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利莫尔:一种来自底栖海洋甲藻利马原甲藻的聚酮化合物。

Limaol: A Polyketide from the Benthic Marine Dinoflagellate Prorocentrum lima.

作者信息

Yang A Reum, Lee Sangbum, Yoo Young Du, Kim Hyung Seop, Jeong Eun Ju, Rho Jung-Rae

机构信息

Department of Marine Biotechnology, Kunsan National University , 558 Daehak-ro, Gunsan 54150, South Korea.

Department of Agronomy & Medicinal Plant Resources, Gyeongnam National University of Science and Technology , JinJu 660-758, South Korea.

出版信息

J Nat Prod. 2017 May 26;80(5):1688-1692. doi: 10.1021/acs.jnatprod.7b00127. Epub 2017 Apr 6.

Abstract

Limaol (1), along with a dinophysistoxin 1 derivative and an okadaic acid (OA) derivative, was isolated from the large-scale cultivation of the benthic marine dinoflagellate Prorocentrum lima. The structure of 1 was determined by a combination of NMR spectroscopy and mass spectrometry and contained tetrahydropyran, 1,3,5,7-tetra(methylene)heptane, and octahydrospiro[pyran-2,2'-pyrano[3,2-b]pyran] moieties. The absolute configuration of 1 was completely elucidated on the basis of ROESY correlations, J-based configuration analysis, and modified Mosher's ester analysis. Limaol showed moderate cytotoxicity when compared to OA against three cancer cell lines.

摘要

利马醇(1)与一种鳍藻毒素-1衍生物和一种冈田酸(OA)衍生物一起,是从底栖海洋甲藻利玛原甲藻的大规模培养物中分离得到的。通过核磁共振光谱和质谱联用确定了1的结构,其含有四氢吡喃、1,3,5,7-四(亚甲基)庚烷和八氢螺[吡喃-2,2'-吡喃并[3,2-b]吡喃]部分。基于旋转 Overhauser 效应光谱(ROESY)相关性、基于 J 的构型分析和改良的莫舍尔酯分析,完全阐明了1的绝对构型。与OA相比,利马醇对三种癌细胞系显示出中等细胞毒性。

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