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爱尔兰深海珊瑚中的Anthoteibinenes A-E：一个胺化难题。

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

机构信息

Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, Florida 33620, United States.

School of Natural Sciences and Ryan Institute, University of Galway, University Road, Galway H91 TK33, Ireland.

出版信息

Org Lett. 2024 Nov 8;26(44):9419-9424. doi: 10.1021/acs.orglett.4c02549. Epub 2024 Sep 3.

DOI:10.1021/acs.orglett.4c02549
PMID:39225686
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11756703/
Abstract

Chemical investigation of extracts from the Irish deep-sea soft coral 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 () exhibited 49% inhibition of respiratory syncytial virus (RSV) at 3.1 μM with no cytotoxicity.

摘要

从爱尔兰深海软珊瑚中提取的化学成分研究表明，含有不寻常二甲胺取代基的卡杜烯型倍半萜烯、anthoteibinenes A-E。结构鉴定采用了 1D/2D NMR 光谱和高分辨率质谱，同时还进行了 NOESY NMR 实验、基于 Gauge Invariant Atomic Orbital (GIAO) NMR 计算结合 DP4+概率测量和 ECD 比较，以提出它们的相对和绝对构型。Anthoteibinene B () 在 3.1 μM 时对呼吸道合胞病毒 (RSV) 的抑制率为 49%，且无细胞毒性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/ad714da4aaa1/nihms-2045354-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/a5c2abe2bfd8/nihms-2045354-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/c9ac63953472/nihms-2045354-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/c1c6781121a2/nihms-2045354-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/54fe7348aaf1/nihms-2045354-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/ad714da4aaa1/nihms-2045354-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/a5c2abe2bfd8/nihms-2045354-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/c9ac63953472/nihms-2045354-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/c1c6781121a2/nihms-2045354-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/54fe7348aaf1/nihms-2045354-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f500/11756703/ad714da4aaa1/nihms-2045354-f0005.jpg

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