Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. II. Structural elucidation.
Pleofungins (formerly called F-15078) A, B, C and D, novel depsipeptide antifungal antibiotics, were found in a mycelium extract of the producing fungus, Phoma sp. SANK 13899. The structures of pleofungins A, B, C and D were elucidated mainly by various NMR studies. The absolute configurations of the amino acids and N-methyl amino acids of pleofungin A constituents in the hydrolysate were determined by the application of advanced Marfey's method in combination with gas chromatography/mass spectrometry analysis of their silylation products with N-methyl-N-(tert-butylsilyl)trifluoroacetamide. Two alpha-hydroxy acid constituents, alpha-hydroxyisocaproic acid and alpha-hydroxyisovaleric acid, were isolated from the hydrolysate and their stereochemistries were determined by their specific rotations.
Aoyagi
Azusa
A
Core Technology Research Laboratories, Sankyo Co., Ltd., Hiromachi, Tokyo, Japan.
Yano
Tatsuya
T
Kozuma
Shiho
S
Takatsu
Toshio
T
D000089:Acetic Anhydrides / Q000737:chemistry; D000468:Alkalies; D001203:Ascomycota / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D047630:Depsipeptides / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D006602:Hexosyltransferases / Q000037:antagonists & inhibitors*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D000432:Methanol / Q000737:chemistry; D008745:Methylation; D008968:Molecular Conformation; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
D000089:Acetic Anhydrides; D000468:Alkalies; D047630:Depsipeptides; D004791:Enzyme Inhibitors; C031800:acetic anhydride; D006602:Hexosyltransferases; C088714:phosphatidylinositol-ceramide phosphoinositol transferase; D000432:Methanol