New phenethylamine derivatives from Arenibacter nanhaiticus sp. nov. NH36AT and their antimicrobial activity

Chen, Yanping; Tang, Jinshan; Tang, Xixiang; Wang, Chuanxi; Lian, Yun-Yang; Shao, Zongze; Yao, Xin‐Sheng; Gao, Hao

doi:10.1038/ja.2013.65

Cited by 13 publications

(8 citation statements)

References 13 publications

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“…Our finding, together with previous reports, indicates that the production of PEA-containing alkaloids is likely a widespread characteristic within the marine flavobacteria. For instance, in a previous report five PEA derivatives were isolated from the flavobacterial strain Arenibacter . In addition, PEA was proposed as a taxonomic biomarker within the free-living Bacteroidetes phylum .…”

Section: Results and Discussionmentioning

confidence: 99%

“…For instance, in a previous report five PEA derivatives were isolated from the flavobacterial strain Arenibacter. 47 In addition, PEA was proposed as a taxonomic biomarker within the free-living Bacteroidetes phylum. 48 These studies together with our findings revealed that the genus Tenacibaculum and other flavobacterial strains are able to produce this type of arylamine.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

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Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

et al. 2022

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The bacterial genus Tenacibaculum has been associated with various ecological roles in marine environments. Members of this genus can act, for example, as pathogens, predators, or episymbionts. However, natural products produced by these bacteria are still unknown. In the present work, we investigated a Tenacibaculum strain for the production of antimicrobial metabolites. Six new phenethylamine (PEA)-containing alkaloids, discolins A and B (1 and 2), dispyridine (3), dispyrrolopyridine A and B (4 and 5), and dispyrrole (6), were isolated from media produced by the predatory bacterium Tenacibaculum discolor sv11. Chemical structures were elucidated by analysis of spectroscopic data. Alkaloids 4 and 5 exhibited strong activity against Gram-positive Bacillus subtilis DSM10, Mycobacterium smegmatis ATCC607, Listeria monocytogenes DSM20600, and Staphylococcus aureus ATCC25923, with minimum inhibitory concentration (MIC) values ranging from 0.5 to 4 μg/mL, and moderate activity against Candida albicans FH2173 and Aspergillus flavus ATCC9170. Compound 6 displayed moderate antibacterial activities against Grampositive bacteria. Dispyrrolopyridine A (4) was active against efflux pump deficient Escherichia coli ATCC25922 ΔtolC, with an MIC value of 8 μg/mL, as well as against Caenorhabditis elegans N2 with an MIC value of 32 μg/mL. Other compounds were inactive against these microorganisms. The biosynthetic route toward discolins A and B (1 and 2) was investigated using in vivo and in vitro experiments. It comprises an enzymatic decarboxylation of phenylalanine to PEA catalyzed by DisA, followed by a nonenzymatic condensation to form the central imidazolium ring. This spontaneous formation of the imidazolium core was verified by means of a synthetic one-pot reaction using the respective building blocks. Six additional strains belonging to three Tenacibaculum species were able to produce discolins, and several DisA analogues were identified in various marine flavobacterial genera, suggesting the widespread presence of PEA-derived compounds in marine ecosystems.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Journal Of Natural Productsmentioning

confidence: 99%

Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

et al. 2022

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“…Phenethylamine derivatives isolated from the strain of Arenibacter nanhaiticus sp. nov. NH36AT consist of antimicrobial activity against Staphylococcus aureus and Bacillus subtilis, Escherichia coli [ 163 ]. Lactobacillus iners also produce a moderate level of lactic acid and prevent BV [ 164 ].…”

Section: Microbiota Metabolites Therapeutic Insight In Ptbmentioning

confidence: 99%

Molecular Mechanism of Microbiota Metabolites in Preterm Birth: Pathological and Therapeutic Insights

Ansari

Bose

You

et al. 2021

IJMS

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Preterm birth (PTB) refers to the birth of infants before 37 weeks of gestation and is a challenging issue worldwide. Evidence reveals that PTB is a multifactorial dysregulation mediated by a complex molecular mechanism. Thus, a better understanding of the complex molecular mechanisms underlying PTB is a prerequisite to explore effective therapeutic approaches. During early pregnancy, various physiological and metabolic changes occur as a result of endocrine and immune metabolism. The microbiota controls the physiological and metabolic mechanism of the host homeostasis, and dysbiosis of maternal microbial homeostasis dysregulates the mechanistic of fetal developmental processes and directly affects the birth outcome. Accumulating evidence indicates that metabolic dysregulation in the maternal or fetal membranes stimulates the inflammatory cytokines, which may positively progress the PTB. Although labour is regarded as an inflammatory process, it is still unclear how microbial dysbiosis could regulate the molecular mechanism of PTB. In this review based on recent research, we focused on both the pathological and therapeutic contribution of microbiota-generated metabolites to PTB and the possible molecular mechanisms.

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“…The antimicrobial activity against E. coli, S. aureus, C. albicans, and A. niger were evaluated by an agar dilution method [19]. The tested strains were cultivated on MH agar plates for bacteria at 35C.…”

Section: Methodsmentioning

confidence: 99%

New Isocoumarins and Related Metabolites from Talaromyces flavus

Yang

et al. 2016

Natural Product Communications

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Two new isocoumarin derivatives, talaisocoumarins A (1) and B (2), and three new related metabolites, talaflavuols A-C (3-5) were isolated from the wetland soil-derived fungus Talaromyces flavus BYD07-13. Their structures were elucidated by spectroscopic (NMR) and MS analyses. The absolute configurations of 1 and 2 were determined by CD and an Rh 2 (OCOCF 3) 4-induced CD method. All compounds were evaluated for cytotoxic and antimicrobial activities. However, none of them showed any activity. The plausible biosynthetic pathways for 1-5 were also proposed.

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New phenethylamine derivatives from Arenibacter nanhaiticus sp. nov. NH36AT and their antimicrobial activity

Cited by 13 publications

References 13 publications

Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11

Molecular Mechanism of Microbiota Metabolites in Preterm Birth: Pathological and Therapeutic Insights

New Isocoumarins and Related Metabolites from Talaromyces flavus

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