Biosynthetic Functional Gene Analysis of Bis-Indole Metabolites from 25D7, a Clone Derived from a Deep-Sea Sediment Metagenomic Library.
This work investigated the metabolites and their biosynthetic functional hydroxylase genes of the deep-sea sediment metagenomic clone 25D7. 5-Bromoindole was added to the 25D7 clone derived Escherichia coli fermentation broth. The new-generated metabolites and their biosynthetic byproducts were located through LC-MS, in which the isotope peaks of brominated products emerged. Two new brominated bis-indole metabolites, 5-bromometagenediindole B (1), and 5-bromometagenediindole C (2) were separated under the guidance of LC-MS. Their structures were elucidated on the basis of 1D and 2D NMR spectra (COSY, HSQC, and HMBC). The biosynthetic functional genes of the two new compounds were revealed through LC-MS and transposon mutagenesis analysis. 5-Bromometagenediindole B (1) also demonstrated moderately cytotoxic activity against MCF7, B16, CNE2, Bel7402, and HT1080 tumor cell lines in vitro.
School of Pharmaceutical Sciences, Xiamen University, South Xiang-An Road, Xiamen 361102, China. yanxia1201@126.com.
Xia
X
Yan
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography State Oceanic Administration, Xiamen 361005, China. tangxixiang@tio.org.cn.|South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Xiamen 361005, China. tangxixiang@tio.org.cn.
Xi-Xiang
XX
Tang
Key Laboratory of Urban Pollutant Conversion, Institute of Urbane Environment, Chinese Academy of Sciences, Xiamen 361021, China. dqin@iue.ac.cn.
Dan
D
Qin
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography State Oceanic Administration, Xiamen 361005, China. yizhiwei@tio.org.cn.|South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Xiamen 361005, China. yizhiwei@tio.org.cn.
Zhi-Wei
ZW
Yi
School of Pharmaceutical Sciences, Xiamen University, South Xiang-An Road, Xiamen 361102, China. fangmj@xmu.edu.cn.
Mei-Juan
MJ
Fang
School of Pharmaceutical Sciences, Xiamen University, South Xiang-An Road, Xiamen 361102, China. wuzhen@xmu.edu.cn.
Zhen
Z
Wu
School of Pharmaceutical Sciences, Xiamen University, South Xiang-An Road, Xiamen 361102, China. qyk@xmu.edu.cn.
Ying-Kun
YK
Qiu
D045744:Cell Line, Tumor; D004926:Escherichia coli / Q000235:genetics* / Q000378:metabolism*; D005285:Fermentation / Q000502:physiology; D019015:Geologic Sediments / Q000737:chemistry*; D006801:Humans; D007211:Indoles / Q000378:metabolism*; D061986:MCF-7 Cells; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008546:Melanoma, Experimental; D056186:Metagenomics / Q000379:methods; D009792:Oceans and Seas
D007211:Indoles; C030374:indole
biosynthetic functional genes; cytotoxicity; deep-sea sediment; diindole derivatives; metagenomic clone; secondary metabolites