cytochalasins

Summary

Summary: 11- to 14-membered macrocyclic lactones with a fused isoindolone. Members with INDOLES attached at the C10 position are called chaetoglobosins. They are produced by various fungi. Some members interact with ACTIN and inhibit CYTOKINESIS.

Top Publications

  1. Pongcharoen W, Rukachaisirikul V, Phongpaichit S, Rungjindamai N, Sakayaroj J. Pimarane diterpene and cytochalasin derivatives from the endophytic fungus Eutypella scoparia PSU-D44. J Nat Prod. 2006;69:856-8 pubmed
    Two pimarane diterpenes, named scopararanes A (1) and B (2), and two cytochalasins, named scoparasins A (3) and B (4), along with 4,8-dihydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochroman-1-one (5) and diaportheins A (6) and B (7) were ..
  2. Schumann J, Hertweck C. Molecular basis of cytochalasan biosynthesis in fungi: gene cluster analysis and evidence for the involvement of a PKS-NRPS hybrid synthase by RNA silencing. J Am Chem Soc. 2007;129:9564-5 pubmed
  3. Gebhardt K, Schimana J, Holtzel A, Dettner K, Draeger S, Beil W, et al. Aspochalamins A-D and aspochalasin Z produced by the endosymbiotic Fungus aspergillus niveus LU 9575. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2004;57:707-14 pubmed
    ..Aspochalamins showed cytostatic effects towards various tumor cell lines and a weak antibacterial activity against Gram-positive bacteria. ..
  4. Wang F, Wei H, Zhu T, Li D, Lin Z, Gu Q. Three new cytochalasins from the marine-derived fungus Spicaria elegans KLA03 by supplementing the cultures with L- and D-tryptophan. Chem Biodivers. 2011;8:887-94 pubmed publisher
    Three new cytochalasins Z(21) -Z(23) (1-3, resp.), together with five analogs, 4-8, were isolated from Spicaria elegans KLA03 by the OSMAC (one strain-many compounds) approach with adding L- and D-tryptophan during its cultivation...
  5. Zhang Y, Tian R, Liu S, Chen X, Liu X, Che Y. Alachalasins A-G, new cytochalasins from the fungus Stachybotrys Podospora vesticola [corrected]. Bioorg Med Chem. 2008;16:2627-34 pubmed
    ..Alachalasin A (1) displayed inhibitory effect on HIV-1LAI replication in C8166 cells with an EC50 of 8.01 microM; alachalasins D (4) and G (7) showed modest antimicrobial activity. ..
  6. Zhou G, Wijeratne E, Bigelow D, Pierson L, VanEtten H, Gunatilaka A. Aspochalasins I, J, and K: three new cytotoxic cytochalasans of Aspergillus flavipes from the rhizosphere of Ericameria laricifolia of the Sonoran Desert. J Nat Prod. 2004;67:328-32 pubmed
    ..All compounds exhibited weak to moderate cytotoxicity against NCI-H460, MCF-7, and SF-268 cancer cell lines, but none showed significant selectivity. ..
  7. Evidente A, Andolfi A, Vurro M, Zonno M, Motta A. Cytochalasins Z1, Z2 and Z3, three 24-oxa[14]cytochalasans produced by Pyrenophora semeniperda. Phytochemistry. 2002;60:45-53 pubmed
    Three new cytochalasans, named cytochalasins Z1, Z2 and Z3, were isolated from the wheat culture of Pyrenophora semeniperda, a fungus proposed to biologically control grass weeds...
  8. Zheng C, Shao C, Wu L, Chen M, Wang K, Zhao D, et al. Bioactive phenylalanine derivatives and cytochalasins from the soft coral-derived fungus, Aspergillus elegans. Mar Drugs. 2013;11:2054-68 pubmed publisher
    ..derivative 4'-OMe-asperphenamate (1), along with one known phenylalanine derivative (2) and two new cytochalasins, aspochalasin A1 (3) and cytochalasin Z24 (4), as well as eight known cytochalasin analogues (5-12) were ..
