| Title: | Petromylidenes A(-)C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus) |
| Author(s): | Li K; Scott AM; Fissette SD; Buchinger TJ; Riedy JJ; Li W; |
| Address: | "Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA. like4@msu.edu. Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA. Scottan7@msu.edu. Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA. fissette@msu.edu. Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA. buching6@msu.edu. Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA. riedyjos@msu.edu. Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA. liweim@msu.edu" |
| ISSN/ISBN: | 1660-3397 (Electronic) 1660-3397 (Linking) |
| 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 5alpha 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" |
| Keywords: | Animals Bile Acids and Salts/chemistry/isolation & purification/*pharmacology Female Limit of Detection Magnetic Resonance Spectroscopy Male Mass Spectrometry Molecular Structure Olfactory Mucosa/*drug effects *Petromyzon Sex Attractants/chemistry/isolati; |
| Notes: | "MedlineLi, Ke Scott, Anne M Fissette, Skye D Buchinger, Tyler J Riedy, Joseph J Li, Weiming eng 137639/Great Lakes Fishery Commission/ Switzerland 2018/09/12 Mar Drugs. 2018 Sep 1; 16(9):308. doi: 10.3390/md16090308" |
