Isolation and structure elucidation of vicenistatin M, and importance of the vicenisamine aminosugar for exerting cytotoxicity of vicenistatin.
A new analogue of vicenistatin was isolated from the producing strain Streptomyces sp. HC-34. A characteristic of the elucidated structure involved the existence of a neutral sugar mycarose instead of an aminosugar vicenisamine of vicenistatin. The absolute stereochemistry of the new analogue (named as vicenistatin M) was determined by the synthesis of D-mycarose and of vicenistatin M itself. Biological testing of vicenistatin M suggested the importance of vicenisamine for exerting the cytotoxicity of vicenistatin.
Matsushima
Y
Y
Department of Chemistry, Tokyo Institute of Technology, Japan.
Nakayama
T
T
Fujita
M
M
Bhandari
R
R
Eguchi
T
T
Shindo
K
K
Kakinuma
K
K
D000606:Amino Sugars / Q000737:chemistry / Q000494:pharmacology; D000617:Aminoglycosides; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D006601:Hexoses / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007769:Lactams / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000606:Amino Sugars; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D006027:Glycosides; D006601:Hexoses; D007769:Lactams; D018942:Macrolides; C427740:vicenistatin M; C082785:vicenistatin; C045835:mycarose