Additionally, marfuraquinocins c and d exhibited antibacterial activity against the methicillinresistant s. This is first report of heliobuphthalmin isolated from this plant. Effects of cytokinin and auxin on in vitro organ development. The main mechanism of action of the naphthoquinones, such as compound 1, operates by inducing apoptosis in t. The noncommunicable disease, cancer, is one of the major causes of death across the world and is forecast to increase by 75% to reach close to 25 million cases over the next two decades. They can be substituted in any position except at the ketone groups. Naphthalene rings which contain two ketone moieties in any position. Juglone, lawsone, and plumbagin are the most widespread compounds. The potential of antimalarial compounds derived from african. Noteworthy secondary metabolites naphthoquinonestheir occurrence, pharmacological properties and analysis article pdf available in current pharmaceutical analysis 5. Chapter 7 structureactivity relationship of naphthoquinones. However, other mechanisms occur, such as inhibitory activities on cysteine and serine protein. All compounds were evaluated for their potential antibacterial and cytotoxic properties.
A survey of the literature has led to a summary of the major findings regarding plantderived compounds from african flora, which have shown antimalarial. Chemical investigation of many bacterial and fungal, as well as plant species has revealed the presence of interesting compounds derived from naphthalene 1,4naphthoquinones and rarely also 1,2naphthoquinones. Naphthoquinones are compounds widely distributed in the environment, both as natural products and as pharmaceutical agents. Article in czech babula p1, adam v, havel l, kizek r. Nov 28, 2018 fungal strains belonging to genus fusarium and aspergillus are known to infect crops, resulting in threatened food security and less agricultural crop yields. There are many targets of cytotoxic action on the cellular level. Naphthoquinones accession number dbcat000382 description. The aim of the current work was to investigate the antimycotoxigenic activity, cytotoxic effect and antioxidant potential of selected south african medicinal plants extracts. Journal of chemical and pharmaceutical research, 2017, 9. Their structures were elucidated on the basis of spectral and chemical analysis.
The naturally occurring 1,2naphthoquinonebased compound. Their mechanism of action often comprises the formation of reactive oxygen species. Naphthoquinones display very significant pharmacological propertiesthey are cytotoxic. Besides these the antioxidant value of this herbal plant has also been reported. Naphthoquinones as allelochemical triggers of programmed. Noteworthy secondary metabolites naphthoquinones their. Quinones are a group of highly reactive organic chemical species that interact with biological systems to promote inflammatory, antiinflammatory, and anticancer actions and to induce toxicities. Redox properties of naturally occurring naphthoquinones.
It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. Synthesis of naphthoquinone derivatives with potential. The potential of antimalarial compounds derived from. A general overview of the principal aspects of lawsone chemistry, the synthesis of its derivatives and their pharmacological activities and mechanism of. Synthesis of naphthoquinones and bisnaphthoquinones. The utilizing of naphthoquinones for medicinal purposes and their occurrence in nature. Drug discovery projects targeting malaria often resort to natural sources in the search for lead compounds. The structure of the naphthoquinones shows that the double ketone motif on carbon 1 and 4 is needed for potency. Pdf noteworthy secondary metabolites naphthoquinonestheir. They have been the subject of much research due to their pharmacological activities. The antimicrobial effect of some naphthoquinones has been reported, including their structureactivity relationship. The chemical biology of naphthoquinones and its environmental.
Dibenzofurans, depsides and depsidones, naphthoquinones, anthraquinones, xanthones and some other specific class compounds showed promising anticancer potential 3,4,5,6. Antiproliferative naphthoquinone esters from rhinacanthus. The study of naphthoquinones and their complexes with dna. Noteworthy secondary metabolites naphthoquinones their occurrence, pharmacological properties and analysis. Naphthoquinones display very significant pharmacological properties they are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, antiinflammatory, and. Universidadefederaldealagoas,institutodequimica e biotecnologia, 57072970 maceio, al, brazil. Naphthoquinones display very significant pharmacological propertiesthey are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, antiinflammatory, and. Of these compounds 1921 exhibited promising prophylactic activity. Naphthoquinones, plants, pharmacology, liquid chromatography, electrochemical detection, uvvis spectrometry. Department of chemistry,pomona college, claremont, ca 91711, usa.
