Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China.
Org Biomol Chem. 2019 Jan 31;17(5):1053-1057. doi: 10.1039/c8ob02775g.
The halogenase gene spmH was putatively involved in the biosynthesis of spiroindimicins/indimicins (SPMs/IDMs), a group of chlorinated tryptophan dimers (TDs) from deep-sea-derived Streptomyces sp. SCSIO 03032. Inactivation of spmH led to six deschloro-analogues of TDs, including four new compounds SPMs G (1) and H (2), and IDMs F (3) and G (4). The structures and absolute configurations of 1-4 were unambiguously determined by the combination of extensive spectroscopic analysis, single-crystal X-ray diffraction and quantum chemical ECD calculations. Compounds 1 and 2 exhibited moderate cytotoxic activities against four cancer cell lines. Additionally, SpmH was biochemically characterized in vitro as an l-tryptophan 5-halogenase.
卤化酶基因 spmH 被推测参与了 spiroindimicins/indimicins（SPMs/IDMs）的生物合成，SPMs/IDMs 是一组来自深海来源的链霉菌 SCSIO 03032 中的氯化色氨酸二聚体（TDs）。spmH 的失活导致了 TDs 的六个去氯类似物，包括四个新的化合物 SPMs G（1）和 H（2）以及 IDMs F（3）和 G（4）。通过广泛的光谱分析、单晶 X 射线衍射和量子化学 ECD 计算的组合，明确确定了 1-4 的结构和绝对构型。化合物 1 和 2 对四种癌细胞系表现出中等的细胞毒性活性。此外，SpmH 在体外被生物化学表征为 l-色氨酸 5-卤化酶。
