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从海绵 Plakinastrella sp. 中分离得到的环状过氧化物的结构阐明、绝对构型和生物评价

Structure elucidation, absolute configuration, and biological evaluation of cyclic peroxides from the sponge Plakinastrella sp.

机构信息

Natural Products Support Group, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 21702-1201, United States.

Natural Products Branch, Developmental Therapeutic Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, MD 21702-1201, United States.

出版信息

Bioorg Med Chem Lett. 2024 Nov 15;113:129963. doi: 10.1016/j.bmcl.2024.129963. Epub 2024 Sep 14.

Abstract

Two cyclic peroxides, plakortides V (1) and W (2) were purified from the organic extract of the sponge Plakinastrella sp. Their planar structures were established based on extensive NMR and MS analysis and the absolute configurations of the three stereogenic centers of the 1,2-dioxane moiety were determined to be 3R,4S,6S by comparative analysis of the H NMR spectral data of the R- or S-MTPA Mosher esters. Compounds 1 and 2 exhibited potent cytotoxic activity against LOX IMVI (melanoma), UO-31 (renal), and HL-60 (TB) (leukemia) cell lines in the NCI-60 cytotoxicity assay.

摘要

两种环过氧化物,即 plakortide V(1)和 W(2),从海绵 Plakinastrella sp 的有机提取物中被分离纯化。它们的平面结构是基于广泛的 NMR 和 MS 分析确定的,1,2-二氧杂环己烷部分的三个立体中心的绝对构型通过 R-或 S-MTPA Mosher 酯的 1H NMR 光谱数据的比较分析被确定为 3R,4S,6S。化合物 1 和 2 在 NCI-60 细胞毒性测定中对 LOX IMVI(黑色素瘤)、UO-31(肾)和 HL-60(TB)(白血病)细胞系表现出强烈的细胞毒性活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d401/11513860/da6954fca083/nihms-2024270-f0002.jpg

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