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Mar. Drugs 2019, 17(1), 22; https://doi.org/10.3390/md17010022

Effect of Pentacyclic Guanidine Alkaloids from the Sponge Monanchora pulchra on Activity of α-Glycosidases from Marine Bacteria

1
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok 690022, Russia
2
Far Eastern Federal University, Russky Island, Vladivostok 690022, Russia
*
Author to whom correspondence should be addressed.
Received: 12 November 2018 / Revised: 9 December 2018 / Accepted: 25 December 2018 / Published: 1 January 2019
(This article belongs to the Special Issue Enzyme Inhibitor from Marine Organisms)
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Abstract

The effect of monanchomycalin B, monanhocicidin A, and normonanhocidin A isolated from the Northwest Pacific sample of the sponge Monanchora pulchra was investigated on the activity of α-galactosidase from the marine γ-proteobacterium Pseudoalteromonas sp. KMM 701 (α-PsGal), and α-N-acetylgalactosaminidase from the marine bacterium Arenibacter latericius KMM 426T (α-NaGa). All compounds are slow-binding irreversible inhibitors of α-PsGal, but have no effect on α-NaGa. A competitive inhibitor d-galactose protects α-PsGal against the inactivation. The inactivation rate (kinact) and equilibrium inhibition (Ki) constants of monanchomycalin B, monanchocidin A, and normonanchocidin A were 0.166 ± 0.029 min−1 and 7.70 ± 0.62 μM, 0.08 ± 0.003 min−1 and 15.08 ± 1.60 μM, 0.026 ± 0.000 min−1, and 4.15 ± 0.01 μM, respectively. The 2D-diagrams of α-PsGal complexes with the guanidine alkaloids were constructed with “vessel” and “anchor” parts of the compounds. Two alkaloid binding sites on the molecule of α-PsGal are shown. Carboxyl groups of the catalytic residues Asp451 and Asp516 of the α-PsGal active site interact with amino groups of “anchor” parts of the guanidine alkaloid molecules. View Full-Text
Keywords: sponge Monanchora pulchra; pentacyclic guanidine alkaloids; GH36 α-galactosidase; GH109 α-N-acetylgalactosaminidase; slow-binding irreversible inhibitor; monanchomycalin B; monanhocidin A; normonanhocidin A sponge Monanchora pulchra; pentacyclic guanidine alkaloids; GH36 α-galactosidase; GH109 α-N-acetylgalactosaminidase; slow-binding irreversible inhibitor; monanchomycalin B; monanhocidin A; normonanhocidin A
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Bakunina, I.; Likhatskaya, G.; Slepchenko, L.; Balabanova, L.; Tekutyeva, L.; Son, O.; Shubina, L.; Makarieva, T. Effect of Pentacyclic Guanidine Alkaloids from the Sponge Monanchora pulchra on Activity of α-Glycosidases from Marine Bacteria. Mar. Drugs 2019, 17, 22.

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