  9. Liu R, Gu Q, Zhu W, Cui C, Fan G, Fang Y, et al. 10-Phenyl-[12]-cytochalasins Z7, Z8, and Z9 from the marine-derived fungus Spicaria elegans. J Nat Prod. 2006;69:871-5 pubmed
    The three new 10-phenyl-[12]-cytochalasins Z7, Z8, and Z9 (1-3), together with two known analogues, cytochalasins E (4) and K (5), were isolated from the marine-derived fungus Spicaria elegans...

More Information

Publications62

  1. Foissner I, Wasteneys G. Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007;48:585-97 pubmed
    Numerous forms of cytochalasins have been identified and, although they share common biological activity, they may differ considerably in potency...
  2. Kim E, Li J, Dang H, Hong J, Lee C, Kim D, et al. Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai. Bioorg Med Chem Lett. 2012;22:3126-9 pubmed publisher
    ..5-30 ?M. The cytochalasin B (5) showed obvious cytotoxicity with IC(50) of 7.9 ?M against HeLa human cervical carcinoma cells. ..
  3. Tomikawa T, Shin ya K, Seto H, Okusa N, Kajiura T, Hayakawa Y. Structure of aspochalasin H, a new member of the aspochalasin family. J Antibiot (Tokyo). 2002;55:666-8 pubmed
  4. Qiao K, Chooi Y, Tang Y. Identification and engineering of the cytochalasin gene cluster from Aspergillus clavatus NRRL 1. Metab Eng. 2011;13:723-32 pubmed publisher
    b>Cytochalasins are a group of fungal secondary metabolites with diverse structures and bioactivities, including cytochalasin E produced by Aspergillus clavatus, which is a potent anti-angiogenic agent...
  5. Corrêa G, Benchimol M. Giardia lamblia behavior under cytochalasins treatment. Parasitol Res. 2006;98:250-6 pubmed
    ..These findings are discussed. ..
  6. Jung G, Titus M, Hammer J. The Dictyostelium type V myosin MyoJ is responsible for the cortical association and motility of contractile vacuole membranes. J Cell Biol. 2009;186:555-70 pubmed publisher
    ..Therefore, myoJ cooperates with plus and minus end-directed microtubule motors to drive the normal distribution and dynamics of the CV complex in Dictyostelium. ..
  7. Rasmussen C, Glass N. Localization of RHO-4 indicates differential regulation of conidial versus vegetative septation in the filamentous fungus Neurospora crassa. Eukaryot Cell. 2007;6:1097-107 pubmed publisher
    ..These data highlight the differences in the regulation of septation during conidiation versus vegetative septation in filamentous fungi...
  8. Liu J. N-containing compounds of macromycetes. Chem Rev. 2005;105:2723-44 pubmed
  9. Jayasuriya H, Herath K, Ondeyka J, Polishook J, Bills G, Dombrowski A, et al. Isolation and structure of antagonists of chemokine receptor (CCR5). J Nat Prod. 2004;67:1036-8 pubmed
    ..Anibamine.TFA competed for the binding of 125I-gp120 to human CCR5 with an IC50 of 1 microM. Ophiobolin C and 19,20-epoxycytochalasin Q exhibited binding IC50) values of 40 and 60 microM, respectively...
  10. Cimmino A, Andolfi A, Berestetskiy A, Evidente A. Production of phytotoxins by Phoma exigua var. exigua, a potential mycoherbicide against perennial thistles. J Agric Food Chem. 2008;56:6304-9 pubmed publisher
    ..demonstrated that the above two strains, grown in liquid and solid cultures, produced p-hydroxybenzaldehyde, cytochalasins B, F, Z2 and Z3, and deoxaphomin. When assayed on the leaves of both C. arvense and S...
  11. Lionetto M, Pedersen S, Hoffmann E, Giordano M, Schettino T. Roles of the cytoskeleton and of protein phosphorylation events in the osmotic stress response in eel intestinal epithelium. Cell Physiol Biochem. 2002;12:163-78 pubmed
    ..It is suggested that NKCC regulation by hypertonic stress involves an interaction between the cytoskeleton and protein phosphorylation events. ..
