Bioactive pyrrole alkaloids isolated from the Red Sea : marine sponge Stylissa carteri
Hamed, Ashraf N. E. and Schmitz, Roland and Bergermann, Anja and Totzke, Frank and Kubbutat, Michael and Müller, Werner E. G. and Youssef, Diaa T.A. and Bishr, Mokhtar M. and Kamel, Mohamed S. and Edrada-Ebel, RuAngelie and Wätjen, Wim and Proksch, Peter (2018) Bioactive pyrrole alkaloids isolated from the Red Sea : marine sponge Stylissa carteri. Zeitschrift fur Naturforschung C, 73 (5-6). pp. 199-210. ISSN 0939-5075 (https://doi.org/10.1515/znc-2017-0161)
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Abstract
Fifteen pyrrole alkaloids were isolated from the Red Sea marine sponge Stylissa carteri and investigated for their biological activities. Four of them were dibrominated [(+) dibromophakelline, Z-3-bromohymenialdisine, (±) ageliferin and 3,4-dibromo-1H-pyrrole-2-carbamide], nine compounds were monobrominated [(-) clathramide C, agelongine, (+) manzacidin A, (-) 3-bromomanzacidin D, Z-spongiacidin D, Z-hymenialdisine, 2-debromostevensine, 2-bromoaldisine and 4-bromo-1H-pyrrole-2-carbamide)] and finally, two compounds were non-brominated derivatives viz., E-debromohymenialdisine and aldisine. The structure elucidations of isolated compounds were based on 1D & 2D NMR spectroscopic and MS studies, as well as by comparison with literature. In-vitro, Z-spongiacidin D exhibited a moderate activity on (ARK5, CDK2-CycA, CDK4/CycD1, VEGF-R2, SAK and PDGFR-beta) protein kinases. Moreover, Z-3-bromohymenialdisine showed nearly similar pattern. Furthermore, Z-hymenialdisine displayed a moderate effect on (ARK5 & VEGF-R2) and (-) clathramide C showed a moderate activity on AURORA-A protein kinases. While, agelongine, (+) manzacidin A, E-debromohymenialdisine and 3,4-dibromo-1H-pyrrole-2-carbamide demonstrated only marginal inhibitory activities. The cytotoxicity study was evaluated in two different cell lines. The most effective secondary metabolites were (+) dibromophakelline and Z-3-bromohymenialdisine on L5178Y. Finally, Z-hymenialdisine, Z-3-bromohymenialdisine and (±) ageliferin exhibited the highest cytotoxic activity on HCT116. No report about inhibition of AURORA-A and B by hymenialdisine/hymenialdisine analogs existed and no reported toxicity of ageliferin existed in literature.
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Item type: Article ID code: 64890 Dates: DateEvent25 April 2018Published20 January 2018Published Online30 November 2017AcceptedSubjects: Medicine > Pharmacy and materia medica Department: Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences Depositing user: Pure Administrator Date deposited: 27 Jul 2018 09:00 Last modified: 02 Oct 2024 00:31 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/64890