They are generally found in plants, fungi and in some animals 2. The medicinal and chemical aspects of naphthoquinones isolated from euclea natalensis a. Due to this, naphthoquinones and their derivatives are at the center of multiple areas of research. Preprints is a multidisciplinary preprint platform that accepts articles from all fields of science and technology, given that the preprint is scientifically sound and can be considered part of academic literature.
The mechanismof their effect is highly large and complexthey bind to dna and inhibit theprocesses of replication, interact with numerous proteins enzymes and disturbcell and mitochondrial. Noteworthy secondary metabolites naphthoquinonestheir occurrence, pharmacological properties and analysis. In this study, methanol extract of henna and a series of synthesized structural analogue of lawsone have been assessed for their antimicrobial activities. In vitro antimicrobial activity of a new series of 1,4naphthoquinones. The phpotential diagrams of these compounds are plotted. Naphthoquinones and their pharmacological properties pdf printer download. Journal of chemical and pharmaceutical research, 2017, 910. A new series of 1,4naphthoquinones, bearing various cyclic and aliphatic amines on c2, was designed and synthesized to identify antiproliferative agents for triplenegative breast cancer, which represents a clinical challenge without targeted therapies. Due to this, naphthoquinones and their derivatives are at. Antimicrobial activities of the henna extract and some. Herbs have proved themselves effective in treating every conceivable type of health problem in tens of millions of patients. Noteworthy secondary metabolites naphthoquinonestheir. And murator 2009 02 pdf the 1, 4naphthoquinone structure constitutes an essential part of these classes of.
Naphthoquinones are industrially used as raw materials for pharmaceuticals, agrochemicals and other chemicals. The in vitro antiproliferative activity against panel of 10 kinds of cancer cells e. Naphthoquinones and their pharmacological properties pubmed. Naphthoquinones and their pharmacological properties. Naphthoquinones from catalpa ovata and their inhibitory effects on the production of nitric oxide. Our results demonstrate that cytotoxic effect of naphthoquinones plumbagin and juglone is caused by their ability to generate reactive oxygen species ros as well as. Their pharmacological activities and mechanisms of action are related to their oxidereduction and acidbase properties, and can be modulated by directly adding a substituted to the 1,4naphthoquinone ring. Two of them, desmethylnovobiocin and 5hydroxynovobiocin fig. Pdf noteworthy secondary metabolites naphthoquinones. Hydrophobicity, molar refractivity, 1,4naphthoquinones, quantitative structureactivity relationships abstract. Nevertheless, their pharmacological properties are still very scarce 3,4. Because of these properties the plants containing them are used in folk medicines, mainly by natives in asia, where. Naphthoquinones definition of naphthoquinones by medical.
Malaria is currently a public health concern in many countries in the world due to various factors which are not yet under check. Due to the cytotoxic properties of naphthoquinones, it is necessary to study the. Streptonigrin is structurally related to the naphthoquinones. The study of naphthoquinones and their complexes with dna by. Oxidation reactions of hydroxy naphthoquinones 107 4. Chitin is the main component of insect exoskeleton, and is also an integral part. Their cytotoxic effect is based on their interactions with dna, especially on. Introduction 1, 4naphthoquinone and their analogues have a variety of biological applications starting from antimicrobial to anti cancerous 1. Here we test the suitability, for pharmaceutical purposes, of two drosera species collected. In aqueous solutions, the quinones are shown to exist each in five forms. Synthesis and preliminary pharmacological evaluation of new 1,4naphthoquinones structurally related to lapachol.
Naphthoquinones, the natural occurring phenolic compounds derived from naphthalene, were tested for cytotoxic properties using plant cell suspension culture of tobacco by2 as. In this work, we propose the synthesis of molecules bearing in their structures these 3 important nuclei figure 1. V 42 23 63 pitchers of the carnivorous plant nepenthes khasiana showed that naphthoquinone production can be induced via colloidal chitin injections into closed n. Naphthoquinones displayvery significant pharmacological propertiesthey are cytotoxic, they havesignificant antibacterial, antifungal, antiviral, insecticidal,antiinflammatory, and antipyretic properties. The naphthoquinones, lawsone, lawsone methyl ether and methylene3,3bilawsone fig. Cisplatin as an important and frequently used anticancer drug forms covalent. Nickel, chromium, iron, copper, and cobaltcontaining metal chelates of 5amino8hydroxy1,4naphtoquinone 2 and its acylderivatives 38 were synthesized and characterized, and their antimicrobial activity was evaluated. Chemical investigation of many bacterial and fungal, as well as plant species has revealed the presence of interesting compounds derived from naphthalene 1,4naphthoquinones and rarely also 1. Naphthoquinones and their pharmacological properties abstract. Due to this fact, the possible cytotoxic mechanisms on cellular. Naphthoquinones as allelochemical triggers of programmed cell.
