Biological activities of marine sesquiterpenoid quinones: structure-activity relationships in cytotoxic and hemolytic assays.
Sesquiterpenoid quinones from marine sponges and their semisynthetic derivatives were compared for cytotoxicity on developing eggs of sea urchin Strongylocentrotus nudus and Ehrlich carcinoma cells, and for hemolytic activities on mice red blood cells. Structure-activity studies showed that activities of these compounds with a hydroxyl group at C-20 ((2), (7)) were higher than their methoxyl ((1), (8)) and amino ((4), (5)) derivatives at this position. Sesquiterpenoid quinones containing a dihydropyran ring ((10)-(12)) had lower activity than noncyclic compounds. The structure of the terpenoid moieties of the compounds had no significant influence on biological activity. There was a direct correlation between cytotoxic and hemolytic activities. This report discusses the mechanism of action employed by these compounds against cell membranes.
Prokof'eva
Nina G
NG
Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok 690022, Russian Federation.
Utkina
Natalia K
NK
Chaikina
Elena L
EL
Makarchenko
Aleksandra E
AE
D000818:Animals; D045744:Cell Line, Tumor; D002462:Cell Membrane / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D008386:Marine Biology; D051379:Mice; D011161:Porifera / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry / Q000494:pharmacology*; D012617:Sea Urchins / Q000166:cytology; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000032:analysis; D015053:Zygote / Q000187:drug effects
D011809:Quinones; D012717:Sesquiterpenes; D013481:Superoxides