A new ansamycin antibiotic, naphthomycin H from a Streptomyces species Y-83,40369.

Mukhopadhyay, T.; Franco, Christopher M. M.; Reddy, G. C. S.; Ganguli, B. N.; Fehlhaber, H.‐W.

doi:10.7164/antibiotics.38.948

Cited by 21 publications

(11 citation statements)

References 3 publications

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“…During an investigation into the early stages of the biosynthesis of naphthalenoid ansamycins (unpublished work), the deuterated N-acetylcysteamine thioesters (11) and (12) (as racemates) were prepared and introduced to separate fermentations of Streptomyces sp. E/784, a bacterium known to produce actamycin (1)9) and naphthomycins D (2),10) H (3),11) and A (4).10,12,13) Examination of the metabolites formed after fermentation for 100 hours showed normal production of the C-30 hydroxylated compounds (1) and (2), but almost undetectable levels of the analogous C-30 chlorinated co-metabolites naphthomycins H (3) and A (4).…”

Section: Resultsmentioning

confidence: 99%

“…E/784 was grown in 250ml baffled Erlenmeyer flasks, each containing a medium (100ml) prepared from dextrose 50g, meat extract 4g, peptone 4g, soybean flour 10g, yeast extract 1g, CaCO3 5g and NaCl 2.5g made up to 1 liter with distilled water, on a Fermentations yielding naphthomycins (5) and (6) flask) of the N-acetylcysteamine thioesters (11) or (12) harvested after 100 hours. Fermentations supplemented cysteine methyl ester (100mg/ml) at 24 and 48 hours afforded naphthomycins (7) and (8) when harvested after 72 hours.…”

Section: Supplementation and Extraction Of Fermentationsmentioning

confidence: 99%

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3-Amino-5-hydroxybenzoic Acid in Antibiotic Biosynthesis. XI. Biological Origins and Semisynthesis of Thionaphthomycins, and the Structures of Naphthomycins I and J.

Hooper

Rickards

1998

J. Antibiot.

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Section: Resultsmentioning

confidence: 99%

Section: Supplementation and Extraction Of Fermentationsmentioning

confidence: 99%

3-Amino-5-hydroxybenzoic Acid in Antibiotic Biosynthesis. XI. Biological Origins and Semisynthesis of Thionaphthomycins, and the Structures of Naphthomycins I and J.

Hooper

Rickards

1998

J. Antibiot.

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“…Members of this subgroup display a range of potent antibacterial and antifungal activities [5]. In our experiments, using disk diffusion testing [10], 1 isolated as the main component showed evident inhibitory activity against P. avellaneum UC-4376, Staphylococcus aureus and Mycobacterium tuberculosis (obtained from Key Laboratory for Conservation and Utilization of Bioresources, Yunnnan University) in dose-dependent manner, respectively (data not shown).…”

mentioning

confidence: 92%

A Novel Ansamycin, Naphthomycin K from Streptomyces sp.

Chen

Shen

2007

J Antibiot

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One novel ansamycin, namely naphthomycin K, together with two known naphthomycins A and E, were isolated from the commensal strain Streptomyces sp. CS of the medicinal plant Maytenus hookeri. Their structures were elucidated by the analysis of NMR and MS data. Naphthomycin K showed evident cytotoxicity against P388 and A-549 cell lines, but no inhibitory activities against Staphylococcus aureus and Mycobacterium tuberculosis.Keywords ansamycin, naphthomycin K, Streptomyces sp. CS In our continuous search for maytansine-producing commensal microorganisms from the medicinal plant Maytenus hookeri, we found that the culture extract of Streptomyces sp. CS [1], one of the commensal microorganisms isolated from the tissue cultures of M. hookeri, showed potent antifungal activity against Penicillium avellaneum UC-4376 by the diffusion assay on agar plates and produced an array of chloride-containing compounds as indicated by LC-ESI-MS detection (data not shown). Naphthomycins A and E (1, 2) were isolated from the fermentation extracts of the strain CS cultivated on ISP2 agar medium (data not shown), and antifungal activity-guided fractionation afforded a new macrolide antibiotic, named 24-demethyl-bafilomycin C 1 , obtained from the extracts of large scale submerged fermentations in ISP2 liquid medium [1]. The presence of chlorinecontaining compounds such as 1 in this strain drew our attention because maytansinoids contain chlorine, and both belong to the type I polyketide family. Guided by analysis of extracts from fermentations in nine different culture media for antifungal activity and LC-ESI-MS profile, ISP3 was selected and used for large-scale solid state fermentation. A novel ansamycin, naphthomycin K (3, Fig. 1) as well as 1 and 2 were isolated from the extract of 14 liters of agar plate fermentation of strain CS.

