Isolation and structure determination of novel phosphatidylinositol turnover inhibitors, piericidin B5 and B5 N-oxide, from Streptomyces sp.
In the course of a screening program for inhibitors of epidermal growth factor (EGF)-induced phosphatidylinositol turnover in human epidermoid carcinoma cell line A431, we discovered two novel compounds of the piericidin family from the culture broth and mycelia of a Streptomyces strain MJ288-OF3. We named them piericidin B5 and B5 N-oxide. By NMR and mass spectrometric analyses, the molecular formulas of piericidin B5 and B5 N-oxide were determined to be C27H41NO4 (MW 443) and C27H41NO5 (MW 459), respectively. Piericidin B5 and B5 N-oxide inhibited phosphatidylinositol turnover of A431 cells with IC50S of 10.0 micrograms/ml and 1.1 micrograms/ml, respectively.
Institute of Microbial Chemistry, Tokyo, Japan.
H
H
Nishioka
T
T
Sawa
Y
Y
Takahashi
H
H
Naganawa
M
M
Hamada
T
T
Takeuchi
K
K
Umezawa
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003497:Cyclic N-Oxides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005285:Fermentation; D008826:Microbial Sensitivity Tests; D010716:Phosphatidylinositols / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011725:Pyridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D003497:Cyclic N-Oxides; D010716:Phosphatidylinositols; D011725:Pyridines; C081410:piericidin B5; C081411:piericidin B5 N-oxide