CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Institution of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Institution of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Southern Marine Science and Engineering Guangdong Laboratory, Guangzhou 511458, China.
Chin J Nat Med. 2020 Apr;18(4):243-249. doi: 10.1016/S1875-5364(20)30029-7.
Mycosphazine A (1), a new iron(III) chelator of coprogen-type siderophore, and mycosphamide A (2), a new cyclic amide benzoate, together with six known aryl amides (3-8), were isolated from the fermentation broth of the deep-sea-derived fungus Mycosphaerella sp. SCSIO z059. Alkaline hydrolysis of 1 afforded a new epimer of dimerum acid, mycosphazine B (1a), and a new bi-fusarinine-type siderophore, mycosphazine C (1b). The planar structures of the new compounds were elucidated by extensive spectroscopic data analysis. The absolute configurations of amino acid residues in 1a and 1b were determined by acid hydrolysis. And the absolute configuration of 2 was established by quantum chemical calculations of the electronic circular dichroism (ECD) spectra. Compound 1 is the first siderophore-Fe(III) chelator incorporating both L-ornithine and D-ornithine unites. Compounds 3-8 were reported as natural products for the first time, and the H and C NMR data of 6 and 8 were assigned for the first time. Compounds 1 and 1a could greatly promote the biofilm formation of bacterium Bacillus amyloliquefaciens with the rate of about 249% and 524% at concentration of 100 μg·mL, respectively.
从深海来源真菌 Mycosphaerella sp. SCSIO z059 的发酵液中分离得到了 Mycosphazine A（1），一种新型的 coprogen 型铁载体螯合剂，和 Mycosphamide A（2），一种新型的环状酰胺苯甲酸酯，以及六种已知的芳基酰胺（3-8）。1 的碱性水解得到了二聚体酸的新差向异构体 Mycosphazine B（1a）和一种新的双 Fusarinine 型铁载体 Mycosphazine C（1b）。通过广泛的光谱数据分析阐明了新化合物的平面结构。通过酸水解确定了 1a 和 1b 中氨基酸残基的绝对构型。通过量子化学计算电子圆二色性（ECD）光谱确定了 2 的绝对构型。化合物 1 是第一个包含 L-鸟氨酸和 D-鸟氨酸单元的铁载体-Fe（III）螯合剂。化合物 3-8 首次被报道为天然产物，并且首次对 6 和 8 的 H 和 C NMR 数据进行了归属。在浓度为 100 μg·mL 时，化合物 1 和 1a 分别可以使细菌解淀粉芽孢杆菌的生物膜形成率提高约 249%和 524%。
