anacardic acids

Summary

Summary: A group of 6-alkyl SALICYLIC ACIDS that are found in ANACARDIUM and known for causing CONTACT DERMATITIS.

Top Publications

  1. Begum P, Hashidoko Y, Islam M, Ogawa Y, Tahara S. Zoosporicidal activities of anacardic acids against Aphanomyces cochlioides. Z Naturforsch C. 2002;57:874-82 pubmed
  2. Eliseeva E, Valkov V, Jung M, Jung M. Characterization of novel inhibitors of histone acetyltransferases. Mol Cancer Ther. 2007;6:2391-8 pubmed
    ..Effects of the new HATi on protein acetylation and HAT activity in vivo make them a suitable tool for discovery of molecular targets of HATs and, potentially, for development of new anticancer therapeutics. ..
  3. Schultz D, Wickramasinghe N, Ivanova M, Isaacs S, Dougherty S, Imbert Fernandez Y, et al. Anacardic acid inhibits estrogen receptor alpha-DNA binding and reduces target gene transcription and breast cancer cell proliferation. Mol Cancer Ther. 2010;9:594-605 pubmed publisher
    ..These data indicate that AnAc 24:1(omega5) inhibits cell proliferation, cell cycle progression, and apoptosis in an ER-dependent manner by reducing ER-DNA interaction and inhibiting ER-mediated transcriptional responses. ..
  4. Toyomizu M, Okamoto K, Akiba Y, Nakatsu T, Konishi T. Anacardic acid-mediated changes in membrane potential and pH gradient across liposomal membranes. Biochim Biophys Acta. 2002;1558:54-62 pubmed
  5. Wu Y, He L, Zhang L, Chen J, Yi Z, Zhang J, et al. Anacardic acid (6-pentadecylsalicylic acid) inhibits tumor angiogenesis by targeting Src/FAK/Rho GTPases signaling pathway. J Pharmacol Exp Ther. 2011;339:403-11 pubmed publisher
  6. Muroi H, Nihei K, Tsujimoto K, Kubo I. Synergistic effects of anacardic acids and methicillin against methicillin resistant Staphylococcus aureus. Bioorg Med Chem. 2004;12:583-7 pubmed
    The synergistic effects of 6-alk(en)ylsalcylic acids, also known as anacardic acids, in combination with methicillin against Staphylococcus aureus ATCC 33591 (MRSA) was investigated...
  7. Masuoka N, Kubo I. Characterization of xanthine oxidase inhibition by anacardic acids. Biochim Biophys Acta. 2004;1688:245-9 pubmed
    ..Salicylic acid moiety and alkenyl side chain in anacardic acid are associated with the cooperative inhibition and hydrophobic binding, respectively. ..
  8. Lee S, Park W, Moon H. Bioassay-guided isolation of antiplasmodial anacardic acids derivatives from the whole plants of Viola websteri Hemsl. Parasitol Res. 2009;104:463-6 pubmed publisher
    ..websteri for the first time. This is the first report on the antiplasmodial activity of the compounds from V. websteri...
  9. Sung B, Pandey M, Ahn K, Yi T, Chaturvedi M, Liu M, et al. Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-kappaB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of . Blood. 2008;111:4880-91 pubmed publisher
    ..Overall, our results demonstrate a novel role for anacardic acid in potentially preventing or treating cancer through modulation of NF-kappaB signaling pathway. ..

More Information

Publications62

  1. Morais T, Pinto N, Carvalho K, Rios J, Ricardo N, Trevisan M, et al. Protective effect of anacardic acids from cashew (Anacardium occidentale) on ethanol-induced gastric damage in mice. Chem Biol Interact. 2010;183:264-9 pubmed publisher
    Cashew nut-shell liquid and the contained anacardic acids (AAs) have been shown to possess antioxidant, lipoxygenase inhibitory, anti-Helicobacter pylori and antitumor properties...
