Nomenclature of a class of biologically active mould metabolites: the cytochalasins, phomins, and zygosporins

Binder, Michael; Tamm, Christoph; Turner, W. B.; Minato, Hitoshi

doi:10.1039/p19730001146

Cited by 39 publications

(32 citation statements)

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“…The metabolites from Helminthosporium species were described as cytochalasins (cytos: cell; chalasis: relaxation). The three groups proposed a systemic nomenclature based on the generic name cytochalasan for the cytochalasins, phomins and zygosporins [166]. Phomin (phomine, cytochalasin B, CB), the first cytochalasin reported, was described in 1966 as a macrolide antibiotic with cytostatic activity produced by a Phoma species [167].…”

Section: Historical Perspective and Producing Fungal Speciesmentioning

confidence: 99%

Mycotoxins: Producing Fungi and Mechanisms of Phytotoxicity

2015

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Abstract:Mycotoxins are secondary fungal metabolites, toxic to humans, animals and plants. Among the hundreds of known mycotoxins, aflatoxins, citrinin, patulin, penicillic acid, tenuazonic acid, ochratoxin A, cytochalasins, deoxynivalenol, fumonisins, fusarin C, fusaric acid, and zearalenone are considered the types that most contaminate cereal grain. The majority of the mycotoxins in these groups are produced by three fungal genera: Aspergillus, Penicillium and Fusarium. These metabolites primarily affect the seed quality, germination, viability, seedling vigour, growth of root and cleoptile. Additionally, since the fungi responsible for the production of these mycotoxins are often endophytes that infect and colonize living plant tissues, accumulation of mycotoxins in the plant tissues may at times be associated with development of plant disease symptoms. The presence of mycotoxins, even in the absence of disease symptoms, may still have subtle biological effects on the physiology of plants. Several studies highlight the toxic effects of mycotoxins on animals and cell lines but little is known about the mode of action of most of these metabolites on plant cells. The most important mycotoxins with phytotoxic effects and their producers in addition to their discovery are briefly outlined below and will be addressed in this article.

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Section: Historical Perspective and Producing Fungal Speciesmentioning

confidence: 99%

Mycotoxins: Producing Fungi and Mechanisms of Phytotoxicity

2015

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“…The thermally induced [2+ 4lcycloaddition of the alkylidene malonic ester 1 to (2 E, 4E)-4-methy1-2,4-hexadien-l-o1 (2) has been shown to be followed immedi- Taken from the <dXplomarbeitenn, by P. St. 1981 andR.…”

Section: Discussionmentioning

confidence: 96%

“…The latter was converted to more stable acetals. Thus, (2 (lo), and (2 E, 4 E)-4-methyl-0-(tert-butyldimethylsilyl)-2,4-hexadien-1-01 (1 1) were prepared starting from the alcohol 2. Oxidation of 2 by pyridinium dichromate [4] afforded 4-methyl-2,4-hexadien-1-a1 (12), a sensitive aldehyde which was characterized by its 2,4-dinitrophenylhydrazone 13.…”

Section: Discussionmentioning

confidence: 99%

Approaches to the synthesis of cytochalasans. Part 5. Studies on the selectivity of the Diels‐Alder reaction leading to the tetrahydroiso‐indolinone sub‐unit

Schmidlin

Gamboni

Strazewski

et al. 1983

Helvetica Chimica Acta

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SummaryThe stereo-and regiochemical course in the [2+ 4lcycloaddition of the chiral alkylidene malonic ester 1 to selected derivatives of (2 E, 4 E)-4-methyl-2,4-hexadien-1-01 (2:) and (2 E, 4 E)-Cmethy1-2,4-hexadien-1-a1 (12) has been investigated. The results are discussed on the basis of semiquantitative PMO theory.The thermally induced [2+ 4lcycloaddition of the alkylidene malonic ester 1 to (2 E, 4E)-4-methy1-2,4-hexadien-l-o1 (2) has been shown to be followed immedi- The numbering of the sub-units corresponds to that used for the cytochalasans 121.

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“…5,11,16,,18 und WCH, zusammen als Essigsaure-9-bromphenacylester (13). Durch Differenzbildung rnit den Resultaten der Abbausequenz 1 lasst sich die Aktivitat der exocyclischen Methylengruppe (C( 12)) bestimmen.…”

Section: -unclassified

Biosynthese der Cytochalasane. Teil II Die Grundbausteine von Cytochalasin D

Lebet

Tamm

1974

Helvetica Chimica Acta

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A number of potential 14C‐ and 3H‐labelled precursors were fed to growing cultures of Zygosporium masonii after the rate of formation of cytochalasin D had been measured. By chemical degradation of [14C]‐ and [3H, 14C]‐cytochalasin D the distribution of the radioactivity originating from incorporated [4′‐3H, U‐14C]‐L‐phenylalanine and [CH3‐14C]‐L‐methionine was determinated. The results demonstrate that the building blocks of cytochalasin D are 1 unit of pheylalanine, 3 units of methionine and acetate units.

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Nomenclature of a class of biologically active mould metabolites: the cytochalasins, phomins, and zygosporins

Abstract: A systematic nomenclature based on the generic name cytochalasan is proposed for the cytochalasins, phomins, and zygosporins.

Cited by 39 publications

References 0 publications

Mycotoxins: Producing Fungi and Mechanisms of Phytotoxicity

Mycotoxins: Producing Fungi and Mechanisms of Phytotoxicity

Approaches to the synthesis of cytochalasans. Part 5. Studies on the selectivity of the Diels‐Alder reaction leading to the tetrahydroiso‐indolinone sub‐unit

Biosynthese der Cytochalasane. Teil II Die Grundbausteine von Cytochalasin D

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