阿普拉毒素D，一种从巴布亚新几内亚采集的海洋蓝藻大鞘丝藻和污鞘丝藻中提取的具有强细胞毒性的环缩肽。

Apratoxin D, a potent cytotoxic cyclodepsipeptide from papua new guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida.

作者信息

Gutiérrez Marcelino, Suyama Takashi L, Engene Niclas, Wingerd Joshua S, Matainaho Teatulohi, Gerwick William H

机构信息

Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, La Jolla, California 92093, USA.

出版信息

J Nat Prod. 2008 Jun;71(6):1099-103. doi: 10.1021/np800121a. Epub 2008 Apr 30.

DOI:10.1021/np800121a

PMID:18444683

Abstract

Cancer cell toxicity-guided fractionation of extracts of the Papua New Guinea marine cyanobacteria Lyngbya majuscula and Lyngbya sordida led to the isolation of apratoxin D (1). Compound 1 contains the same macrocycle as apratoxins A and C but possesses the novel 3,7-dihydroxy-2,5,8,10,10-pentamethylundecanoic acid as the polyketide moiety. The planar structures and stereostructures of compound 1 were determined by extensive 1D and 2D NMR and MS data analyses and by comparison with the spectroscopic data of apratoxins A and C. Apratoxin D (1) showed potent in vitro cytotoxicity against H-460 human lung cancer cells with an IC 50 value of 2.6 nM.

摘要

对巴布亚新几内亚海洋蓝藻巨大鞘丝藻（Lyngbya majuscula）和污鞘丝藻（Lyngbya sordida）提取物进行癌细胞毒性导向分级分离，从而分离出了阿普拉毒素D（1）。化合物1与阿普拉毒素A和C含有相同的大环，但具有新型的3,7 - 二羟基 - 2,5,8,10,10 - 五甲基十一烷酸作为聚酮部分。通过广泛的一维和二维核磁共振及质谱数据分析，并与阿普拉毒素A和C的光谱数据进行比较，确定了化合物1的平面结构和立体结构。阿普拉毒素D（1）对H - 460人肺癌细胞显示出强大的体外细胞毒性，IC50值为2.6 nM。