Hispidospermidin, a novel phospholipase C inhibitor produced by Chaetosphaeronema hispidulum (Cda) Moesz NR 7127. II. Isolation, characterization and structural elucidation.
Hispidospermidin (1) is a novel phospholipase C inhibitor produced by Chaetosphaeronema hispidulum (Cda) Moesz NR 7127. Its structure (C25H47N3O) has been elucidated as a cage compound with a trimethylspermidine side chain based on various NMR studies, including 1H-1H COSY, 13C-1H COSY, HOHAHA, HMBC, COLOC and long range J C-H resolved 2D spectroscopy. The absolute configuration of 1 has been elucidated by modified Mosher's method on the (R)- and (S)-MTPA amides of a derivative of 1.
Ohtsuka
T
T
Nippon Roche Research Center, Kamakura, Japan.
Itezono
Y
Y
Nakayama
N
N
Sakai
A
A
Shimma
N
N
Yokose
K
K
Seto
H
H
D002597:Chaetomium / Q000378:metabolism*; D011083:Polycyclic Compounds / Q000737:chemistry* / Q000302:isolation & purification*; D013095:Spermidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D010738:Type C Phospholipases / Q000037:antagonists & inhibitors*
D011083:Polycyclic Compounds; C086148:hispidospermidin; D010738:Type C Phospholipases; D013095:Spermidine