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“…12B), an active inhibitor of a number of gram-positive and gram-negative bacteria (82), and the corresponding mercapturic acid, naphthomycin G, which lacks biological activity (78). This constitutes an example where MSH and Mca likely function in a detoxification mode.…”

Section: Fig 10 Msh-dependent Detoxification Of Thiol-reactive Drugmentioning

confidence: 99%

Biosynthesis and Functions of Mycothiol, the Unique Protective Thiol of Actinobacteria

Newton

Buchmeier

Fahey

2008

Microbiol Mol Biol Rev

316

293

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SUMMARY Mycothiol (MSH; AcCys-GlcN-Ins) is the major thiol found in Actinobacteria and has many of the functions of glutathione, which is the dominant thiol in other bacteria and eukaryotes but is absent in Actinobacteria. MSH functions as a protected reserve of cysteine and in the detoxification of alkylating agents, reactive oxygen and nitrogen species, and antibiotics. MSH also acts as a thiol buffer which is important in maintaining the highly reducing environment within the cell and protecting against disulfide stress. The pathway of MSH biosynthesis involves production of GlcNAc-Ins-P by MSH glycosyltransferase (MshA), dephosphorylation by the MSH phosphatase MshA2 (not yet identified), deacetylation by MshB to produce GlcN-Ins, linkage to Cys by the MSH ligase MshC, and acetylation by MSH synthase (MshD), yielding MSH. Studies of MSH mutants have shown that the MSH glycosyltransferase MshA and the MSH ligase MshC are required for MSH production, whereas mutants in the MSH deacetylase MshB and the acetyltransferase (MSH synthase) MshD produce some MSH and/or a closely related thiol. Current evidence indicates that MSH biosynthesis is controlled by transcriptional regulation mediated by σB and σR in Streptomyces coelicolor. Identified enzymes of MSH metabolism include mycothione reductase (disulfide reductase; Mtr), the S-nitrosomycothiol reductase MscR, the MSH S-conjugate amidase Mca, and an MSH-dependent maleylpyruvate isomerase. Mca cleaves MSH S-conjugates to generate mercapturic acids (AcCySR), excreted from the cell, and GlcN-Ins, used for resynthesis of MSH. The phenotypes of MSH-deficient mutants indicate the occurrence of one or more MSH-dependent S-transferases, peroxidases, and mycoredoxins, which are important targets for future studies. Current evidence suggests that several MSH biosynthetic and metabolic enzymes are potential targets for drugs against tuberculosis. The functions of MSH in antibiotic-producing streptomycetes and in bioremediation are areas for future study.

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A new ansamycin antibiotic, naphthomycin H from a Streptomyces species Y-83,40369.

Cited by 21 publications

References 3 publications

3-Amino-5-hydroxybenzoic Acid in Antibiotic Biosynthesis. XI. Biological Origins and Semisynthesis of Thionaphthomycins, and the Structures of Naphthomycins I and J.

3-Amino-5-hydroxybenzoic Acid in Antibiotic Biosynthesis. XI. Biological Origins and Semisynthesis of Thionaphthomycins, and the Structures of Naphthomycins I and J.

A Novel Ansamycin, Naphthomycin K from Streptomyces sp.

Biosynthesis and Functions of Mycothiol, the Unique Protective Thiol of Actinobacteria

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