Structure of fredericamycin A, an antitumor antibiotic of a novel skeletal type; spectroscopic and mass spectral characterization.
IR, UV-visible spectroscopy, circular dichroism, 1H and 13C NMR studies, high resolution electron impact, field desorption, and fast atom bombardment mass spectral studies are reported for fredericamycin A (NSC-305263), a novel antitumor antibiotic of acid-base indicator type produced by Streptomyces griseus (FCRC-48). The spectral data are correlated with the structure obtained by X-ray crystallography as (E,E)-6',7'-dihydro-4,9,9'-trihydroxy-6-methoxy-3'-(1,3-pentadienyl++ +)-spiro- [2H-benz[f]indene-2,8'-[8H]-cyclopent-[g]-isoquinoline]-1,1', 3,5,8(2'H)-pentone. The novel spiro ring antibiotic exhibits unusual 1H and 13C NMR spectroscopic and chemical behavior, not previously observed in other antibiotic structures.
D000107:Acetylation; D000903:Antibiotics, Antineoplastic; D055598:Chemical Phenomena; D002621:Chemistry; D002942:Circular Dichroism; D003460:Crystallization; D007546:Isoquinolines; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013141:Spiro Compounds; D013305:Streptomyces griseus / Q000378:metabolism*
D000903:Antibiotics, Antineoplastic; D007546:Isoquinolines; D013141:Spiro Compounds; C016660:fredericamycin A