Quinones

Rapanone (2,5-Dihydroxy-3-tridecyl-[1,4]benzoquinone) is a natural benzoquinone that is a potent and selective inhibitor of human synovial PLA2.

Applications 2-Hydroxy-1,4-naphthoquinone-5,6,7,8-d4 is the isotope labelled analog of 2-Hydroxy-1,4-naphthoquinone (Lawsone) (H949535); the active ingredient of Lawsonia inermis (henna) leaves extract. Lawsone has potential antimicrobial activity and can be used for the detection of latent fingermarks on paper surfaces. References Tekin, V., et al.: J. Radioanal. Nucl. Ch., (2014); Rahmoun, N.M., et al.: Am. J. Med. Biol. Res., 1, 16 (2013); Jelly, R., et al.: Chem. Commun., 30, 3513 (2008)

Natural glycoside

2,6-Dimethoxyhydroquinone is an organic compound that functions primarily as an antioxidant. It is derived from natural sources such as specific plant species and can also be synthesized chemically. This compound operates by donating electrons to reactive oxygen species, effectively neutralizing them and preventing oxidative stress within biological systems. The mode of action involves disrupting the free radical chain reactions, which can otherwise lead to cellular damage. The uses and applications of 2,6-Dimethoxyhydroquinone are extensive in scientific research due to its antioxidant properties. It is investigated for its potential in reducing oxidative damage in various biochemical pathways and systems. Applications in the cosmetic industry and pharmaceuticals have also been proposed, given its ability to mitigate oxidative stress-related aging processes and diseases. Researchers continue to explore its potential as an additive in formulations aimed at extending shelf life or enhancing the stability of other compounds susceptible to oxidation. This compound's multifaceted role in inhibiting oxidative mechanisms makes it a subject of interest across multiple scientific disciplines.

Quinone

Natural glycoside

Natural glycoside

Xyloidone (NSC-106453) is an antifungal that halts growth of several pathogens at 0.4-33.3 mg/L.

Ferruginin A is a marine-derived compound, classified as a natural iron chelator. It is isolated from various marine organisms, particularly sponges and seaweeds, known for their complex secondary metabolites. As an iron chelator, Ferruginin A functions by binding to free iron ions in biological systems, thereby reducing oxidative stress and preventing metal-catalyzed radical formation. This action is crucial, particularly in cellular environments where excess free iron can lead to detrimental oxidative damage. Ferruginin A's primary applications are within the field of neuroprotective research, where iron dysregulation is implicated in neurodegenerative diseases such as Alzheimer's and Parkinson's. By modulating iron homeostasis, Ferruginin A can provide insights into therapeutic strategies aimed at mitigating oxidative damage in neuronal cells. Additionally, its role in exploring the pathology of these diseases makes it a valuable tool for scientists investigating the intricate balance of metal ions in the human brain. As part of a broader quest to understand neurodegeneration, Ferruginin A aids in unraveling the complex interplay between molecular structures and their physiological impacts.

Hydroquinone

Quinone

Oxygen-heterocyclic compound

Maesaquinone is a naturally occurring quinone compound derived from the plant genus Maesa, which is widely studied in the context of its phytochemical properties. This compound exerts its biological effects primarily through modulation of cellular redox states, leading to the generation of reactive oxygen species (ROS) and subsequent induction of apoptosis in cancer cells. By targeting cellular antioxidant mechanisms, Maesaquinone effectively disrupts the redox balance, triggering programmed cell death pathways. The potential applications of Maesaquinone are particularly significant in the field of oncology. Its ability to selectively induce apoptosis in transformed cells while sparing normal cells highlights its promise as a therapeutic agent. Beyond its role in cancer research, Maesaquinone may also serve as a prototype for the development of new chemical entities aimed at modulating redox-sensitive pathways. The ongoing research into its molecular targets and mechanisms continues to offer insights into its broader pharmacological potential.

Auramycin B is an anthracycline antibiotic with notable antibacterial activity against Gram-positive bacteria. Additionally, Auramycin B exhibits antitumor properties in mouse models of P388 and L1210 leukemia.

1,4,6,8-Tetrahydroxy-3-methylanthraquinone is a specialized anthraquinone derivative, which is isolated primarily from certain plant sources, showcasing its botanical origin. This compound belongs to the anthraquinone family, known for their characteristic aromatic structures and hydroxyl functionalities. The mode of action of 1,4,6,8-Tetrahydroxy-3-methylanthraquinone primarily involves its potential as a redox-active molecule due to its hydroxy groups. These groups facilitate electron transfer processes, enabling the compound to act as an antioxidant or potentially interfere with biological redox cycles. In scientific research, it has garnered interest due to its diverse biological activities. Its applications span from being an intriguing candidate for anti-inflammatory studies to exploring its role in anticancer research due to its ability to induce apoptosis in certain cell lines. Furthermore, the compound’s behavior as a natural dye has sparked investigation into its use in industrial applications, particularly in eco-friendly textile processing. The multifaceted nature of 1,4,6,8-Tetrahydroxy-3-methylanthraquinone makes it an invaluable subject of study for advancing both biochemical understanding and practical applications.

Natural glycoside

Alldimycin A is an anthracycline compound that inhibits the synthesis of RNA and DNA. It effectively hampers the growth of mouse leukemia L1210 cells and reduces DNA and RNA synthesis, with IC50 values of 0.05 μg/mL, 0.92 μg/mL, and 0.47 μg/mL, respectively.

Quinone

Natural glycoside

Quinone

Lawsone, a red-orange dye, found in henna leaves and water hyacinth flowers, is also 2-hydroxy-1,4-naphthoquinone.

