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Weiming Li - One of the best experts on this subject based on the ideXlab platform.

  • petromylidenes a c 2 alkylidene bile salt derivatives isolated from sea lamprey Petromyzon marinus
    Marine Drugs, 2018
    Co-Authors: Ke Li, Anne M. Scott, Joseph J. Riedy, Skye Fissette, Tyler J Buchinger, Weiming Li
    Abstract:

    Three novel bile acid derivatives, petromylidenes A–C (1–3), featuring uncommon alkylidene adductive scaffolds, were isolated from water conditioned with sexually mature male sea lampreys (Petromyzon marinus). Their structures were elucidated by mass spectrometry and NMR spectroscopy, and by comparison to spectral data of related structures. The identification of compounds 1–3, further illustrates the structural diversity of the 5α bile salt family. Compounds 1–3 exhibited notable biological properties as well, including high olfactory potencies in adult sea lampreys and strong behavioral attraction of ovulated female sea lampreys. Electro-olfactogram recordings indicated that the limit of detection for 1 was 10−9 M, 2 was 10−11 M, and 3 was less than 10−13 M. These results suggested 1–3 were likely male pheromones, which guide reproductive behaviors in the sea lamprey.

  • Three Novel Bile Alcohols of Mature Male Sea Lamprey (Petromyzon marinus) Act as Chemical Cues for Conspecifics
    Journal of Chemical Ecology, 2017
    Co-Authors: Ke Li, Anne M. Scott, Joseph J. Riedy, Skye Fissette, Zoe E. Middleton, Weiming Li
    Abstract:

    Sea lamprey, Petromyzon marinus , rely heavily on chemical cues that mediate their life history events, such as migration and reproduction. Here, we describe Petromyzone A–C ( 1 – 3 ), three novel bile alcohols that are highly oxidized and sulfated, isolated from water conditioned with spermiated male sea lamprey. Structures of these compounds were unequivocally established by spectroscopic analyses and by comparison with spectra of known compounds. Electro-olfactogram recordings showed that 1 at 10^−11 M was stimulatory to the adult sea lamprey olfactory epithelium, while 2 and 3 were stimulatory at 10^−13 M. Behavioral assays indicated that 1 is attractive, 2 is not attractive or repulsive, and 3 is repulsive to ovulated female sea lamprey. The results suggest that 1 and 2 may be putative pheromones that mediate chemical communication in sea lamprey. The identification of these three components enhances our understanding of the structures and functions of sex pheromone components in this species and may provide useful behavioral manipulation tools for the integrated management of sea lamprey, a destructive invader in the Laurentian Great Lakes.

  • chemical cues and pheromones in the sea lamprey Petromyzon marinus
    Frontiers in Zoology, 2015
    Co-Authors: Tyler J Buchinger, Cory O Brant, Barbara S Zielinski, Michael J Siefkes, Weiming Li
    Abstract:

    Chemical cues and pheromones guide decisions in organisms throughout the animal kingdom. The neurobiology, function, and evolution of olfaction are particularly well described in insects, and resulting concepts have driven novel approaches to pest control. However, aside from several exceptions, the olfactory biology of vertebrates remains poorly understood. One exception is the sea lamprey (Petromyzon marinus), which relies heavily upon olfaction during reproduction. Here, we provide a broad review of the chemical cues and pheromones used by the sea lamprey during reproduction, including overviews of the sea lamprey olfactory system, chemical cues and pheromones, and potential applications to population management. The critical role of olfaction in mediating the sea lamprey life cycle is evident by a well-developed olfactory system. Sea lamprey use chemical cues and pheromones to identify productive spawning habitat, coordinate spawning behaviors, and avoid risk. Manipulation of olfactory biology offers opportunities for management of populations in the Laurentian Great Lakes, where the sea lamprey is a destructive invader. We suggest that the sea lamprey is a broadly useful organism with which to study vertebrate olfaction because of its simple but well-developed olfactory organ, the dominant role of olfaction in guiding behaviors during reproduction, and the direct implications for vertebrate pest management.

