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来自一种海洋兼性曲霉属物种的二氧代吗啉及其衍生物。

Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species.

作者信息

Aparicio-Cuevas Manuel A, Rivero-Cruz Isabel, Sánchez-Castellanos Mariano, Menéndez Daniel, Raja Huzefa A, Joseph-Nathan Pedro, González María Del Carmen, Figueroa Mario

机构信息

Genome Integrity and Structural Biology Laboratory, National Institute of Environmental Health Sciences, NIH , Research Triangle Park, North Carolina 27709, United States.

Department of Chemistry and Biochemistry, University of North Carolina at Greensboro , Greensboro, North Carolina 27402, United States.

出版信息

J Nat Prod. 2017 Aug 25;80(8):2311-2318. doi: 10.1021/acs.jnatprod.7b00331. Epub 2017 Aug 10.

DOI:10.1021/acs.jnatprod.7b00331
PMID:28796494
Abstract

Two new dioxomorpholines, 1 and 2, three new derivatives, 3-5, and the known compound PF1233 B (6) were isolated from a marine-facultative Aspergillus sp. MEXU 27854. Their structures were established by 1D and 2D NMR and HRESIMS data analysis. The absolute configuration of 1 and 2 was elucidated by comparison of experimental and DFT-calculated vibrational circular dichroism spectra. Compounds 3, 5, and 6 were noncytotoxic to a panel of human cancer cell lines with different functional status for the tumor-suppressor protein p53, but were inhibitors of P-glycoprotein-reversing multidrug resistance in a doxorubicin-resistant cell line.

摘要

从一株海洋兼性曲霉Aspergillus sp. MEXU 27854中分离得到了两种新的二氧代吗啉（1和2）、三种新的衍生物（3 - 5）以及已知化合物PF1233 B（6）。通过一维和二维核磁共振以及高分辨电喷雾电离质谱数据分析确定了它们的结构。通过比较实验和密度泛函理论计算的振动圆二色光谱阐明了1和2的绝对构型。化合物3、5和6对一组具有不同肿瘤抑制蛋白p53功能状态的人癌细胞系无细胞毒性，但在多柔比星耐药细胞系中是P - 糖蛋白逆转多药耐药的抑制剂。