Biologically Active Acetylenic Amino Alcohol and N -Hydroxylated 1,2,3,4-Tetrahydro-β-carboline Constituents of the New Zealand Ascidian Pseudodistoma opacum

Jiayi Wang (1) , A. Norrie Pearce (1) , Susanna Chan (1) , Richard Taylor (1) , Michael Page (2) , Alexis Valentin (3) , Marie-Lise Bourguet-Kondracki (4) , James Dalton (1) , Siouxsie Wiles (1) , Brent Copp (1)

1 University of Auckland [Auckland]
2 NIWA - National Institute of Water and Atmospheric Research [Auckland]
3 PHARMA-DEV - Pharmacochimie et Biologie pour le Développement
4 MCAM - Molécules de Communication et Adaptation des Micro-organismes

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.

Mots clés: New Zealand; Plasmodium falciparum / drug effects; Staphylococcus aureus / drug effects; Urochordata / chemistry; Alkynes / chemistry; Alkynes / isolation & purification; Alkynes / pharmacology; Animals; Antimalarials / chemistry; Antimalarials / isolation & purification; Antimalarials / pharmacology; Carbolines / chemistry; Carbolines / isolation & purification; Carbolines / pharmacology; Chloroquine / pharmacology; Drug Resistance; Bacterial / drug effects; Escherichia coli / drug effects; Inhibitory Concentration 50; Microbial Sensitivity Tests; Molecular Structure; Mycobacterium tuberculosis / drug effects

Domaines: Sciences du Vivant [q-bio]

Jiayi Wang, A. Norrie Pearce, Susanna Chan, Richard Taylor, Michael Page, et al.. Biologically Active Acetylenic Amino Alcohol and N -Hydroxylated 1,2,3,4-Tetrahydro-β-carboline Constituents of the New Zealand Ascidian Pseudodistoma opacum. Journal of Natural Products, 2015, 79 (3), pp.607-610. ⟨10.1021/acs.jnatprod.5b00770⟩. ⟨hal-03184421⟩