Anthoteibinenes A-E from the Irish Deep-Sea Coral Anthothela grandiflora: An Amination Puzzle.

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-11-08 Epub Date: 2024-09-03 DOI:10.1021/acs.orglett.4c02549
Stine S H Olsen, Sam Afoullouss, Ryan M Young, Mark Johnson, A Louise Allcock, Michael N Teng, Kim C Tran, Bill J Baker
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Abstract

Chemical investigation of extracts from the Irish deep-sea soft coral Anthothela grandiflora revealed cadinene-like sesquiterpenes, anthoteibinenes A-E, bearing unusual dimethylamine substitution. Structure elucidation was accomplished using 1D/2D NMR spectroscopy and high-resolution mass spectrometry, while NOESY NMR experiments, gauge invariant atomic orbital (GIAO) NMR calculations coupled with DP4+ probabilities measures, and ECD comparisons were incorporated to propose their relative and absolute configurations. Anthoteibinene B (2) exhibited 49% inhibition of respiratory syncytial virus (RSV) at 3.1 μM with no cytotoxicity.

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爱尔兰深海珊瑚 Anthothela grandiflora 中的蒽醌 A-E:氨化之谜。
对爱尔兰深海软珊瑚Anthothela grandiflora的提取物进行的化学研究发现了具有不寻常二甲基胺取代作用的类似卡地宁的倍半萜类化合物--anthoteibinenes A-E。利用一维/二维 NMR 光谱和高分辨率质谱法完成了结构阐释,同时结合 NOESY NMR 实验、量规不变原子轨道 (GIAO) NMR 计算以及 DP4+ 概率测量和 ECD 比较,提出了它们的相对和绝对构型。在 3.1 μM 的浓度下,蒽替比奈 B (2) 对呼吸道合胞病毒(RSV)的抑制率为 49%,且无细胞毒性。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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