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来自深海软珊瑚的异叶烷型和异叶内酯型二萜类化合物

Xeniaphyllane and Xeniolide Diterpenes from the Deep-Sea Soft Coral .

作者信息

Afoullouss Sam, Young Ryan M, Jennings Laurence K, Doyle Jason, Croke Karen, Livorsi Debora, Adams John H, Johnson Mark P, Thomas Olivier P, Allcock A Louise

机构信息

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

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

出版信息

ACS Omega. 2024 Sep 25;9(40):41914-41922. doi: 10.1021/acsomega.4c06361. eCollection 2024 Oct 8.

DOI:10.1021/acsomega.4c06361
PMID:39398151
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11465450/
Abstract

As exploration of ocean depths >1000 m is only possible by expensive remotely operated underwater vehicles, deep-sea invertebrates represent a largely untapped source of marine metabolites for potential applications in medicine. Our current study aims to investigate these deep-sea invertebrates in Ireland to discover new biological and chemical diversity. Here, we investigate the bubble gum coral, , collected at 1500 m depth from Whittard canyon in the Northeastern Atlantic. This species was selected following chemical profiling and biological screening. The isolation and structure elucidation of the main metabolites yielded three new diterpenes, namely, miolenol () and epoxymiolenol () characterized by the rare bicyclo[7.2.0]undec-4-ene skeleton, and the xeniolide epoxycoraxeniolide A (), together with five known diterpenes. The structures of the new compounds were identified through extensive NMR analysis with their absolute configurations assigned by comparison between experimental and TDDFT-calculated ECD. The eight compounds were screened for cytotoxicity and antimalarial activity, and none displayed noteworthy bioactivity.

摘要

由于只有通过昂贵的遥控水下航行器才能对深度超过1000米的海洋深处进行探索,深海无脊椎动物在很大程度上仍是未开发的海洋代谢产物来源,具有在医学领域潜在应用的可能性。我们当前的研究旨在调查爱尔兰的这些深海无脊椎动物,以发现新的生物和化学多样性。在此,我们研究了从东北大西洋惠特德峡谷1500米深处采集的泡泡糖珊瑚。该物种是在进行化学分析和生物筛选后选定的。主要代谢产物的分离和结构解析产生了三种新的二萜类化合物,即具有罕见的双环[7.2.0]十一碳-4-烯骨架的米奥醇()和环氧米奥醇(),以及异戊二烯内酯环氧珊瑚异戊二烯内酯A(),同时还有五种已知的二萜类化合物。通过广泛的核磁共振分析鉴定了新化合物的结构,并通过实验ECD与TDDFT计算的ECD比较确定了它们的绝对构型。对这八种化合物进行了细胞毒性和抗疟疾活性筛选,结果均未显示出显著的生物活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/a87730288803/ao4c06361_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/81a3a88a216f/ao4c06361_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/6b8adcf9b00f/ao4c06361_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/486c41d6282a/ao4c06361_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/2adf3cad8a3c/ao4c06361_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/d8bed6378637/ao4c06361_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/a87730288803/ao4c06361_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/81a3a88a216f/ao4c06361_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/6b8adcf9b00f/ao4c06361_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/486c41d6282a/ao4c06361_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/2adf3cad8a3c/ao4c06361_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/d8bed6378637/ao4c06361_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0beb/11465450/a87730288803/ao4c06361_0006.jpg

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Bathyptilones: Terpenoids from an Antarctic Sea Pen, (Verrill, 1879).
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