The structure of ravidomycin

Findlay, John A.; Liu, Jia-Sen; Radics, L.; Rakhit, Suman

doi:10.1139/v81-438

Cited by 51 publications

(30 citation statements)

References 3 publications

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“…As was observed with other photosensitizers (13), activation of ravidomycin and desacetylravidomycin seems to be optimal at wavelengths (362 and 400 nm) close to their absorption maxima (350 and 392 nm) (8). The same absorption peaks were retained when these drugs were tested in the presence of DNA (data not shown).…”

Section: Discussionsupporting

confidence: 78%

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Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin

Greenstein¹,

Monji²,

Yeung³

et al. 1986

Antimicrob Agents Chemother

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The antitumor antibiotics ravidomycin and desacetylravidomycin were studied by the biochemical A prophage induction assay. In this assay, induction of the enzyme j8-galactosidase is measured as a specific indication of the ability of an agent to directly or indirectly damage DNA. Induction was observed only when these two antibiotics were irradiated with light in the presence of the indicator organism. Drug treated with light followed by incubation with the indicator organism in the dark did not cause induction. Light in both the near UV and visible wave length ranges activated these antibiotics; near UV and visible blue wavelengths were most effective, while 597-nm light was totally ineffective. The amount of induction caused by these drugs varied directly with the dosage of light provided. Bacterial growth inhibition, as well as cytotoxicity for a human colon carcinoma cell line, was also dramatically enhanced by light. These data suggest that ravidomycin and desacetylravidomycin are potent photosensitizing, DNA-damaging agents.

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Section: Discussionsupporting

confidence: 78%

“…Ravidomycin (8,20,21), desacetylravidomycin (20), the gilvocarcins (1,15,25), and the chrysomycins (24,29) constitute a recently described class of structurally related antitumor antibiotics. These compounds ( Fig.…”

mentioning

confidence: 99%

Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin

Greenstein¹,

Monji²,

Yeung³

et al. 1986

Antimicrob Agents Chemother

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“…18,19 Both antibiotics contain a common angucyclinone-derived tetracyclic aromatic benzo[ d ]naptho[1,2- b ]pyran-6-one core moiety, which is connected to their respective sugar residues at C-4 position through a C–C bond (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Characterization of the TDP-d-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-d-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate

2011

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Ravidomycin V and related compounds, e.g., FE35A-B, exhibit potent anticancer activities against various cancer cell lines in the presence of visible light. The amino sugar moieties (d-ravidosamine and its analogues, respectively) in these molecules contribute to the higher potencies of ravidomycin and analogues when compared to closely related compounds with neutral or branched sugars. Within the ravidomycin V biosynthetic gene cluster, five putative genes encoding NDP-d-ravidosamine biosynthetic enzymes were identified. Through the activities of the isolated enzymes in vitro, it is demonstrated that ravD, ravE, ravIM, ravAMT and ravNMT encode TDP-d-glucose synthase, TDP-4-keto-6-deoxy-d-glucose-4,6-dehydratase, TDP-4-keto-6-deoxy-d-glucose-3,4-ketoisomerase, TDP-3-keto-6-deoxy-d-galactose-3-aminotransferase, and TDP-3-amino-3,6-dideoxy-d-galactose-N,N-dimethyl-transferase, respectively. A protocol for a one-pot enzymatic synthesis of TDP-d-ravidosamine has been developed. The results presented here now set the stage to produce TDP-d-ravidosamine routinely for glycosylation studies.

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“…It was isolated from Streptomyces ravidus NRRL 11,300, cultured from Guatemalan soil [183][184][185]. The structure of ravidomycin was initially assigned based on NMR spectrometry [186,187]. However, the Clinked sugar was incorrectly identified as 3,6-dideoxy-3-(N,N-dimethylamino)-4-O-acetyl-C-altropyranose in this work.…”

Section: Fig (34) Chrysomycin Derivatives From a Japanese Soil Strementioning

confidence: 99%

Bioactive C-Glycosides from Bacterial Secondary Metabolism

Hultin

2005

CTMC

122

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C-Glycosides are commonly regarded as unusual structures, but they are far more prevalent among natural products than is imagined. This review discusses the C-glycosidic compounds produced by various bacteria, particularly the "biosynthetically talented" Streptomyces. The major structure types are presented, along with brief descriptions of the known biological and pharmacological properties of the compounds. Recent work has uncovered the genetic basis for the biosynthesis of several bacterial C-glycosides, and emphasis is placed on those cases where it has been possible to identify (at least provisionally) the C-glycosyltransferase in the pathway. Prospects for biosynthetic engineering, combinatorial biosynthesis, or glycorandomization in C-glycosidic natural products are briefly discussed.

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The structure of ravidomycin

Abstract: The structure 1a is proposed for ravidomycin on the basis of chemical and spectroscopic data.

Cited by 51 publications

References 3 publications

Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin

Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin

Characterization of the TDP-d-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-d-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate

Bioactive C-Glycosides from Bacterial Secondary Metabolism

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