STRUCTURAL ELUCIDATION OF ACULEXIMYCIN I. FURTHER PURIFICATION AND GLYCOSIDIC BOND CLEAVAGE OF ACULEXIMYCIN

• Published in: Journal of antibiotics Vol. 42; no. 5; pp. 691 - 700
• Main Authors: MURATA, HIDEAKI, KOJIMA, NORIKO, HARADA, KEN-ICHI, SUZUKI, MAKOTO, IKEMOTO, TAKAYA, SHIBUYA, TOSHIRO, HANEISHI, TATSUO, TORIKATA, AKIO
• Format: Journal Article
• Language: English
• Published: Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1989; Japan Antibiotics Research Association
• Subjects: Actinomycetales - metabolism; Aminoglycosides; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - metabolism; Biological and medical sciences; Bridged Bicyclo Compounds; Bridged Bicyclo Compounds, Heterocyclic; Chemical Phenomena; Chemistry, Physical; Chromatography; Chromatography, High Pressure Liquid; Glycosides; Insecticides; Macrolides; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Molecular Weight; Pesticides, fertilizers and other agrochemicals toxicology; Spectrophotometry; Streptosporangium albidum; Toxicology; Binding; Insecticide; Molecular structure; Streptosporangium; Pesticides; NMR spectrometry; Actinomycetales; Antibiotic; Production; Bacteria; Isolation; Actinomycetes; Glycoside; Actinoplanaceae
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.42.691

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 l, 8-diazabicyclo[5, 4, 0]undecene-7 caused a glycosidic bond cleavage to give aculexitriose, pseudoaglycones I and II.