  2. Tamura S, Nitoda T, Kubo I. Effects of salicylic acid on mushroom tyrosinase and B16 melanoma cells. Z Naturforsch C. 2007;62:227-33 pubmed
    ..Neither acid showed noticeable effects on cultured murine B16-F10 melanoma cells except weak cytotoxicity. ..
  3. Sun Y, Jiang X, Chen S, Price B. Inhibition of histone acetyltransferase activity by anacardic acid sensitizes tumor cells to ionizing radiation. FEBS Lett. 2006;580:4353-6 pubmed
    ..These results demonstrate a central role for HATs such as Tip60 in regulating the DNA damage response. HAT inhibitors provide a novel therapeutic approach for increasing the sensitivity of tumors to radiation therapy. ..
  4. Logrado L, Santos C, Romeiro L, Costa A, Ferreira J, Cavalcanti B, et al. Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids. Eur J Med Chem. 2010;45:3480-9 pubmed publisher
    This work is part of a large program, which seeks to discover new antitumor isobenfuranones designed from anacardic acids. The synthetic strategy for the construction of the title compounds takes into consideration the use of inexpensive ..
  5. Ha T, Kubo I. Lipoxygenase inhibitory activity of anacardic acids. J Agric Food Chem. 2005;53:4350-4 pubmed
    ..The alk(en)yl side chain of anacardic acids is essential to elicit the inhibitory activity...
  6. Kubo I, Nihei K, Tsujimoto K. Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA). J Agric Food Chem. 2003;51:7624-8 pubmed
    The structural and antibacterial activity relationship of 6-alk(en)ylsalicylic acids, also known as anacardic acids, was investigated against Gram-positive bacteria, emphasizing the methicillin resistant Staphylococcus aureus ATCC 33591 (..
  7. Carvalho A, Annoni R, Silva P, Borelli P, Fock R, Trevisan M, et al. Acute, subacute toxicity and mutagenic effects of anacardic acids from cashew (Anacardium occidentale Linn.) in mice. J Ethnopharmacol. 2011;135:730-6 pubmed publisher
    ..cashew) is a Brazilian plant that is usually consumed in natura and is used in folk medicine. Anacardic acids (AAs) in the cashew nut shell liquid are biologically active as gastroprotectors, inhibitors of the activity ..
  8. Seong Y, Shin P, Kim G. Anacardic acid induces mitochondrial-mediated apoptosis in the A549 human lung adenocarcinoma cells. Int J Oncol. 2013;42:1045-51 pubmed publisher
    ..This study will be helpful in revealing the cell death mechanisms and in developing potential drugs for lung cancer using AA. ..
  9. Balasubramanyam K, Swaminathan V, Ranganathan A, Kundu T. Small molecule modulators of histone acetyltransferase p300. J Biol Chem. 2003;278:19134-40 pubmed
    ..These compounds would be useful as biological switching molecules for probing into the role of p300 in transcriptional studies and may also be useful as new chemical entities for the development of anticancer drugs. ..
  10. Park W, Ma E. Inhibition of PCAF histone acetyltransferase and cytotoxic effect of N-acylanthranilic acids. Arch Pharm Res. 2012;35:1379-86 pubmed publisher
    ..The cytotoxicity, against one normal cell line (HSF) and eight cancer cell lines (HT-29, HCT-116, MDA-231, A-549, Hep3B, Caski, HeLa and Caki), were evaluated by the SRB method. ..
  11. Tsujimoto K, Hayashi A, Ha T, Kubo I. Anacardic acids and ferric ion chelation. Z Naturforsch C. 2007;62:710-6 pubmed
    ..Anacardiaceae), commonly known as anacardic acids, inhibited the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11...
  12. Farias D, Cavalheiro M, Viana S, De Lima G, da Rocha Bezerra L, Ricardo N, et al. Insecticidal action of sodium anacardate from Brazilian cashew nut shell liquid against Aedes aegypti. J Am Mosq Control Assoc. 2009;25:386-9 pubmed
    ..3 g/kg body weight), this compound did not cause any adverse effects on mice, suggesting that this compound is safe to mammals. Therefore, sodium anacardate may be a viable low-cost alternative to help combat Ae. aegypti. ..
  13. Muroi H, Kubo I. Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus. J Appl Bacteriol. 1996;80:387-94 pubmed
    ..The time-kill curves demonstrated synergistic bactericidal activities for these combinations. ..
  14. Fukuda I, Ito A, Hirai G, Nishimura S, Kawasaki H, Saitoh H, et al. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chem Biol. 2009;16:133-40 pubmed publisher
  15. Oliveira M, Morais S, Magalhães D, Batista W, Vieira I, Craveiro A, et al. Antioxidant, larvicidal and antiacetylcholinesterase activities of cashew nut shell liquid constituents. Acta Trop. 2011;117:165-70 pubmed publisher
    ..Based on the results, these multipotent compounds represent promising agents in the control of Ae. aegypti, the main dengue vector in Brazil. ..
  16. Tedong L, Madiraju P, Martineau L, Vallerand D, Arnason J, Desire D, et al. Hydro-ethanolic extract of cashew tree (Anacardium occidentale) nut and its principal compound, anacardic acid, stimulate glucose uptake in C2C12 muscle cells. Mol Nutr Food Res. 2010;54:1753-62 pubmed publisher
    ..In addition, the dysfunction of mitochondrial oxidative phosphorylation may enhance glycolysis and contribute to increased glucose uptake. These results collectively suggest that CSE may be a potential anti-diabetic nutraceutical. ..
  17. Sun Y, Sahbaie P, Liang D, Li W, Li X, Shi X, et al. Epigenetic regulation of spinal CXCR2 signaling in incisional hypersensitivity in mice. Anesthesiology. 2013;119:1198-208 pubmed publisher
    ..The spinal CXCR2 signaling pathway is one epigenetically regulated pathway controlling early and latent sensitization after incision. ..
  18. Liu Z, Luo X, Liu L, Zhao W, Guo S, Guo Y, et al. Histone acetyltransferase p300 promotes MKL1-mediated transactivation of catechol-O-methyltransferase gene. Acta Biochim Biophys Sin (Shanghai). 2013;45:1002-10 pubmed publisher
  19. Hollands A, Corriden R, Gysler G, Dahesh S, Olson J, Raza Ali S, et al. Natural Product Anacardic Acid from Cashew Nut Shells Stimulates Neutrophil Extracellular Trap Production and Bactericidal Activity. J Biol Chem. 2016;291:13964-73 pubmed publisher
    ..Neutrophil extracellular traps produced in response to anacardic acid are bactericidal and complement select direct antimicrobial activities of the compound. ..
  20. Souto J, Conte M, Alvarez R, Nebbioso A, Carafa V, Altucci L, et al. Synthesis of benzamides related to anacardic acid and their histone acetyltransferase (HAT) inhibitory activities. ChemMedChem. 2008;3:1435-42 pubmed publisher
    ..Moreover, an analogue with the shortest alkyl chain induced significant apoptosis at 50 microM in U937 leukemia cells. ..
  21. Kubo J, Lee J, Kubo I. Anti-Helicobacter pylori agents from the cashew apple. J Agric Food Chem. 1999;47:533-7 pubmed
    b>Anacardic acids and (E)-2-hexenal characterized from the cashew Anacardium occidentale L...
  22. Colussi C, Rosati J, Straino S, Spallotta F, Berni R, Stilli D, et al. N?-lysine acetylation determines dissociation from GAP junctions and lateralization of connexin 43 in normal and dystrophic heart. Proc Natl Acad Sci U S A. 2011;108:2795-800 pubmed publisher
    ..These results suggest that Cx43 N(?)-lysine acetylation may have physiopathological consequences for cell to cell coupling and cardiac function. ..
  23. George J, Kuttan R. Mutagenic, carcinogenic and cocarcinogenic activity of cashewnut shell liquid. Cancer Lett. 1997;112:11-6 pubmed
    ..2 ml acetone) demonstrated that it has no cocarcinogenic potency on mouse skin tumour model when applied along with 2 x 10(-6)% benzo(a)pyrene in acetone up to a period of 20 weeks. ..
