2015
DOI: 10.1021/acs.jnatprod.5b00770
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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, Staphylo… Show more

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Cited by 34 publications
(59 citation statements)
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“…M. tuberculosis reference strain ATCC 27294 and M. tuberculosis clinical isolate Rangipo N were similarly tagged and designated BSG001 and BSG002, respectively (Colangeli et al, 2014; Wang et al, 2016). All strains were grown at 37 °C, with 200 rpm agitation where appropriate.…”
Section: Methodsmentioning
confidence: 99%
“…M. tuberculosis reference strain ATCC 27294 and M. tuberculosis clinical isolate Rangipo N were similarly tagged and designated BSG001 and BSG002, respectively (Colangeli et al, 2014; Wang et al, 2016). All strains were grown at 37 °C, with 200 rpm agitation where appropriate.…”
Section: Methodsmentioning
confidence: 99%
“…In this study we used M. tuberculosis BSG001 (Wang et al, 2016), a stable bioluminescent derivative of H37Rv transformed with the integrating plasmid pMV306hspLuxABG13CDE (Andreu et al, 2010). Cultures of BSG001 were grown at 37 °C with gentle shaking (100 rpm) in Middlebrook 7H9 broth (Fort Richard, Auckland) supplemented with 10% Middlebrook ADC enrichment media (Fort Richard) and 0.5% glycerol (Sigma-Aldrich), or on 7H11 agar (Fort Richard) supplemented with 10% Middlebrook OADC enrichment media (Fort Richard) and 0.5% glycerol.…”
Section: Methodsmentioning
confidence: 99%
“…Wang et al actioned the isolation and identification of a new N-hydroxy-1, 2, 3, 4-tetrahydroβ-carboline, together with the first example of an acetylenic 1-amino-2-alcohol lipid, distaminolyne A (1) from ascidian, Pseudodistoma opacum. The compounds showed moderate activity against pathogens and compound 2 displayed antimalarial activity against a chloroquine-resistant strain (FcB1) of P. falciparum (IC 50 3.82 ± 0.2 µM) [125]. Another chloroquine-resistant Dd2 strain of P. falciparum was very susceptible to known antimalarial sesquiterpenoids (Table 2) produced by marine sponge, Hyrtios erectus [4].…”
Section: Marine-derived Antimicrobial Compounds From Invertebratesmentioning
confidence: 99%