Cinatrins, a novel family of phospholipase A2 inhibitors. I. Taxonomy and fermentation of the producing culture; isolation and structures of cinatrins.
Cinatrins A, B, C1, C2 and C3, a family of phospholipase A2 inhibitors were isolated from the fermentation broth of Circinotrichum falcatisporum RF-641. They were found to be novel spiro-gamma-dilactones and gamma-lactones derived from 1,2,3,5-tetra or 1,2,3(or 1,2,4)-trihydroxypentadecane-1,2,3-tricarboxylic acids. Structures were elucidated by MS and NMR studies and chemical transformations. The structure of cinatrin C3 was confirmed by X-ray crystallographic analysis, and its absolute configuration was determined by comparison of the CD spectra with related compounds.
Itazaki
H
H
Shionogi Research Laboratory, Shionogi & Co., Ltd., Osaka, Japan.
Nagashima
K
K
Kawamura
Y
Y
Matsumoto
K
K
Nakai
H
H
Terui
Y
Y
D002845:Chromatography; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005285:Fermentation; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D003904:Mitosporic Fungi / Q000145:classification / Q000378:metabolism*; D008968:Molecular Conformation; D015394:Molecular Structure; D010741:Phospholipases A / Q000037:antagonists & inhibitors*; D054467:Phospholipases A2; D012995:Solubility; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014961:X-Ray Diffraction
D007783:Lactones; C073567:cinatrin A; C073568:cinatrin B; C073569:cinatrin C1; C073570:cinatrin C2; C073571:cinatrin C3; D010741:Phospholipases A; D054467:Phospholipases A2