Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida.
A review of results of bioactivity and reactivity examinations of marine sesquiterpene (hydro)quinones is presented. The article is focused mostly on friedo- rearranged drimane structural types, isolated from sponges of the order Dictyoceratida. Examples of structural correlations are outlined. Available results on the mechanism of redox processes and examinations of chemo- and regioselectivity in addition reactions are presented and, where possible, analyzed in relation to established bioactivities. Most of the bioactivity examinations are concerned with antitumor activities and the mechanism thereof, such as DNA damage, arylation of nucleophiles, tubulin assembly inhibition, protein kinase inhibition, inhibition of the arachidonic cascade, etc. Perspectives on marine drug development are discussed with respect to biotechnological methods and synthesis. Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed.
Sladić
Dusan
D
Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, POB 158, 11001 Belgrade, Serbia and Montenegro. dsladic@chem.bg.ac.yu
Gasić
Miroslav J
MJ
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D004249:DNA Damage; D006056:Golgi Apparatus / Q000187:drug effects; D006873:Hydroquinones / Q000737:chemistry / Q000378:metabolism; D008954:Models, Biological; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry*; D047428:Protein Kinase Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D011494:Protein Kinases / Q000378:metabolism; D011499:Protein Processing, Post-Translational / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D014404:Tubulin / Q000187:drug effects / Q000378:metabolism
D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D006873:Hydroquinones; D047428:Protein Kinase Inhibitors; D012717:Sesquiterpenes; D014404:Tubulin; D011494:Protein Kinases; C023663:avarol; C031927:hydroquinone