Fatty-acid derivative acts as a sea lamprey migratory pheromone

29Citations
Citations of this article
35Readers
Mendeley users who have this article in their library.

Abstract

Olfactory cues provide critical information for spatial orientation of fish, especially in the context of anadromous migrations. Born in freshwater, juveniles of anadromous fish descend to the ocean where they grow into adults before migrating back into freshwater to spawn. The reproductive migrants, therefore, are under selective pressures to locate streams optimal for offspring survival. Many anadromous fish use olfactory cues to orient toward suitable streams. However, no behaviorally active compounds have been identified as migratory cues. Extensive studies have shown that the migratory adult sea lampreys (Petromyzon marinus), a jawless fish, track a pheromone emitted by their stream-dwelling larvae, and, consequently, enter streams with abundant larvae. We fractionated extracts of larval sea lamprey washings with guidance from a bioassay that measures in-stream migratory behaviors of adults and identified four dihydroxylated tetrahydrofuran fatty acids, of which (+)-(2S,3S,5R)-tetrahydro-3-hydroxy-5-[(1R)-1-hydroxyhexyl]-2-furanoctanoic acid was shown as a migratory pheromone. The chemical structure was elucidated by spectroscopies and confirmed by chemical synthesis and X-ray crystallography. The four fatty acids were isomer-specific and enantiomer-specific in their olfactory and behavioral activities. A synthetic copy of the identified pheromone was a potent stimulant of the adult olfactory epithelium, and, at 5 × 10−13 M, replicated the extracts of larval washings in biasing adults into a tributary stream. Our results reveal a pheromone that bridges two distinct life stages and guides orientation over a large space that spans two different habitats. The identified molecule may be useful for control of the sea lamprey.

References Powered by Scopus

Nuclear Magnetic Resonance Enantiomer Regents. Configurational Correlations via Nuclear Magnetic Resonance Chemical Shifts of Diastereomeric Mandelate, O-Methylmandelate, and α-Methoxy-α-trifluoromethylphenylacetate (MTPA) Esters

3076Citations
N/AReaders
Get full text

'Pheromones': A new term for a class of biologically active substances

930Citations
N/AReaders
Get full text

Mosher ester analysis for the determination of absolute configuration of stereogenic (Chiral) carbinol carbons

645Citations
N/AReaders
Get full text

Cited by Powered by Scopus

Scientists' warning on invasive alien species

1292Citations
N/AReaders
Get full text

Maintenance management and eradication of established aquatic invaders

70Citations
N/AReaders
Get full text

High predation of native sea lamprey during spawning migration

41Citations
N/AReaders
Get full text

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Cite

CITATION STYLE

APA

Li, K., Brant, C. O., Huertas, M., Hessler, E. J., Mezei, G., Scott, A. M., … Li, W. (2018). Fatty-acid derivative acts as a sea lamprey migratory pheromone. Proceedings of the National Academy of Sciences of the United States of America, 115(34), 8603–8608. https://doi.org/10.1073/pnas.1803169115

Readers over time

‘18‘19‘20‘21‘22‘23‘24036912

Readers' Seniority

Tooltip

PhD / Post grad / Masters / Doc 9

50%

Professor / Associate Prof. 5

28%

Researcher 4

22%

Readers' Discipline

Tooltip

Agricultural and Biological Sciences 7

41%

Chemistry 4

24%

Environmental Science 4

24%

Computer Science 2

12%

Article Metrics

Tooltip
Mentions
News Mentions: 2
Social Media
Shares, Likes & Comments: 1

Save time finding and organizing research with Mendeley

Sign up for free
0