Cyclopiazonic acid imine

In 1973, Abe and co-workers 193) isolated cyclopiazonic acid (130, a-CA), mp 245-246°C, cyclopiazonic acid imine (131), mp 277-278°C, and bissecode-hydrocyclopiazonic acid (132, p-CA), mp 168-169°C, from the combined extracts of mycelia and culture filtrates of Asp. versicolor. Cyclopiazonic acid was also isolated from Asp. flavus 194) and Asp. oryzae 195) by other groups. Penicillium cyclopium Westling 196) also produced the above metabolites as well as the intermediate, a-acetyl-7-(P-indolyl)methyltetramic acid (133), mp 164-165°C. Cyclopiazonic acid is known to cause acute toxicosis in ducklings and rats 197). 

Ohmomo, S., Sugita, M. and Abe, M. (1973) Isolation of cyclopiazonic acid, cyclopiazonic acid imine and bissecodehydrocyclopiazonic acid from the cultures of Aspergillus versicolor (Vuill) Tarabschi. J. Agr. Chem. Soc. Jap., 47, 83-89. 

Holzapfel and Schabort (1977) recently presented evidence that position 5 of aCA has the L-configuration. Earlier, Holzapfel et al. (1970) isolated two metabolites chemically related to aCA from shake cultures of P. cyclo-pium. These compounds, cyclopiazonic acid imine and bissecodehydro-cyclopiazonic acid [also designated jS-cyclopiazonic acid (jSCA)], have the structures 8 and 9, respectively. 

A close biogenetic relationship to ergoline alkaloids can be easily recognized in the case of cyclopiazonic acid (269-271) and its imine and bisse-codehydro derivatives (272,273) (Fig. 21), which were isolated from P. cyclopium and A. versicolor. 

A. versicolor cyclopiazonic acid, bis-secodehydrocyclopiazonic acid, imine cyclopiazonic acid Ohmrtmo et al. (1973)... 

P. cyclopium cyclopiazonic acid, bi ss ecodehyd rocyclo-piazonic acid, imine cyclopiazonic acid Hermansen et al. (1984) Holzapfel (1968) Holzapfel (1970)... 

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