Phenalinolactones A–D, terpenoglycoside antibiotics from Streptomyces sp. Tü 6071

Gebhardt, Klaus; Meyer, S.; Schinko, Jochen; Bringmann, Gerhard; Zeeck, Axel; Fiedler, Hans‐Peter

doi:10.1038/ja.2010.165

Cited by 21 publications

(34 citation statements)

References 11 publications

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“…Diterpenes are comprised of four isoprene units and 16 glycosylated diterpenoids have been reported as metabolites of Strepomyces and Nocardia including the phenalinolactones, 1259 lucensimycins, 1260 brasillicardins, 1261,1262 platensimycins, 1263 and platencins. 1264,1265 Phenalinolactones, C-4 glycosides of a methylated α-L-amicetose ( 97 ) (Fig.…”

Section: Terpenes and Sterolsmentioning

confidence: 99%

“…58), display moderate activity against Gram positive bacteria. 1259 In contrast, brasillicardins are C-2 (α-L-rhamnose 46 ) glycosides which, in brasillicardins A and B, are further modified at the rhamnose C-3′ with N -acetyl-β-D-glucosamine ( 153 ). 1261,1262 The latter sugar is believed to be essential for the immunosuppressive activity of brasillicardin A.…”

Section: Terpenes and Sterolsmentioning

confidence: 99%

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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: Terpenes and Sterolsmentioning

confidence: 99%

Section: Terpenes and Sterolsmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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“…Aglycone diversity is based on the fact that GNPs are found in almost all major biosynthetic classes of natural products (Fig. 1A), e.g., nonribosomal (6) and ribosomal peptides (7), polyketides (8), terpenes (9), and alkaloids (10). Glycosylation diversity arises through sugar monomers and sugar attachment.…”

mentioning

confidence: 99%

Glycogenomics as a mass spectrometry-guided genome-mining method for microbial glycosylated molecules

Kersten

Ziemert

Gonzalez³

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

103

107

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Glycosyl groups are an essential mediator of molecular interactions in cells and on cellular surfaces. There are very few methods that directly relate sugar-containing molecules to their biosynthetic machineries. Here, we introduce glycogenomics as an experimentguided genome-mining approach for fast characterization of glycosylated natural products (GNPs) and their biosynthetic pathways from genome-sequenced microbes by targeting glycosyl groups in microbial metabolomes. Microbial GNPs consist of aglycone and glycosyl structure groups in which the sugar unit(s) are often critical for the GNP's bioactivity, e.g., by promoting binding to a target biomolecule. GNPs are a structurally diverse class of molecules with important pharmaceutical and agrochemical applications. Herein, O-and N-glycosyl groups are characterized in their sugar monomers by tandem mass spectrometry (MS) and matched to corresponding glycosylation genes in secondary metabolic pathways by a MS-glycogenetic code. The associated aglycone biosynthetic genes of the GNP genotype then classify the natural product to further guide structure elucidation. We highlight the glycogenomic strategy by the characterization of several bioactive glycosylated molecules and their gene clusters, including the anticancer agent cinerubin B from Streptomyces sp. SPB74 and an antibiotic, arenimycin B, from Salinispora arenicola CNB-527.secondary metabolite | drug discovery | microbial genomics | deoxysugar | polyketide

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“…isolated the PLs A–D using ethyl acetate extraction and chromatographic separation on diol‐modified silica gel, Sephadex LH‐20 and preparative RP‐HPLC. Structures were investigated on the basis of detailed NMR and MS analyses using ESI‐MS and HR‐ESI‐MS, but information about putative intermediates remains elusive . Conventional methods for the elucidation of biosynthetic pathways are time‐consuming since they rely primarily on feeding experiments with isotope‐labelled precursors and on the investigation of biosynthetic enzymes.…”

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confidence: 99%

Metabolic pathway monitoring of phenalinolactone biosynthesis from Streptomyces sp. Tü6071 by liquid chromatography/mass spectrometry coupling

Kiske

Erxleben

Lucas

et al. 2014

Rapid Comm Mass Spectrometry

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A precise analytical method was established for the identification of phenalinolactones by combining purification from Streptomyces using SPE prior to LC/ESI-MS/MS. By optimising LC/ESI-MS/MS settings, this method has been successfully applied for pathway monitoring of secondary metabolites. Application of a precursor ion scan allowed for the identification of unknown intermediates in biosynthetic pathways.

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Phenalinolactones A–D, terpenoglycoside antibiotics from Streptomyces sp. Tü 6071

Cited by 21 publications

References 11 publications

A comprehensive review of glycosylated bacterial natural products

A comprehensive review of glycosylated bacterial natural products

Glycogenomics as a mass spectrometry-guided genome-mining method for microbial glycosylated molecules

Metabolic pathway monitoring of phenalinolactone biosynthesis from Streptomyces sp. Tü6071 by liquid chromatography/mass spectrometry coupling

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