  12. Giannoutsou E, Apostolakos P, Galatis B. Actin filament-organized local cortical endoplasmic reticulum aggregations in developing stomatal complexes of grasses. Protoplasma. 2011;248:373-90 pubmed publisher
    ..The probable role(s) of the local ER aggregations are discussed. ..
  13. Henics T, Nagy E, Szekeres Bartho J. Interaction of AU-rich sequence binding proteins with actin: possible involvement of the actin cytoskeleton in lymphokine mRNA turnover. J Cell Physiol. 1997;173:19-27 pubmed
    ..Moreover, disruption of the microfilament network by cytochalasins produces increased immunoprecipitable actin-AUBP complexes in the detergent-resistant cytoplasmic subfractions ..
  14. Hill D, Strome S. An analysis of the role of microfilaments in the establishment and maintenance of asymmetry in Caenorhabditis elegans zygotes. Dev Biol. 1988;125:75-84 pubmed
  15. Gooding L, Sofola I, Tollefson A, Duerksen Hughes P, Wold W. The adenovirus E3-14.7K protein is a general inhibitor of tumor necrosis factor-mediated cytolysis. J Immunol. 1990;145:3080-6 pubmed
    ..The 14.7K protein was found in both the nuclear and cytosol fractions of TNF resistant as well as all spontaneously sensitive cells suggesting that 14.7K may have more than one site of action within the cell. ..
  16. Masai K, Maruyama J, Nakajima H, Kitamoto K. Effects of protein transport inhibitors on the distribution and secretion of the fusion protein RntA-EGFP in Aspergillus oryzae. Biosci Biotechnol Biochem. 2004;68:1569-73 pubmed
    ..In addition, quantitative analysis was performed using the RntA-EGFP visualization system to analyze the relative amount of RntA-EGFP secreted into the culture medium during treatment with the protein transport inhibitors. ..
  17. Astuya A, Caprile T, Castro M, Salazar K, García M, Reinicke K, et al. Vitamin C uptake and recycling among normal and tumor cells from the central nervous system. J Neurosci Res. 2005;79:146-56 pubmed
    ..This recycling model may work as an efficient system for the salvage of vitamin C by avoiding the hydrolysis of dehydroascorbic acid produced by antioxidative protection. ..
  18. Song X, Ma Q, Hao X, Li H. Roles of the actin cytoskeleton and an actin-binding protein in wheat resistance against Puccinia striiformis f. sp. tritici. Protoplasma. 2012;249:99-106 pubmed publisher
    ..Both pharmacological and gene expression results collectively support the notion that the compromise of the actin microfilament is linked to the compatible interaction between the stripe rust fungus and the leaves of its wheat host. ..
  19. Maruoka N, Steele D, Au B, Dan P, Zhang X, Moore E, et al. alpha-actinin-2 couples to cardiac Kv1.5 channels, regulating current density and channel localization in HEK cells. FEBS Lett. 2000;473:188-94 pubmed
    ..The ion channels and alpha-actinin-2 co-localize at the membrane in HEK cells, where disruption of the actin cytoskeleton and antisense constructs to alpha-actinin-2 modulate the ion and gating current density. ..
  20. Quinlan M, Hyatt J. Establishment of the circumferential actin filament network is a prerequisite for localization of the cadherin-catenin complex in epithelial cells. Cell Growth Differ. 1999;10:839-54 pubmed
    ..A similar result was observed with dominant negative rac1. These data suggest that the status of cortical actin is assessed and transduced and thereby regulates the transport and delivery of cadherin and catenins to the cell surface. ..
  21. Ocampo M, Rodriguez D, Curtidor H, Vanegas M, Patarroyo M, Patarroyo M. Peptides derived from Mycobacterium tuberculosis Rv2301 protein are involved in invasion to human epithelial cells and macrophages. Amino Acids. 2012;42:2067-77 pubmed publisher
    ..These findings are of vital importance for the rational selection of Rv2301 HABPs, to be included as components of an antituberculosis vaccine. ..
