一种睡莲生物碱的对映体特异性合成及生物学研究：海狸香成分的推测结构
Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.
作者信息
Seki Hajime, Georg Gunda I
机构信息
Departments of Chemistry and Medicinal Chemistry, Institute for Therapeutics Discovery and Development, College of Pharmacy, University of Minnesota, 717 Delaware St. SE, Minneapolis MN 55414 U.S.A.
出版信息
European J Org Chem. 2014 Jun 1;2014(18):3777-3783. doi: 10.1002/ejoc.201402232.
An enantiospecific synthesis of a Nuphar alkaloid was achieved in 9 steps from -Boc-(L)-proline. The alkaloid is a minor component of castoreum, the dried scent glands of the beaver. During the course of our study, the stereochemistry of three synthetic intermediates was verified by X-ray analysis, which contributes to resolving existing discrepancies among the literature reports regarding the synthesis of this particular compound. Based on our synthesis, we propose the structure of the natural product. Also, intrigued by castoreum's therapeutic effect, which was used in ancient Greece and Rome for gynecological and other purposes, biological screening was conducted. We found that the alkaloid has affinity for the oxytocin receptor.
从 -Boc-(L)-脯氨酸出发，经9步反应实现了一种睡莲生物碱的对映体特异性合成。该生物碱是海狸干燥的气味腺——海狸香的次要成分。在我们的研究过程中，通过X射线分析验证了三种合成中间体的立体化学，这有助于解决文献报道中关于该特定化合物合成的现有差异。基于我们的合成，我们提出了天然产物的结构。此外，受古希腊和罗马将海狸香用于妇科及其他用途的治疗效果的启发，我们进行了生物筛选。我们发现该生物碱对催产素受体具有亲和力。
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