Benzanthrins A and B, a new class of quinone antibiotics. I Discovery, fermentation and antibacterial activity.

Theriault, Robert J.; Rasmussen, Ronald R.; Kohl, William L.; Prokop, Joseph F.; Hutch, Thomas B.; Barlow, Grant J.

doi:10.7164/antibiotics.39.1509

Cited by 23 publications

(6 citation statements)

References 15 publications

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“…The fact that there were only two unassigned aromatic protons indicated, by default, that the angolosamine was equatorially (J2-3'ax =10.5 Hz) linked to the benz[a]anthraquinone skeleton through carbon rather than oxygen. This also was in agreement with the generic structure of the Zn dust distillation product (1). The chemical shift of C-2' (6 76.4) in the CSCM which correlated with H-2' (6 5.2) is the expected value for carbon 2 of a C-glycoside13).…”

Section: Structure Determinationsupporting

confidence: 86%

Benzanthrins A and B, a new class of quinone antibiotics. II Isolation, elucidation of structure and potential antitumor activity.

Rasmussen¹,

Nuss

Scherr

et al. 1986

J. Antibiot.

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The benzanthrins, which were produced by Nocardia lurida, were extracted from the fermentation broth with CH2Cl2. Subsequent purification on Sephadex LH-20 and diolbonded silica gel, followed by countercurrent chromatography, afforded analytically pure benzanthrins A and B. FAB-MS revealed that benzanthrins A and B were isomeric. It was demonstrated through degradative and spectroscopic studies that the benzanthrins were di- Fermentation studies with Nocardia lurida, a known producer of the ristocetins, resulted in the additional production of two new antibiotics, benzanthrins A and B. The discovery, fermentation and antibacterial activity of the benzanthrins is the subject of the preceding paper1). This paper will deal with the isolation, structure determination and antitumor activity of these novel antibiotics. ExperimentalGeneral Procedures NMR spectra were obtained with a General Electric GN 500 MHz spectrometer. The samples were run in CD2Cl2 and referenced on the lock solvent (5.32 ppm). The 2D proton-carbon chemical shift correlation (CSCM) experiment was performed on the GN 500 using a 5 mm C-13 probe and a model 1280 computer. The CSCM pulse sequence employed for the experiment was essentially that of FREEMAN and MORRIS2) modified to deliver a composite 180 degree pulse. Ninety degree pulse widths on the 5 mm C-13 probe were 15 pseconds for carbon and 30 useconds for proton. Fixed delays, delta 1 and delta 2, were set to 3.3 and 1.7 mseconds, respectively, with phase-cycling providing quadrature in both dimensions. The 2D homonuclear J-correlation experiment (COSY)3) was run on the GN 500 spectrometer using the 5 mm H-1 probe. The ninety degree proton pulse for this probe was 12 pseconds. Mass spectra were determined on a Kratos MS-50 spectrometer. High resolution measurements were made at 10,000 resolving power. UV spectra were determined with a Perkin-Elmer Lambda 3B UV/VIS spectrophotometer and IR spectra were measured with a PerkinElmer Model 521 grating spectrometer.

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Section: Structure Determinationsupporting

confidence: 86%

Benzanthrins A and B, a new class of quinone antibiotics. II Isolation, elucidation of structure and potential antitumor activity.

Rasmussen¹,

Nuss

Scherr

et al. 1986

J. Antibiot.

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“…In addition to the above described angucyclines, a number of additional miscellaneous angucyclines have been reported and are organized herein based upon the regiospecificity of glycosylation. Angucyline C-1 or C-2 glycosylation is relatively rare with the benzanthrins from Nocardia, 129,130 pseudonocardones from Pseudonocardia (associated with the fungusgrowing ant Apterostigma dentigerum) 131 and P371A1/A2 from Streptomyces 132,133 as the only representative bacterial metabolites within this subset. Members display variant activities including antibacterial, antiplasmodial, and/or cancer cell line cytotoxicity as well as inhibition of gastric acid secretion.…”

Section: Other Related Aquayamycin-type Angucyclinesmentioning

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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“…lurida in 1986 [124,125]. They are atypical of the angucycline family, and no other compounds of their type have been discovered.…”

Section: Benzanthrinsmentioning

confidence: 98%

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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Benzanthrins A and B, a new class of quinone antibiotics. I Discovery, fermentation and antibacterial activity.

Abstract: Nocardia lurida has been shown to produce two novel quinone antibiotics, benzanthrins

Cited by 23 publications

References 15 publications

Benzanthrins A and B, a new class of quinone antibiotics. II Isolation, elucidation of structure and potential antitumor activity.

Benzanthrins A and B, a new class of quinone antibiotics. II Isolation, elucidation of structure and potential antitumor activity.

A comprehensive review of glycosylated bacterial natural products

Bioactive C-Glycosides from Bacterial Secondary Metabolism

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