2013
DOI: 10.1021/np400448y
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Cytotoxic Psammaplysin Analogues from a Suberea sp. Marine Sponge and the Role of the Spirooxepinisoxazoline in Their Activity

Abstract: Seventeen bromotyrosine-derived metabolites, including eight new compounds, were isolated from a Micronesian sponge of the genus Suberea. Four of the new compounds were psammaplysin derivatives (10-13), and the other four were ceratinamine derivatives (14-17). Of the compounds obtained, the psammaplysins exhibited cytotoxicity against human cancer cell lines (GI₅₀ values down to 0.8 μM), while the ceratinamine and moloka'iamine analogues showed almost no activity. These results suggest that the spirooxepinisox… Show more

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Cited by 32 publications
(73 citation statements)
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“…Only psammaplysin X 691 and the 19-hydroxy derivative 692 showed activity against six HTCLs. 705 Sesquibastadin 699 (Ianthella basta, Ambon, Indonesia) is a trimer of hemibastadin that inhibited a variety of protein kinases from a panel of 24 enzymes, but had no effect on the proliferation of murine lymphoma cells (L5178Y). 706 The Verongid sponges Ianthella basta and Aplysina cavernicola were examined for the presence of brominated skeletal components within their organic and siliceous matrices.…”
Section: Spongesmentioning
confidence: 99%
“…Only psammaplysin X 691 and the 19-hydroxy derivative 692 showed activity against six HTCLs. 705 Sesquibastadin 699 (Ianthella basta, Ambon, Indonesia) is a trimer of hemibastadin that inhibited a variety of protein kinases from a panel of 24 enzymes, but had no effect on the proliferation of murine lymphoma cells (L5178Y). 706 The Verongid sponges Ianthella basta and Aplysina cavernicola were examined for the presence of brominated skeletal components within their organic and siliceous matrices.…”
Section: Spongesmentioning
confidence: 99%
“…11 The relative configuration of psammaplysin A (1) was first determined as (6S*,7S*) in 1985 by single-crystal X-ray crystallographic analysis of its diacetyl derivative (2). 3 Subsequent reports on the relative configuration of psammaplysins C−H were made by comparing their specific rotation values with those of psammaplysin A, 4,8,9,11,12 by chemical shift comparisons, [5][6][7]11 or by ROESY/NOESY correlation data. 8−10 The potent biological activities of the psammaplysins, together with their unusual 1,6-dioxa-2-azaspiro [4.6]undeca-2,7,9-triene motif, clearly justify efforts to resolve their absolute configuration, an aspect of their structure elucidation that could not be pursued in the original X-ray crystallographic work due to inferior crystal quality.…”
mentioning
confidence: 99%
“…Psammaplysin analogs (118-121) displayed their cytotoxicity against several human cancer cell lines with a GI 50 value down to 0.8 mM. These results suggest that the spirooxepinisoxazoline ring is necessary for cytotoxicity [54].…”
Section: Othersmentioning
confidence: 89%