Abstract
Three new azaphilones, chaetomugilin S (1), 7,5'-bis-epi-chaetoviridin A (2), and 7-epi-chaetoviridin E (3), and two new chlorinated phenolic glycosides, globosumoside A (4) and globosumoside B (5), were isolated from the crude extract of the fungal strain Chaetomium elatum No. 89-1-3-1. Their structures were determined by detailed NMR and MS spectroscopic analyses. The absolute configurations of C-7 in chaetomugilin S (1), 7,5'-bis-epi-chaetoviridin A (2), and 7-epi-chaetoviridin E (3) were assigned by CD experiments, and the absolute configurations of 1 and 2 were established by X-ray crystallography. Compounds 1-3 are the first examples of 7R-configurated azaphilones with a chlorinated isochromen from Chaetomium spp. In addition, compounds 1-3 showed inhibitory activity in the cysteine aspartyl-specific protease-3 (caspase-3) enzymatic assay, with IC₅₀ values of 20.6, 10.9, and 7.9 µM, respectively.
Georg Thieme Verlag KG Stuttgart · New York.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Benzopyrans / chemistry
-
Benzopyrans / isolation & purification
-
Benzopyrans / pharmacology*
-
Caspase 3 / drug effects
-
Caspase Inhibitors / chemistry
-
Caspase Inhibitors / isolation & purification
-
Caspase Inhibitors / pharmacology*
-
Cell Extracts / chemistry
-
Cell Extracts / isolation & purification
-
Cell Extracts / pharmacology*
-
Chaetomium / chemistry*
-
Crystallography, X-Ray
-
Glycosides / chemistry
-
Glycosides / isolation & purification
-
Glycosides / pharmacology*
-
Halogenation
-
Inhibitory Concentration 50
-
Magnetic Resonance Spectroscopy
-
Medicine, Chinese Traditional
-
Models, Molecular
-
Molecular Structure
-
Phenols / chemistry
-
Phenols / isolation & purification
-
Phenols / pharmacology*
-
Pigments, Biological / chemistry
-
Pigments, Biological / isolation & purification
-
Pigments, Biological / pharmacology*
-
Recombinant Proteins
Substances
-
Benzopyrans
-
Caspase Inhibitors
-
Cell Extracts
-
Glycosides
-
Phenols
-
Pigments, Biological
-
Recombinant Proteins
-
azaphilone
-
Caspase 3