Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation

Toxicon : Official Journal of the International Society on Toxinology
Ulf BickmeyerMichael Assmann

Abstract

Seven pyrrole alkaloids isolated from Agelas sponges were tested for interactions with the cellular calcium homeostasis. Brominated pyrrole alkaloids reduced voltage dependent calcium elevation in PC12 cells. Dibromosceptrin was the most potent alkaloid with a half maximal concentration of 2.8 microM followed by sceptrin (67.5 microM) and oroidin (75.8 microM). 4,5-Dibromopyrrole-2-carboxylic acid reduced calcium elevation at concentrations exceeding 30 microM but did not eliminate calcium elevation at concentrations up to 1 mM. 4-Bromopyrrole-2-carboxylic acid and pyrrole-2-carboxylic acid were not active in this respect. The aminoimidazole group appeared to have a significant effect on voltage dependent calcium elevation shown by the comparison of oroidin with 4,5-dibromopyrrole-2-carboxylic acid. The degree of bromination of the pyrrole moiety is another important factor, as was shown by the comparison of 4,5-dibromopyrrole-2-carboxylic acid with 4-bromopyrrole-2-carboxylic acid, as well as oroidin with hymenidin and dibromosceptrin with sceptrin. The previously reported feeding deterrent activity of brominated pyrrole alkaloids in Agelas sponges against predatory reef fish may partly be explained by a general interaction of...Continue Reading

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Citations

Apr 7, 2006·Frontiers in Zoology·Adrian WertzUlf Bickmeyer
Jan 26, 2010·Marine Drugs·Barbara ForteGianluca Papeo
Apr 20, 2010·Organic & Biomolecular Chemistry·Sven W MeyerMatthias Köck
Aug 25, 2011·Journal of the American Chemical Society·Ian B SeiplePhil S Baran
Nov 11, 2011·Marine Drugs·Sean D StoweJohn Cavanagh
Sep 1, 2009·Integrative and Comparative Biology·Erik E SotkaKristen E Whalen
Oct 20, 2010·Biochemical and Biophysical Research Communications·Ulf BickmeyerPeter Karuso
Jun 9, 2009·Comparative Biochemistry and Physiology. Toxicology & Pharmacology : CBP·Ann-Katrin LüdersUlf Bickmeyer
Jun 16, 2007·Toxicon : Official Journal of the International Society on Toxinology·Ulf BickmeyerMatthias Köck
Jul 1, 2008·Biochemical and Biophysical Research Communications·Ulf BickmeyerMatthias Köck
Oct 24, 2013·European Journal of Medicinal Chemistry·Žiga HodnikDanijel Kikelj
Jul 12, 2011·Toxicon : Official Journal of the International Society on Toxinology·Haiyan MaAllan Cembella
Dec 2, 2014·Bioorganic & Medicinal Chemistry Letters·Xiuxiu SunKequan Zhou
Nov 9, 2017·Marine Drugs·Huawei ZhangPhillip Crews
Feb 5, 2008·The Journal of Experimental Biology·Staci A Padove CohenNael A McCarty
Dec 25, 2009·ACS Chemical Biology·Angel CipresKristiina Vuori
Nov 13, 2013·Journal of Chemical Information and Modeling·Tihomir TomašićDanijel Kikelj
Mar 6, 2007·Journal of Natural Products·Ivette C PiñaPhillip Crews
Sep 27, 2021·Mycopathologia·Antonio Carlos Vital JúniorVânia Sousa Andrade

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