1998
DOI: 10.1021/np970462z
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Cytotoxic Scalarane Sesterterpenes from a Sponge, Hyrtios erecta

Abstract: Novel scalarane sesterterpenes (1-4) were isolated from a sponge, Hyrtios erecta (order Dictyoceratida). They were characterized by means of spectral analyses, X-ray crystallography, and chemical reactions. Compound 1 showed potent in vitro and in vivo antitumor activities. In addition, the structure-activity relationship was also discussed using computer-assisted structure matching of 1 and aragusterols.

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Cited by 32 publications
(55 citation statements)
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“…The results of these assays (see Table 3) show that all four compounds inhibit cell proliferation (GI 50 5-27 µM), with 4 being 3 times more potent than the other compounds at inhibiting cell growth. Considering our results in light of those from an SAR study by Sato et al, 21 who compared the anticancer activity of two tetraoxygenated sclaranes with aragusterols, confirms that a 3-keto group enhances activity over a 3R-or 3 -hydroxyl functional group. Oxygenation at C-3 appears to be necessary, as well as placement of If there is no hydroxyl group at any of these latter positions, aragusterols become inactive, 22 while multiple oxidation (hydroxyl and/or epoxide functionality) seems to enhance biological activity.…”
Section: Resultssupporting
confidence: 85%
“…The results of these assays (see Table 3) show that all four compounds inhibit cell proliferation (GI 50 5-27 µM), with 4 being 3 times more potent than the other compounds at inhibiting cell growth. Considering our results in light of those from an SAR study by Sato et al, 21 who compared the anticancer activity of two tetraoxygenated sclaranes with aragusterols, confirms that a 3-keto group enhances activity over a 3R-or 3 -hydroxyl functional group. Oxygenation at C-3 appears to be necessary, as well as placement of If there is no hydroxyl group at any of these latter positions, aragusterols become inactive, 22 while multiple oxidation (hydroxyl and/or epoxide functionality) seems to enhance biological activity.…”
Section: Resultssupporting
confidence: 85%
“…In vivo, animals inoculated i.p. with P388 cells and injected i.p.with 0.5 to 8 mg/Kg of compound 1 on days 1, 5 and 9 after P388 cells injection lengthened their life span by 24%-74% [67]. Another sponge compound that demonstrated potent in vivo anticancer activity is B6.…”
Section: Spongesmentioning
confidence: 99%
“…Scalarane sesterterpenes are characteristic secondary metabolites of some sponges. From a sponge, Hyrtios erecta, new eight scalarane sesterterpenes 307-314 have been isolated [111,112]. Generally, they are not functionalized on A-B-ring carbons, while antitumor compounds obtained from this sponge contain unique 3-oxygenated structures.…”
Section: Sesterterpenes (Table 11)mentioning
confidence: 99%