the terminal reductase complex in anaerobic sulfate respiration. (PubMed, Proc Natl Acad Sci U S A) - "Here, we present studies revealing that the DsrMKJOP complex of the sulfate reducer Archaeoglobus fulgidus works as a menadiol:DsrC-trisulfide oxidoreductase. Our results reveal a close interaction between the DsrC-trisulfide and the DsrMKJOP complex and show that electrons from the quinone pool reduce consecutively the DsrM hemes b, the DsrK noncubane [4Fe-4S] catalytic center, and finally the DsrC-trisulfide with concomitant release of sulfide. These results clarify the role of this widespread respiratory membrane complex and support the suggestion that DsrMKJOP contributes to energy conservation upon reduction of the DsrC-trisulfide in the last step of DSR."

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Cryo-EM structure of HQNO-bound Alternative Complex III from the anoxygenic phototrophic bacterium Chloroflexus aurantiacus. (PubMed, Plant Cell) - "We here determined cryogenic electron microscopy structures of photosynthetic ACIII isolated from Chloroflexus aurantiacus (CaACIIIp), in apo-form and in complexed form bound to a menadiol analog 2-heptyl-4-hydroxyquinoline-N-oxide (HQNO)...A unique insertion loop in ActE was shown to function in determining the binding specificity of CaACIIIp for downstream electron acceptors. This study broadens our understanding of the structural diversity and molecular evolution of ACIIIs, enabling further investigation of the (mena)quinol oxidoreductases evolved coupling mechanism in bacterial energy conservation."

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The effect of vitamin K4 supplementation on insulin resistance in individuals with type 2 diabetes: a double-blind randomised placebo-controlled clinical trial. (PubMed, Eur J Nutr) - P=N/A | "Vitamin K4 supplementation for 24 weeks is capable of improving insulin resistance and TG levels in individuals with type 2 diabetes. In addition, the improvement in insulin resistance was reflected in the decrease in antidiabetic medication doses. However, it did not affect fasting plasma glucose (FPG) or glycated haemoglobin (HbAc)."

Clinical • Journal • Diabetes • Dyslipidemia • Metabolic Disorders • Type 2 Diabetes Mellitus

Production of Superoxide Radicals and Hydrogen Peroxide by NADH- Ubiquinone Reductase and Ubiquinol-Cytochrome c Reductase from Beef-Heart Mitochondria. (PubMed, Arch Biochem Biophys) - "Additional evidence for the role of ubiquinone as peroxide generator is provided by the generation of O and HO during autoxidation of quinols. In oxygenated buffers, ubiquinol (QH), benzoquinol, duroquinol and menadiol generated Owith k values of 0.1 to 1.4 M s and HO with k values of 0.009 to 4.3 m·s."

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Vitamin derivatives as effective light controlled biocidal agents for food contact surfaces (ACS-Sp 2022) - "Recent research and development have revealed that certain vitamin compound and derivatives, including phylloquinone (VK1), menatetrenone (VK2), menadione (VK3) menadiol diacetate (VK4), menadione sodium bisulfite (MSB, soluble VK3 derivative), riboflavin (RF, VB2), and flavin mononucleotide (FMN, VB2 derivative), are photo-active and can produce reactive oxygen species (ROS) under daylight or UVA illuminations...In this presentation, the photo-induced biocidal mechanisms of representative compounds are discussed with computational modeling and experimental results. Creative applications of the agents in food preservation and reduction of biofilms under varied lighting conditions will be illustrated."

Vitamin K supplementation and vascular health after kidney transplantation. (PubMed, Am J Transplant) - "The authors conclude that in their randomized controlled trial in kidney transplant recipients (KTRs), vitamin K supplementation (menadiol diphosphate 5 mg thrice-weekly) did not affect aortic distensibility or coronary artery calcium score. Although the authors deserve credit for their 'Viktory' of completing this trial, and notwithstanding the relevance to publish null trial results, we question if their conclusions apply to all KTRs."

Journal • Transplantation

Menadione inhibits thioredoxin reductase 1 via arylation at the Sec residue and enhances both NADPH oxidation and superoxide production in Sec to Cys substitution. (PubMed, Free Radic Biol Med) - "TrxR1 has been reported to reduce menadione to menadiol and to produce superoxide anion radicals...In summary, our results demonstrate that TrxR1 catalyzes the reduction of menadione in a Sec-independent manner, which highly dependent on Cys instead of N-terminal redox motif, and the Sec of TrxR1 is the primary target of menadione. The interaction between menadione and TrxR1 revealed in this study may provide a valuable reference for the development of anticancer drugs targeting selenoprotein TrxR1."

