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Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H

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Abstract

An endophytic fungus was isolated that produces a series of volatile natural products, including terpenes and odd chain polyenes. Phylogenetic analysis of the isolate using five loci suggests that it is closely related to Nigrograna mackinnonii CBS 674.75. The main component of the polyene series was purified and identified as (3E,5E,7E)-nona-1,3,5,7-tetraene (NTE), a novel natural product. Non-oxygenated hydrocarbons of this chain length are uncommon and desirable as gasoline-surrogate biofuels. The biosynthetic pathway for NTE production was explored using metabolic labeling and gas chromatography time of flight mass spectometer (GCMS). Two-carbon incorporation 13C acetate suggests that it is derived from a polyketide synthase (PKS) followed by decarboxylation. There are several known mechanisms for such decarboxylation, though none have been discovered in fungi. Towards identifying the PKS responsible for the production of NTE, the genome of N. mackinnonii E5202H (ATCC SD-6839) was sequenced and assembled. Of the 32 PKSs present in the genome, 17 are predicted to contain sufficient domains for the production of NTE. These results exemplify the capacity of endophytic fungi to produce novel natural products that may have many uses, such as biologically derived fuels and commodity chemicals.

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Acknowledgments

This research was performed with a collecting and research permit provided to SAS by the Ministerio del Ambiente of Ecuador. The authors would like to thank Percy Vargas Nunez for help with collection and identification of the host plant, Gary Strobel for the M. albus isolate used for the selection, Joseph Wolenski for providing the microscope facilities, Nicholas J. Carriero, and Robert D. Bjornson in the Yale University Biomedical High Performance Computing Center funded by NIH grants RR19895 and RR029676-01, and the Office of Assistant Secretary of Defense for Research and Engineering NSSEFF grant N00244-09-1-0070 awarded to SAS. DJS and BFD were supported in part by the NIH Cell and Molecular Biology training grant number T32 GM007223.

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Authors and Affiliations

  1. Department of Molecular Biophysics and Biochemistry, Yale University, New Haven, CT, 06511, USA

    Jeffery J. Shaw, Daniel J. Spakowicz, Rahul S. Dalal, Jared H. Davis, Nina A. Lehr, Brian F. Dunican & Scott A. Strobel

  2. Laboratorio de Biotecnología Vegetal, Pontificia Universidad Católica del Ecuador, Quito, Ecuador

    Esteban A. Orellana & Alexandra Narváez-Trujillo

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  9. Scott A. Strobel
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Correspondence to Scott A. Strobel.

Additional information

Jeffery J. Shaw and Daniel J. Spakowicz contributed equally to this work.

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Shaw, J.J., Spakowicz, D.J., Dalal, R.S. et al. Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H. Appl Microbiol Biotechnol 99, 3715–3728 (2015). https://doi.org/10.1007/s00253-014-6206-5

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  • DOI: https://doi.org/10.1007/s00253-014-6206-5

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