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从养殖物中分离并鉴定冈田酸和鳍藻毒素-1新二醇酯的结构

Isolation and Structural Identification of New Diol Esters of Okadaic Acid and Dinophysistoxin-1 from the Cultured .

作者信息

Ji Yeong Kwang, Moon Semin, Lee Sangbum, Kim Yun Na, Jeong Eun Ju, Rho Jung-Rae

机构信息

Department of Oceanography, Kunsan National University, 558 Daehak-ro, Gunsan 54150, Republic of Korea.

Department of Plant & Biomaterials Science, Gyeongsang National University, Jinju 52725, Republic of Korea.

出版信息

Toxins (Basel). 2025 Jan 7;17(1):28. doi: 10.3390/toxins17010028.

DOI:10.3390/toxins17010028
PMID:39852981
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11768745/
Abstract

, a dinoflagellate responsible for producing diarrhetic shellfish poisoning (DSP) toxins, poses significant threats to marine ecosystems, aquaculture industries, and human health. DSP toxins, including okadaic acid (OA), dinophysis toxin (DTX), and their diverse derivatives, continue to be identified and characterized. In this study, we report the isolation of four new diol esters of OA/DTX-1 from large-scale cultures of . Their chemical structures were elucidated through comprehensive NMR and MS analyses, along with structural comparisons with the well-known OA. Notably, compound featured an additional ester group within the diol unit, while compound was revealed to be a C11 diol ester. The cytotoxicity of these newly isolated derivatives was evaluated against three cell lines: Neuro2a (mouse), HCT116 (human), and HepG2 (human). All diol esters exhibited cytotoxic effects, with compound displaying toxicity comparable to OA. These results expand our understanding of DSP toxin diversity and provide valuable insight into the structural variations and biological activity of diol esters of OA/DTX-1.

摘要

一种导致腹泻性贝类中毒(DSP)毒素产生的甲藻,对海洋生态系统、水产养殖业和人类健康构成重大威胁。包括冈田酸(OA)、鳍藻毒素(DTX)及其多种衍生物在内的DSP毒素不断被鉴定和表征。在本研究中,我们报告了从大规模培养的[甲藻名称未给出]中分离出四种新的OA/DTX - 1二醇酯。通过全面的核磁共振(NMR)和质谱(MS)分析以及与著名的OA进行结构比较,阐明了它们的化学结构。值得注意的是,化合物[具体编号未给出]在二醇单元内有一个额外的酯基,而化合物[具体编号未给出]被揭示为一种C11二醇酯。针对三种细胞系:Neuro2a(小鼠)、HCT116(人)和HepG2(人)评估了这些新分离衍生物的细胞毒性。所有二醇酯均表现出细胞毒性作用,化合物[具体编号未给出]显示出与OA相当的毒性。这些结果扩展了我们对DSP毒素多样性的理解,并为OA/DTX - 1二醇酯的结构变异和生物活性提供了有价值的见解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/13443f368238/toxins-17-00028-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/9e350bfaab3d/toxins-17-00028-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/bae534757624/toxins-17-00028-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/13443f368238/toxins-17-00028-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/9e350bfaab3d/toxins-17-00028-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/bae534757624/toxins-17-00028-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5ec/11768745/13443f368238/toxins-17-00028-g003a.jpg

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本文引用的文献

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Toxicon. 2023 Aug 15;232:107224. doi: 10.1016/j.toxicon.2023.107224. Epub 2023 Jul 10.
2
Nontarget Screening and Toxicity Evaluation of Diol Esters of Okadaic Acid and Dinophysistoxins Reveal Intraspecies Difference of .非靶标筛查和 okadaic 酸与麻痹性贝毒的二醇酯的毒性评估揭示了种内差异。
Environ Sci Technol. 2020 Oct 6;54(19):12366-12375. doi: 10.1021/acs.est.0c03691. Epub 2020 Sep 20.
3
The toxic benthic dinoflagellate Prorocentrum maculosum Faust is a synonym of Prorocentrum hoffmannianum Faust.
有毒底栖甲藻夜光藻 Faust 是 Faust 氏拟菱形藻的同义词。
Harmful Algae. 2018 Sep;78:1-8. doi: 10.1016/j.hal.2018.06.009. Epub 2018 Jul 11.
4
Sulfated diesters of okadaic acid and DTX-1: Self-protective precursors of diarrhetic shellfish poisoning (DSP) toxins.**硫酸酯**:**冈田酸**和 DTX-1:腹泻性贝类毒素(DSP)的自我保护前体。
Harmful Algae. 2017 Mar;63:85-93. doi: 10.1016/j.hal.2017.01.012. Epub 2017 Feb 11.
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Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts.超越DP4:利用核磁共振位移的量子化学计算改进异构体化合物立体化学归属的概率
J Org Chem. 2015 Dec 18;80(24):12526-34. doi: 10.1021/acs.joc.5b02396. Epub 2015 Dec 10.
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J Sep Sci. 2012 Apr;35(7):782-9. doi: 10.1002/jssc.201100914.
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