Abstract
The cytochalasans are a group of structurally diverse fungal metabolites exhibiting a wide range of biological activities. Their name is derived from Greek (κύτος, kytos, cell; χάλασις, chalasis, relaxation) due to their most well-known effect, namely, the influence on actin filament networks in eukaryotic cells, which results in a deterioration of the dynamic processes involving the cytoskeleton formation. Together with some other biological properties, the cytochalasans represent a group of potential drug candidates, especially as anticancer agents.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Bräse S, Encinas A, Keck J, Nising CF (2009) Chemistry and biology of mycotoxins and related fungal metabolites. Chem Rev 109:3903
Rothweiler W, Tamm C (1966) Isolation and structure of phomin. Experientia 22:750
Aldridge DC, Armstrong JJ, Speake RN, Turner WB (1967) Cytochalasins, a new class of biologically active mold metabolites. Chem Commun 26
Binder M, Kiechel JR, Tamm C (1970) Zur Biogenese des Antibioticums Phomin. 1. Teil: Die Grundbausteine. Helv Chim Acta 53:1797
Scherlach K, Boettger D, Remme N, Hertweck C (2010) The chemistry and biology of cytochalasans. Nat Prod Rep 27:869
Binder M, Tamm C, Turner WB, Minato H (1973) Nomenclature of a class of biologically active mold metabolites. Cytochalasins, phomins, and zygosporins. J Chem Soc Perkin Trans 1:1146
Liu R, Lin Z, Zhu T, Fang Y, Gu Q, Zhu W (2008) Novel open-chain cytochalasins from the marine-derived fungus Spicaria elegans. J Nat Prod 71:1127
Lin Z, Zhu T, Wei H, Zhang G, Wang H, Gu Q (2009) Spicochalasin A and new aspochalasins from the marine-derived fungus Spicaria elegans. Eur J Org
Horn WS, Simmonds MSJ, Blaney WM (1995) Phomopsichalasin, a novel antimicrobial agent from an endophytic Phomopsis sp. Tetrahedron 51:3969
Numata A, Takahashi C, Ito Y, Minoura K, Yamada T, Matsuda C, Nomoto K (1996) Penochalasins, a novel class of cytotoxic cytochalasans from a Penicillium species separated from a marine alga: structure determination and solution conformation. J Chem Soc Perkin Trans 1:239
Evidente A, Cimmino A, Andolfi A, Berestetskiy A, Motta A (2011) Phomachalasins A–D, 26-oxa[16] and [15]cytochalasans produced by Phoma exigua var. exigua, a potential mycoherbicide for Cirsium arvense biocontrol. Tetrahedron 67:1557
Spudich JA, Lin S (1972) Cytochalasin B, its interaction with actin and actomyosin from muscle. Proc Nat Acad Sci USA 69:442
Carter SB (1967) Effects of cytochalasins on mammalian cells. Nature 213:261
Peterson JR, Mitchison TJ (2002) Small molecules, big impact: a history of chemical inhibitors and the cytoskeleton. Chem Biol 9:1275
Bonder EM, Mooseker MS (1986) Cytochalasin B slows but does not prevent monomer addition at the barbed end of the actin filament. J Cell Biol 102:282
Sampath P, Pollard TD (1991) Effects of cytochalasin, phalloidin, and pH on the elongation of actin filaments. Biochemistry 30:1973
Goddette DW, Frieden C (1986) Actin polymerization. The mechanism of action of cytochalasin D. J Biol Chem 261:15974
Nair UB, Joel PB, Wan Q, Lowey S, Rould MA, Trybus KM (2008) Crystal structures of monomeric actin bound to cytochalasin D. J Mol Biol 384:848
Sekita S, Yoshihira K, Natori S, Udagawa S, Sakabe F, Kurata K, Umeda M (1982) Chaetoglobosins, cytotoxic 10-(Indol-3-yl)-[13]cytochalasans from Chaetomium spp. I. Production, isolation and some cytological effects of chaetoglobosins A–J. Chem Pharm Bull 30:1609
