Dataset Information

Petromylidenes A?C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus).

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 5? 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.

SUBMITTER: Li K

PROVIDER: S-EPMC6163752 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Publications

Petromylidenes A⁻C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus).

Li Ke K Scott Anne M AM Fissette Skye D SD Buchinger Tyler J TJ Riedy Joseph J JJ Li Weiming W

Marine drugs 20180901 9

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 < ...[more]

PMID: 30200427

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Project description:The sea lamprey, Petromyzon marinus, is an anadromous, semelparous species that is vulnerable to endangered in parts of its native range due in part to loss of spawning habitat because of man-made barriers. The ability of lampreys to return to the ocean or estuary and search out alternative spawning river systems would be limited by their osmoregulatory ability in seawater. A reduction in tolerance to salinity has been documented in migrants, although the underlying mechanisms have not been characterized. We examined the capacity for marine osmoregulation in upstream spawning migrants by characterizing the physiological effects of salinity challenge from a molecular perspective. Estuarine-captured migrants held in freshwater (FW) for ∼1 week (short-term acclimation) or 2 months (long-term acclimation) underwent an incremental salinity challenge until loss of equilibrium occurred and upper thresholds of 25 and 17.5, respectively, occurred. Regardless of salinity tolerance, all lamprey downregulated FW ion-uptake mechanisms [gill transcripts of Na(+):Cl(-) cotransporter (NCC/slc12a3) and epithelial Na(+) channel (ENaC/scnn1) and kidney Na(+)/K(+)-ATPase (NKA) protein and activity but not transcript]. At their respective salinity limits, lamprey displayed a clear osmoregulatory failure and were unable to regulate [Na(+)] and [Cl(-)] in plasma and intestinal fluid within physiological limits, becoming osmocompromised. A >90% drop in haematocrit indicated haemolysis, and higher plasma concentrations of the cytosolic enzymes alanine aminotransferase, aspartate aminotransferase and lactate dehydrogenase indicated damage to other tissues, including liver. However, >80% of short-term FW-acclimated fish were able to osmoregulate efficiently, with less haemolysis and tissue damage. This osmoregulatory ability was correlated with significant upregulation of the secretory form of Na(+):K(+):2Cl(-) cotransporter (NKCC1/slc12a2) transcript levels and the re-emergence of seawater-type ionocytes detected through immunohistochemical NKA immunoreactivity in the gill, the central ionoregulatory organ. This work sheds light on the molecular and physiological limits to the potential return to seawater for lampreys searching for alternative FW systems in which to spawn.

Dataset Information

Petromylidenes A?C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus).

Publications

Petromylidenes A⁻C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (<i>Petromyzon marinus</i>).

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