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海洋环胍生物碱单锚菌素B和乌鲁波西丁A作为瞬时受体电位香草酸亚型1（TRPV1）、瞬时受体电位香草酸亚型2（TRPV2）和瞬时受体电位香草酸亚型3（TRPV3）的抑制剂，但不是瞬时受体电位锚蛋白1（TRPA1）受体的抑制剂。

Marine Cyclic Guanidine Alkaloids Monanchomycalin B and Urupocidin A Act as Inhibitors of TRPV1, TRPV2 and TRPV3, but not TRPA1 Receptors.

作者信息

Korolkova Yuliya, Makarieva Tatyana, Tabakmakher Kseniya, Shubina Larisa, Kudryashova Ekaterina, Andreev Yaroslav, Mosharova Irina, Lee Hyi-Seung, Lee Yeon-Ju, Kozlov Sergey

机构信息

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya Street, 16/10, Moscow 117997, Russia.

G.B. Elyakov Pacific Institute of Bioorganic Chemistry (PIBOC), Russian Academy of Sciences, Prospect 100 let Vladivostoku, 159, Vladivostok 690022, Russia.

出版信息

Mar Drugs. 2017 Mar 23;15(4):87. doi: 10.3390/md15040087.

DOI:10.3390/md15040087
PMID:28333079
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5408233/
Abstract

Marine sponges contain a variety of low-molecular-weight compounds including guanidine alkaloids possessing different biological activities. Monanchomycalin B and urupocidin A were isolated from the marine sponge We found that they act as inhibitors of the TRPV1, TRPV2, and TRPV3 channels, but are inactive against the TRPA1 receptor. Monanchomycalin B is the most active among all published marine alkaloids (EC 6.02, 2.84, and 3.25 μM for TRPV1, TRPV2, and TRPV3, correspondingly). Moreover, monanchomycalin B and urupocidin A are the first samples of marine alkaloids affecting the TRPV2 receptor. Two semi-synthetic urupocidin A derivatives were also obtained and tested against TRP (Transient Receptor Potential) receptors that allowed us to collect some data concerning the structure-activity relationship in this series of compounds. We showed that the removal of one of three side chains or double bonds in the other side chains in urupocidin A led to a decrease of the inhibitory activities. New ligands specific to the TRPV subfamily may be useful for the design of medicines as in the study of TRP channels biology.

摘要

海洋海绵含有多种低分子量化合物，包括具有不同生物活性的胍生物碱。从海洋海绵中分离出了莫南乔米卡林B和乌鲁波西丁A。我们发现它们可作为瞬时受体电位香草酸亚型1（TRPV1）、瞬时受体电位香草酸亚型2（TRPV2）和瞬时受体电位香草酸亚型3（TRPV3）通道的抑制剂，但对瞬时受体电位锚蛋白1（TRPA1）受体无活性。莫南乔米卡林B是所有已发表的海洋生物碱中活性最强的（对TRPV1、TRPV2和TRPV3的半数有效浓度分别为6.02、2.84和3.25 μM）。此外，莫南乔米卡林B和乌鲁波西丁A是影响TRPV2受体的首批海洋生物碱样品。还获得了两种乌鲁波西丁A的半合成衍生物，并对其进行了针对瞬时受体电位（TRP）受体的测试，这使我们能够收集有关该系列化合物构效关系的一些数据。我们表明，去除乌鲁波西丁A中三条侧链之一或另一侧链中的双键会导致抑制活性降低。TRPV亚家族的新配体可能有助于药物设计，如在TRP通道生物学研究中。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43c4/5408233/f05db246d707/marinedrugs-15-00087-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43c4/5408233/fe5659a0230c/marinedrugs-15-00087-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43c4/5408233/f05db246d707/marinedrugs-15-00087-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43c4/5408233/fe5659a0230c/marinedrugs-15-00087-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43c4/5408233/f05db246d707/marinedrugs-15-00087-g002.jpg

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