Jiao W, Feng Y, Blunt JW, Cole AL, Munro MH (2004) Chaetoglobosins Q, R, and T, three further new metabolites from Chaetomium globosum. J Nat Prod 67:1722
Alvi KA, Nair B, Pu H, Ursino R, Gallo C, Mocek U (1997) Phomacins: three novel antitumor cytochalasan constituents produced by a Phoma sp. J Org Chem 62:2148
Gan Y, Au JL, Lu J, Wientjes MG (1998) Antiproliferative and cytotoxic effects of geldanamycin, cytochalasin E, suramin and thiacetazone in human prostate xenograft tumor histocultures. Pharm Res 15:1760
Udagawa T, Yuan J, Panigrahy D, Chang YH, Shah J, D’Amato RJ (2000) Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth. J Pharmacol Exp Ther 294:421
Stehn JR, Schevzov G, O’Neill GM, Gunning PW (2006) Specialisation of the tropomyosin composition of actin filaments provides new potential targets for chemotherapy. Curr Cancer Drug Targets 6:245
Betina V, Micekova D, Nemec P (1972) Antimicrobial properties of cytochalasins and their alteration of fungal morphology. J Gen Microbiol 71:343
Cunningham D, Schafer D, Tanenbaum SW, Flashner M (1979) Physiological responses of bacteria to cytochalasin a: effects on growth, transport, and enzyme induction. J Bacteriol 137:925
Makioka A, Kumagai M, Kobayashi S, Takeuchi T (2004) Different effects of cytochalasins on the growth and differentiation of Entamoeba invadens. Parasitol Res 93:68
Rampal AL, Pinkofsky HB, Jung CY (1980) Structure of cytochalasins and cytochalasin B binding sites in human erythrocyte membranes. Biochemistry 19:678
Kletzien RF, Springer A, Perdue JF (1972) Cytochalasin A and B: inhibition of sugar uptake in cultured cells. J Biol Chem 247:2964
Estensen RD, Plagemann PGW (1972) Cytochalasin B: inhibition of glucose and glucosamine transport. Proc Natl Acad Sci USA 69:1430
Bloch R (1973) Inhibition of the glucose transport in the human erythrocyte by cytochalasin B. Biochemistry 12:4799
Griffin JF, Rampal AL, Jung CY (1982) Inhibition of glucose transport in human erythrocytes by cytochalasin: a model based on diffraction studies. Proc Natl Acad Sci USA 79:3759
Schofield JG (1971) Cytochalasin B and realease of growth hormone. Nature New Biol 234:215
Williams JA, Wolff J (1971) Cytochalasin B inhibits thyroid secretion. Biochem Biophys Res Commun 44:422
http://www.plantesygdomme.dk/Penicillium%20aeble/target5.htmlbyMagnusGammelgaard
Andersen B, Smedsgaard J, Frisvad JC (2004) Penicillium expansum: consistent production of patulin, chaetoglobosins, and other secondary metabolites in culture and their natural occurrence in fruit products. J Agric Food Chem 52:2421
Vesely D, Veselá D, Jelínek R (1995) Penicillium aurantiogriseum dierckx produces chaetoglobosin A toxic to embryonic chickens. Mycopathologia 132:31
Springer JP, Clardy J, Wells JM, Cole RJ, Kirksey JW, MacFarlane RD, Torgerson DF (1976) Isolation and structure determination of the mycotoxin chaetoglobosin C, a new (13) cytochalasin. Tetrahedron Lett 17:1355
Cherton JC, Jallal A, Lhommet G, Loutelier C, Dardoize F, Lacoste L, Subileau C (1994) Unexpected production of chaetoglobosins from maize incubated by Phomopsis lepstromiformis. I. Isolation and optimization of the production in liquid media by LC monitoring. Analysis 22:210
Sekita S, Yoshihira K, Natori S, Udagawa S, Sakabe F, Kurata H, Umeda M (1982) Chaetoglobosins, cytotoxic 10-(indol-3-yl)-[13]cytochalasans from Chaetomium spp. I. Production, isolation and some cytological effects of chaetoglobosin A-J. Chem Pharm Bull 30:1609
