Department of Fisheries and Wildlife, Michigan State University , Room 13 Natural Resources Building, 480 Wilson Road, East Lansing, Michigan 48824, United States.
Department of Chemistry, University of Minnesota , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Org Lett. 2017 Sep 1;19(17):4444-4447. doi: 10.1021/acs.orglett.7b01921. Epub 2017 Aug 17.
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.
两种新型的磺化胆甾烷二烯酮,分别具有独特的重排侧链或甾体 C 环上罕见的顺式 11,12-二醇,分别命名为 petromyzene A(1)和 B(2),从产卵雄性七鳃鳗(Petromyzon marinus;一种无颌脊椎动物)的水条件中分离得到。这些天然产物的结构通过质谱和 NMR 光谱法阐明。Petromyzenes A 和 B 对成年七鳃鳗表现出高嗅觉效力,并对产卵雌性具有强烈的行为吸引力。