Cottoquinazoline A and Cotteslosins A and B, Metabolites from an Australian Marine-Derived Strain of Aspergillus versicolor
- 26 February 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 72 (4), 666-670
- https://doi.org/10.1021/np800777f
Abstract
An Australian marine-derived isolate of Aspergillus versicolor (MST-MF495) yielded the known fungal metabolites sterigmatocystin, violaceol I, violaceol II, diorcinol, (-)-cyclopenol, and viridicatol, along with a new alkaloid, cottoquinazoline A (1), and two new cyclopentapeptides, cotteslosins A (2) and B (3). Structures for 1-3 and the known compounds were determined by spectroscopic analysis. The absolute configurations of 1-3 were addressed by chemical degradation and application of the C(3) Marfey's method. The use of "cellophane raft" high-nutrient media as a device for up-regulating secondary metabolite diversity in marine-derived fungi is discussed. The antibacterial properties displayed by A. versicolor (MST-MF495) were attributed to the phenols violaceol I, violaceol II, and diorcinol, while cotteslosins 2 and 3 were identified as weak cytotoxic agents.Keywords
This publication has 32 references indexed in Scilit:
- Acremolides A−D, Lipodepsipeptides from an Australian Marine-Derived Fungus, Acremonium sp.Journal of Natural Products, 2008
- Citromycetins and Bilains A–C: New Aromatic Polyketides and Diketopiperazines from Australian Marine-Derived and Terrestrial Penicillium spp.Journal of Natural Products, 2007
- Phenyl Ethers from Cultured Lichen Mycobionts of Graphis scripta var. serpentina and G. rikuzensisCHEMICAL & PHARMACEUTICAL BULLETIN, 2003
- Antifungal Metabolite with a New Carbon Skeleton from Keissleriella sp. YS4108, a Marine Filamentous FungusPlanta Medica, 2002
- A New Azaphilone, Falconensin H, from Emericella falconensis.CHEMICAL & PHARMACEUTICAL BULLETIN, 1993
- Structure determination of violaceol-I and -II, new fungal metabolites from a strain of Emericella violacea.CHEMICAL & PHARMACEUTICAL BULLETIN, 1982
- The isolation and structure determination of violaceic acid, a new biphenyl ether type metabolite from Emericella violacea.CHEMICAL & PHARMACEUTICAL BULLETIN, 1982
- Stoffwechselprodukte von Kiroorganismen, 171. Ethericin A; Isolierung, Charakterisierung und Strukturaufklärung eines neuen, antibiotisch wirksamen DiphenylethersEuropean Journal of Organic Chemistry, 1978
- A NEW METABOLITE, ASPERMUTARUBROL, FROM ASPERGILLUS SYDOWIChemistry Letters, 1978
- The biosynthesis of phenols—XVII : Some phenolic metabolites of mutant strains of Aspergillus regulosusPhytochemistry, 1968