cardanol and anacardic-acid

The cashew nut releases a substance that is known as cashew nut shell liquid (CNSL). There are both natural (iCNSL) and technical (tCNSL) cashew nut shell liquids. This study used an Artemia salina bioassay to evaluate the toxic effects of iCNSL and tCNSL cashew nut shell liquids. It also evaluated the toxicity, cytotoxicity, and mutagenicity of CNSL and its effects on the damage induced by copper sulfate (CuSO4·5H2O) on the meristems' root of Allium cepa. Effects of the damage induced by CuSO4·5H2O were evaluated before (pre-), during (co-), and after (post-) treatments. The iCNSL contained 94.5% anacardic acid, and the tCNSL contained 91.3% cardanol. The liquids were toxic to A. salina. Toxicity, cytotoxicity, and mutagenicity were observed with iCNSL compared with the negative control. Similarly, iCNSL failed to inhibit the toxicity and cytotoxicity of CuSO4·5H2O. The tCNSL was not toxic, cytotoxic, or mutagenic in any of the concentrations. However, the lowest iCNSL concentrations and all of the tCNSL concentrations had preventive, antimutagenic, and reparative effects on micronuclei and on chromosomal aberrations in the A. cepa. Therefore, protective, modulating, and reparative effects may be observed in the A. cepa, depending on the concentration and type of CNSL used.

Topics: Anacardic Acids; Anacardium; Animals; Antimutagenic Agents; Artemia; Biological Assay; Biological Factors; Mutagens; Nuts; Onions; Phenols

Anacardic acid, cardanol and cardol, the main constituents of natural cashew nut shell liquid (CNSL), were obtained by solvent extraction and assayed for antioxidant, larvicidal and antiacetylcholinesterase activity. Their relative percent composition was obtained by HPLC analysis. Antioxidant activity was assessed using the DPPH and ABTS(+) tests, which showed cardanol as the most active, followed by cardol and anacardic acid. The three CNSL components demonstrated good larvicidal activity against Aedes aegypti (LC(50)=12.40 for anacardic acid, 10.22 for cardol and 14.45 for cardanol) and exhibited inhibition zones for acetylcholinesterase enzymes in the TLC test similar to carbachol, which was used as standard. Based on the results, these multipotent compounds represent promising agents in the control of Ae. aegypti, the main dengue vector in Brazil.

Topics: Acetylcholinesterase; Aedes; Anacardic Acids; Anacardium; Animals; Antioxidants; Brazil; Chromatography, High Pressure Liquid; Dengue; Dengue Virus; Disease Vectors; Inhibitory Concentration 50; Larva; Mosquito Control; Nuts; Phenols; Resorcinols

On the basis of antibacterial anacardic acids, 6-pentadecenylsalicylic acids, isolated from the cashew apple, Anacardium occidentale L. (Anacardiaceae), a series of 6-alk(en)ylsalicylic acids were synthesized and tested for their antibacterial activity against Streptococcus mutans ATCC 25175. Among them, 6-(4',8'-dimethylnonyl)salicylic acid was found to exhibit the most potent antibacterial activity against this cariogenic bacterium with the minimum inhibition concentration (MIC) of 0.78 microg/ml.

Topics: Anacardic Acids; Anti-Bacterial Agents; Dental Caries; Drug Design; Drug Evaluation, Preclinical

The cashew tree (Anacardium occidentale) represents one of the major cheapest sources of non-isoprenoid phenolic lipids, which have a variety of biological properties: they can act as molluscicides, insecticides, fungicides, have anti-termite properties, have medicinal applications, and demonstrate antioxidant activity in vitro. Immature cashew nut-shell liquid (iCNSL) is a unique natural source of unsaturated long-chain phenols. Their use has stimulated much research in order to prepare drug analogues for application in several fields. The objective of the present study was to determine whether iCNSL has antioxidant properties when used in strains of the yeast Saccharomyces cerevisiae and to measure the inhibitory activity of acetylcholinesterase. The constituents were identified using thin-layer chromatography, gas chromatography-mass spectrometry, Fourier transform infrared spectroscopy, and (1)H and (13)C nuclear magnetic resonance. The iCNSL contains anacardic acid, cardanol, cardol, and 2-methyl cardol. Immature cashew nut oil contains triacylglycerols, fatty acids, alkyl-substituted phenols, and cholesterol. The main constituents of the free fatty acids are palmitic (C(16:0)) and oleic acid (C(18:1)). iCNSL has excellent protective activities in strains of S. cerevisiae against oxidative damage induced by hydrogen peroxide and inhibits acetylcholinesterase activity. iCNSL may have an important role in protecting DNA against damage induced by reactive oxygen species, as well as hydrogen peroxide, generated by intra- and extracellular mechanisms.

