Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. II. Structure elucidation of purpactins A, B and C.
The structure of purpactins, novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors, was determined by spectroscopic analyses. Purpactin A was deduced to be 3-1'-acetoxy-11-hydroxy-4-methoxy-9-methyl-3'-methylbutyl-5H, 7H-dibenzo[b,g]-1,5-dioxocin-5-one, purpactin B was 5-1''-acetoxy-6'-hydroxymethyl-4-methoxy-4'-methyl-3''-methylbutyl-spiro [benzofuran-2,1'-cyclohexa-3',5'-diene]-2',3(2H)-dione and purpactin C was 5-1''-acetoxy-6'-formyl-4-methoxy-4'-methyl-3''-methylbutyl-spiro [benzofuran-2,1'-cyclohexa-3',5'-diene]-2',3(2H)-dione. Purpactin A was attributed to 1'-O-acetylpenicillide.
Nishida
H
H
Research Center for Biological Function, Kitasato Institute, Tokyo, Japan.
Tomoda
H
H
Cao
J
J
Okuda
S
S
Omura
S
S
D001572:Benzofurans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D008970:Molecular Weight; D002785:Sterol O-Acyltransferase / Q000037:antagonists & inhibitors*
D001572:Benzofurans; D006571:Heterocyclic Compounds; D006575:Heterocyclic Compounds, 3-Ring; C068086:purpactin A; C068087:purpactin B; C068088:purpactin C; D002785:Sterol O-Acyltransferase