  24. Kubo I, Kinst Hori I, Yokokawa Y. Tyrosinase inhibitors from Anacardium occidentale fruits. J Nat Prod. 1994;57:545-51 pubmed
    b>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...
  25. Pena A, Tominaga K, Pereira Smith O. MRG15 activates the cdc2 promoter via histone acetylation in human cells. Exp Cell Res. 2011;317:1534-40 pubmed publisher
    ..These results suggest that MRG15 is acting in a HAT complex involving Tip60 to modify chromatin via acetylation of histone H4 at the cdc2 promoter to activate transcription. ..
  26. Paramashivappa R, Phani Kumar P, Subba Rao P, Srinivasa Rao A. Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition. J Agric Food Chem. 2002;50:7709-13 pubmed
    ..The synthesized compounds were characterized by spectral studies and tested for PDE(5) inhibition, and the results were compared with those obtained with sildenafil. ..
  27. Pandey D, Chen F, Patel A, Wang C, Dimitropoulou C, Patel V, et al. SUMO1 negatively regulates reactive oxygen species production from NADPH oxidases. Arterioscler Thromb Vasc Biol. 2011;31:1634-42 pubmed publisher
    ..Together, these results suggest that SUMO is an important regulatory mechanism that indirectly represses the production of ROS to ameliorate cellular stress. ..
  28. Wisastra R, Ghizzoni M, Boltjes A, Haisma H, Dekker F. Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases. Bioorg Med Chem. 2012;20:5027-32 pubmed publisher
    ..In addition, another derivative (21) caused non-essential activation of potato 5-LOX. This suggests the presence of an allosteric binding site that regulates the lipoxygenase activity. ..
  29. Jain S, Wei J, Mitrani L, Bishopric N. Auto-acetylation stabilizes p300 in cardiac myocytes during acute oxidative stress, promoting STAT3 accumulation and cell survival. Breast Cancer Res Treat. 2012;135:103-14 pubmed publisher
    ..Our results suggest that HDAC inhibitors could potentially reduce acute anthracycline-mediated cardiotoxicity by promoting p300 auto-acetylation. ..
  30. Rivero Cruz B, Esturau N, Sanchez Nieto S, Romero I, Castillo Juarez I, Rivero Cruz J. Isolation of the new anacardic acid 6-[16'Z-nonadecenyl]-salicylic acid and evaluation of its antimicrobial activity against Streptococcus mutans and Porphyromonas gingivalis. Nat Prod Res. 2011;25:1282-7 pubmed publisher
    ..Compounds 1-4 exhibited antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis with minimum inhibitory concentrations ranging from 7 to 104?µg?mL and from 12 to 126?µg?mL, respectively. ..
  31. Trevisan M, Pfundstein B, Haubner R, Wurtele G, Spiegelhalder B, Bartsch H, et al. Characterization of alkyl phenols in cashew (Anacardium occidentale) products and assay of their antioxidant capacity. Food Chem Toxicol. 2006;44:188-97 pubmed
    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...
  32. Mamidyala S, Ramu S, Huang J, Robertson A, Cooper M. Efficient synthesis of anacardic acid analogues and their antibacterial activities. Bioorg Med Chem Lett. 2013;23:1667-70 pubmed publisher
    ..The novel compounds were screened for antibacterial activity and cytotoxicity. Although substitution on the salicylic head group enhanced antibacterial activities they also enhanced cytotoxicity. ..
  33. Philip J, Da Cruz Francisco J, Dey E, Buchweishaija J, Mkayula L, Ye L. Isolation of anacardic acid from natural cashew nut shell liquid (CNSL) using supercritical carbon dioxide. J Agric Food Chem. 2008;56:9350-4 pubmed publisher
  34. Azad M, Kikusato M, Zulkifli I, Toyomizu M. Electrolysed reduced water decreases reactive oxygen species-induced oxidative damage to skeletal muscle and improves performance in broiler chickens exposed to medium-term chronic heat stress. Br Poult Sci. 2013;54:503-9 pubmed publisher
    ..4. In conclusion, this study suggests that ERW could partially inhibit ROS-induced oxidative damage to skeletal muscle and improve growth performance in broiler chickens under medium-term chronic heat treatment. ..
