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Mar. Drugs 2016, 14(6), 107; doi:10.3390/md14060107

Biosynthetic Functional Gene Analysis of Bis-Indole Metabolites from 25D7, a Clone Derived from a Deep-Sea Sediment Metagenomic Library

1,†
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2,3,†
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4
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2,3
,
1
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1,* and 1,*
1
School of Pharmaceutical Sciences, Xiamen University, South Xiang-An Road, Xiamen 361102, China
2
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography State Oceanic Administration, Xiamen 361005, China
3
South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Xiamen 361005, China
4
Key Laboratory of Urban Pollutant Conversion, Institute of Urbane Environment, Chinese Academy of Sciences, Xiamen 361021, China
These authors contribute equally to this paper.
*
Authors to whom correspondence should be addressed.
Academic Editor: Danielle Skropeta
Received: 25 December 2015 / Revised: 10 May 2016 / Accepted: 13 May 2016 / Published: 1 June 2016
(This article belongs to the Special Issue Deep-Sea Natural Products)
View Full-Text   |   Download PDF [1494 KB, uploaded 1 June 2016]   |  

Abstract

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. View Full-Text
Keywords: deep-sea sediment; metagenomic clone; secondary metabolites; diindole derivatives; biosynthetic functional genes; cytotoxicity deep-sea sediment; metagenomic clone; secondary metabolites; diindole derivatives; biosynthetic functional genes; cytotoxicity
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MDPI and ACS Style

Yan, X.; Tang, X.-X.; Qin, D.; Yi, Z.-W.; Fang, M.-J.; Wu, Z.; Qiu, Y.-K. Biosynthetic Functional Gene Analysis of Bis-Indole Metabolites from 25D7, a Clone Derived from a Deep-Sea Sediment Metagenomic Library. Mar. Drugs 2016, 14, 107.

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