Naturally-occurring nitro compounds

Parry, Ronald J.; Nishino, Shirley F.; Spain, Jim C.

doi:10.1039/c0np00024h

Cited by 143 publications

(122 citation statements)

References 197 publications

(269 reference statements)

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“…The marine acorn worm produces 10 different chlorinated and brominated phenols (48). Naturally occurring nitrophenols are less common, but include o-nitrophenol (46) and a variety of more complex nitrophenols with additional substituents synthesized by some bacteria and fungi (49). Degradation pathways for only a handful of substituted phenols that are degraded via benzoquinone intermediates have been reported.…”

Section: Discussionmentioning

confidence: 99%

Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol

Yadid

Rudolph

Hlouchová

et al. 2013

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

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Microbes in contaminated environments often evolve new metabolic pathways for detoxification or degradation of pollutants. In some cases, intermediates in newly evolved pathways are more toxic than the initial compound. The initial step in the degradation of pentachlorophenol by Sphingobium chlorophenolicum generates a particularly reactive intermediate; tetrachlorobenzoquinone (TCBQ) is a potent alkylating agent that reacts with cellular thiols at a diffusion-controlled rate. TCBQ reductase (PcpD), an FMN-and NADH-dependent reductase, catalyzes the reduction of TCBQ to tetrachlorohydroquinone. In the presence of PcpD, TCBQ formed by pentachlorophenol hydroxylase (PcpB) is sequestered until it is reduced to the less toxic tetrachlorohydroquinone, protecting the bacterium from the toxic effects of TCBQ and maintaining flux through the pathway. The toxicity of TCBQ may have exerted selective pressure to maintain slow turnover of PcpB (0.02 s −1 ) so that a transient interaction between PcpB and PcpD can occur before TCBQ is released from the active site of PcpB.biodegradation | molecular evolution | channeling | quinone reductase

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Section: Discussionmentioning

confidence: 99%

Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol

Yadid

Rudolph

Hlouchová

et al. 2013

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

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“…Pyrrolomycin A, another recently-discovered nitrated compound, is produced by Actinosporangium vitaminophilum SF-2080. It demonstrates activity against Gram-positive and Gram-negative bacteria as well as some fungi [60]. Aureothin, alloaureothin, spectinabilin (neoaureothin) and luteoreticulin (griseulin) are structurally related nitrophenyl pyrones which express various bioactivities and are produced by Streptomyces spp.…”

Section: Antimicrobial Properties Of Novel Antibioticsmentioning

confidence: 99%

“…ALAA 2000 was discovered to produce ayamycin, a monocyclic nitrated aromatic compound, which exhibits antibacterial and antifungal activity [59,60]. Pyrrolomycin A, another recently-discovered nitrated compound, is produced by Actinosporangium vitaminophilum SF-2080.…”

Section: Antimicrobial Properties Of Novel Antibioticsmentioning

confidence: 99%

“…Aureothin, alloaureothin, spectinabilin (neoaureothin) and luteoreticulin (griseulin) are structurally related nitrophenyl pyrones which express various bioactivities and are produced by Streptomyces spp. [60]. Aureothin demonstrates anti-Helicobacter pylori, antitumour and antifungal activity, whereas luteoreticulin possesses mosquitocidal and nematocidal properties [60].…”

Section: Antimicrobial Properties Of Novel Antibioticsmentioning

confidence: 99%

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Biologically active secondary metabolites from Actinomycetes

Solecka¹,

Zajko²,

Postek³

et al. 2012

Open Life Sciences

113

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AbstractSecondary metabolites obtained from Actinomycetales provide a potential source of many novel compounds with antibacterial, antitumour, antifungal, antiviral, antiparasitic and other properties. The majority of these compounds are widely used as medicines for combating multidrug-resistant Gram-positive and Gram-negative bacterial strains. Members of the genus Streptomyces are profile producers of previously-known secondary metabolites. Actinomycetes have been isolated from terrestrial soils, from the rhizospheres of plant roots, and recently from marine sediments. This review demonstrates the diversity of secondary metabolites produced by actinomycete strains with respect to their chemical structure, biological activity and origin. On the basis of this diversity, this review concludes that the discovery of new bioactive compounds will continue to pose a great challenge for scientists.

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“…[24][25][26], Myxococcus fulvus [27], and Enterobacter agglomerans [28]. It shows antibacterial activity against Gram-positive pathogens, in particular against certain Streptomyces species, such as S. antibioticus and S. violaceoruber (MIC = 0.89 µM), against fungal strains, such as Paecilomyces variotii and Penicillium puberulum (MIC in the range 8.9-26.9 µM) [29], and against a range of mycobacteria, including Mycobacterium tuberculosis (MIC in the range 17.9-35.9 µM) [30].…”

Section: Halogenated Pyrroles Related To Pyrrolomycinsmentioning

confidence: 99%

Pharmaceutical Potential of Synthetic and Natural Pyrrolomycins

et al. 2015

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Abstract:The emergence of antibiotic resistance is currently considered one of the most important global health problem. The continuous onset of multidrug-resistant Gram-positive and Gram-negative bacterial strains limits the clinical efficacy of most of the marketed antibiotics. Therefore, there is an urgent need for new antibiotics. Pyrrolomycins are a class of biologically active compounds that exhibit a broad spectrum of biological activities, including antibacterial, antifungal, anthelmintic, antiproliferative, insecticidal, and acaricidal activities. In this review we focus on the antibacterial activity and antibiofilm activity of pyrrolomycins against Gram-positive and Gram-negative pathogens. Their efficacy, combined in some cases with a low toxicity, confers to these molecules a great potential for the development of new antimicrobial agents to face the antibiotic crisis.

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Naturally-occurring nitro compounds

Abstract: Naturally-occurring nitro compounds display great structural diversity, and a wide range of biological activities. This review summarizes current information on the structures of naturally-occurring nitro compounds and on the biosynthesis of the nitro group.

Cited by 143 publications

References 197 publications

Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol

Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol

Biologically active secondary metabolites from Actinomycetes

Pharmaceutical Potential of Synthetic and Natural Pyrrolomycins

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