The structure of the olivomycin-chromomycin antibiotics

Berlin, Yu. A.; Esipov, S. E.; Kolosov, M. N.; Shemyakin, M. M.

doi:10.1016/s0040-4039(01)99770-9

Cited by 35 publications

(17 citation statements)

References 3 publications

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“…Mithramycin 314 is the prototypical member of the aureolic acid family of antitumor antibiotics that also includes chromomycins, 323 olivomycins, 324–326 durhamycins, 327 SR1768A, 328 UCH9, 329,330 chromocyclomycin, 325,331 02-3D and 02-3G, 332 and variamycins 333,334 from Streptomyces and Actinoplanes as well as several other analogs ( e.g. , ketopremithramycins and ketomithramycins) 335 generated by pathway engineering.…”

Section: Anthracyclines Tetracyclines Quinones and Tricyclinesmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.

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Section: Anthracyclines Tetracyclines Quinones and Tricyclinesmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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“…1a) [11][12][13][14] . Nevertheless, the α,β-unsaturated ketone of D-ring is generally retained in the nal products except aureolic acid compounds including mithramycin [15][16][17][18] , whose scaffolds are formed via cleaving the D-ring of tetracycline precursors through Baeyer-Villiger oxidation (Supplementary Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

Characterization of Highly Reductive Modification of Tetracycline D-Ring Reveals Enzymatic Conversion of Enone to Alkane

Nie

et al. 2021

Preprint

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Tetracyclines are an eminent family of type II polyketides which possess a variety of decoration on the skeletons. However, apart from the oxidative modification in aureolic acid compounds, there are few cases on the further conversion of α, β-unsaturated ketones in the tetracycline D-ring. Here, we identified two reductases (TjhO5 and TjhD4) that highly reduced the α,β-unsaturated ketone of D-ring in the biosynthesis of unconventional tetracyclines. By identifying related intermediates and conducting isotope incorporation experiments, we demonstrated that the entire transformation could be accomplished by TjhO5 and TjhD4 collectively via two distinct pathways involving different enzymatic mechanisms. A distinctive deoxygenation mechanism was possibly involved in the TjhO5-mediated continuous reduction of C = O to CH2. These findings highlight the unprecedent post-modification of tetracyclines and facilitate further engineering to enrich the structural diversities.

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“…The active fraction with an UV profile λ max 230, 283, 315 and 420 nm and IR absorption bands at 3420 and 1730 cm -1 was determined to be a mixture of at least six components (1)(2)(3)(4)(5)(6) which exhibited properties characteristic of the aureolic acids group. Aureolic acids represent a family of antitumor antibiotics [6,7] that include mithramycin [8,9], olivomycins A and B, chromomycins A 2 and A 3 [10][11][12], UCH9 [13,14], and durhamycin A [15]. These compounds are glycosylated aromatic polyketides containing a tricyclic aglycone with an aliphatic side chain attached at C-3.…”

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confidence: 99%

The Antitumor Antibiotics Complex of Aureolic Acids from the Marine Sediment-associated Strain of Streptomyces sp. KMM 9048

Kalinovskaya

Romanenko

Kalinovsky

et al. 2017

Natural Product Communications

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A new antibiotic complex of six aureolic acids was isolated from the marine sediment-associated strain Streptomyces sp. KMM 9048. Four of the compounds (3-6) were found to be similar but not identical to the known chromomycins A 2 , A 3 , demethyl chromomycin A 3 and A 4. The two remaining compounds, A 2-1 (1) and A 3-1 (2), were established as novel chromomycin analogs, which did not contain sugar B. Spectroscopic methods including 1D and 2D NMR, and HRMS and MS/MS were applied for structure elucidation. Compounds 1-5 showed strong antimicrobial activity against Gram-positive indicatory bacteria Enterococcus faecium, Staphylococcus aureus, S. epidermidis, and Bacillus subtilis. Antitumor assay indicated that all tested compounds, in different manners, inhibited colony formation of RPMI-7951 and SK-Mel-28 cancer cells. This is the first study reporting the inhibitory effects of chromomycin analogs 1-5 on the colony formation of the investigated cancer cell lines. Compound 3, in a concentration of 5 nM, inhibited colony formation of RPMI-7951 and SK-Mel-28 cells by 82 % and 72 %, respectively. Our finding indicated that, of the compounds tested, 3 and 4 are promising anticancer and antimicrobial agents.

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The structure of the olivomycin-chromomycin antibiotics

Cited by 35 publications

References 3 publications

A comprehensive review of glycosylated bacterial natural products

A comprehensive review of glycosylated bacterial natural products

Characterization of Highly Reductive Modification of Tetracycline D-Ring Reveals Enzymatic Conversion of Enone to Alkane

The Antitumor Antibiotics Complex of Aureolic Acids from the Marine Sediment-associated Strain of Streptomyces sp. KMM 9048

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