Streptomyces refuineus

Anthramycin is a benzodiazepine alkaloid with potent antitumor and antibiotic activity produced by the thermophilic actinomycete Streptomyces refuineus sbsp. thermotolerans. Using a genome-scanning approach, the biosynthesis was found to involve condensation of 4 methyl-3-hydroxy anthranilic acid 136 and a... 

Anthramycin (95), produced by Streptomyces refuineus [171], is active in vivo against sarcome 180, Ehrlich solid and Ehrlich ascites carcinomas, Waker 256 carcinosarcoma and human epithelioma no. 3 [172]. As mentioned before, anthramycin (95) inhibits nucleic acid synthesis through covalent attachment via Cl 1 to DNA at N2 of guanidine [173]. The right-handed twist of anthramycin (95) allows it to fit entirely within the minor groove of DNA [174]. Its synthesis has been carried out by two groups [170,175],... 

Anthramycin.—The aromatic ring of tyrosine suffers minor modification on incorporation into securinine (see above) whilst utilization in betalain biosynthesis results in ring cleavage between C-3 and C-4 after hydroxylation to dopa (see below). Similar degradation of tyrosine occurs in the biosynthesis of anthramycin (166), an antibiotic produced by Streptomyces refuineus. var thermotolerans. ... 

Anthramycin is an antibiotic with antitumor activity. It is isolated from the growth of Streptomyces refuineus. Anthramycin (3.36) is unique in having the 7-membered azepine ring (partially reduced) present, fused to a pyrroline ring (a dihydropyrrole). 

The broth of Streptomyces refuineus has afforded the antibiotic anthramycin (XXVIIIa) with antitumour activity. The constitution of the compound was established by spectroscopic methods [I32J. It has been synthesised [133] from V-benzoyloxy-4-methyl-2-nitrobenzoyl-L-hydroxyproline methyl ester... 

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