title: Didemnidines A and B, indole spermidine alkaloids from the New Zealand ascidian Didemnum sp.
abstract: Two new indole spermidine alkaloids, didemnidines A (1) and B (2), have been isolated from the New Zealand ascidian Didemnum sp. The structures of the metabolites, determined by analysis of 2D NMR spectra and confirmed via synthesis, embody an indole-3-glyoxylamide moiety linked to the N(1) position of spermidine, the latter motif being particularly rare among marine natural products. Didemnidine B and a synthetic precursor exhibited mild in vitro growth inhibition of Plasmodium falciparum with IC(50)'s of 15 and 8.4 μM, respectively.
authors.affiliation: Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
authors.forename: Rhys
authors.initials: R
authors.lastname: Finlayson
authors.forename: A Norrie
authors.initials: AN
authors.lastname: Pearce
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Page
authors.forename: Marcel
authors.initials: M
authors.lastname: Kaiser
authors.forename: Marie-Lise
authors.initials: ML
authors.lastname: Bourguet-Kondracki
authors.forename: Jacquie L
authors.initials: JL
authors.lastname: Harper
authors.forename: Victoria L
authors.initials: VL
authors.lastname: Webb
authors.forename: Brent R
authors.initials: BR
authors.lastname: Copp
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007893:Leishmania donovani / Q000187:drug effects; D015394:Molecular Structure; D009520:New Zealand; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects; D013095:Spermidine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014345:Trypanosoma / Q000187:drug effects; D014561:Urochordata / Q000737:chemistry*
chemical_list: D000981:Antiprotozoal Agents; D026121:Indole Alkaloids; C559172:didemnidine A; C559173:didemnidine B; D013095:Spermidine