Rubrosides A-H, new bioactive tetramic acid glycosides from the marine sponge Siliquariaspongia japonica
Rubrosides A-H, new bioactive tetramic acid glycosides from the marine sponge Siliquariaspongia japonica
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Rubrosides A-H，来自海洋海绵 Siliquariaspongia japonica 的新型生物活性特特拉姆酸苷
DOI：
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发表时间：
1999
期刊：
影响因子：
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通讯作者：
N. Fusetani
中科院分区：
文献类型：
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作者：
N. Sata;S. Wada;S. Matsunaga;S. Watabe;R. V. VAN SOEST;N. Fusetani
从海生海绵 Siliquariaspongia japonica 中分离出八种新的特特拉姆酸苷，命名为红糖苷 A−H。它们的结构根据光谱数据被阐明为含有以4-氯-2-甲基四氢呋喃环封端的多烯的特特拉姆酸糖苷。两种主要代谢物红苷 D 和 F 中呋喃官能团的绝对立体化学通过 NMR 方法测定，使用手性各向异性试剂对 RuO4 氧化衍生的四氢-2-糠酸进行测定。通过化学降解产物的手性 GC 分析推导出特特拉姆酸和所有红苷中糖部分的绝对立体化学。浓度为 0.5−1.0 μg/mL 的红苷在 3Y1 大鼠成纤维细胞中诱导大量大的细胞内空泡，红苷 A、C、D 和 E 对 P388 小鼠白血病细胞具有细胞毒性，IC50 值为 0.046−0.21 μg/mL。大多数红苷对烟曲霉和白色念珠菌具有抗真菌活性。
Eight new tetramic acid glycosides named rubrosides A−H have been isolated from the marine sponge Siliquariaspongia japonica. Their structures were elucidated on the basis of spectral data as tetramic acid glycosides containing polyenes terminating in a 4-chloro-2-methyltetrahydrofuran ring. The absolute stereochemistry of the furan functionality in the two major metabolites, rubrosides D and F, was determined by the NMR method using chiral anisotropic reagents for tetrahydro-2-furoic acid derived by RuO4 oxidation. The absolute stereochemistry of tetramic acid and of the sugar moieties in all rubrosides was deduced by chiral GC analysis of chemical degradation products. The rubrosides induced numerous large intracellular vacuoles in 3Y1 rat fibroblasts at concentrations of 0.5−1.0 μg/mL, and rubrosides A, C, D, and E were cytotoxic against P388 murine leukemia cells with IC50 values of 0.046−0.21 μg/mL. Most rubrosides show antifungal activity against Aspergillus fumigatus and Candida albicans.