  22. Dudas P, Pelis R, Braun E, Renfro J. Transepithelial urate transport by avian renal proximal tubule epithelium in primary culture. J Exp Biol. 2005;208:4305-15 pubmed
    ..MK571 had no effect from the interstitial side. RT-PCR revealed mRNA for OAT1-, OAT3-, MRP2- and MRP4-like organic anion transporters in chicken proximal epithelium. ..
  23. Benkovic V, Kopjar N, Horvat Knezevic A, Dikic D, Basic I, Ramic S, et al. Evaluation of radioprotective effects of propolis and quercetin on human white blood cells in vitro. Biol Pharm Bull. 2008;31:1778-85 pubmed
    ..However, to clarify the underlying mechanisms of their cyto/radioprotective activities, additional studies are necessary at both in vitro and in vivo levels. ..
  24. Song Y, Wang J, Li S, Cheng B, Li L, Chen B, et al. Metabolites of the mangrove fungus Xylaria sp. BL321 from the South China Sea. Planta Med. 2012;78:172-6 pubmed publisher
    ..Compounds 4-7 displayed cytotoxicity against human breast cancer cell lines MCF-7 and MDA-MB-435, while compounds 1- 3 were inactive (IC(50) >?50?µM). ..
  25. Dichtl K, Ebel F, Dirr F, Routier F, Heesemann J, Wagener J. Farnesol misplaces tip-localized Rho proteins and inhibits cell wall integrity signalling in Aspergillus fumigatus. Mol Microbiol. 2010;76:1191-204 pubmed publisher
    ..After farnesol treatment this localization is rapidly lost, which is accompanied by swelling of the hyphal tips. Parallel displacement of tropomyosin from the tips suggests a concomitant disorganization of the apical actin cytoskeleton...
  26. Dos Santos T, VARELA J, Lynch I, Salvati A, Dawson K. Effects of transport inhibitors on the cellular uptake of carboxylated polystyrene nanoparticles in different cell lines. PLoS ONE. 2011;6:e24438 pubmed publisher
    ..A strong reduction of NP uptake was observed after chlorpromazine treatment only in the case of 1321N1 cells. These outcomes suggested that the same NP might exploit different uptake mechanisms to enter different cell types. ..
  27. Callaini G, Riparbelli M, Dallai R. The distribution of cytoplasmic bacteria in the early Drosophila embryo is mediated by astral microtubules. J Cell Sci. 1994;107 ( Pt 3):673-82 pubmed
  28. Naruse N, Yamamoto H, Murata S, Sawada Y, Fukagawa Y, Oki T. Aspochalasin E, a new antibiotic isolated from a fungus. J Antibiot (Tokyo). 1993;46:679-81 pubmed
  29. Kuromi H, Kidokoro Y. The optically determined size of exo/endo cycling vesicle pool correlates with the quantal content at the neuromuscular junction of Drosophila larvae. J Neurosci. 1999;19:1557-65 pubmed
    ..The results suggest that vesicles in the exo/endo cycling pool primarily participate in evoked exocytosis of vesicles. ..
  30. Ottonello L, Arduino N, Bertolotto M, Dapino P, Mancini M, Dallegri F. In vitro inhibition of human neutrophil histotoxicity by ambroxol: evidence for a multistep mechanism. Br J Pharmacol. 2003;140:736-42 pubmed
    ..Thus, ambroxol appears to be a good candidate for raising attempts to develop new therapeutic histoprotective approaches to inflammatory bronchopulmonary diseases...
  31. Gvakharia B, Bebas P, Cymborowski B, Giebultowicz J. Disruption of sperm release from insect testes by cytochalasin and beta-actin mRNA mediated interference. Cell Mol Life Sci. 2003;60:1744-51 pubmed
    ..Combined results of RNAi experiments at physiological, cellular and molecular levels identified unique cells that are critically involved in the mechanism of sperm release. ..
  32. Lunn J, Jacamo R, Rozengurt E. Preferential phosphorylation of focal adhesion kinase tyrosine 861 is critical for mediating an anti-apoptotic response to hyperosmotic stress. J Biol Chem. 2007;282:10370-9 pubmed
  33. Clemens D, Horwitz M. Uptake and intracellular fate of Francisella tularensis in human macrophages. Ann N Y Acad Sci. 2007;1105:160-86 pubmed
    ..Further research is needed to determine the mechanisms underlying looping phagocytosis, and the maturational arrest, fibrillar coat formation, and disruption of the phagosome. ..
