title: Biologically Active Acetylenic Amino Alcohol and N-Hydroxylated 1,2,3,4-Tetrahydro-β-carboline Constituents of the New Zealand Ascidian Pseudodistoma opacum.
abstract: The first occurrence of an acetylenic 1-amino-2-alcohol, distaminolyne A (1), isolated from the New Zealand ascidian Pseudodistoma opacum, is reported. The isolation and structure elucidation of 1 and assignment of absolute configuration using the exciton coupled circular dichroism technique are described. In addition, a new N-9 hydroxy analogue (2) of the known P. opacum metabolite 7-bromohomotrypargine is also reported. Antimicrobial screening identified modest activity of 1 toward Escherichia coli, Staphylococcus aureus, and Mycobacterim tuberculosis, while 2 exhibited a moderate antimalarial activity (IC50 3.82 μM) toward a chloroquine-resistant strain (FcB1) of Plasmodium falciparum.
authors.forename: Jiayi
authors.initials: J
authors.lastname: Wang
authors.forename: A Norrie
authors.initials: AN
authors.lastname: Pearce
authors.forename: Susanna T S
authors.initials: ST
authors.lastname: Chan
authors.affiliation: Leigh Marine Laboratory, Institute of Marine Science, University of Auckland , PO Box 349, Warkworth 0941, New Zealand.
authors.forename: Richard B
authors.initials: RB
authors.lastname: Taylor
authors.affiliation: National Institute of Water & Atmospheric Research (NIWA) Ltd , PO Box 893, Nelson 7010, New Zealand.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Page
authors.affiliation: Université Paul Sabatier, PHARMA-DEV, UMR 152 IRD-UPS, Université de Toulouse , 118 Route de Narbonne, F-31062 Toulouse Cedex 9, France.
authors.forename: Alexis
authors.initials: A
authors.lastname: Valentin
authors.affiliation: Laboratoire Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS, Muséum National d'Histoire Naturelle , 57 Rue Cuvier (C.P. 54), 75005 Paris, France.
authors.forename: Marie-Lise
authors.initials: ML
authors.lastname: Bourguet-Kondracki
authors.forename: James P
authors.initials: JP
authors.lastname: Dalton
authors.forename: Siouxsie
authors.initials: S
authors.lastname: Wiles
authors.forename: Brent R
authors.initials: BR
authors.lastname: Copp
mesh_terms: D000480:Alkynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002243:Carbolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002738:Chloroquine / Q000494:pharmacology; D024881:Drug Resistance, Bacterial / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D009520:New Zealand; D010963:Plasmodium falciparum / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D014561:Urochordata / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000962:Antimalarials; D002243:Carbolines; C009804:tryptoline; D002738:Chloroquine