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

Research paper by Jiayi Wang, A. Norrie Pearce, Susanna T. S. Chan, Richard B. Taylor, Michael J. Page, Alexis Valentin, Marie-Lise Bourguet-Kondracki, James P. Dalton, Siouxsie Wiles, Brent R. Copp

Indexed on: 09 Mar '16Published on: 15 Dec '15Published in: Journal of Natural Products


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.

Figure 10.1021/acs.jnatprod.5b00770.2.jpg
Figure 10.1021/acs.jnatprod.5b00770.3.jpg