Rearranged and Unrearranged Angucyclinones from Indonesian Streptomyces spp.

Fotso, Serge; Mahmud, Taifo; Zabriskie, T. Mark; Santosa, Dwi Andreas; Sulastri, Sulastri; Protea, Philip J

doi:10.1038/ja.2008.61

Cited by 31 publications

(22 citation statements)

References 17 publications

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“…Five structurally related compounds were isolated from the culture broth and identified as known anthraquinones, 1 to 5. [16][17][18][19] Among them, 4 and 5 were found to show dose-dependent white zones (9, 11 mm for 4 and 18, 26 mm for 5) at 5.0 and 10 μg/disk, respectively (Table 3). Thus, 5 exhibited potent inhibition of yellow pigment production with this assay, but also showed growth inhibition at 10 μg/disk.…”

Section: Screening Resultsmentioning

confidence: 99%

“…Moreover, five anthraquinones, SM-196B (1), 16) 1-deoxo-1-hydroxy-8-O-methylrabelomycin (2), 17) 8-O-methylrabelomycin (3), 18) 6-deoxy-8-O-methylrabelomycin (4) 18) and tetrangomycin (5) 19) (Fig. 1), previously reported as antibiotics, [16][17][18][19] were isolated from the culture broth of actinomycete strain Streptomyces badius 4-6. Among them, 4 and 5 showed inhibitory activity of MRSA staphyloxanthin production in the paper disk assay.…”

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confidence: 99%

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Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

Sakai

Koyama

Fukuda

et al. 2012

Biological & Pharmaceutical Bulletin

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Staphyloxanthin, a yellow pigment produced by methicillin-resistant Staphylococcus aureus (MRSA), is a virulent factor escaping from the host immune system. A new screening method for inhibitors of staphyloxanthin production by MRSA was established using paper disks. By this screening method, inhibitors of staphyloxanthin production were selected from the natural product library (ca. 300) and from actinomycete culture broths (ca. 1000). From the natural product library, four known inhibitors of lipid metabolism, cerulenin, dihydrobisvertinol, xanthohumol and zaragozic acid, were found to inhibit staphyloxanthin production; however, typical antibiotics used clinically, including vancomycin, had no effect on staphyloxanthin production. From actinomycete culture broths, two known anthraquinones, 6-deoxy-8-O-methylrabelomycin and tetrangomycin, were found to inhibit staphyloxanthin production by MRSA in the paper disk assay. These results suggested that this screening method is useful and effective to find compounds targeting staphyloxanthin production, leading to a new type of chemotherapeutics against MRSA infection.

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Section: Screening Resultsmentioning

confidence: 99%

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confidence: 99%

Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

Sakai

Koyama

Fukuda

et al. 2012

Biological & Pharmaceutical Bulletin

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“…The microbial natural product tetrangulol methyl ether was first reported by Kuntsmann and Mitscher in 196623 and is known to exhibit antibiotic properties 24. The inhibition of QR-2 by tetrangulol methyl ether also suggests that it may have chemoprevention activity.…”

Section: Resultsmentioning

confidence: 99%

Screening Natural Products for Inhibitors of Quinone Reductase-2 Using Ultrafiltration LC−MS

et al. 2010

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Inhibitors of quinone reductase-2 (NQO2; QR-2) can have anti-malarial activity and anti-tumor activities or can function as chemoprevention agents by preventing the metabolic activation of toxic quinones such as menadione. To expedite the search for new natural product inhibitors of QR-2, we developed a screening assay based on ultrafiltration liquid chromatography-mass spectrometry that is compatible with complex samples such as bacterial or botanical extracts. Human QR-2 was prepared recombinantly, and the known QR-2 inhibitor, resveratrol, was used as a positive control and as a competitive ligand to eliminate false positives. Ultrafiltration LC-MS screening of extracts of marine sediment bacteria resulted in the discovery of tetrangulol methyl ether as an inhibitor of QR-2. When applied to the screening of hop extracts from the botanical, Humulus lupulus L., xanthohumol and xanthohumol D were identified as ligands of QR-2. Inhibition of QR-2 by these ligands was confirmed using a functional enzyme assay. Furthermore, binding of xanthohumol and xanthohumol D to the active site of QR-2 were confirmed using Xray crystallography. Ultrafiltration LC-MS was shown to be a useful assay for the discovery of inhibitors of QR-2 in complex matrices such as extracts of bacteria and botanicals.

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“…This conversion was studied by HPLC. NMR afforded an ultimate proof for proposed structure of metabolite 3 as 8-O-methyl-7-deoxo-7-hydroxytetrangomycin, which was recently isolated from an Indonesian Streptomyces [24]. So far none angucyclinone has been described as a metabolite of N. dassonvillei, only indole neosidomycin [25] and indolocarbazole type metabolites [26] have been isolated from this microorganism.…”

Section: Structures Determinationmentioning

confidence: 99%

Isolation, structure elucidation and biological activity of angucycline antibiotics from an epiphytic yew streptomycete

Maruna

Šturdíková

Liptaj

et al. 2010

J. Basic Microbiol.

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In the course of study of epiphytic microorganisms occurring on the surface of roots of Taxus baccata L. a new strain Streptomyces sp. AC113 was isolated. According to 16S ribosomal DNA-based identification the new strain is 99% identical with Streptomyces flavidofuscus. This strain cultivated in an arginine glycerol medium produced three major metabolites identified as (-)-8-O -methyltetrangomycin (1), 8-O -methyltetrangulol (2) and 8-O -methyl-7-deoxo-7-hydroxytetrangomycin (3). The chemical structures of these angucyclines were elucidated by 1D and 2D NMR as well as by mass spectrometry. Isolated angucycline metabolites showed significant antimicrobial activity against Bacillus cereus and Listeria mocytogenes. Cytotoxic activities of compounds 1, 2 and 3 against four cell lines (B16, HT-29 and non - tumor V79, L929) were evaluated. Compound 3 was the most potent anticancer agents with IC(50) 0.054 microg/ml against cell line B16.

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Rearranged and Unrearranged Angucyclinones from Indonesian Streptomyces spp.

Cited by 31 publications

References 17 publications

Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

Screening Natural Products for Inhibitors of Quinone Reductase-2 Using Ultrafiltration LC−MS

Isolation, structure elucidation and biological activity of angucycline antibiotics from an epiphytic yew streptomycete

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