Chemistry and Biology of the Pyrrole–Imidazole Alkaloids

Lindel, Thomas

doi:10.1016/bs.alkal.2016.12.001

Cited by 35 publications

(67 citation statements)

References 229 publications

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“…Pyrroleimidazole alkaloids encompass a large group of heterocyclic natural products isolated from marine sponges. 233 Perhaps one of the most famous pyrrole-imidazole alkaloids is palau 'amine (125). Discovered by Scheuer et al in 1993, 234 researchers reported that palau 'amine displayed cytotoxic activity.…”

Section: Rsc Chemical Biologymentioning

confidence: 99%

Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors

Hubbell

Tepe

2020

RSC Chem. Biol.

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Section: Rsc Chemical Biologymentioning

confidence: 99%

Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors

Hubbell

Tepe

2020

RSC Chem. Biol.

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“…Sponges belonging to the genus Agelas constitute an important source of marine pyrrole-imidazole alkaloids [7,8]. Since the structural elucidation of the first alkaloid, dibromophakellin, almost 50 years ago [9], more than 200 analogues isolated from a variety of tropical sponges have been found to display a wide range of biological properties including antitumor, antifungal and antibacterial activities [10,11].…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa

et al. 2020

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The pyrrole-imidazoles, a group of alkaloids commonly found in marine sponges belonging to the genus Agelas, display a wide range of biological activities. Herein, we report the first chemical study of the secondary metabolites of the sponge A. dilatata from the coastal area of the Yucatan Peninsula (Mexico). In this study, we isolated eight known alkaloids from an organic extract of the sponge. We used NMR and MS analysis and comparison with existing databases to characterize the alkaloids: ageliferin (1), bromoageliferin (2), dibromoageliferin (3), sceptrin (4), nakamuric acid (5), 4-bromo-1H-pyrrole-2-carboxylic acid (6), 4,5-dibromopyrrole-2-carboxylic acid (7) and 3,7-dimethylisoguanine (8). We also evaluated, for the first time, the activity of these alkaloids against the most problematic multidrug-resistant (MDR) pathogens, i.e., the Gram-negative bacteria Pseudomonas aeruginosa, Klebsiella pneumoniae and Acinetobacter baumannii. Bromoageliferin (2) displayed significant activity against P. aeruginosa. Comparison of the antibacterial activity of ageliferins 1–3 (of similar structure) against P. aeruginosa revealed some relationship between structure and activity. Furthermore, in in vitro assays, 2 inhibited growth and biofilm production in clinical strains of P. aeruginosa. Moreover, 2 increased the survival time in an in vivo Galleria mellonella model of infection. The findings confirm bromoageliferin (2) as a potential lead for designing new antibacterial drugs.

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“…One epibacterial defense strategy for sponge-symbiont community is to produce bioactive secondary metabolites in order to outcompete other bacteria in the water column from causing infection or biofouling [ 9 , 10 , 11 , 12 , 13 , 14 ]. Among the sponge-derived active metabolites, pyrrole-imidazole alkaloids are a class of structurally unique natural products with a range of ecological and significant pharmacological bioactivities [ 15 , 16 , 17 ]. For instance, oroidin and stevensine were demonstrated to possess antifeedant properties, while oroidin and its analogues have been extensively studied as biofilm inhibitors [ 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Bromopyrrole Alkaloids with the Inhibitory Effects against the Biofilm Formation of Gram Negative Bacteria

Sun

et al. 2018

Marine Drugs

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Anti-biofilm assay guided fractionation of the marine sponge Stylissa massa revealed the butanol soluble fraction that was possessing the inhibitory activity toward the biofilm formation of bacterium E. coli. Chromatographic separation of the bioactive fraction resulted in the isolation of 32 bromopyrrole alkaloids, including six new alkaloids, named stylisines A–F (1–6). The structures of new alkaloids were established by comprehensive analyses of the two-dimensional (2D) NMR (COSY, HMQC, and HMBC) and the high resolution electrospray ionization mass spectroscopy (HRESIMS) data, while the absolute configurations were determined by the X-ray diffraction and the electronic circular dichroism (ECD) data. Bioassay results indicated that phakellin-based alkaloids, including dibromoisophakellin and dibromophakellin, significantly reduced the biofilm formation of the bacterium E. coli. Present work provided a group of new natural scaffolds for the inhibitory effects against the biofilm formation of E. coli.

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Chemistry and Biology of the Pyrrole–Imidazole Alkaloids

Cited by 35 publications

References 229 publications

Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors

Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors

In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa

Bromopyrrole Alkaloids with the Inhibitory Effects against the Biofilm Formation of Gram Negative Bacteria

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