R. P. Maskey, I. Grün-wollny, H. Laatsch
May 24, 2005
Citations
2
Influential Citations
71
Citations
Quality indicators
Journal
Journal of natural products
Abstract
In our screening of microorganisms for new natural products, the fungus Penicillium notatum delivered further members of the sorbicillin family, namely, the sohirnones A [3, 1-(2,4-dihydroxy-5-methylphenyl)hex-4-en-1-one], B [4a, 1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hexa-2,4-dien-1-one], and C [5, 1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hex-4-en-1-one]. A stable tautomer of oxosorbicillinol (7) was characterized as 6, and the recently described 7-deacetoxyyanuthone (8) was reisolated. The additionally isolated rezishanones A-D (12-13c) are the first natural Diels-Alder products of sorbicillinol (1) with dienophiles not related with 1. The monomers and dimers showed weak antibacterial activity, but were inactive against fungi and algae. The structures were determined by spectroscopic methods and by comparison of the NMR data with those of the structurally related 2',3'-dihydrosorbicillin (2) and, in the case of 4a, by transformation into the known sorrentanone (4b).