  35. Wang D, Girard T, Kasten T, LaChance R, Miller Wideman M, Durley R. Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex. J Nat Prod. 1998;61:1352-5 pubmed
    ..compounds were found to be linolenic, linoleic, and oleic acids from roots of Salvia miltiorrhiza; and two anacardic acids, 6-(8'Z-pentadecenyl)- and 6-(10'Z-heptadecenyl)-salicylic acids, from leaves of Ginkgo biloba...
  36. Park M, Upton D, Blackmon M, Dixon V, Craver S, Neal D, et al. Anacardic acid inhibits pancreatic cancer cell growth, and potentiates chemotherapeutic effect by Chmp1A - ATM - p53 signaling pathway. BMC Complement Altern Med. 2018;18:71 pubmed publisher
    ..Our data suggests that Anacardic Acid might be a promising complementary supplement to slow the initiation or progression of pancreatic cancer. ..
  37. Davidson S, Townsend P, Carroll C, Yurek George A, Balasubramanyam K, Kundu T, et al. The transcriptional coactivator p300 plays a critical role in the hypertrophic and protective pathways induced by phenylephrine in cardiac cells but is specific to the hypertrophic effect of urocortin. Chembiochem. 2005;6:162-70 pubmed
  38. Schmeck B, Lorenz J, N Guessan P, Opitz B, van Laak V, Zahlten J, et al. Histone acetylation and flagellin are essential for Legionella pneumophila-induced cytokine expression. J Immunol. 2008;181:940-7 pubmed
    ..In summary, histone acetylation seems to be important for the regulation of proinflammatory gene expression in L. pneumophila infected lung epithelial cells. These pathways may contribute to the host response in Legionnaires' disease. ..
  39. Chandregowda V, Kush A, Reddy G. Synthesis of benzamide derivatives of anacardic acid and their cytotoxic activity. Eur J Med Chem. 2009;44:2711-9 pubmed publisher
    ..02 microM, 13.55 microM, 15.29 microM on HeLa cell line. Their activities are comparable with garcinol which is a cell permeable histone acetyltransferase (HAT) inhibitor and 10 fold more active than p300 HAT activators so far reported. ..
  40. Mantelingu K, Kishore A, Balasubramanyam K, Kumar G, Altaf M, Swamy S, et al. Activation of p300 histone acetyltransferase by small molecules altering enzyme structure: probed by surface-enhanced Raman spectroscopy. J Phys Chem B. 2007;111:4527-34 pubmed
  41. Kubo I, Nitoda T, Tocoli F, Green I. Multifunctional cytotoxic agents from Anacardium occidentale. Phytother Res. 2011;25:38-45 pubmed publisher
    The effects of anacardic acids and cardols isolated from the cashew nut and apple Anacardium occidentale (Anacardiaceae) on murine B16-F10 melanoma cells were tested...
  42. Cesla P, Blomberg L, Hamberg M, Jandera P. Characterization of anacardic acids by micellar electrokinetic chromatography and mass spectrometry. J Chromatogr A. 2006;1115:253-9 pubmed
    A possibility of using capillary electrophoresis for separation of anacardic acids (6-alkylsalicylic acids) has been studied...
  43. Ghizzoni M, Boltjes A, Graaf C, Haisma H, Dekker F. Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative. Bioorg Med Chem. 2010;18:5826-34 pubmed publisher
    ..Ten new derivatives were synthesized using a novel synthetic route. One compound showed a twofold improved inhibitory potency for the PCAF HAT activity and a twofold improved inhibition of histone acetylation in HEP G2 cells. ..