  34. Meuth S, Kanyshkova T, Landgraf P, Pape H, Budde T. Influence of Ca2+-binding proteins and the cytoskeleton on Ca2+-dependent inactivation of high-voltage activated Ca2+ currents in thalamocortical relay neurons. Pflugers Arch. 2005;450:111-22 pubmed
  35. Nolz J, Fernandez Zapico M, Billadeau D. TCR/CD28-stimulated actin dynamics are required for NFAT1-mediated transcription of c-rel leading to CD28 response element activation. J Immunol. 2007;179:1104-12 pubmed
    ..Overall, these findings establish that disrupting actin cytoskeletal dynamics impairs TCR/CD28-mediated calcium flux required for NFAT1-mediated c-rel transcription and, thus, activation of the CD28RE/AP. ..
  36. Giordana B, Milani A, Grimaldi A, Farneti R, Casartelli M, Ambrosecchio M, et al. Absorption of sugars and amino acids by the epidermis of Aphidius ervi larvae. J Insect Physiol. 2003;49:1115-24 pubmed
    ..ervi larvae further corroborate the general idea that the pre-imaginal stages of endophagous koinobiont Hymenoptera, like Metazoan parasites, show a high degree of physiological integration with their hosts. ..
  37. Tzima E, Trotter P, Hastings A, Orchard M, Walker J. Investigation of the relocation of cytosolic phospholipase A2 and annexin V in activated platelets. Thromb Res. 2000;97:421-9 pubmed
    ..The incorporation of cytosolic phospholipase A(2) into the membrane fraction of thrombin-activated platelets parallels that of annexin V, which suggests an interaction between the two proteins. ..
  38. Castro M, Caprile T, Astuya A, Millan C, Reinicke K, Vera J, et al. High-affinity sodium-vitamin C co-transporters (SVCT) expression in embryonic mouse neurons. J Neurochem. 2001;78:815-23 pubmed
    ..Vitamin C that is found at high concentration in fetal brain may function in preventing oxidative free radical damage, because antioxidant radical enzymes mature only late in the developing brain. ..
  39. Takamatsu S, Zhang Q, Schrader K, ElSohly H, Walker L. Characterization of Mycotypha metabolites found to be inhibitors of cell adhesion molecules. J Antibiot (Tokyo). 2002;55:585-92 pubmed
    ..All these components inhibited adhesion of HL-60 cells to CHO-ICAM-1 cells at IC50 values of 30 micrograms/ml for 1, 75 micrograms/ml for 2, and 90 micrograms/ml for 3. ..
  40. Takagi S, Kong S, Mineyuki Y, Furuya M. Regulation of actin-dependent cytoplasmic motility by type II phytochrome occurs within seconds in Vallisneria gigantea epidermal cells. Plant Cell. 2003;15:331-45 pubmed
    ..Although the phytochrome-dependent cytoplasmic motility was blocked by exogenously applied latrunculin B or cytochalasins, treatment of the dark-adapted cells with Ca(2+)-chelating reagents induced the cytoplasmic motility...
  41. Mellersh D, Foulds I, Higgins V, Heath M. H2O2 plays different roles in determining penetration failure in three diverse plant-fungal interactions. Plant J. 2002;29:257-68 pubmed
  42. Rochfort S, Ford J, Ovenden S, Wan S, George S, Wildman H, et al. A novel aspochalasin with HIV-1 integrase inhibitory activity from Aspergillus flavipes. J Antibiot (Tokyo). 2005;58:279-83 pubmed
    ..Structure elucidation of 1 was accomplished by detailed spectroscopic data analyses and by comparison with related cytochalasins. Aspochalasin L demonstrated activity against HIV integrase with an IC50 of 71.7microM.
  43. Taheri Talesh N, Horio T, Araújo Bazán L, Dou X, Espeso E, Peñalva M, et al. The tip growth apparatus of Aspergillus nidulans. Mol Biol Cell. 2008;19:1439-49 pubmed publisher
    ..Microtubules are important for delivering vesicles to the tip area and for holding the tip growth apparatus in position...
