Bioconversion of alkaloids to high-value chemicals: Comparative analysis of newly isolated lupanine degrading strains

Parmaki, Stella; Vyrides, Ioannis; Vasquez, Marlen I.; Hartman, Viki; Zacharia, Irene; Hadjiadamou, Ioanna; Barbeitos, Catarina B.M.; Ferreira, Frederico Castelo; Afonso, Carlos A. M.; Drouza, Chryssoula; Koutinas, Michalis

doi:10.1016/j.chemosphere.2017.10.165

Cited by 17 publications

(21 citation statements)

References 37 publications

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“…In this study, the enantioselective degradation of racemic lupanine was investigated during fermentation of three microorganisms (P. putida LPK411, R. rhodochrous LPK211, Rhodococcus sp. LPK311), which are capable of utilizing racemic lupanine as single carbon substrate [15]. The results demonstrate that all microorganisms could perform resolution degrading faster D-(+)-lupanine ( Fig.…”

Section: Biocatalytic Resolution Of Lupanine Enantiomeric Mixturementioning

confidence: 80%

“…Santana et al [17] demonstrated that the molecules 3-hydroxylupanine, 13-hydroxylupanine, 17-oxosparteine, 3,4-dehydrolupanine and α-isolupanine can be produced during lupanine bioconversion by unidentified microorganisms. Moreover, bioconversion experiments of racemic lupanine using LPK111 and LPK311 generated the same compound (lupanine N-oxide) as final metabolic product [15]. However, the use of P. putida LPK411 resulted in accumulation of three metabolic products from racemic lupanine biodegradation (17-oxolupanine and two derivatives incorporating open ring structures).…”

Section: Biodegradation Of Lupanine Enantiomers By P Putida Lpk411mentioning

confidence: 99%

“…However, ecotoxicological studies in mice report that racemic anabasine expressed higher toxicity as compared to the enantiomers [36]. The EC 50 values calculated for racemic lupanine on Α. fischeri have been previously determined for 5 min and 15 min of exposure as 89 mg L −1 and 47 mg L −1 respectively [15]. Thus, the results presented here indicate that lupanine enantiomers are less toxic as compared to racemic lupanine, confirming the presence of a strong synergistic effect in the toxicity action of these molecules when they exist in the form of a racemic mixture.…”

Section: Toxicological Assessment Of Lupanine Enantiomers With Marinementioning

confidence: 99%

“…Racemic and enantiopure lupanine was obtained following a procedure previously described [13,15]. The purity of lupanine isolated from the above processes was also determined by 1 H NMR spectroscopy.…”

Section: Purification Of Lupanine Racemate and Enantiomersmentioning

confidence: 99%

“…Previous research has reported that different strains are capable of degrading racemic lupanine [15][16][17]. However, studies on microbial resolution of racemic alkaloids and the metabolic properties of the microorganisms employed are still lacking.…”

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confidence: 99%

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Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization

et al. 2020

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Background: Lupanine is a plant toxin contained in the wastewater of lupine bean processing industries, which could be used for semi-synthesis of various novel high added-value compounds. This paper introduces an environmental friendly process for microbial production of enantiopure lupanine.Results: Previously isolated P. putida LPK411, R. rhodochrous LPK211 and Rhodococcus sp. LPK311, holding the capacity to utilize lupanine as single carbon source, were employed as biocatalysts for resolution of racemic lupanine. All strains achieved high enantiomeric excess (ee) of L-(−)-lupanine (> 95%), while with the use of LPK411 53% of the initial racemate content was not removed. LPK411 fed with lupanine enantiomers as single substrates achieved 92% of D-(+)-lupanine biodegradation, whereas L-(−)-lupanine was not metabolized. Monitoring the transcriptional kinetics of the luh gene in cultures supplemented with the racemate as well as each of the enantiomers supported the enantioselectivity of LPK411 for D-(+)-lupanine biotransformation, while (trans)-6-oxooctahydro-1H-quinolizine-3-carboxylic acid was detected as final biodegradation product from D-(+)-lupanine use. Ecotoxicological assessment demonstrated that lupanine enantiomers were less toxic to A. fischeri compared to the racemate exhibiting synergistic interaction. Conclusions:The biological chiral separation process of lupanine presented here constitutes an eco-friendly and low-cost alternative to widely used chemical methods for chiral separation.

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Section: Biocatalytic Resolution Of Lupanine Enantiomeric Mixturementioning

confidence: 80%

Section: Biodegradation Of Lupanine Enantiomers By P Putida Lpk411mentioning

confidence: 99%

Section: Toxicological Assessment Of Lupanine Enantiomers With Marinementioning

confidence: 99%

Section: Purification Of Lupanine Racemate and Enantiomersmentioning

confidence: 99%

mentioning

confidence: 99%

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Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization

et al. 2020

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Genome Sequence Analysis of Two Pseudomonas putida Strains to Identify a 17-Hydroxylase Putatively Involved in Sparteine Degradation

2018

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Two strains of Pseudomonas putida, Psp-LUP and Psp-SPAR, capable of growth on the quinolizidine alkaloids, lupanine and sparteine respectively, were studied here. We report the isolation of Psp-SPAR and the complete genome sequencing of both bacteria. Both were confirmed to belong to P. putida, Psp-LUP close to the type isolate of the species (NBRC14164T) and Psp-SPAR close to strains KT2440 and F1. Psp-SPAR did not grow on lupanine but did contain a gene encoding a putative quinolizidine-17-hydroxylase peptide which exhibited high similarity (76%identity) to the lupanine-17-hydroxylase characterised from Psp-LUP.

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Comparison of different cultures and culturing conditions for the biological deterioration of organic load from real saline bilge wastewater: microbial diversity insights and ecotoxicity assessment

Mazioti

Vasquez

Vyrides

2021

Environ Sci Pollut Res

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Bilge wastewater is a high strength, typically saline wastewater, originating from operation of ships. In this study, the treatment of real bilge wastewater was tested using pure isolated aerobic strains and mixed cultures (aerobic and anaerobic). The Chemical Oxygen Demand (COD) and ecotoxicity decrease were monitored over time, while the microbial dynamics alterations in mixed cultures were also recorded. The isolated strains Pseudodonghicola xiamenensis, Halomonas alkaliphila and Vibrio antiquaries were shown to significantly biodegrade bilge wastewater. Reasonable COD removal rates were achieved by aerobic mixed cultures (59%, 9 days), while anaerobic mixed cultures showed lower performance (34%, 51 days). The genus Pseudodonghicola was identified as dominant under aerobic conditions both in the mixed cultures and in the control sample (raw wastewater), after exposure to bilge wastewater, demonstrating natural proliferation of the genus and potential contribution to COD reduction. Biodegradation rates were higher when initial organic load was high, while the toxicity of raw wastewater partially decreased after treatment.

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Bioconversion of alkaloids to high-value chemicals: Comparative analysis of newly isolated lupanine degrading strains

Cited by 17 publications

References 37 publications

Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization

Resolution of alkaloid racemate: a novel microbial approach for the production of enantiopure lupanine via industrial wastewater valorization

Genome Sequence Analysis of Two Pseudomonas putida Strains to Identify a 17-Hydroxylase Putatively Involved in Sparteine Degradation

Comparison of different cultures and culturing conditions for the biological deterioration of organic load from real saline bilge wastewater: microbial diversity insights and ecotoxicity assessment

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