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Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of (1)H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.
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| http://dx.doi.org/10.1021/acs.jnatprod.6b00168 | DOI Listing |
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Article Synopsis
- * A total of 53 compounds were annotated, including 22 newly discovered analogues and 4 new homologous series, suggesting significant diversity in crambescin compounds.
- * The research highlights the effectiveness of combining manual and computational methods for detailed metabolomic analysis, underscoring its potential for high-throughput identification in similar studies.
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