Structures, biosynthesis, and bioactivities of prodiginine natural products

Li, Peishan; He, Shufen; Zhang, Xuejiao; Gao, Qi; Liu, Yanan; Liu, Liwei

doi:10.1007/s00253-022-12245-x

Cited by 7 publications

(3 citation statements)

References 91 publications

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“…Prodigiosin has recently received interest due to its antioxidant activity (which improves the immune system), its antimicrobial activity against bacterial, fungal and yeast species [ 15 , 27 , 28 , 29 ], and its antiproliferative effect on cancer cells [ 29 , 30 , 31 ]. Antimicrobial activity (although low level) against some bacterial strains was demonstrated in agar diffusion tests in the present study, as it was against other members of Enterobacteriaceae under experimental cheesemaking conditions.…”

Section: Discussionmentioning

confidence: 99%

Prodigiosin-Producing Serratia marcescens as the Causal Agent of a Red Colour Defect in a Blue Cheese

Rodrı́guez

Lobato

Vázquez

et al. 2023

Foods

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Technological defects in the organoleptic characteristics of cheese (odour, colour, texture, and flavour) reduce quality and consumer acceptance. A red colour defect in Cabrales cheese (a traditional, blue-veined, Spanish cheese made from raw milk) occurs infrequently but can have a notable economic impact on family-owned, artisanal cheesemaking businesses. This work reports the culture-based determination of Serratia marcescens as the microbe involved in the appearance of red spots on the surface and nearby inner areas of such cheese. Sequencing and analysis of the genome of one S. marcescens isolate, RO1, revealed a cluster of 16 genes involved in the production of prodigiosin, a tripyrrole red pigment. HPLC analysis confirmed the presence of prodigiosin in methanol extracts of S. marcescens RO1 cultures. The same was also observed in extracts from red areas of affected cheeses. The strain showed low survival rates under acidic conditions but was not affected by concentrations of up to 5% NaCl (the usual value for blue cheese). The optimal conditions for prodigiosin production by S. marscescens RO1 on agar plates were 32 °C and aerobic conditions. Prodigiosin has been reported to possess antimicrobial activity, which agrees with the here-observed inhibitory effect of RO1 supernatants on different bacteria, the inhibition of Enterobacteriaceae, and the delayed development of Penicillium roqueforti during cheesemaking. The association between S. marcescens and the red colour defect was strengthened by recreating the fault in experimental cheeses inoculated with RO1. The data gathered in this study point towards the starting milk as the origin of this bacterium in cheese. These findings should help in the development of strategies that minimize the incidence of pigmenting S. marcescens in milk, the red defect the bacterium causes in cheese, and its associated economic losses.

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Section: Discussionmentioning

confidence: 99%

Prodigiosin-Producing Serratia marcescens as the Causal Agent of a Red Colour Defect in a Blue Cheese

Rodrı́guez

Lobato

Vázquez

et al. 2023

Foods

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“…Within the extensive prodiginine family, PG holds the distinction of being the first discovered and most widely recognized member. Other prodiginine family members, including cycloprodigosin, undecylprodigiosin (UP), metacycloprodigiosin, and streptorubin B, exhibit distinct molecular weights or structures compared to PG but share bioactive functions suitable for medical and clinical applications ( Li et al, 2022 ).…”

Section: Introductionmentioning

confidence: 99%

Prodigiosin: unveiling the crimson wonder – a comprehensive journey from diverse bioactivity to synthesis and yield enhancement

Lu,

Liu,

Jiang

et al. 2024

Front. Microbiol.

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Prodigiosin (PG) is a red tripyrrole pigment from the prodiginine family that has attracted widespread attention due to its excellent biological activities, including anticancer, antibacterial and anti-algal activities. The synthesis and production of PG is of particular significance, as it has the potential to be utilized in a number of applications, including those pertaining to clinical drug development, food safety, and environmental management. This paper provides a systematic review of recent research on PG, covering aspects like chemical structure, bioactivity, biosynthesis, gene composition and regulation, and optimization of production conditions, with a particular focus on the biosynthesis and regulation of PG in Serratia marcescens. This provides a solid theoretical basis for the drug development and production of PG, and is expected to promote the further development of PG in medicine and other applications.

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“…Prodiginines are a group of bacterial secondary metabolites with diverse remarkable bioactivities, among which anticancer and antimicrobial effects have perhaps been described in most detail thus far ( Fürstner, 2003 ; Stankovic et al, 2014 ; Hu et al, 2016 ; Sakai-Kawada et al, 2019 ; Yip et al, 2019 ; Berning et al, 2021 ; Li et al, 2022 ). Notably, prodiginine-producing bacteria such as Streptomyces and Serratia species also dwell in the rhizosphere, the dynamic micro-biosphere around the plant roots and site of manifold chemical interactions between the bacteria and plants ( Berg, 2009 ; Lugtenberg and Kamilova, 2009 ; Meschke et al, 2012 ).…”

Section: Introductionmentioning

confidence: 99%

Production of tailored hydroxylated prodiginine showing combinatorial activity with rhamnolipids against plant-parasitic nematodes

Kossmann,

Huang,

Weihmann

et al. 2023

Front. Microbiol.

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Bacterial secondary metabolites exhibit diverse remarkable bioactivities and are thus the subject of study for different applications. Recently, the individual effectiveness of tripyrrolic prodiginines and rhamnolipids against the plant-parasitic nematode Heterodera schachtii, which causes tremendous losses in crop plants, was described. Notably, rhamnolipid production in engineered Pseudomonas putida strains has already reached industrial implementation. However, the non-natural hydroxyl-decorated prodiginines, which are of particular interest in this study due to a previously described particularly good plant compatibility and low toxicity, are not as readily accessible. In the present study, a new effective hybrid synthetic route was established. This included the engineering of a novel P. putida strain to provide enhanced levels of a bipyrrole precursor and an optimization of mutasynthesis, i.e., the conversion of chemically synthesized and supplemented monopyrroles to tripyrrolic compounds. Subsequent semisynthesis provided the hydroxylated prodiginine. The prodiginines caused reduced infectiousness of H. schachtii for Arabidopsis thaliana plants resulting from impaired motility and stylet thrusting, providing the first insights on the mode of action in this context. Furthermore, the combined application with rhamnolipids was assessed for the first time and found to be more effective against nematode parasitism than the individual compounds. To obtain, for instance, 50% nematode control, it was sufficient to apply 7.8 μM hydroxylated prodiginine together with 0.7 μg/ml (~ 1.1 μM) di-rhamnolipids, which corresponded to ca. ¼ of the individual EC50 values. In summary, a hybrid synthetic route toward a hydroxylated prodiginine was established and its effects and combinatorial activity with rhamnolipids on plant-parasitic nematode H. schachtii are presented, demonstrating potential application as antinematodal agents. Graphical Abstract

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Structures, biosynthesis, and bioactivities of prodiginine natural products

Cited by 7 publications

References 91 publications

Prodigiosin-Producing Serratia marcescens as the Causal Agent of a Red Colour Defect in a Blue Cheese

Prodigiosin-Producing Serratia marcescens as the Causal Agent of a Red Colour Defect in a Blue Cheese

Prodigiosin: unveiling the crimson wonder – a comprehensive journey from diverse bioactivity to synthesis and yield enhancement

Production of tailored hydroxylated prodiginine showing combinatorial activity with rhamnolipids against plant-parasitic nematodes

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