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

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

1
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya Street, 16/10, Moscow 117997, Russia
2
G.B. Elyakov Pacific Institute of Bioorganic Chemistry (PIBOC), Russian Academy of Sciences, Prospect 100 let Vladivostoku, 159, Vladivostok 690022, Russia
3
Sechenov First Moscow State Medical University, Institute of Molecular Medicine, Trubetskaya str.8, bld. 2, Moscow 119991, Russia
4
Korea Institute of Ocean Science & Technology, Marine Natural Products Laboratory, Ansan 426-744, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Kirsten Benkendorff
Received: 16 January 2017 / Revised: 28 February 2017 / Accepted: 20 March 2017 / Published: 23 March 2017
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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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 Monanchora pulchra. 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 (EC50 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. View Full-Text
Keywords: guanidine alkaloids; sponge; Monanchora pulchra; TRPV1; TRPV2; TRPV3; TRPA1 guanidine alkaloids; sponge; Monanchora pulchra; TRPV1; TRPV2; TRPV3; TRPA1
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Korolkova, Y.; Makarieva, T.; Tabakmakher, K.; Shubina, L.; Kudryashova, E.; Andreev, Y.; Mosharova, I.; Lee, H.-S.; Lee, Y.-J.; Kozlov, S. Marine Cyclic Guanidine Alkaloids Monanchomycalin B and Urupocidin A Act as Inhibitors of TRPV1, TRPV2 and TRPV3, but not TRPA1 Receptors. Mar. Drugs 2017, 15, 87.

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