Auramycins and sulfurmycins,new anthracycline antibiotics: Characterization of aglycones,auramycinone and sulfurmycinone.

The Journal of Antibiotics
1981.0

Abstract

In the screening for new antitumor anthracycline antibiotics, anthracycline glycosides with novel aglycones were isolated from Streptomyces sp. OBB-111 (classified as S. galilaeus), a strain isolated from a soil sample in Bayern, West Germany. The strain was cultured in a medium containing glucose, soluble starch, S-3 meat, yeast extract, K₂HPO₄, MgSO₄·7H₂O, NaCl, and CaCO₃, with shaking at 180 rpm and 27°C for 7 days. Yellow antibiotics were extracted using a chloroform-methanol (1:1) mixture and recovered in the chloroform layer. Crude extracts contained multiple components, with major ones identified as aclacinomycin A, B, and their analogues (MA144-M1, -N1, -S1, -T1). Mass fragmentation analysis revealed anthracyclines with two distinct aglycones, named auramycins and sulfurmycins. Hydrolysis of the glycosides yielded the aglycones aklavinone, auramycinone, and sulfurmycinone. Auramycinone (C₂₁H₁₈O₈) exhibited a melting point (m.p.) of 153.5°C, a specific rotation ([α]²⁰ᴰ) of -178° (c 0.1, CHCl₃), and elemental analysis consistent with its molecular formula. Sulfurmycinone (C₂₃H₂₀O₉) had a m.p. of 159°C, [α]ᴰ of +232.2° (c 0.1, CHCl₃), and matching elemental analysis. Chromatographic (HPLC, TLC), UV, IR, ¹H-NMR, and ¹³C-NMR data indicated auramycinone possesses a methyl group at C-9 (replacing the ethyl group in aklavinone), while sulfurmycinone contains an additional carbonyl group and an acetonyl side chain at C-9. The absolute configuration at C-7, C-9, and C-10—determined via ORD and CD spectra—matched that of aklavinone. Auramycinone and sulfurmycinone are unique anthracycline aglycones: auramycinone has a methyl group at C-9, sulfurmycinone an acetonyl group, and both bear a carbomethoxy group at C-10, distinguishing them from known anthracycline aglycones.

Knowledge Graph

Similar Paper

Auramycins and sulfurmycins,new anthracycline antibiotics: Characterization of aglycones,auramycinone and sulfurmycinone.
The Journal of Antibiotics 1981.0
New anthracycline antibiotics, auramycins and sulfurmycins. I. Isolation and characterization of auramycins A and B, and sulfurmycins A and B.
The Journal of Antibiotics 1982.0
New anthracycline antibiotics, 1-hydroxyauramycins and 1-hydroxysulfurmycins.
The Journal of Antibiotics 1981.0
New anthracycline antibiotics, auramycins and sulfurmycins. II. Isolation and characterization of 10 minor components (C-G).
The Journal of Antibiotics 1982.0
New anthracycline antibiotics, auramycins and sulfurmycins. II. Isolation and characterization of 10 minor components (C-G).
The Journal of Antibiotics 1982.0
Antitumor anthracycline antibiotics, aclacinomycin A and analogues. II. Structural determination.
The Journal of Antibiotics 1979.0
Antitumor anthracycline antibiotics, aclacinomycin A and analogues. I. Taxonomy, production, isolation and physicochemical properties.
The Journal of Antibiotics 1979.0
Aurantimycins, New Depsipeptide Antibiotics from Streptomyces aurantiacus IMET 43917 Production, Isolation, Structure Elucidation, and Biological Activity.
The Journal of Antibiotics 1995.0
Biosynthesis of anthracycline antibiotics by Streptomyces galilaeus. II. Structure of new anthracycline antibiotics obtained by microbial glycosidation and biological activity.
The Journal of Antibiotics 1980.0
MICROBIAL CONVERSION OF ANTHRACYCLINE ANTIBIOTICS I. MICROBIAL CONVERSION OF ACLACINOMYCIN BTO ACLACINOMYCIN A
The Journal of Antibiotics 1983.0