Ohtsubo K, Saito M, Sekita S, Yoshihira K, Natori S (1978) Acute toxic effects of chaetoglobosin a, a new cytochalasan compound produced by Chaetomium globosum. Jpn J Exp Med 48:105
Thomas EJ (1991) Cytochalasan synthesis: macrocycle formation via intramolecular Diels-Alder reactions. Acc Chem Res 24:229
Vedejs E, Reid JG (1984) Total synthesis of carbocyclic cytochalasans. J Am Chem Soc 106:4617
Stork G, Nakahara Y, Nakahara Y, Greenlee WJ (1978) Total synthesis of cytochalasin B. J Am Chem Soc 100:7775
Stork G, Nakamura J (1983) A simplified total synthesis of cytochalasins via an intramolecular Diels-Alder reaction. J Am Chem Soc 105:5510
Haidle HM, Myers AG (2004) An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci USA 101:12048
Beaulieu PL, Wernic D (1996) Preparation of aminoalkyl chlorohydrin hydrochlorides: key building blocks for hydroxyethylamine-based HIV protease inhibitors. J Org Chem 61:3635
Barbier P, Benezra C (1986) Allergenic α-methylene-γ-butyrolactones. Study of the capacity of β-acetoxy- and β-hydroxy-α-methylene-γ-butyrolactone to induce allergic contact dermatitis in Guinea pigs. J Med Chem 29:868
Tapolczay DJ, Thomas EJ, Whitehead JWF (1985) Total synthesis of proxiphomin, a naturally occuring [13]cytochalasan. H. J Chem Soc Chem Commun 143
Thomas EJ, Whitehead JWF (1989) Cytochalasan synthesis: total synthesis of the naturally occurring [13]cytochalasan proxiphomin. J Chem Soc Perkin Trans I:499
Thomas EJ, Whitehead JWF (1986) Cytochalasan synthesis: synthesis of an [11]-membered ring precursor of cytochalasin H. J Chem Soc Chem Commun 724
Thomas EJ, Whitehead JWF (1986) Cytochalasan synthesis: totalsynthesis of cytochalasin H. J Chem Soc Chem Commun 727
Thomas EJ, Whitehead JWF (1989) Cytochalasan synthesis: total synthesis of cytochalasin H. J Chem Soc Perkin Trans I:507
Sauter R, Thomas EJ, Watts JP (1989) Cytochalasan synthesis: an alternative approach to cytochalasin H. J Chem Soc Perkin Trans I:519
Dyke H, Sauter R, Steel P, Thomas EJ (1986) Cytochalasan synthesis: total synthesis of cytochalasin G. J Chem Soc Chem Commun 1447
Dyke H, Steel PG, Thomas EJ (1989) Cytochalasan synthesis: total synthesis of cytochalasin G. J Chem Soc Perkin Trans I:525
Merifield E, Thomas EJ (1990) Cytochalasan synthesis: total synthesis of cytochalasin D. J Chem Soc Chem Commun 464
Merifield E, Thomas EJ (1999) Total synthesis of cytochalasin D: total synthesis and full structural assignment of cytochalasin O. J Chem Soc Perkin Trans 1:3269
. Trost BM, Ohmori M, Boyd SA, Okawara H, Brickner SJ (1989) Pd-catalyzed Synthesis of Macrocycles. A Total Synthesis of (–)-Aspochalasin B. J Am Chem Soc 111: 8281
Vedejs E, Rodgers JD, Wittenberger SJ (1988) A sulfur-mediated total synthesis of zygosporin E. J Am Chem Soc 110:4822
Vedejs E, Wittenberger SJ (1990) The total synthesis of dl-zygosporin E and dl-C18-desmethylcytochalasin D. J Am Chem Soc 112:4357
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2013 Springer-Verlag Wien
About this chapter
Cite this chapter
Bräse, S. et al. (2013). Cytochalasans. In: The Chemistry of Mycotoxins. Progress in the Chemistry of Organic Natural Products, vol 97. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1312-7_14
Download citation
DOI: https://doi.org/10.1007/978-3-7091-1312-7_14
Published:
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-1311-0
Online ISBN: 978-3-7091-1312-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)