  44. Toyomizu M, Okamoto K, Ishibashi T, Chen Z, Nakatsu T. Uncoupling effect of anacardic acids from cashew nut shell oil on oxidative phosphorylation of rat liver mitochondria. Life Sci. 2000;66:229-34 pubmed
    b>Anacardic acids are one of natural products found in not only the cashew nut shell oil but also the nut and fruit juice...
  45. Kanojia R, Murray W, Bernstein J, Fernandez J, Foleno B, Krause H, et al. 6-oxa isosteres of anacardic acids as potent inhibitors of bacterial histidine protein kinase (HPK)-mediated two-component regulatory systems. Bioorg Med Chem Lett. 1999;9:2947-52 pubmed
    A series of 6-oxa isosteres of anacardic acids (6-higher alkyl/alkenyl-2-hydroxybenzoic acids) was synthesised and several members were discovered to be among the most potent inhibitors (IC50 values < or = 5 microM) of the bacterial ..
  46. Souto J, Benedetti R, Otto K, Miceli M, Alvarez R, Altucci L, et al. New anacardic acid-inspired benzamides: histone lysine acetyltransferase activators. ChemMedChem. 2010;5:1530-40 pubmed publisher
    ..These activities correlate with the enzymatic activation of histone lysine acetyltransferases (KATs): CBP and PCAF. ..
  47. Sukumari Ramesh S, Singh N, Jensen M, Dhandapani K, Vender J. Anacardic acid induces caspase-independent apoptosis and radiosensitizes pituitary adenoma cells. J Neurosurg. 2011;114:1681-90 pubmed publisher
    ..These findings warrant further exploration of anacardic acid as a single agent or as an adjunct to radiation therapy for the treatment of pituitary tumors. ..
  48. Kubo I, Ha T, Shimizu K. Lipoxygenase inhibitory activity of 6-pentadecanylsalicylic acid without prooxidant effect. Nat Prod Commun. 2010;5:85-90 pubmed
    ..The inhibition of anacardic acid (C15:0) can be explained by a combination of iron ion-chelation and hydrophobic interaction abilities because of its specific structural feature. ..
  49. Song C, Kanthasamy A, Anantharam V, Sun F, Kanthasamy A. Environmental neurotoxic pesticide increases histone acetylation to promote apoptosis in dopaminergic neuronal cells: relevance to epigenetic mechanisms of neurodegeneration. Mol Pharmacol. 2010;77:621-32 pubmed publisher
  50. Green I, Tocoli F, Lee S, Nihei K, Kubo I. Molecular design of anti-MRSA agents based on the anacardic acid scaffold. Bioorg Med Chem. 2007;15:6236-41 pubmed
    ..This activity was superior to that of the most potent antibacterial anacardic acid isolated from the cashew Anacardium occidentale (Anacardiaceae), apple and nut, that is, the 6-[8'(Z),11'(Z),14'-pentadecatrienyl]salicylic acid. ..
  51. Kishore A, Vedamurthy B, Mantelingu K, Agrawal S, Reddy B, Roy S, et al. Specific small-molecule activator of Aurora kinase A induces autophosphorylation in a cell-free system. J Med Chem. 2008;51:792-7 pubmed publisher
    ..This data thus indicate anacardic acid as the first small-molecule activator of Aurora kinase, which could be highly useful for probing the function of hyperactive (overexpressed) Aurora kinase A. ..
  52. Ravnskjaer K, Hogan M, Lackey D, Tora L, Dent S, Olefsky J, et al. Glucagon regulates gluconeogenesis through KAT2B- and WDR5-mediated epigenetic effects. J Clin Invest. 2013;123:4318-28 pubmed publisher
    ..Administration of a small-molecule KAT2B antagonist lowered circulating blood glucose concentrations in insulin resistance, suggesting that this enzyme may be a useful target for diabetes treatment. ..
  53. Wu J, Xie N, Wu Z, Zhang Y, Zheng Y. Bisubstrate Inhibitors of the MYST HATs Esa1 and Tip60. Bioorg Med Chem. 2009;17:1381-6 pubmed publisher