  • Petromyzonin a hexahydrophenanthrene sulfate isolated from the larval sea lamprey Petromyzon marinus l
    Organic Letters, 2013
    Co-Authors: Ke Li, Cory O Brant, Mar Huertas, Weiming Li
    Abstract:

    A new hexahydrophenanthrene sulfate was identified from water conditioned with sea lamprey larvae (Petromyzon marinus) and named Petromyzonin. Its structure was unequivocally elucidated on the basis of spectroscopic analyses including comparison with spectra of known compounds. The absolute configuration was determined by electronic circular dichroism. Petromyzonin may function as a chemical signal, as it elicited responses in electro-olfactogram recording with a dynamic concentration–response relationship and a detection threshold of 10–11 M.

  • identification of squalamine in the plasma membrane of white blood cells in the sea lamprey Petromyzon marinus
    Journal of Lipid Research, 2007
    Co-Authors: Weiming Li
    Abstract:

    It is well established that innate mechanisms play an important role in the immunity of fish. Antimicrobial peptides have been isolated and characterized from several species of teleosts. Here, we report the isolation of an anti- microbialcompoundfromthebloodofbacteriallychallenged sea lamprey, Petromyzon marinus. An acetic acid extract from theblood cells ofchallenged fish was subjectedtosolid-phase extraction, cation-exchange chromatography, gel-filtration chromatography, and reverse-phase high-performance liquid chromatography, with the purified fractions assayed for anti- microbial activity. Surprisingly, antimicrobial activity in these fractions originated from squalamine, an aminosterol previ- ouslyidentifiedinthedogfishshark,Squalusacanthias.Further chromatographic and mass spectrometric analyses confirmed the identity of squalamine, an antimicrobial and antiangio- genic agent, in the active fraction from the sea lamprey blood cells. Immunocytochemical analysis localized squalamine to the plasma membrane of white blood cells. Therefore, we postulate that squalamine has an important role in the innate immunity that defends the lamprey against microbial invasion. The full biochemical and immunological roles of squalamine in the white blood cell membrane remain to be investigated.—Yun, S-S. and W. Li. Identification of squalamine in the plasma membrane of white blood cells in the sea lamprey, Petromyzon marinus. J. Lipid Res. 2007. 48: 2579-2586.

A P Scott - One of the best experts on this subject based on the ideXlab platform.

  • the sea lamprey Petromyzon marinus has a receptor for androstenedione
    Biology of Reproduction, 2007
    Co-Authors: Mara B Bryan, A P Scott, Weiming Li
    Abstract:

    The use of nuclear steroid receptors as ligand-activated transcription factors is a critical event in vertebrate evolution. It is believed that nuclear steroid receptors arose at or before the vertebrate radiation, except for an androgen receptor (Ar) that evolved only in the gnathostome line. We report an androgen-Ar complex in the male sea lamprey (Petromyzon marinus), an extant jawless vertebrate. The androgen with the highest affinity is not testosterone, but its direct precursor, androstenedione (Ad). To establish that the binding moiety in lamprey testis is a receptor—and not an ‘‘androgen-binding protein’’—we have shown that it can be extracted from the nucleus as well as the cytosol, that the Ad-receptor complex binds to DNA, and that the receptor is approximately twice the size of an androgenbinding protein extracted from the Atlantic salmon testis. The capacity (and high affinity) of binding of the lamprey Ar is such that much of the Ad present in male lampreys becomes sequestered within the testis (as opposed to circulating in the plasma). Concentrations of Ad (but not of testosterone) in plasma and testis tissue are upregulated by injection of lamprey GnRH. Implantation of male lampreys with exogenous Ad significantly accelerates the development of the testis and growth of at least one secondary male characteristic. It appears that all classes of steroid hormones have contributed to the evolution of the regulatory complexity of steroid receptors found in modern vertebrates.

