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具有新颖骨架或罕见取代模式的胆盐二烯酮可作为成体海七鳃鳗的化学线索。

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

机构信息

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.

出版信息

Org Lett. 2017 Sep 1;19(17):4444-4447. doi: 10.1021/acs.orglett.7b01921. Epub 2017 Aug 17.

DOI:10.1021/acs.orglett.7b01921
PMID:28816048
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.

摘要

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。

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