By Hartmut Laatsch, Serge Fotso (auth.), Karsten Krohn (eds.)
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Additional info for Anthracycline Chemistry and Biology I: Biological Occurence and Biosynthesis, Synthesis and Chemistry
They exhibited cytotoxic activity Naturally Occurring Anthracyclines 33a 33b 33c 33d 23 R1 R2 α-Roa α-Roa α-Roa β-Roa α-Me α-CH2 -COMe α-Et β-Et against leukemia L1210 cells and inhibited gram-positive and gram-negative bacteria . , the antimycobacterial nothramicin (34c) was reported, the reduced form of the 10-ketone 34a. 8 1,4,11- and 1,6,11-Trihydroxyanthracyclines Two aglycones were reported in the small group of 1,4,11-trihydroxylated anthracyclines, α2-rhodomycinone (35a) and δ-rhodomycinone (Fo 214).
To date, only the aglycone stefﬁmycinone (36a) 36a 36b 36c 36d R1 R2 H mRha 2,4-mRha 2,4-mRha O O O H, H Naturally Occurring Anthracyclines 25 and monoglycosylated derivatives such as stefﬁmycin A (36b), B (36c), and C (36d) have been isolated . In contrast to the stefﬁmycinone derivatives, the 2-hydroxyaklavinones have (9R)-ethyl groups at C-9 position. Compounds of the aclacinomycin group, such as 2-hydroxyaclacinomycin-A (37b), B (37c), and N (37d), were reported from S. galilaeus KE 303 (FERM-P 4808) [56, 57].
They may be, however, precursors of the unique nogarol group, which is described in Sect. 12. 9 2,4,6-Trihydroxyanthracyclines The small group of 2,4,6-trioxyanthracyclines is represented by the stefﬁmycinone (36a) derivatives and the 2-hydroxyaklavinone (37a) family. All stefﬁmycinones possess a carbonyl group at C-10 and a (9S)-methyl group with a stereochemistry opposite to that of “normal” anthracycline and anthracyclinone antibiotics. Another characteristic feature of this family is the presence of 2,8-dimethoxy groups.