Gephyromycin, the first bridged angucyclinone, from Streptomyces griseus strain NTK 14.
The new, highly oxygenated angucyclinone gephyromycin was isolated from an extract of a Streptomyces griseus strain. Its unprecedented ether-bridged structure was elucidated by NMR methods and substantiated by single crystal X-ray analysis. The absolute configuration was evidenced by quantum chemical CD calculations. Gephyromycin exhibits glutaminergic activity towards neuronal cells. Furthermore, the known compounds fridamycin E and dehydrorabelomycin were identified.
Bringmann
Gerhard
G
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Lang
Gerhard
G
Maksimenka
Katja
K
Hamm
Andreas
A
Gulder
Tobias A M
TA
Dieter
Anke
A
Bull
Alan T
AT
Stach
James E M
JE
Kocher
Niko
N
Müller
Werner E G
WE
Fiedler
Hans-Peter
HP
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002118:Calcium / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D008958:Models, Molecular; D015394:Molecular Structure; D009474:Neurons / Q000187:drug effects / Q000378:metabolism; D051381:Rats; D013305:Streptomyces griseus / Q000737:chemistry*
D000880:Anthraquinones; D001952:Bridged-Ring Compounds; C504085:gephyromycin; D002118:Calcium