Bile Salt-like Dienones Having a Novel Skeleton or a Rare Substitution Pattern Function as Chemical Cues in Adult Sea Lamprey

Ke Li, Anne M. Scott, Cory O. Brant, Skye D. Fissette, Joseph J. Riedy, Thomas R. Hoye, Weiming Li

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Two novel sulfated bile salt-like dienones, featuring either a unique, rearranged side chain or a rare cis-11,12-diol on the steroidal C-ring, herein named petromyzene A (1) and B (2), respectively, were isolated from water conditioned with spawning male sea lamprey (Petromyzon marinus; a jawless vertebrate animal). The structures of these natural products were elucidated by mass spectrometry and NMR spectroscopy. Petromyzenes A and B exhibited high olfactory potency for adult sea lamprey and strong behavioral attraction for spawning females.

Original languageEnglish (US)
Pages (from-to)4444-4447
Number of pages4
JournalOrganic Letters
Volume19
Issue number17
DOIs
StatePublished - Sep 1 2017

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