The Anthracyclinic Complex Retamycin, 1. Structure Determination of the Major Constituents

Bieber, Lothar W.; Filho, Álvaro A. Da Silva; Silva, Ely C.; Mello, J. F. De; Lyra, Franciso D. A.; Nascimento, Márcia Silva do; Botta, Bruno; Angelis, Francesco De

doi:10.1021/np50062a029

Cited by 14 publications

(12 citation statements)

References 7 publications

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“…These compounds are produced by Streptomyces olindensis originally described as a producer of an anthracycline complex called retamycin (Gonçalves de Lima et al 1969). It was initially proposed that retamycin consisted of a γ-rhodomycinone aglycone with a trisaccharide attached at 10-position (Bieber et al 1989). However, more recently, we have verified that some of the compounds of the retamycin complex have the same structure of some cosmomycins (Furlan et al 2004).…”

Section: Introductionmentioning

confidence: 58%

Insights in the glycosylation steps during biosynthesis of the antitumor anthracycline cosmomycin: characterization of two glycosyltransferase genes

Garrido

Lombó

Baig

et al. 2006

Appl Microbiol Biotechnol

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Glycosylation pattern in cosmomycins is a distinctive feature among anthracyclines. These antitumor compounds possess two trisaccharide chains attached at C-7 and C-10, each of them with structural variability, mainly at the distal deoxysugar moieties. We have characterized a 14-kb chromosomal region from Streptomyces olindensis containing 13 genes involved in cosmomycin biosynthesis. Two of the genes, cosG and cosK, coding for glycosyltransferase were inactivated with the generation of five new derivatives. Structural elucidation of these compounds showed altered glycosylation patterns indicating the capability of both glycosyltransferases of transferring deoxysugars to both sides of the aglycone and the flexibility of CosK with respect to the deoxysugar donor. A model is proposed for the glycosylation steps during cosmomycins biosynthesis.

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Section: Introductionmentioning

confidence: 58%

Insights in the glycosylation steps during biosynthesis of the antitumor anthracycline cosmomycin: characterization of two glycosyltransferase genes

Garrido

Lombó

Baig

et al. 2006

Appl Microbiol Biotechnol

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“…Hence, in the present work, image analysis techniques were applied to characterize the morphology of Streptomyces olindensis in submerged culture, which is a good producer of the antibiotic retamycin, an anthracyclin complex with high antitumour activity (2). The morphology was classified into four classes: pellets, clumps (or entangled filaments), branched, and unbranched free filaments (9), through a criterion developed to classify the microorganism into these classes, based on its dimensions (perimeter and convex perimeter).…”

Section: Introductionmentioning

confidence: 99%

Applications of image analysis in the characterization of Streptomyces olindensis in submerged culture

Pamboukian¹,

Guimarães²,

Facciotti³

2002

Braz. J. Microbiol.

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The morphology of Streptomyces olindensis (producer of retamycin, an antitumor antibiotic) grown in submerged culture was assessed by image analysis. The morphology was differentiated into four classes: pellets, clumps (or entangled filaments), branched and unbranched free filaments. Four morphological parameters were initially considered (area, convex area, perimeter, and convex perimeter) but only two parameters (perimeter and convex perimeter) were chosen to automatically classify the cells into the four morphological classes, using histogram analysis. Each morphological class was evaluated during growth carried out in liquid media in fermenter or shaker. It was found that pellets and clumps dominated in early growth stages in fermenter (due to the inoculum coming from a shaker cultivation) and that during cultivation, the breakage of pellets and clumps caused an increase in the percentage of free filaments. The criteria of morphological classification by image analysis proposed were useful to quantify the percentage of each morphological class during fermentations and may help to establish correlations between antibiotic production and microorganism morphology.

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“…Anthracyclines are potent antitumoral agents synthesized by streptomycetes through the polyketide pathway (3). Polyketides constitute a large group of complex natural products with great structural diversity (4,5).…”

Section: Introductionmentioning

confidence: 99%

“…acetyl-CoA, propionyl-CoA, malonyl-CoA) (5). Daunorubicin polyketide synthase (PKS) is primed with propionyl-CoA and uses malonyl-CoA as elongation unit (3).…”

Section: Introductionmentioning

confidence: 99%

Carbon catabolite repression of retamycin production by Streptomyces olindensis ICB20

Inoue¹,

Netto²,

Padilla³

et al. 2007

Braz. J. Microbiol.

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Retamycin is an anthracyclinic antitumoral complex produced by Streptomyces olindensis ICB20. In this work the influence of different glucose concentrations in the feed medium on the production of retamycin was studied. Chemostat cultures employing glucose concentration varying between 10 g/L and 25 g/L showed that use of high glucose concentration resulted in catabolite repression of the biosynthesis of the antitumoral. The highest specific retamycin production rate, qRTM = 7.8 mg/g.h, was obtained when glucose concentration was 10 g/L. The lowest value of qRTM, 2.5 mg/g.h, was observed when glucose concentration was 20 and 25 g/L. The residual glucose concentration varied from 0 to 13 g/L, as the glucose concentration in the feed was increased from 10 to 25 g/L.

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The Anthracyclinic Complex Retamycin, 1. Structure Determination of the Major Constituents

Cited by 14 publications

References 7 publications

Insights in the glycosylation steps during biosynthesis of the antitumor anthracycline cosmomycin: characterization of two glycosyltransferase genes

Insights in the glycosylation steps during biosynthesis of the antitumor anthracycline cosmomycin: characterization of two glycosyltransferase genes

Applications of image analysis in the characterization of Streptomyces olindensis in submerged culture

Carbon catabolite repression of retamycin production by Streptomyces olindensis ICB20

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