Biosynthesis of antitumor antibiotic, cytogenin.
The biosynthesis of antitumor antibiotic cytogenin, 3-hydroxymethyl-6-methoxy-8-hydroxy-isocoumarin, was studied by feeding 14C- or 13C-labeled compounds to culture of the producing organism, Streptoverticillium eurocidicum MI43-37F11. 14C-Acetate and 14C-methionine were efficiently incorporated into cytogenin as precursors. 13C NMR studies proved that the carbon skeleton of cytogenin is derived from pentaketide intermediate due to head-to-tail condensation of five acetate units and methyl group of 6-OCH3 is derived from methionine. It was suggested that 3-hydroxymethyl and/or 6-methoxy group of cytogenin were metabolized by hydroxylation and/or methylation from three intermediates.
Kumagai
H
H
Institute for Chemotherapy, M.C.R.F., Shizuoka, Japan.
Amemiya
M
M
Naganawa
H
H
Sawa
T
T
Ishizuka
M
M
Takeuchi
T
T
D000085:Acetates / Q000378:metabolism; D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000737:chemistry / Q000378:metabolism; D003470:Culture Media; D006900:Hydroxylation; D049934:Isocoumarins; D009682:Magnetic Resonance Spectroscopy; D008715:Methionine / Q000378:metabolism; D008745:Methylation; D011355:Prodrugs; D013056:Spectrophotometry, Ultraviolet; D013306:Streptomycetaceae / Q000378:metabolism*
D000085:Acetates; D000903:Antibiotics, Antineoplastic; D003374:Coumarins; D003470:Culture Media; D049934:Isocoumarins; D011355:Prodrugs; C066806:cytogenin; D008715:Methionine