Article

Trachycladindoles A-G: cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer.

Institute for Molecular Bioscience, The University of Queensland, St Lucia, Queensland, Australia.
Organic & Biomolecular Chemistry (Impact Factor: 3.57). 08/2008; 6(15):2765-71. DOI: 10.1039/b803455a
Source: PubMed

ABSTRACT A southern Australian marine sponge, Trachycladus laevispirulifer, yielded the cytotoxic agents trachycladindoles A-G (1-7) as a selection of novel indole-2-carboxylic acids bearing a 2-amino-4,5-dihydroimidazole moiety. The trachycladindoles displayed promising selective cytotoxicity against a panel of human cancer cell lines and their structures were assigned on the basis of detailed spectroscopic analysis. Preliminary structure activity relationship (SAR) investigations by co-metabolite defined structural features key to the trachycladindole pharmacophore, highlighting an unusual bioactive molecular motif deserving of future investigation.

0 Bookmarks
 · 
89 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: This review covers the literature published in 2011 for marine natural products, with 870 citations (558 for the period January to December 2011) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1152 for 2011), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.
    Natural Product Reports 02/2011; 28(2):196-268. · 10.18 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: A great number of structurally diverse natural products containing five-membered heterocyclic subunits, such as imidazole, oxazole, thiazole, and their saturated congeners, are abundant in nature. These naturally occurring metabolites often exhibit extensive and pharmacologically important biological activities. The latest progress in the isolation, biological activities, chemical synthetic studies, and biosynthetic pathways on these natural products is summarized in this review.
    Natural Product Reports 04/2011; 28(6):1143-91. · 10.18 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Four new tris-bromoindole cyclic guanidine alkaloids, araiosamines A-D, were isolated from the methanol extract of a marine sponge, Clathria (Thalysias) araiosa, collected from Vanuatu. Their carbon skeletons delineate a new class of indole alkaloids apparently derived from a linear polymerization process involving a carbon-carbon bond formation. Comparison of the structures including the relative configurations suggests a common intermediate containing a dihydroaminopyrimidine moiety capable of undergoing various modalities of conjugate addition to yield unprecedented ring systems.
    The Journal of Organic Chemistry 04/2011; 76(14):5515-23. · 4.56 Impact Factor