  • pheromones of the male sea lamprey Petromyzon marinus l structural studies on a new compound 3 keto allocholic acid and 3 keto Petromyzonol sulfate
    Steroids, 2003
    Co-Authors: A P Scott, Weiming Li
    Abstract:

    This study reports the results of chemical and chromatographic studies which establish the presence of 3-keto allocholic acid (3kACA) in water extracts from spermiating male sea lamprey, Petromyzon marinus. This is the second compound to be isolated and identified from these extracts. The first was 3-keto Petromyzonol sulfate (3kPZS), which was shown to act as strong pheromonal attractant for ovulated females. Some new characterization data on 3kPZS (utilizing an only recently available synthetic preparation of the compound) is also included. The possibility that a mixture of 3kACA and 3kPZS might be a more potent pheromonal attractant than either compound alone is discussed.

Mara B Bryan - One of the best experts on this subject based on the ideXlab platform.

  • the sea lamprey Petromyzon marinus has a receptor for androstenedione
    Biology of Reproduction, 2007
    Co-Authors: Mara B Bryan, A P Scott, Weiming Li
    Abstract:

    The use of nuclear steroid receptors as ligand-activated transcription factors is a critical event in vertebrate evolution. It is believed that nuclear steroid receptors arose at or before the vertebrate radiation, except for an androgen receptor (Ar) that evolved only in the gnathostome line. We report an androgen-Ar complex in the male sea lamprey (Petromyzon marinus), an extant jawless vertebrate. The androgen with the highest affinity is not testosterone, but its direct precursor, androstenedione (Ad). To establish that the binding moiety in lamprey testis is a receptor—and not an ‘‘androgen-binding protein’’—we have shown that it can be extracted from the nucleus as well as the cytosol, that the Ad-receptor complex binds to DNA, and that the receptor is approximately twice the size of an androgenbinding protein extracted from the Atlantic salmon testis. The capacity (and high affinity) of binding of the lamprey Ar is such that much of the Ad present in male lampreys becomes sequestered within the testis (as opposed to circulating in the plasma). Concentrations of Ad (but not of testosterone) in plasma and testis tissue are upregulated by injection of lamprey GnRH. Implantation of male lampreys with exogenous Ad significantly accelerates the development of the testis and growth of at least one secondary male characteristic. It appears that all classes of steroid hormones have contributed to the evolution of the regulatory complexity of steroid receptors found in modern vertebrates.

Stephen D Mccormick - One of the best experts on this subject based on the ideXlab platform.

Barbara S Zielinski - One of the best experts on this subject based on the ideXlab platform.

  • chemical cues and pheromones in the sea lamprey Petromyzon marinus
    Frontiers in Zoology, 2015
    Co-Authors: Tyler J Buchinger, Cory O Brant, Barbara S Zielinski, Michael J Siefkes, Weiming Li
    Abstract:

    Chemical cues and pheromones guide decisions in organisms throughout the animal kingdom. The neurobiology, function, and evolution of olfaction are particularly well described in insects, and resulting concepts have driven novel approaches to pest control. However, aside from several exceptions, the olfactory biology of vertebrates remains poorly understood. One exception is the sea lamprey (Petromyzon marinus), which relies heavily upon olfaction during reproduction. Here, we provide a broad review of the chemical cues and pheromones used by the sea lamprey during reproduction, including overviews of the sea lamprey olfactory system, chemical cues and pheromones, and potential applications to population management. The critical role of olfaction in mediating the sea lamprey life cycle is evident by a well-developed olfactory system. Sea lamprey use chemical cues and pheromones to identify productive spawning habitat, coordinate spawning behaviors, and avoid risk. Manipulation of olfactory biology offers opportunities for management of populations in the Laurentian Great Lakes, where the sea lamprey is a destructive invader. We suggest that the sea lamprey is a broadly useful organism with which to study vertebrate olfaction because of its simple but well-developed olfactory organ, the dominant role of olfaction in guiding behaviors during reproduction, and the direct implications for vertebrate pest management.

  • the morphology of the olfactory epithelium in larval juvenile and upstream migrant stages of the sea lamprey Petromyzon marinus
    Brain Behavior and Evolution, 1995
    Co-Authors: Jamie Vandenbossche, James G Seelye, Barbara S Zielinski
    Abstract:

    The structure of the olfactory epithelium in the larval, juvenile and upstream migrant stages of the sea lamprey, Petromyzon marinus, was investigated by light microscopy and by sca