  44. Litjens T, Harland M, Roberts M, Barritt G, Rychkov G. Fast Ca(2+)-dependent inactivation of the store-operated Ca2+ current (ISOC) in liver cells: a role for calmodulin. J Physiol. 2004;558:85-97 pubmed
    ..It is hypothesized that CaM is tethered to the channel itself and therefore protected from chemical inhibitors. ..
  45. Jarosch B, Collins N, Zellerhoff N, Schaffrath U. RAR1, ROR1, and the actin cytoskeleton contribute to basal resistance to Magnaporthe grisea in barley. Mol Plant Microbe Interact. 2005;18:397-404 pubmed
    ..Application of the actin agonist cytochalasin E promoted cell wall penetration by M. grisea in a dose-dependent manner, demonstrating an involvement of the actin cytoskeleton in penetration resistance. ..
  46. Xiao L, Liu H, Wu N, Liu M, Wei J, Zhang Y, et al. Characterization of the high cytochalasin E and rosellichalasin producing-Aspergillus sp. nov. F1 isolated from marine solar saltern in China. World J Microbiol Biotechnol. 2013;29:11-7 pubmed publisher
    ..5 ?M. Considering the high cytochalasin production and the simple and economical fermentation of Aspergillus sp. nov. F1, the strain could be used as potential strain for large scale production of the cytochalasin E and rosellichalasin. ..
  47. Zutz C, Gacek A, Sulyok M, Wagner M, Strauss J, Rychli K. Small chemical chromatin effectors alter secondary metabolite production in Aspergillus clavatus. Toxins (Basel). 2013;5:1723-41 pubmed publisher
    ..Interestingly, AZA influenced some SM cluster genes and SM production although no Aspergillus species has yet been shown to carry detectable DNA methylation. ..
  48. Delebassée S, Mambu L, Pinault E, Champavier Y, Liagre B, Millot M. Cytochalasin E in the lichen Pleurosticta acetabulum. Anti-proliferative activity against human HT-29 colorectal cancer cells and quantitative variability. Fitoterapia. 2017;121:146-151 pubmed publisher
    ..LC-MS quantitation of cytochalasin E in different samples of P. acetabulum demonstrated quantitative variations of cytochalasin E production in the lichen and especially high concentrations in apothecia. ..
  49. Nightingale T, White I, Doyle E, Turmaine M, Harrison Lavoie K, Webb K, et al. Actomyosin II contractility expels von Willebrand factor from Weibel-Palade bodies during exocytosis. J Cell Biol. 2011;194:613-29 pubmed publisher
    ..This study therefore demonstrates how discrete actin cytoskeleton functions within a single cellular system explain actin filament-based prevention and promotion of specific exocytic steps during regulated secretion. ..
  50. Huang J, Ye Z, Hu X, Lu L, Luo Z. Electrical stimulation induces calcium-dependent release of NGF from cultured Schwann cells. Glia. 2010;58:622-31 pubmed publisher
  51. Ortiz E, Pasquini L, Soto E, Pasquini J. Apotransferrin and the cytoskeleton of oligodendroglial cells. J Neurosci Res. 2005;82:822-30 pubmed
    ..This mechanism may be of importance in the increased formation of the myelin membrane induced by aTf. ..
  52. Rappaport R. Absence of furrowing activity following regional cortical tension reduction in sand dollar blastomere and fertilized egg fragment surfaces. Dev Growth Differ. 1999;41:441-7 pubmed
    ..The results strongly suggest that establishment of the division mechanism by simple gradients of tension at the surface is unlikely. ..
  53. Tang X, Lancelle S, Hepler P. Fluorescence microscopic localization of actin in pollen tubes: comparison of actin antibody and phalloidin staining. Cell Motil Cytoskeleton. 1989;12:216-24 pubmed
    ..A similar pattern of MFs is evident after RP staining. When pollen tubes are treated with cytochalasins (CB or CD) cytoplasmic streaming is inhibited, as is tube elongation...