Aspergillazines A-E: novel heterocyclic dipeptides from an Australian strain of Aspergillus unilateralis

Capon, R. J., Ratnayake, R., Stewart, M., Lacey, E., Tennant, S. and Gill, J. H. (2005) Aspergillazines A-E: novel heterocyclic dipeptides from an Australian strain of Aspergillus unilateralis. Organic & Biomolecular Chemistry, 3 1: 123-129. doi:10.1039/b413440k


Author Capon, R. J.
Ratnayake, R.
Stewart, M.
Lacey, E.
Tennant, S.
Gill, J. H.
Title Aspergillazines A-E: novel heterocyclic dipeptides from an Australian strain of Aspergillus unilateralis
Journal name Organic & Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
Publication date 2005
Sub-type Article (original research)
DOI 10.1039/b413440k
Open Access Status Not Open Access
Volume 3
Issue 1
Start page 123
End page 129
Total pages 7
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2005
Language eng
Abstract Biological and chemical pro ling of an Australian strain of the fungus Aspergillus unilateralis (MST-F8675), isolated from a soil sample collected near Mount Isa, Queensland, revealed a complex array of metabolites displaying broad chemotherapeutic properties. Noteworthy among these metabolites were a unique series of highly modified dipeptides aspergillazines A-E, incorporating a selection of unprecedented and yet biosynthetically related heterocyclic systems. Co-occurring with the aspergillazines was the recently described marine-derived fungal metabolite trichodermamide A (cf. penicillazine), whereas re-fermentation of A. unilateralis in NaCl (1%) enriched media resulted in co-production of the only other known example of this structure class, the marine-derived fungal metabolite trichodermamide B. Further investigation of A. unilateralis returned the known terrestrial fungal metabolite viridicatumtoxin as the cytotoxic and antibacterial principle, together with E-2-decenedioic acid, ferulic acid, (7E,7'E)-5,5'-diferulic acid and (7E,7'E)-8,5'-diferulic acid. The aromatic diacids have previously been reported from the chemical and enzymatic (esterase) treatment of plant cell wall material, with their isolation from A. unilateralis being their first apparent reported occurrence as natural products. Structures for all metabolites were determined by detailed spectroscopic analysis and, where appropriate, comparison to literature data and/or authentic samples.
Keyword Chemistry, Organic
Penicillium Sp
Viridicatumtoxin
Toxin
Acid
Q-Index Code C1

 
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Created: Wed, 15 Aug 2007, 06:27:43 EST