title: Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. III. Chemical modification of purpactin A.
abstract: Acylated derivatives of the C-1' and/or C-11 hydroxy group(s) of penicillide were synthesized and their inhibitory activity against acyl-CoA:cholesterol acyltransferase (ACAT) was studied. Introduction of long acyl group into either or both hydroxy residue(s) decreased the inhibitory activity. A small acyl moiety such as acetyl or n-butyryl at the C-1' hydroxy group is responsible for potent inhibitory activity against ACAT. The 1'-O-acetyl-11-O-tetrahydropyranyl derivative (11-O-2''-tetrahydropyranylpurpactin A) showed high selectivity (cytotoxic dose vs. effective dose) in a cell assay using J774 macrophages.
authors.affiliation: Research Center for Biological Function, Kitasato Institute, Tokyo, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Nishida
authors.forename: H
authors.initials: H
authors.lastname: Tomoda
authors.forename: J
authors.initials: J
authors.lastname: Cao
authors.forename: S
authors.initials: S
authors.lastname: Araki
authors.forename: S
authors.initials: S
authors.lastname: Okuda
authors.forename: S
authors.initials: S
authors.lastname: Omura
mesh_terms: D000818:Animals; D002460:Cell Line; D006571:Heterocyclic Compounds / Q000378:metabolism*; D006575:Heterocyclic Compounds, 3-Ring; D008264:Macrophages / Q000201:enzymology; D008862:Microsomes, Liver / Q000201:enzymology; D051381:Rats; D002785:Sterol O-Acyltransferase / Q000037:antagonists & inhibitors*
chemical_list: D006571:Heterocyclic Compounds; D006575:Heterocyclic Compounds, 3-Ring; C068086:purpactin A; D002785:Sterol O-Acyltransferase