Cytotoxic guanidine alkaloids from the French Polynesian sponge Monanchora n. sp.

A Al-Mourabit (1) , A El-Demerdash , C Moriou (1) , M-T Martin , A Rodrigues-Stien , Sylvain Petek (2) , Marina Demoy-Schneider (3) , K Hall (4) , J Hooper , Cécile Debitus (2)

1 ICSN - Institut de Chimie des Substances Naturelles
2 EIO - Ecosystèmes Insulaires Océaniens (UMR 241)
3 University of French Polynesia
4 University of Calgary

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 1H 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.

Mots clés: MARINE NATURAL-PRODUCTS; CRAMBE-CRAMBE; PTILOMYCALIN-A; PULCHRA; CRAMBESCIDINS; SPICULIFER; CHEMISTRY; ARBUSCULA; FUSION; FRENCH POLYNESIA

Mots clés: PRODUITS NATURELS MARINS; CHIMIE; EPONGES; POLYNESIE FRANCAISE

Domaines: Biologie végétale; Pharmacologie

A Al-Mourabit, A El-Demerdash, C Moriou, M-T Martin, A Rodrigues-Stien, et al.. Cytotoxic guanidine alkaloids from the French Polynesian sponge Monanchora n. sp.. Journal of Natural Products, 2016, 79, p. 1929-1937. ⟨10.1021/acs.jnatprod.6b00168⟩. ⟨hal-01584556⟩