Semi-quantitative assay for polyketide prymnesins isolated from Prymnesium parvum (Haptophyta) cultures

Claire, John W. La; Manning, Schonna R.; Talarski, Aimee

doi:10.1016/j.toxicon.2015.06.002

Cited by 11 publications

(10 citation statements)

References 25 publications

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“…Using ANOVA statistical analysis it was determined that this difference in karmitoxin production between the two growth media was statistically significant ( p < 0.0001) ( Table S2 ), however, it is possible that this observed 23% increase in karmitoxin concentration in mixotrophic cultures is associated with increased nutrition from R. salina rather than being a predator-prey induced phenomenon. This proportional production of karmitoxin in relationship to cell concentration seen here with K. armiger is in contrast to a semi-quantification study on another ichthyotoxic microalgae, the haptophyte Prymnesium parvum , in relation to the ichthyotoxins prymnesin 1 and 2, which found that the concentration of these large polyketides was not directly proportional to cell concentration [ 20 ].…”

Section: Resultscontrasting

confidence: 99%

“…For common algal toxins which affect humans there are numerous quantitative and semi-quantitative methods, however, for ichthyotoxic metabolites there are few [ 19 , 20 ], with the exception of ichthyotoxins, which also effect humans. This is certainly the case for the brevetoxin and ciguatoxin class of neurotoxins, which are routinely monitored with enzyme-linked immunosorbent assays and high-performance liquid chromatography (HPLC) coupled to tandem mass spectrometry (MS/MS) [ 21 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

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HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger

et al. 2017

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Being able to quantify ichthyotoxic metabolites from microalgae allows for the determination of ecologically-relevant concentrations that can be simulated in laboratory experiments, as well as to investigate bioaccumulation and degradation. Here, the ichthyotoxin karmitoxin, produced by Karlodinium armiger, was quantified in laboratory-grown cultures using high-performance liquid chromatography (HPLC) coupled to electrospray ionisation high-resolution time-of-flight mass spectrometry (HRMS). Prior to the quantification of karmitoxin, a standard of karmitoxin was purified from K. armiger cultures (80 L). The standard was quantified by fluorescent derivatisation using Waters AccQ-Fluor reagent and derivatised fumonisin B1 and fumonisin B2 as standards, as each contain a primary amine. Various sample preparation methods for whole culture samples were assessed, including six different solid phase extraction substrates. During analysis of culture samples, MS source conditions were monitored with chloramphenicol and valinomycin as external standards over prolonged injection sequences (>12 h) and karmitoxin concentrations were determined using the response factor of a closely eluting iturin A2 internal standard. Using this method the limit of quantification was 0.11 μg·mL−1, and the limit of detection was found to be 0.03 μg·mL−1. Matrix effects were determined with the use of K. armiger cultures grown with 13C-labelled bicarbonate as the primary carbon source.

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Section: Resultscontrasting

confidence: 99%

Section: Introductionmentioning

confidence: 99%

HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger

et al. 2017

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“… 11 Detection of prymnesins typically relies upon LC-MS analysis 10 , 11 or labelling of the conserved amine group with ninhydrin and phenylacetaldehyde to give a fluorescent adduct. 12 We were drawn to consider whether the conserved terminal bis-alkyne on prymnesin toxins might prove to be a useful chemical handle for the detection of prymnesins via the ubiquitous bioorthogonal copper-catalysed alkyne-azide cycloaddition (CuAAC) ‘click’ reaction, which has been deployed in a number of diagnostic contexts. 13 The detection of a terminal alkyne-based plant natural product using this approach was reported recently.…”

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confidence: 99%

CuAAC click chemistry for the enhanced detection of novel alkyne-based natural product toxins

et al. 2018

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“…A semi-quantitative method utilizing the primary amine of prymnesins for quantitation has been previously developed by La Claire II et al [17]. However, instead of fluorescence labeling the prymnesins directly from the biomass extract, they carried out a series of purification steps prior to quantitating the total amount of amines using a ninhydrin reaction and fluorescence detection.…”

Section: Resultsmentioning

confidence: 99%

“…Quantitative analytical methods for algal toxins that are harmful to humans, like those accumulating in shellfish, are in general well established [15]. However, only few quantitative and semi-quantitative analytical methods have been developed for ichthyotoxic metabolites [16,17,18]. Themost limiting factor in developing analytical methods is the lack of commercially available standards [19] or reliable standards at all.…”

Section: Introductionmentioning

confidence: 99%

Development of an Indirect Quantitation Method to Assess Ichthyotoxic B-Type Prymnesins from Prymnesium parvum

Svenssen

Binzer

Medić

et al. 2019

Toxins

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Harmful algal blooms of Prymnesium parvum have recurrently been associated with the killing of fish. The causative ichthyotoxic agents of this haptophyte are believed to be prymnesins, a group of supersized ladder-frame polyether compounds currently divided into three types. Here, the development of a quantitative method to assess the molar sum of prymnesins in water samples and in algal biomass is reported. The method is based on the derivatization of the primary amine group and subsequent fluorescence detection using external calibrants. The presence of prymnesins in the underivatized sample should be confirmed by liquid chromatography mass spectrometry. The method is currently only partly applicable to water samples due to the low amounts that are present. The growth and cellular toxin content of two B-type producing strains were monitored in batch cultures eventually limited by an elevated pH. The cellular toxin contents varied by a factor of ~2.5 throughout the growth cycle, with the highest amounts found in the exponential growth phase and the lowest in the stationary growth/death phases. The strain K-0081 contained ~5 times more toxin than K-0374. Further investigations showed that the majority of prymnesins were associated with the biomass (89% ± 7%). This study provides the basis for further investigations into the toxicity and production of prymnesins.

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Semi-quantitative assay for polyketide prymnesins isolated from Prymnesium parvum (Haptophyta) cultures

Cited by 11 publications

References 25 publications

HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger

HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger

CuAAC click chemistry for the enhanced detection of novel alkyne-based natural product toxins

Development of an Indirect Quantitation Method to Assess Ichthyotoxic B-Type Prymnesins from Prymnesium parvum

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