title: Cytotoxic Guanidine Alkaloids from a French Polynesian Monanchora n. sp. Sponge.
abstract: 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.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.|Organic Chemistry Division, Chemistry Department, Faculty of Science, Mansoura University , Mansoura 35516, Egypt.
authors.forename: Amr
authors.initials: A
authors.lastname: El-Demerdash
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Moriou
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Alice de Souza
authors.initials: Ade S
authors.lastname: Rodrigues-Stien
authors.affiliation: Institut de Recherche pour le Développement (IRD) , UMR-241 EIO, BP529, 98713, Papeete, Tahiti, French Polynesia.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Petek
authors.affiliation: Université de la Polynésie Française , UMR-241 EIO, BP 6570, 98702 Faa'a Aéroport, Tahiti, French Polynesia.
authors.forename: Marina
authors.initials: M
authors.lastname: Demoy-Schneider
authors.affiliation: Queensland Museum , PO Box 3300, South Brisbane BC, Queensland 4101, Australia.
authors.forename: Kathryn
authors.initials: K
authors.lastname: Hall
authors.affiliation: Queensland Museum , PO Box 3300, South Brisbane BC, Queensland 4101, Australia.|Eskitis Institute for Drug Discovery, Griffith University , Nathan, Queensland 4111, Australia.
authors.forename: John N A
authors.initials: JN
authors.lastname: Hooper
authors.affiliation: Institut de Recherche pour le Développement (IRD) , UMR-241 EIO, BP529, 98713, Papeete, Tahiti, French Polynesia.
authors.forename: Cécile
authors.initials: C
authors.lastname: Debitus
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D047089:Axinella / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006146:Guanidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D045325:HCT116 Cells; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D008386:Marine Biology; D019906:Nuclear Magnetic Resonance, Biomolecular; D011114:Polynesia
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D006146:Guanidines