关键词: 5-debromopurealidin H Ianthella NatureBank alkaloid anthelmintic biodiscovery bromotyrosine sponge

来  源:   DOI:10.3762/bjoc.18.164   PDF(Pubmed)

Abstract:
In order to further expand the NatureBank open access compound library, chemical investigations of the Australian marine sponge, Ianthella basta, were undertaken since 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, which included psammaplysins F (3) and H (4), bastadins 4 (5), 8 (6) and 13 (7), aerothionin (8) and hexadellin A (9), were evaluated for their nematocidal activity against exsheathed third-stage larvae of Haemonchus contortus, a highly pathogenic parasite of ruminants. Of the nine compounds, bastadin 8 (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.
摘要:
为了进一步扩大NatureBank开放存取复合库,澳大利亚海洋海绵的化学研究,Ianthellabasta,因为从该海绵的提取物的UHPLC-MS分析表明存在新的生物碱。对CH2Cl2/MeOHI.basta提取物的大规模提取和质量导向分离研究导致了一种新的溴酪氨酸衍生生物碱的纯化,5-去溴氰尿苷H(1),连同已知的海洋天然产品,ianthesineE(2).在详细的光谱和光谱数据分析之后确定新化合物的化学结构。这两种化合物(1和2)以及以前从NatureBank开放访问库报道的七个海洋溴酪氨酸生物碱,其中包括psammaplysinsF(3)和H(4),bastadins4(5),8(6)和13(7)气硫素(8)和六adellinA(9),评估了它们对出鞘的第三期幼虫的杀线虫活性,反刍动物的高致病性寄生虫。在九种化合物中,bastadin8(6),hexadellinA(9)和bastadin4(5)在暴露72小时后显示出对幼虫运动的抑制作用,IC50值为1.6µM,10.0µM和33.3µM,分别。
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