Brauers G, Edrada R A, Ebel R, Proksch P, Wray V, Berg A, Gräfe U, Schächtele C, Totzke F, Finkenzeller G, Marme D, Kraus J, Münchbach M, Michel M, Bringmann G, Schaumann K
Heinrich-Heine-Universität, Lehrstuhl für Pharmazeutische Biologie, Universitätsstrasse 1, Geb. 26.23, D-40225 Düsseldorf, Germany.
J Nat Prod. 2000 Jun;63(6):739-45. doi: 10.1021/np9905259.
An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6, 8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the (1)H and (13)C NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.
从地中海海绵嗜气海绵（Aplysina aerophoba）中分离出一种未描述过的小孢拟盘多毛孢属真菌，它产生了两种新的β-烯酮衍生物（1, 2）和三种新的1,3,6,8-四羟基蒽醌同系物（5 - 7）。这些化合物的结构是根据核磁共振光谱和质谱数据以及圆二色光谱确定的。这是首次基于二维核磁共振光谱对β-烯酮同系物的¹H和¹³C核磁共振数据进行全面且明确的归属。此外，我们通过对1-(2'-蒽醌基)乙醇（如5和6）的圆二色性（CD）进行量子化学计算并与实验测量光谱进行比较，首次阐明了它们的绝对构型。此外，研究表明化合物1、5、6和7是蛋白激酶C-ε、细胞周期蛋白依赖性激酶4（CDK4）和表皮生长因子受体酪氨酸激酶的抑制剂。