Sennidine B is a natural anthraquinone compound, which is derived from the plant species of the genus Senna. This compound functions primarily by promoting peristalsis in the colon, thus facilitating bowel movements. Sennidine B achieves this by modulating ion transport in the intestinal epithelium, enhancing water and electrolyte secretion, and stimulating the colonic muscles. Sennidine B is primarily used in its role as a laxative, aiding in the treatment of constipation and related gastrointestinal disorders. Its applications are particularly valuable in clinical settings where patients require relief from intestinal stasis. The compound’s efficacy in promoting colon motility makes it a critical component in formulations designed to alleviate conditions associated with slow colonic transit. This anthraquinone derivative is subject to ongoing research focusing on optimizing dosage forms and understanding its pharmacodynamics and pharmacokinetics to enhance its therapeutic potential and minimize adverse effects.

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Natural glycoside

Oxygen-heterocyclic compound

2,3-Dimethoxyhydroquinone is a chemical compound classified as a methoxy derivative of hydroquinone, which is commonly sourced through chemical synthesis from hydroquinone and methanol under specific catalytic conditions. This compound exhibits its mode of action through the donation of electrons, serving as a potent antioxidant by neutralizing free radicals. Its applications are widespread in various scientific fields, primarily in the study of antioxidant mechanisms and potential therapeutic interventions. Researchers explore its potential in mitigating oxidative stress in biological systems, owing to its ability to inhibit radical-mediated damage at the molecular level. This feature makes it a candidate for further research in pharmacological and biochemical studies related to cellular protection and aging. Additionally, 2,3-Dimethoxyhydroquinone serves as a reference compound in analytical chemistry, providing insights into the behavior of similar structures under oxidative conditions. Its role in the stabilization of sensitive compounds through radical scavenging further underscores its significance in experimental and applied sciences.

2,6-Dihydroxyanthraquinone is an anthraquinone derivative, which is an organic compound derived from the naturally occurring anthraquinone compound. It is primarily obtained through the oxidation of anthracene or can be synthesized via various organic synthesis methods that incorporate hydroxyl groups at the 2 and 6 positions on the anthraquinone backbone. The mode of action of 2,6-Dihydroxyanthraquinone involves its ability to coordinate with metal ions, engage in redox reactions, and function as a chelating agent. Its chemical structure allows it to participate in electron transfer processes, making it valuable in various oxidation-reduction reactions. This compound is commonly utilized in diverse fields such as dye synthesis, analytical chemistry, and pharmaceuticals. In dye synthesis, it serves as a precursor for the formulation of vat dyes due to its stability and coloration properties. In analytical chemistry, it is employed in the development of reagents for metal ion detection and quantification. Furthermore, its ability to undergo redox reactions makes it of interest in biological research, particularly in studies relating to cellular oxidative stress and the development of redox-active pharmaceuticals. Overall, 2,6-Dihydroxyanthraquinone is a versatile compound with significant implications in both chemical and biological research contexts.

Quinone

Quinone

Laxative; induces intestinal smooth muscle contraction; antineoplastic

Auramycin A is an anthracycline antibiotic with significant antibacterial activity against Gram-positive bacteria. Additionally, Auramycin A demonstrates antitumor activity against mouse leukemia models P388 and L1210.

Chrysophanic acid is a naturally occurring anthraquinone compound, which is typically extracted from plants such as rhubarb and senna. It is commonly found in species within the Polygonaceae family. This compound functions primarily through mechanisms that involve modulating cellular pathways, possessing anti-inflammatory, antimicrobial, and potential anticancer properties. The primary mode of action of chrysophanic acid involves inhibition of pro-inflammatory cytokines and enzymes, disrupting microbial cell walls, and interfering with cellular proliferation by inducing apoptosis in various cancer cell lines. The compound's efficacy is linked to its ability to interfere with oxidative stress and enhance the body's antioxidant response. Chrysophanic acid finds applications in the pharmaceutical industry due to its therapeutic potential in managing conditions such as skin disorders (e.g., psoriasis) and infections. It is also a subject of research for its potential use in cancer therapies. Scientists are exploring its utility in developing new drugs and treatment regimens, taking advantage of its natural origin and multifaceted biological activities.

Natural glycoside

Natural glycoside

Quinone

Natural glycoside

2,3-Dimethoxy-5-methyl-1,4-hydroquinone is an organic compound belonging to the class of hydroquinones, which is a type of phenolic antioxidant. It is synthesized through chemical reactions involving methoxylation and methylation of hydroquinone precursors. This compound acts primarily as an electron donor, efficiently reducing reactive oxygen species (ROS) and stabilizing free radicals by donating electrons, thereby exhibiting potent antioxidant activity. Due to its antioxidative properties, 2,3-Dimethoxy-5-methyl-1,4-hydroquinone has been investigated for various applications, particularly in fields where oxidative stress is a concern. It is utilized in pharmaceutical research for developing treatments that mitigate oxidative damage associated with chronic diseases. Additionally, it is explored in the development of cosmetics to enhance skin protection against environmental stressors. Its role as an antioxidant also makes it a candidate in food preservation techniques, aiming to prolong shelf life by preventing oxidative degradation. The potential therapeutic and industrial applications continue to attract scientific interest, highlighting the importance of thorough investigation into its biochemical interactions and efficacy.

Applications Acetylshikonin is the main ingredient of Zicao, which has used in clinics as a traditional Chinese for thousands of years. It exerts anti-obesity and anti-NAFLD effects through the regulation of lipid metabolism and anti-inflammatory effects. Also, it is a 1,4-naphthoquinone pigment extracted from the roots of Lithospermum erythrorhizon with anti-tumor effects. Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package References Su, M., et al.: Mol., 21, 976/1-976/14 (2016); Koike, A., et al.: Biol. Pharm. Bull., 39, 969-976 (2016)