SF2809 compounds, novel chymase inhibitors from Dactylosporangium sp. 2. Structural elucidation.
Novel chymase inhibitors, SF2809-I, II, III, IV, V and VI, were isolated from the fermentation broth of Dactylosporangium sp. SF2809, and their structures were determined by spectroscopic analyses. SF2809 compounds commonly contain a substituted indole moiety and a quinolinone moiety. The two moieties are connected to a methylene carbon in SF2809-I and III. The other compounds, SF2809-II, IV, V and VI, have an additional moiety, a p-hydroxyphenyl group or a phenyl group. In these compounds, all of three moieties are connected to a methine carbon. Furthermore, studies concerning the stereochemistry of SF2809-V revealed that the isolated compound was racemic, and the isomer possessing (R)-configuration was about thirty times more potent than another isomer.
Tani
Masato
M
Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd. Morooka-Cho 760, Kohoku-Ku, Yokohama 222-8567, Japan. masato_tani@meiji.co.jp
Harimaya
Kenzo
K
Gyobu
Yasuhiro
Y
Sasaki
Toru
T
Takenouchi
Osami
O
Kawamura
Takashi
T
Kamimura
Takashi
T
Harada
Toshiaki
T
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D053818:Chymases; D018360:Crystallography, X-Ray; D006868:Hydrolysis; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008970:Molecular Weight; D015363:Quinolones / Q000737:chemistry*; D012697:Serine Endopeptidases / Q000378:metabolism*; D015842:Serine Proteinase Inhibitors / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D007211:Indoles; D015363:Quinolones; D015842:Serine Proteinase Inhibitors; D012697:Serine Endopeptidases; D053818:Chymases