• Medientyp: E-Artikel
  • Titel: Bioactive pyrrole alkaloids isolated from the Red Sea: marine sponge Stylissa carteri
  • Beteiligte: Hamed, Ashraf N.E.; Schmitz, Roland; Bergermann, Anja; Totzke, Frank; Kubbutat, Michael; Müller, Werner E.G.; Youssef, Diaa T.A.; Bishr, Mokhtar M.; Kamel, Mohamed S.; Edrada-Ebel, RuAngelie; Wätjen, Wim; Proksch, Peter
  • Erschienen: Walter de Gruyter GmbH, 2018
  • Erschienen in: Zeitschrift für Naturforschung C
  • Sprache: Englisch
  • DOI: 10.1515/znc-2017-0161
  • ISSN: 1865-7125; 0939-5075
  • Schlagwörter: General Biochemistry, Genetics and Molecular Biology
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  • Beschreibung: <jats:title>Abstract</jats:title> <jats:p>Fifteen pyrrole alkaloids were isolated from the Red Sea marine sponge <jats:italic>Stylissa carteri</jats:italic> and investigated for their biological activities. Four of them were dibrominated [(+) dibromophakelline, <jats:italic>Z</jats:italic>-3-bromohymenialdisine, (±) ageliferin and 3,4-dibromo-1<jats:italic>H</jats:italic>-pyrrole-2-carbamide], nine compounds were monobrominated [(−) clathramide C, agelongine, (+) manzacidin A, (−) 3-bromomanzacidin D, <jats:italic>Z</jats:italic>-spongiacidin D, <jats:italic>Z</jats:italic>-hymenialdisine, 2-debromostevensine, 2-bromoaldisine and 4-bromo-1<jats:italic>H</jats:italic>-pyrrole-2-carbamide)] and finally, two compounds were non-brominated derivatives viz., <jats:italic>E</jats:italic>-debromohymenialdisine and aldisine. The structure elucidations of isolated compounds were based on 1D &amp; 2D NMR spectroscopic and MS studies, as well as by comparison with literature. In-vitro, <jats:italic>Z</jats:italic>-spongiacidin D exhibited a moderate activity on (ARK5, CDK2-CycA, CDK4/CycD1, VEGF-R2, SAK and PDGFR-beta) protein kinases. Moreover, <jats:italic>Z</jats:italic>-3-bromohymenialdisine showed nearly similar pattern. Furthermore, <jats:italic>Z</jats:italic>-hymenialdisine displayed a moderate effect on (ARK5 &amp; VEGF-R2) and (−) clathramide C showed a moderate activity on AURORA-A protein kinases. While, agelongine, (+) manzacidin A, <jats:italic>E</jats:italic>-debromohymenialdisine and 3,4-dibromo-1<jats:italic>H</jats:italic>-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 <jats:italic>Z</jats:italic>-3-bromohymenialdisine on L5178Y. Finally, <jats:italic>Z</jats:italic>-hymenialdisine, <jats:italic>Z</jats:italic>-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.</jats:p>