Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, Düsseldorf 40225, Germany; Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt.
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt.
Fitoterapia. 2018 Jul;128:258-264. doi: 10.1016/j.fitote.2018.05.019. Epub 2018 May 17.
Chemical investigation of a freshwater sediment-derived fungus, Penicillium sp. (S1a1), led to the isolation of three new tanzawaic acid derivatives, including penitanzchroman (1), tanzawaic acids Y (2) and Z (3), along with six known tanzawaic acid analogues (4-9), three known isochromans (10-12) and two known benzoquinones (13 and 14). The structures of the new compounds were established based on high-resolution mass spectrometry, and detailed analysis of one- and two-dimensional NMR spectroscopy. The relative configuration of the new compounds was assigned on the basis of NMR spectroscopic data including ROESY spectra. The absolute configuration was determined based on the specific optical rotation, in addition to biogenetic considerations in comparison with related co-isolated known metabolites. Penitanzchroman (1) constitutes a hitherto unprecedented skeleton, formed of tanzawaic acid A (5) and (3S)-6-hydroxy-8-methoxy-3,5-dimethylisochroman (10) linked by a CC bond. Moreover, all compounds were evaluated for their antibacterial and cytotoxic activities.
从淡水沉积物来源的真菌Penicillium sp. (S1a1) 中进行化学研究，分离得到三个新的坦扎瓦酸衍生物，包括 penitanzchroman (1)、tanzawaic 酸 Y (2) 和 Z (3)，以及六个已知的坦扎瓦酸类似物 (4-9)、三个已知的异苯并呋喃 (10-12) 和两个已知的苯醌 (13 和 14)。新化合物的结构是基于高分辨率质谱和一维和二维 NMR 光谱的详细分析确定的。新化合物的相对构型是根据包括 ROESY 谱在内的 NMR 光谱数据确定的。绝对构型是基于比旋光度确定的，此外还考虑了与相关共分离的已知代谢物的生物发生。Penitanzchroman (1) 由坦扎瓦酸 A (5) 和 (3S)-6-羟基-8-甲氧基-3,5-二甲基异苯并呋喃 (10) 通过 CC 键连接而成，构成了一个前所未有的骨架。此外，还评估了所有化合物的抗菌和细胞毒性活性。
