New anthracycline glycosides from Micromonospora. II. Isolation, characterization and biological properties.

Abstract

Four glycosides, designated A, B, C and D, are the main components of the anthracyclinc complex produced by cultures of Micromonospora sp. nov. They were extracted by solvent partition, separated by column chromatography and characterized by chemical and physical met-lods as I 1-deoxy analogues of daunorubicin. Among these new anthracyclines, displaying antibacterial and cytotoxic activity in vitro, l I-deoxydaunorubicin and 11-deoxydoxorubicin are also active against P388 leukemia in mice.

A comprehensive review of glycosylated bacterial natural products

“…18 Regiospecificity of O-glycosylation among these metabolites is restricted to the 4-and 6-positions of the phenazine ring as well as the less common glycosyl esters which occur at a phenazine 6-carboxylic acid. Only three sugars were observed among the corresponding glycosides where a-L-quinovose (194) and b-L-quinovose (297), a sugar common to saponin glycosides, 1125 were found as sugars with free reducing termini attached as sugar 2 0 /or 3 0 -esters of the phenazine C6-carboxylic acid [phenazine a-L-quinovose 2 0 -ester (194, C-6), phenazine a-L-quinovose 3 0 -ester (194, C-6), phenazine b-L-quinovose 2 0 -ester (297, C-6) and phenazine b-L-quinovose 3 0 -ester (297, C-6)] in metabolites of a marine Streptomyces. 1126 The remaining glycosylated phenazines (aestivophoenins A-C, 1127,1128 izuminosides A-C, 1129 and phenazoviridin [1130][1131][1132] from Streptomyces) are mono-glycosylated with a-L-rhamnose (46) at the phenazine C-4-or C-6-position, or as anomeric glycosyl esters of the phenazine 6-carboxylic acid similar to that described above (Fig.…”

The genus Micromonospora as a model microorganism for bioactive natural product discovery

“…120 Recently in 2018, further rakicidin analogues (E and G-I) (141-144) were recovered from the marine M. chalcea FIM 02-523. 121 In 1997, a novel bioactive depsipeptide, thiocoraline (145), was characterized from the culture broth of a marine Micromonospora strain. This unique compound showed exceptional cytotoxicity against a panel of cancer cell lines (IC 50 0.002 mg mL À1 ) and strong antibacterial activity against Gram-positive bacteria (MIC 0.03 mg mL À1 ).…”

“…This metabolite exhibited antibacterial activity against both Grampositive and Gram-negative bacteria with MIC values range 0. 145 Later, a unique antitumor nitroanthracycline analog, cororubicin (169) derived from a marine Micromonospora strain, was able to inhibit the growth of many cancer cell lines (IC 50 0.8-4 mg mL À1 ) by generating intracellular active superoxide radicals. 146 From the endophytic strain M. lupini, two new anthraquinones lupinacidins A and B (170, 171) were isolated.…”

Genetic improvement of processes yielding microbial products

“…New anthracyclines and aglycones have been isolated from blocked mutants of the daunorubicin and doxorubicin producers (Cassinelli et al , 1980; McGuire et al , 1981). By adding carminomycinone or 13‐dihydrocarminomycinone to an idiotroph of Streptomyces galilaeus (the producer of aclacinomycin), the aglycones were glycosylated to form a new trisaccharide anthracycline, trisarubicionol (Yoshimoto et al , 1981).…”