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

Li, Weiming

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

Posted on 2017-08-16 - 21:12

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.

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Li, Ke; Scott, Anne M.; Brant, Cory O.; Fissette, Skye D.; Riedy, Joseph J.; Hoye, Thomas R.; et al. (2017). Bile Salt-like Dienones Having a Novel Skeleton or a Rare Substitution Pattern Function as Chemical Cues in Adult Sea Lamprey. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01921

https://doi.org/10.1021/acs.orglett.7b01921

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