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Research Project: Fungal Endophytes of Maize: Gene Products Conferring Resistance to Aflatoxin and Fumonisin

Location: Mycotoxin Research

Title: Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor

Authors
item Greshock, Thomas - COLORADO STATE UNIV
item Grubbs, Alan - COLORADO STATE UNIV
item Jiao, Ping - UNIVERSITY OF IOWA
item Wicklow, Donald
item Gloer, James - UNIVERSITY OF IOWA
item Williams, Robert - COLORADO STATE UNIV

Submitted to: Angewandte Chemie
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 22, 2008
Publication Date: April 3, 2008
Citation: Greshock, T.J., Grubbs, A.W., Jiao, P., Wicklow, D.T., Gloer, J.B., Williams, R.M. 2008. Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor. Angewandte Chemie. 47(19):3573-3577.

Interpretive Summary: Fungi that parasitize and kill other fungi offer a potential source of novel antifungal agents useful to agriculture and medicine. The fungus Aspergillus versicolor NRRL 35600, encountered as a colonist of a wood decay fungus in Hawaii, was examined for its ability to produce antifungal agents and other bioactive metabolites. Versicolamide B is reported as new metabolite belonging to a family of alkaloids known for its myriad of biological activities. The total synthesis of versicolamide B is reported and the implications of its rare stereochemistry are discussed.

Technical Abstract: A new prenylated indole alkaloid, versicolamide B, was isolated from cultures of Aspergillus versicolor NRRL 35600. The structure was assigned by 2D NMR data, and confirmed by a biomimetic total synthesis. Versicolamide B is the first member of the paraherquamide-stephacidin family of alkaloids found to possess the anti-relative stereochemistry at C19. Ent-Stephacidin A and ent-notoamide B were also isolated for the first time from these cultures.

   

 
Project Team
Wicklow, Donald
Kendra, David
Naumann, Todd
Brown, Daren
 
Publications
   Publications
 
Related National Programs
  Food Safety, (animal and plant products) (108)
 
Related Projects
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   New Biologically Active Natural Products from Fungi
 
 
Last Modified: 05/13/2009
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