Quinone moieties are present in many drugs such as anthracyclines. Some studies indicate that the antibacterial activity of a family of isoxazolylnaphthoquinones requires a free keto group at position 1, and the substituent at position 2 must be a hydroxyl group 10. Antimicrobial activity of 1,4naphthoquinones by metal. A wide spectrum of biological activity of secondary metabolites is known so far. Essential oils and phenol compounds obtained from the plant extracts are the active principles responsible for their use 5. Pharmacological effects tocardiovascular and reproductive systems have been demonstrated too. It is fairly rapidly reduced by qr, 41 but no information on the rate of autoxidation of the hydroquinone is available. Thermodynamic parameters for all redox and acidbase equilibria between conjugated forms are.
A quinone derivative of naphthalene, reducible to naphthohydroquinone. In vitro antimicrobial activity of a new series of 1,4. It is a quinolinequinone, with carbon5 of the aromatic ring being replaced by nitrogen. Aug 19, 2019 secondary metabolites are classified by their biosynthetic origins and chemical structures. Redox properties of two naturally occurring naphthoquinones, vitamin k220 and lapochol, are examined by thinlayer voltammetry on a pyrolytic graphite electrode. Naphthoquinone derivatives exert their antitrypanosomal activity via a multitarget mechanism simone pieretti 1,2,3. Naphthoquinones are encountered in some bacteria and in the leaves, seeds, and woody parts of higher plants. The effect of metal complexation on the antimicrobial activity of 1,4 naphthoquinones was investigated. Bisnaphthoquinones are biologically important and number of synthetic routes has. Pdf naphthoquinones and their pharmacological properties. The fact that naphthoquinones are potent inhibitors of respiration in parasitized rbcs, characterised by an abnormal content of coenzyme q ubiquinone, 18 16, a variety of heterocyclic quinones have been tested for their antimalarial activity 1926.
Naphthoquinone pdf plants containing naphthoquinones have been employed for the treatment of various. The naphthoquinones are of particular interest because of their. Naphthoquinones and their pharmacological properties pdf printer read online naphthoquinones may cause oxidative stress in exposed cells and, therefore, affect redox signaling. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. Naphthoquinones display very significant pharmacological propertiesthey are cytotoxic, they have significant antibacterial, antifungal, antiviral.
In recent times, quinone derivatives including vitamin k, plumbagin, juglone, lawsone and shikonin attracted the. The medicinal and chemical aspects of naphthoquinones. Radiotherapy and surgical approaches have been unsuccessful in controlling the incidence of most cancers. Naphthoquinones and their pharmacological properties pdf. The aqueous and organic extracts of the leaves from selected. A class of compounds containing the naphthoquinone 1 structure.
Naphthofurans synthesized from naphthoquinones have attracted the attention owing to their well pronounced activities such as antifungal and cytotoxic 17. Among naphthoquinones, 2a and 3a inhibited the proliferation of mdamb231 cells ec50 1. The effect of metal complexation on the antimicrobial activity of 1,4naphthoquinones was investigated. Naphthoquinones represent the group of plant secondary metabolites with cytotoxic properties based on their ability to generate reactive oxygen species and interfere with the processes of cell respiration. They are soluble in organic solvents and have been used extensively as dyes for fabrics. Pdf chemical investigation of many bacterial and fungal, as well as plant species. Preprints is a multidisciplinary preprint platform that accepts articles from all fields of science and technology, given that the preprint is scientifically sound and can be considered part of. The anticancer activities of naphthoquinones have been the focus of much research to discover novel anticancer agents. Naphthoquinone definition of naphthoquinone by medical. Understanding cancer and the anticancer activities of.
Kb, hep2, mcf7, hepg2, hela, siha, c32, llc, colon26 and p388 and nontumorigenic vero cells were then. They can be recovered as yellow, orange, red, or purple crystals. Four of them were determined as new novobiocin analogues. Research has revealed some of the most diverse pharmacological effects, including antibacterial, antifungal, antiviral. Quantitative hplc determination of naphthoquinones in. The activity declines dramatically when the ketone is reduced to the corresponding hydroxyl group e.
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