Journal • Oncology

Association of NQO2 With UDP-Glucuronosyltransferases Reduces Menadione Toxicity in Neuroblastoma Cells. (PubMed, Front Pharmacol) - "Those results confirmed that the cooperation of the two enzymes plays a fundamental role during the cells' detoxification process. The fluorescence measurements of the variation of redox homeostasis of each cell line and the detection of a glucuronide form of menadiol in the cells co-expressing NQO2 and UGT1A6 enzymes further confirmed our findings."

Journal • Neuroblastoma • Oncology • Solid Tumor

Menadione sodium bisulfite alleviated chromium effects on wheat by regulating oxidative defense, chromium speciation, and ion homeostasis. (PubMed, Environ Sci Pollut Res Int) - "We also compared the effects of water-soluble MSB with that of water-insoluble menadiol diacetate (MD)...Consequently, MSB enhanced wheat growth by lessening oxidative damage, total Cr contents in aerial parts, and strengthening antioxidant enzyme activities. MD was not effective in mediating defense responses in wheat under Cr toxicity."

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The ViKTORIES trial: a randomised, double-blind, placebo-controlled trial of vitamin K supplementation to improve vascular health in kidney transplant recipients. (PubMed, Am J Transplant) - "KTR were recruited between September 2017 and June 2018, and randomised 1:1 to vitamin K (Menadiol diphosphate 5mg; n=45) or placebo (n=45) thrice-weekly...In this heterogeneous cohort of prevalent KTR, vitamin K supplementation did not reduce vascular stiffness or calcification over 1 year. Improving vascular health in KTR is likely to require a multifaceted approach."

Clinical • Journal • Cardiovascular • Transplantation • MRI

A novel approach combining metabolomics and molecular pharmacology to study the effect of Gei Herba on mouse hematopoietic function. (PubMed, Biomed Pharmacother) - "In the present study, a novel approach combining LC-MS metabolomics and molecular pharmacology was developed to investigate the hematopoietic effect and mechanism of LBZ on hematopoietic dysfunction (HD) caused by cyclophosphamide (CTX) in treated mice...Fourteen potential biomarkers were identified in the spleen by metabolic profiles analysis, including 5-hydroxymethyluracil, ascorbalamic acid, adenosine 5'-monophosphate, menadiol disulfate, l-homocysteine sulfonic acid and l-carnitine...The present study combines metabolomic and molecular pharmacological methods to elucidate mechanisms for the protective effect of LBZ on mouse HD following CTX-induced damage. This approach may be useful for exploring mechanisms of action of other drugs."

Journal • Preclinical • Hematological Disorders • CASP3 • CASP9

Vitamin K for kidney transplant organ recipients: investigating vessel stiffness (ViKTORIES): study rationale and protocol of a randomised controlled trial. (PubMed, Open Heart) - "This trial may identify a novel, inexpensive and low-risk treatment to improve surrogate markers of cardiovascular risk in RTR."

Clinical • Journal • Atrial Fibrillation • Cardiovascular • Nephrology • Renal Disease • Transplantation • MRI

Combination of double-mediator system with large-scale integration-based amperometric devices for detecting NAD(P)H:quinone oxidoreductase 1 activity of cancer cell aggregates. (PubMed, ACS Sens) - "Since MD can diffuse into cells due to its hydrophobicity, it is reduced into menadiol by intracellular NQO1...In addition, NQO1 and respiration activities were simultaneously imaged using the detection system that was further combined with electrochemicolor imaging. Thus, the double-mediator system was proven to be useful for evaluating intracellular redox activity of cell aggregates."

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Oxidant Generation Resulting from the Interaction of Copper with Menadione (Vitamin K3)-a Model for Metal-mediated Oxidant Generation in Living Systems. (PubMed, J Inorg Biochem) - "...In this study, the kinetics and mechanism of the oxidation of menadiol (MNHQ, the reduced form of MNQ) in the absence and presence of copper (Cu) over the pH range 6.0-7.5 was examined...Oxygen not only facilitated the catalytic role of Cu(II) by rapidly regenerating Cu(II) but also effectively removed MSNQ, generating the important chain-propagating species O. The model demonstrated that Cu(I) was a significant sink of O resulting in the generation of HO with subsequent generation of highly oxidative intermediates including Cu(III). These results provide considerable insight into the clinical significance of the biological activation and detoxification of MNQ with the kinetic model developed of use in identifying key processes in the generation of harmful oxidants in living systems."

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