Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (<i>Petromyzon </i><i>marinus</i>) Migratory Pheromone

Hoye, Thomas R.; Dvornikovs, Vadims; Fine, Jared M.; Anderson, Kari R.; Jeffrey, Christopher S.; Muddiman, David C.; Shao, Feng; Sorensen, Peter W.; Wang, Jizhou

doi:10.1021/jo070957l

Cited by 41 publications

(24 citation statements)

References 10 publications

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“…The MS/MS fragmentation showed a 96.9603 fragment, which corresponds to HSO 4 − . The 13 C chemical shift for C-24 ( δ C 69.4 ppm) was similar to a sulfate half-ester OSO 3 Na [17]. The 1 H NMR spectrum, (See Figure S1, S2, S3, S4, S5, S6, S7), showed two deshielded methyl singlets ( δ H 1.17, s, H-18; δ H 1.24, s, H-19) and one methyl doublet ( δ H 0.87, d) with chemical shifts corresponding to methyl groups H 3 -21.…”

Section: Resultsmentioning

confidence: 80%

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: Resultsmentioning

confidence: 80%

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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“…The generated peak lists were searched against databases such as METLIN 53 and LIPID MAPS 54 , and putative compound identification was made possible by using the accurate mass in tandem with fundamental mass spectrometry concepts such as spectral accuracy 55,56 and sulfur counting. 57,58 …”

Section: Methodsmentioning

confidence: 99%

“…53 B) Confident identification of analyte by utilizing concepts such as spectral accuracy 55,56 and sulfur counting 57,58 in tandem with accurate mass to confidently identify an analyte observed in tissue.…”

Section: Figurementioning

confidence: 99%

Polarity switching mass spectrometry imaging of healthy and cancerous hen ovarian tissue sections by infrared matrix-assisted laser desorption electrospray ionization (IR-MALDESI)

Nazari

Muddiman

2016

Analyst

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Mass spectrometry imaging (MSI) is a rapidly evolving field for monitoring the spatial distribution and abundance of analytes in biological tissue sections. It allows for direct and simultaneous analysis of hundreds of different compounds in a label-free manner. In order to obtain a comprehensive metabolite and lipid data, a polarity switching MSI method using infrared matrix assisted laser desorption electrospray ionization (IR-MALDESI) was developed and optimized where the electrospray polarity was alternated from one voxel to the next. Healthy and cancerous ovarian hen tissue sections were analyzed using this method. Distribution and relative abundance of different metabolites and lipids within each tissue section were discerned, and differences between the two were revealed. Additionally, the utility of using mass spectrometry concepts such as spectral accuracy and sulfur counting for confident identification of analytes in an untargeted method are discussed.

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“…Marshall and coworkers used sulfur-counting as a means to characterize the p16 tumor suppressor protein [11], and also later in the study of glycosphingolipids [13]. Hoye and coworkers applied sulfur-counting to the study of sea lamprey pheromones [12]. …”

Section: Introductionmentioning

confidence: 99%

Spectral Accuracy and Sulfur Counting Capabilities of the LTQ-FT-ICR and the LTQ-Orbitrap XL for Small Molecule Analysis

Blake

Walker

Muddiman

et al. 2011

J. Am. Soc. Mass Spectrom.

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Color Index Disperse Yellow 42 (DY42), a high-volume disperse dye for polyester, was used to compare the capabilities of the LTQ-Orbitrap XL and the LTQ-FT-ICR with respect to mass measurement accuracy (MMA), spectral accuracy, and sulfur counting. The results of this research will be used in the construction of a dye database for forensic purposes; the additional spectral information will increase the confidence in the identification of unknown dyes found in fibers at crime scenes. Initial LTQ-Orbitrap XL data showed MMAs greater than 3 ppm and poor spectral accuracy. Modification of several Orbitrap installation parameters (e.g., deflector voltage) resulted in a significant improvement of the data. The LTQ-FT-ICR and LTQ-Orbitrap XL (after installation parameters were modified) exhibited MMA ≤ 3 ppm, good spectral accuracy (chi-square values for the isotopic distribution ≤ 2), and were correctly able to ascertain the number of sulfur atoms in the compound at all resolving powers investigated for AGC targets of 5.00×105 and 1.00×106.

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Details of the Structure Determination of the Sulfated Steroids PSDS and PADS: New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

Cited by 41 publications

References 10 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)

Polarity switching mass spectrometry imaging of healthy and cancerous hen ovarian tissue sections by infrared matrix-assisted laser desorption electrospray ionization (IR-MALDESI)

Spectral Accuracy and Sulfur Counting Capabilities of the LTQ-FT-ICR and the LTQ-Orbitrap XL for Small Molecule Analysis

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