NW-G03, a related cyclic hexapeptide compound of NW-G01, produced by Streptomyces alboflavus 313

Guo, Zhengyan; Shen, Ling; Zhang, Jiwen; Xin, Hongmei; Liu, Wei; Ji, Zhiqin; Wu, Wenjun

doi:10.1038/ja.2011.88

Cited by 13 publications

(4 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…NW-G01, G05, and piperazimycin even coincide with hytramycins in the positions of two R -form and one S -form piperazic acids. The results obtained in the present study are consistent with the strong antibacterial activity of the cyclic piperazic acid-containing NW-Gs − against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus , and lack of activity against Gram-negative species and extend this profile to include activity against M. tb . In fact, we obtained NW-G01 from Dr. Hatakeyama at Nagasaki University and determined its anti-TB MIC to be 18.6 μg/mL in the MABA, only slightly higher than that of the hytramycins.…”

Section: Resultssupporting

confidence: 89%

“…First discovered in 1959, natural products containing a piperazic acid moiety have been isolated and proven to exhibit extraordinary biological activities . The anticancer agents himastatin − and chloptosin, in the form of dimers, as well as a recently reported hexadepsipeptide, piperazimycin, share great structural similarity with 1 and 2 , together with a series of hexapeptide antibiotics, the NW-G compounds (NW-Gs), isolated from Streptomyces alboflavus 313 strain. − Himastatin, chloptosin, and NW-Gs all have a cyclic structure with six amino acids and contain a hydroxyhexahydropyrroloindole carboxylic acid motif, which in 1 and 2 is substituted by a leucine. All NW-Gs, piperazimycin, and the hytramycins 1 and 2 have three piperazic acid moieties in the cyclic structure, two adjacent and the third flanked by another amino acid.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Hytramycins V and I, Anti-Mycobacterium tuberculosis Hexapeptides from a Streptomyces hygroscopicus Strain

Cai¹,

Napolitano²,

McAlpine³

et al. 2013

J. Nat. Prod.

View full text Add to dashboard Cite

Thirty-five thousand actinomycete extracts were screened for anti-Mycobacterium tuberculosis (M. tb) activity, followed by C18 cartridge fractionation of 37 prioritized extracts. Based on MICs against replicating and nonreplicating M. tb, and IC50 values against Vero cells to generate selectivity indices, seven fractions from seven different strains were selected for further examination. When cultured in G.S.S. media and extracted with ethyl acetate, the Streptomyces hygroscopicus strain ECUM 14046 yielded an extract with promising anti-M. tb activity and a well-defined chromatographic profile. Fractionation by preparative HPLC and subsequent structure elucidation of two active fractions using 1D- and 2D-NMR and MS methods revealed the presence of two cyclohexapeptides, hytramycins V and I, each containing three unusual piperazic acid moieties. The use of (1)H iterative full spin analysis (HiFSA) on both hytramycins confirmed that quantum mechanics-simulated spectra match the experimental data, and all J(H,H) and δH values are consistent with the proposed structures. The absolute configuration of each amino acid moiety was determined by Marfey's method. The MICs against replicating and, more importantly, nonreplicating M. tb fall into the range of some existing second-line anti-TB drugs, such as streptomycin and capreomycin, respectively. The activities were maintained against M. tb strains that represent the major global clades, as well as H37Rv-isogenic strains that are resistant to individual clinical anti-TB drugs.

show abstract

Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Hytramycins V and I, Anti-Mycobacterium tuberculosis Hexapeptides from a Streptomyces hygroscopicus Strain

Cai¹,

Napolitano²,

McAlpine³

et al. 2013

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…Pseudo‐monomers of himastatin ( 13 ) and chloptosin ( 14 ) were also identified in fungi. For example, the NW‐G family was isolated from Streptomyces alboflavus 313 . The NW‐G family encompasses at least nine members.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3a‐hydroxyhexahydropyrrolo[2,3‐B]Indole‐2‐carboxamide, an oxidation product of tryptophan present in natural products

Blanc

Perrin

2018

Peptide Science

View full text Add to dashboard Cite

The 3a‐hydroxyhexahydropyrrolo[2,3‐b]indole‐2‐carboxamide (HO‐HPIC) is formed from the oxidation of tryptophan residues and is well represented in peptide‐based natural products. These natural products exhibit potential medicinal activities and thus have caught the attention of chemists and biologists over the past few years. Considerable effort has been marshaled toward the synthesis of HO‐HPIC‐containing natural products, but only a few of these peptides have been successfully synthetically prepared. This review briefly describes a few choice natural products containing the HO‐HPIC motif, summarizes the biological activities and synthetic routes of selected natural compounds containing HO‐HPIC, and emphasizes the use of dimethyldioxirane (DMDO) in the oxidation of tryptophan and its derivatives to HO‐HPIC‐containing motifs.

show abstract

“…1 In our previous investigation of natural products from microorganisms for drug discovery, nine pyrroloindoline-containing cyclic hexapeptides, NW-G01, NW-G03 and NW-G05-NW-G11, were discovered in the fermentation broth of Streptomyces alboflavus 313. [2][3][4][5][6][7] They are structurally related to himastatin and chloptosin ( Figure 1), two cyclic hexapeptides antibiotics produced by strains of Streptomyces. They all contain the common rare amino acids, piperazine-3-carboxylic acid and pyrroloindoline derivative, especially for chloptosin, it has the identical Trp-Val-PA 3 -PA 2 moiety in its structure with that of NW-series cyclic hexapeptides.…”

Section: Introductionmentioning

confidence: 99%

Identification of pyrroloindoline-containing cyclic hexapeptides in the metabolites of Streptomyces alboflavus 313 by HPLC-DAD-ESI-MS/MS

Gang

et al. 2013

J Antibiot

Self Cite

View full text Add to dashboard Cite

To investigate the chemical biodiversity of biologically active cyclic hexapeptides in the metabolites from microorganisms, the fermentation broth of Streptomyces alboflavus 313 was analyzed using HPLC, equipped with a diode array detector (DAD), coupled with ESI tandem MS (HPLC-DAD-ESI-MS/MS). In the mass spectra of cyclic hexapeptides, predominant ions [M+H](+), as well as [M-18+H](+), [M-28+H](+) and [M+Na](+), were observed and used to determine the molecular masses, while fragmentation reactions of [M+H](+) were recorded to provide information on the contents of amino acids and their linkage sequence. Based on the fragmentation patterns and comparison with standards, 15 pyrroloindoline-containing natural cyclic hexapeptides, cp01-15, were identified from the microorganism and six of these are reported for the first time.

show abstract

NW-G03, a related cyclic hexapeptide compound of NW-G01, produced by Streptomyces alboflavus 313

Cited by 13 publications

References 14 publications

Hytramycins V and I, Anti-Mycobacterium tuberculosis Hexapeptides from a Streptomyces hygroscopicus Strain

Hytramycins V and I, Anti-Mycobacterium tuberculosis Hexapeptides from a Streptomyces hygroscopicus Strain

Synthesis of 3a‐hydroxyhexahydropyrrolo[2,3‐B]Indole‐2‐carboxamide, an oxidation product of tryptophan present in natural products

Identification of pyrroloindoline-containing cyclic hexapeptides in the metabolites of Streptomyces alboflavus 313 by HPLC-DAD-ESI-MS/MS

Contact Info

Product

Resources

About