Organic Letters
Organic Letters
5 years ago

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

Bile Salt-like Dienones Having a Novel Skeleton or a Rare Substitution Pattern Function as Chemical Cues in Adult Sea Lamprey
Weiming Li, Thomas R. Hoye, Anne M. Scott, Joseph J. Riedy, Cory O. Brant, Skye D. Fissette, Ke Li
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01921

DOI: 10.1021/acs.orglett.7b01921

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