Biosynthesis of antitumor antibiotic, cytogenin. 1994

H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
Institute for Chemotherapy, M.C.R.F., Shizuoka, Japan.

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.

UI MeSH Term Description Entries
D008715 Methionine A sulfur-containing essential L-amino acid that is important in many body functions. L-Methionine,Liquimeth,Methionine, L-Isomer,Pedameth,L-Isomer Methionine,Methionine, L Isomer
D008745 Methylation Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed) Methylations
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D011355 Prodrugs A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. Drug Precursor,Drug Precursors,Pro-Drug,Prodrug,Pro-Drugs,Precursor, Drug,Precursors, Drug,Pro Drug,Pro Drugs
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D003374 Coumarins Synthetic or naturally occurring substances related to coumarin, the delta-lactone of coumarinic acid. 1,2-Benzopyrone Derivatives,1,2-Benzopyrones,Coumarin Derivative,Coumarine,1,2-Benzo-Pyrones,Benzopyran-2-ones,Coumarin Derivatives,Coumarines,1,2 Benzo Pyrones,1,2 Benzopyrone Derivatives,1,2 Benzopyrones,Benzopyran 2 ones,Derivative, Coumarin,Derivatives, 1,2-Benzopyrone,Derivatives, Coumarin
D003470 Culture Media Any liquid or solid preparation made specifically for the growth, storage, or transport of microorganisms or other types of cells. The variety of media that exist allow for the culturing of specific microorganisms and cell types, such as differential media, selective media, test media, and defined media. Solid media consist of liquid media that have been solidified with an agent such as AGAR or GELATIN. Media, Culture
D006900 Hydroxylation Placing of a hydroxyl group on a compound in a position where one did not exist before. (Stedman, 26th ed) Hydroxylations
D000085 Acetates Derivatives of ACETIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxymethane structure. Acetate,Acetic Acid Esters,Acetic Acids,Acids, Acetic,Esters, Acetic Acid
D000903 Antibiotics, Antineoplastic Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. Antineoplastic Antibiotics,Cytotoxic Antibiotics,Antibiotics, Cytotoxic

Related Publications

H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
February 1995, The Journal of antibiotics,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
November 1990, The Journal of antibiotics,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
May 2009, Applied and environmental microbiology,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
January 1989, Journal of natural products,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
August 2002, Science (New York, N.Y.),
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
January 1985, Biochemistry,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
March 1998, The Journal of antibiotics,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
April 1983, The Journal of antibiotics,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
September 1979, Biochemistry,
H Kumagai, and M Amemiya, and H Naganawa, and T Sawa, and M Ishizuka, and T Takeuchi
January 2022, Frontiers in bioengineering and biotechnology,
Copied contents to your clipboard!