Two new karlotoxins found in Karlodinium veneficum (strain GM2) from the East China Sea

Cai, Pengjie; He, Shan; Zhou, Chengxu; Place, Allen R.; Haq, Saddef; Ding, Lijian; Chen, Haimin; Jiang, Ying; Guo, Cheng; Xu, Yaru; Zhang, Jinrong; Yan, Xiaojun

doi:10.1016/j.hal.2016.08.001

Cited by 37 publications

(13 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…301 The macrolides iriomoteolide-10a 708 and -12a 709 were obtained from an Amphidinium sp. 302 Three new brevisulcatic acids (BSXs), ladder-frame polyethers 710-712 were isolated from Karenia brevisculcata, 303 two new karlotoxins, polyketides 713 and 714 were obtained from Karlodinium ven-ecum, 304 and the ladder-frame polyether prymnesin-B1 715 was obtained from the microalga Prymnesium parvum. 305 The relative conguration of the C-3-C-12 portion of amphirionin-5 716 was assigned by stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product.…”

Section: Dinoagellatesmentioning

confidence: 99%

Marine natural products

et al. 2018

View full text Add to dashboard Cite

Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

show abstract

Section: Dinoagellatesmentioning

confidence: 99%

Marine natural products

et al. 2018

View full text Add to dashboard Cite

show abstract

“…The dinoflagellate Karlodinium armiger produces karmitoxin [ 30 ], an ichthyotoxic metabolite structurally related to the karlotoxins, amphidinols, and others ( Table S1 ) [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 ]. Presented here is a method for the quantitative analysis of karmitoxin in laboratory-grown cultures of K. armiger using iturin A2 as an internal standard by HPLC-QTOF-MS.…”

Section: Introductionmentioning

confidence: 99%

HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger

et al. 2017

View full text Add to dashboard Cite

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.

show abstract

“…The toxic strain of K. veneficum (GM2, in which toxin had been demonstrated by Cai et al . ) was used as a positive control in this study. Algal cultures grown to exponential phases in sterile natural seawater (25 psu) enriched with f/2‐Si medium were used for the toxicity and karlotoxin detection analyses.…”

Section: Methodsmentioning

confidence: 99%

Biochemical characteristics support the recently described species Karlodinium zhouanum (Gymnodiniales, Dinophyceae)

Zhu

Zhou

Meng

et al. 2019

Phycological Research

Self Cite

View full text Add to dashboard Cite

SUMMARY The small athecate dinoflagellate Karlodinium zhouanum is a species recently described in the coastal waters of China. K. zhouanum is morphologically similar to Karlodinium veneficum, a typical ichthyotoxic blooming karlotoxin‐producing species, and it is impossible to distinguish between these two species based on light microscopy. In this study, strains of K. zhouanum isolated from the East China Sea were studied. By analyzing toxins, toxicity, lipid characteristics and typical molecular and physiological traits of this species, K. zhouanum was shown to be nontoxic to brine shrimp and widely spread over the coastal waters of China. No karlotoxin‐like toxin was detected by liquid chromatography‐mass spectrometry (LC–MS). Instead of gymnodinosterol, the critical sterol in toxic K. veneficum, 27(nor)‐24S‐4α‐Methyl‐5α‐ergosta‐8(14)‐en‐3β‐ol (NEE) was dominant in K. zhouanum, while gymnodinosterol was absent. These sterol characteristics may provide not only support for the species separation between toxic and nontoxic species of Karlodinium but also environmental survey tools to differentiate the contribution of nontoxic Karlodinium strains, which has been unclear until now.

show abstract

Two new karlotoxins found in Karlodinium veneficum (strain GM2) from the East China Sea

Cited by 37 publications

References 29 publications

Marine natural products

Marine natural products

HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger

Biochemical characteristics support the recently described species Karlodinium zhouanum (Gymnodiniales, Dinophyceae)

Contact Info

Product

Resources

About