Structural elucidation of aculeximycin. I. Further purification and glycosidic bond cleavage of aculeximycin.
A new insecticidal antibiotic, aculeximycin (ACM), was produced by an actinomycete identified as Streptosporangium albidum. ACM has been successfully isolated from culture filtrate by a combination of Diaion HP-20, Amberlite CG-50, reversed phase silica gel and Sephadex LH-20 chromatographies. It was found that ACM is a basic glycosidic antibiotic with a molecular weight of 1,672 including five monosaccharide units, three double bonds and a hemiketal ring by preliminary spectral analyses. Treatment of ACM with 1,8-diazabicyclo[5,4,0]undecene-7 caused a glycosidic bond cleavage to give aculexitriose, pseudoaglycones I and II.
Murata
H
H
Faculty of Pharmacy, Meijo University, Nagoya, Japan.
Kojima
N
N
Harada
K
K
Suzuki
M
M
Ikemoto
T
T
Shibuya
T
T
Haneishi
T
T
Torikata
A
A
D000192:Actinomycetales / Q000378:metabolism; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000378:metabolism; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002845:Chromatography; D002851:Chromatography, High Pressure Liquid; D006027:Glycosides; D007306:Insecticides; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008970:Molecular Weight; D013053:Spectrophotometry
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006027:Glycosides; D007306:Insecticides; D018942:Macrolides; C039610:aculeximycin; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene