Beilstein J. Org. Chem.2022,18, 1544–1552, doi:10.3762/bjoc.18.164
UHPLC–MS analysis of the extract from this sponge indicated the presence of a new alkaloid. Large-scale extraction and mass-directed isolation studies on the CH2Cl2/MeOH I. basta extract resulted in the purification of a new bromotyrosine-derived alkaloid, 5-debromopurealidin H (1), along with the known
marine natural product, ianthesine E (2). The chemical structure of the new compound was determined following detailed spectroscopic and spectrometric data analysis. These two compounds (1 and 2) along with seven previously reported marine bromotyrosine alkaloids from the NatureBank open access library
(6), hexadellin A (9) and bastadin 4 (5) showed inhibition towards larval motility after 72 h of exposure with IC50 values of 1.6 µM, 10.0 µM and 33.3 µM, respectively.
Keywords: alkaloid; anthelmintic; biodiscovery; bromotyrosine; 5-debromopurealidin H; Ianthella; NatureBank; sponge; Introduction
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Graphical Abstract
Figure 1:
UHPLC–UV chromatogram (254 nm) of the CH2Cl2/MeOH extract of Ianthella basta (NB6021519); retention...
Beilstein J. Org. Chem.2015,11, 2334–2342, doi:10.3762/bjoc.11.254
Qun Gothel Thanchanok Sirirak Matthias Kock Alfred-Wegener-Institut, Helmholtz-Zentrum für Polar- und Meeresforschung, Am Handelshafen 12, 27570 Bremerhaven, Germany 10.3762/bjoc.11.254 Abstract Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and
of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2) exhibited cytotoxicity against MCF-7 cells.
Keywords: alkaloids; Aplysina lacunosa; bromotyrosine; marine natural
products; NMR spectroscopy; Introduction
Bromotyrosine-derived alkaloids are unique brominated metabolites which were isolated mainly from marine sponges of the order Verongida. For more than 50 years, bromotyrosine alkaloids raised the interests of synthetic and natural products chemists due to their
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Graphical Abstract
Figure 1:
Three new bromotyrosine derivatives isolated from sponge Aplysina lacunosa: 14-debromo-11-deoxyfist...