Xanthoascin
Application Notes
Xanthoascin is a member of the rare class of isocyanides related to xanthocillin. Xanthoascin was first reported from Aspergillus candidus by Takahashi and coworkers in 1976. Structually, xanthoascin is derived from two molecules of tyrosine where the amine groups are enzymatically transformed into isocyano functionalities and one aromatic ring prenylated, subsequently undergoing an intramolecular cyclisation. Xanthoascin is a potent antibacterial, altering the permeability of the cell membrane and leading to cell leakage. Xanthoascin is also active against tumor cell lines but has been reported to cause severe toxicity in in vivo studies.
References
- Ohtsubo H. et al. (1976). Hepato- and cardiotoxicity of xanthoascin, a new metabolite of A. candidus Link, to mice. I. Blood chemistry and histological changes in mice. Jpn. J. Exp. Med., 46, 277.
- Takahashi C. et al. (1976). The structures of toxic metabolites of Aspergillus candidus. II. The compound B (xanthoascin), a hepato- and cardio-toxic xanthocillin analog. Chem. Pharm. Bull., 24, 2317.
- Zhang W. et al. (2015). Natural phenolic metabolites from endophytic Aspergillus sp. IFB-YXS with antimicrobial activity. BMCL, 25, 2698.