Topics: Acetylcholinesterase; Anacardic Acids; Anacardium; Cholesterol; Chromatography, Thin Layer; Enzyme Activation; Fatty Acids; Magnetic Resonance Spectroscopy; Oxidation-Reduction; Phenols; Plant Oils; Plant Preparations; Resorcinols; Saccharomyces cerevisiae; Saccharomyces cerevisiae Proteins; Seeds; Triglycerides

In this study the content of anacardic acids, cardanols and cardols in cashew apple, nut (raw and roasted) and cashew nut shell liquid (CNSL) were analysed. The higher amounts (353.6 g/kg) of the major alkyl phenols, anacardic acids were detected in CNSL followed by cashew fibre 6.1 g/kg) while the lowest (0.65 g/kg) amounts were detected in roasted cashew nut. Cashew apple and fibre contained anacardic acids exclusively, whereas CNSL also contained an abundance of cardanols and cardols. Cashew nut (raw and roasted) also contained low amounts of hydroxy alkyl phenols. Cashew nut shell liquid was used for a basic fractionation of the alkyl phenol classes and the individual anacardic acids, major cardanols and cardols were purified to homogeneity from these fractions by semi-preparative HPLC and definitively identified by nano-ESI-MS-MS, GC-MS and NMR analyses. The hexane extracts (10 mg/ml) of all cashew products tested plus CNSL, displayed significant antioxidant capacity. Cashew nut shell liquid was the more efficient (inhibition=100%) followed by the hexane extract of cashew fibre (94%) and apple (53%). The antioxidant capacity correlated significantly (P<0.05) with the concentration of alkyl phenols in the extracts. A mixture of anacardic acids (10.0 mg/ml) showed the higher antioxidant capacity (IC50=0.60 mM) compared to cardols and cardanols (IC50>4.0 mM). The data shows that of these substances, anacardic-1 was by far the more potent antioxidant (IC50=0.27 mM) compared to cardol-1 (IC50=1.71 mM) and cardanol-1 (IC50>4.0 mM). The antioxidant capacity of anacardic acid-1 is more related to inhibition of superoxide generation (IC50=0.04 mM) and xanthine oxidase (IC50=0.30 mM) than to scavenging of hydroxyl radicals. At present a substantial amount of cashew fibre is mostly used in formulations of animal or poultry feeds. The data presented in this study, indicates that this waste product along with CNSL, both of which contain high contents of anacardic acids, could be better utilized in functional food formulations and may represent a cheap source of cancer chemopreventive agents.

Topics: Anacardic Acids; Anacardium; Antioxidants; Chromatography, High Pressure Liquid; Deoxyguanosine; Enzyme Inhibitors; Gas Chromatography-Mass Spectrometry; Indicators and Reagents; Magnetic Resonance Spectroscopy; Phenols; Resorcinols; Spectrometry, Mass, Electrospray Ionization; Superoxides; Xanthine Oxidase

Anacardic acids, 2-methylcardols, and cardols isolated from various parts of the cashew [Anacardium occidentale] (Anacardiaceae) fruit have been found to exhibit tyrosinase inhibitory activity. Kinetic studies with the two principal active compounds, 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid and 5-[8(Z),11(Z),14-pentadecatrienyl]resorcinol, have indicated that both of these phenolic compounds exhibit characteristic competitive inhibition of the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) by mushroom tyrosinase.

Topics: Anacardic Acids; Basidiomycota; Kinetics; Levodopa; Monophenol Monooxygenase; Nuts; Oxidation-Reduction; Resorcinols; Salicylates; Structure-Activity Relationship