6-bromohypaphorine from marine nudibranch mollusk Hermissenda crassicornis is an agonist of human α7 nicotinic acetylcholine receptor

Marine Drugs
Igor E KasheverovVictor I Tsetlin

Abstract

6-Bromohypaphorine (6-BHP) has been isolated from the marine sponges Pachymatisma johnstoni, Aplysina sp., and the tunicate Aplidium conicum, but data on its biological activity were not available. For the nudibranch mollusk Hermissenda crassicornis no endogenous compounds were known, and here we describe the isolation of 6-BHP from this mollusk and its effects on different nicotinic acetylcholine receptors (nAChR). Two-electrode voltage-clamp experiments on the chimeric α7 nAChR (built of chicken α7 ligand-binding and glycine receptor transmembrane domains) or on rat α4β2 nAChR expressed in Xenopus oocytes revealed no action of 6-BHP. However, in radioligand analysis, 6-BHP competed with radioiodinated α-bungarotoxin for binding to human α7 nAChR expressed in GH4C1 cells (IC50 23 ± 1 μM), but showed no competition on muscle-type nAChR from Torpedo californica. In Ca2+-imaging experiments on the human α7 nAChR expressed in the Neuro2a cells, 6-BHP in the presence of PNU120596 behaved as an agonist (EC50 ~80 μM). To the best of our knowledge, 6-BHP is the first low-molecular weight compound from marine source which is an agonist of the nAChR subtype. This may have physiological importance because H. crassicornis, with its simple...Continue Reading

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Citations

Dec 2, 2017·Scientific Reports·Thomas DurekVictor I Tsetlin
Nov 15, 2017·Natural Product Reports·Lewis J Dean, Michèle R Prinsep
Sep 3, 2020·International Journal of Molecular Sciences·Evgeny P BarykinAlexander A Makarov
Nov 7, 2016·Doklady. Biochemistry and Biophysics·I E KasheverovV I Tsetlin
Mar 16, 2017·Natural Product Reports·John W BluntMichèle R Prinsep
Dec 30, 2020·Marine Drugs·Conxita Avila, Carlos Angulo-Preckler
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Taitusi TaufaRobert A Keyzers
Jan 27, 2019·Journal of Medicinal Chemistry·Dina ManettiMaria Novella Romanelli

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Methods Mentioned

BETA
column chromatography
glycosylation
transfection

Software Mentioned

ORIGIN
WinWCP

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