A novel indole alkaloid from deep-sea sediment metagenomic clone-derived Escherichia coli fermentation broth

Abstract

To explore secondary metabolites in deep-sea sediment metagenomic clone-derived Escherichia coli fermentation broth, different kinds of chromatography methods were used in the isolation procedures, while the structures of the isolated compounds were assigned based on the MS analysis and their ¹H and ¹³C NMR spectra including 2D NMR techniques such as COSY, HMQC, and HMBC experiments. As a result, a novel compound was isolated and characterized as N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide (1). In addition, eight known compounds were also obtained. Fatty acid amide hydrolase and monoacylglycerol lipase were used to screen analgesic activity, and the new compound showed analgesic activity to some extent in pharmacological test.

Keywords:

• deep-sea sediment
• metagenomic clone
• N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide
• indole alkaloids

Acknowledgements

The authors would like to acknowledge the financial support from National High Technology Research and Development Plan (863) of China (2007AA091904) and China Ocean Mineral Resources R&D Association Fund (DYXM-115-02-2-9). Tian-hua Zhong of the Third Institute of Oceanography was appreciated for his kind help in NMR experiments.

Notes

^† These authors contributed equally to this paper.