Multiplex quantification of lamprey specific bile acid derivatives in environmental water using UHPLC–MS/MS

Li, Ke; Wang, Jianji; Brant, Cory O.; Ahn, SangChun; Li, Weiming

doi:10.1016/j.jchromb.2011.10.039

Cited by 20 publications

(21 citation statements)

References 60 publications

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“…The dwell time established for each transition was 0.2 s, and interscan delay was set at 20 ms. Data acquisition was carried out by Masslynx 4.1 software (Waters). To mimic the composition of sea lamprey SMW, the concentration of 3 KPZS was determined following methods developed by Li et al [32].…”

Section: Methodsmentioning

confidence: 99%

Characterization of a Novel Bile Alcohol Sulfate Released by Sexually Mature Male Sea Lamprey (Petromyzon marinus)

Brant

Siefkes

et al. 2013

PLoS ONE

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A sulphate-conjugated bile alcohol, 3,12-diketo-4,6-petromyzonene-24-sulfate (DKPES), was identified using bioassay-guided fractionation from water conditioned with sexually mature male sea lamprey (Petromyzon marinus). The structure and relative stereochemistry of DKPES was established using spectroscopic data. The electro-olfactogram (EOG) response threshold of DKPES was 10−7 Molar (M) and that of 3-keto petromyzonol sulfate (3 KPZS; a known component of the male sea lamprey sex pheromone) was 10−10 M. Behavioural studies indicated that DKPES can be detected at low concentrations by attracting sexually mature females to nests when combined with 3 KPZS. Nests baited with a mixture of DKPES and 3 KPZS (ratio 1∶29.8) attracted equal numbers of sexually mature females compared to an adjacent nest baited with 3 KPZS alone. When DKPES and 3 KPZS mixtures were applied at ratios of 2∶29.8 and 10∶29.8, the proportion of sexually mature females that entered baited nests increased to 73% and 70%, respectively. None of the sexually mature females released were attracted to nests baited with DKPES alone. These results indicated that DKPES is a component of the sex pheromone released by sexually mature male sea lamprey, and is the second biologically active compound identified from this pheromone. DKPES represents the first example that a minor component of a vertebrate pheromone can be combined with a major component to elicit critical sexual behaviors. DKPES holds considerable promise for increasing the effectiveness of pheromone-baited trapping as a means of sea lamprey control in the Laurentian Great Lakes.

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Section: Methodsmentioning

confidence: 99%

Characterization of a Novel Bile Alcohol Sulfate Released by Sexually Mature Male Sea Lamprey (Petromyzon marinus)

Brant

Siefkes

et al. 2013

PLoS ONE

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“…Bile acid analyses followed the method developed by Li et al [ 74 ] with minor modification. The analysis method was validated and exceeds the minimum standards recommended in the Food and Drug Administration guidance.…”

Section: Methodsmentioning

confidence: 99%

Hsp90 and hepatobiliary transformation during sea lamprey metamorphosis

et al. 2015

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BackgroundBiliary atresia (BA) is a human infant disease with inflammatory fibrous obstructions in the bile ducts and is the most common cause for pediatric liver transplantation. In contrast, the sea lamprey undergoes developmental BA with transient cholestasis and fibrosis during metamorphosis, but emerges as a fecund adult. Therefore, sea lamprey liver metamorphosis may serve as an etiological model for human BA and provide pivotal information for hepatobiliary transformation and possible therapeutics.ResultsWe hypothesized that liver metamorphosis in sea lamprey is due to transcriptional reprogramming that dictates cellular remodeling during metamorphosis. We determined global gene expressions in liver at several metamorphic landmark stages by integrating mRNA-Seq and gene ontology analyses, and validated the results with real-time quantitative PCR, histological and immunohistochemical staining. These analyses revealed that gene expressions of protein folding chaperones, membrane transporters and extracellular matrices were altered and shifted during liver metamorphosis. HSP90, important in protein folding and invertebrate metamorphosis, was identified as a candidate key factor during liver metamorphosis in sea lamprey. Blocking HSP90 with geldanamycin facilitated liver metamorphosis and decreased the gene expressions of the rate limiting enzyme for cholesterol biosynthesis, HMGCoA reductase (hmgcr), and bile acid biosynthesis, cyp7a1. Injection of hsp90 siRNA for 4 days altered gene expressions of met, hmgcr, cyp27a1, and slc10a1. Bile acid concentrations were increased while bile duct and gall bladder degeneration was facilitated and synchronized after hsp90 siRNA injection.ConclusionsHSP90 appears to play crucial roles in hepatobiliary transformation during sea lamprey metamorphosis. Sea lamprey is a useful animal model to study postembryonic development and mechanisms for hsp90-induced hepatobiliary transformation.Electronic supplementary materialThe online version of this article (doi:10.1186/s12861-015-0097-2) contains supplementary material, which is available to authorized users.

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“…Thus, the systematic variability of BAs in fish may lead to taxaspecific BAs in the water surrounding an individual. While many studies have determined the electrophysiological responses of fish to BAs, few have investigated the release of BAs into the water [6,7,12]. To further characterize the role of BAs as chemical cues in fish, simple, specific, rapid, and sensitive analytical methods for the quantification of BAs are needed.…”

Section: Introductionmentioning

confidence: 99%

“…Several analytical methods have been used to identify and quantify BAs in biological matrices by gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) [12][13][14][15][16][17][18][19]. The advantage of GC-MS in BA quantification lies in the reference method to ascertain structure and assign the position and stereochemistry of the hydroxyl groups on the cholane cycle [20,21].…”

Section: Introductionmentioning

confidence: 99%

“…However, GC-MS is time-consuming because of the multiple steps required for processing samples, including the cleavage of amido-and sulfo-conjugates and the methylation of carboxylic and hydroxyl groups [14,15]. For routine quantification of biological samples, ultra-high performance liquid chromatography with tandem mass spectrometry (UHPLC-MS/MS) appears to be the most sensitive and reliable method for the rapid and simultaneous determination of both non-conjugated (free) and conjugated BAs as native metabolites [12,16,17]. UHPLC provides effective chromatographic separation, while MS can efficiently ionize BAs, especially in the negative electrospray ionization (ESI) mode due to the presence of either a carboxylic function (free and glycine conjugated BAs) or sulfate function (taurine conjugated BAs).…”

Section: Introductionmentioning

confidence: 99%

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Quantification of 15 bile acids in lake charr feces by ultra-high performance liquid chromatography–tandem mass spectrometry

Buchinger

Bussy

et al. 2015

Journal of Chromatography B

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Multiplex quantification of lamprey specific bile acid derivatives in environmental water using UHPLC–MS/MS

Cited by 20 publications

References 60 publications

Characterization of a Novel Bile Alcohol Sulfate Released by Sexually Mature Male Sea Lamprey (Petromyzon marinus)

Characterization of a Novel Bile Alcohol Sulfate Released by Sexually Mature Male Sea Lamprey (Petromyzon marinus)

Hsp90 and hepatobiliary transformation during sea lamprey metamorphosis

Quantification of 15 bile acids in lake charr feces by ultra-high performance liquid chromatography–tandem mass spectrometry

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