Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H
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 wa...
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| Veröffentlicht in: | Applied microbiology and biotechnology 2015-04, Vol.99 (8), p.3715-3728 |
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| creator | Shaw, Jeffery J Spakowicz, Daniel J Dalal, Rahul S Davis, Jared H Lehr, Nina A Dunican, Brian F Orellana, Esteban A Narváez-Trujillo, Alexandra Strobel, Scott A |
| description | 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 incorporation¹³C 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. |
| doi_str_mv | 10.1007/s00253-014-6206-5 |
| format | Article |
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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 incorporation¹³C 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.</description><identifier>ISSN: 0175-7598</identifier><identifier>EISSN: 1432-0614</identifier><identifier>DOI: 10.1007/s00253-014-6206-5</identifier><identifier>PMID: 25672844</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>acetates ; Analysis ; Antibiotics ; Ascomycota - classification ; Ascomycota - genetics ; Ascomycota - isolation & purification ; Ascomycota - metabolism ; biochemical pathways ; Biodiesel fuels ; Bioenergy and Biofuels ; Biofuels ; Biomedical and Life Sciences ; Biosynthesis ; Biotechnology ; Chromatography ; Cladistic analysis ; decarboxylation ; DNA, Fungal - chemistry ; DNA, Fungal - genetics ; endophytes ; Endophytes - classification ; Endophytes - genetics ; Endophytes - isolation & purification ; Endophytes - metabolism ; Fungi ; Gas chromatography ; Gas Chromatography-Mass Spectrometry ; Gasoline ; Genes ; genome ; Genome, Fungal ; Genomes ; genomics ; Hydrocarbons ; Influence ; Isotope Labeling ; Life Sciences ; loci ; Metabolic Networks and Pathways - genetics ; Metabolism ; Metabolites ; Microbial Genetics and Genomics ; Microbiology ; Molecular Sequence Data ; Natural products ; Phylogenetics ; phylogeny ; Physiological aspects ; polyenes ; Polyenes - metabolism ; polyketide synthases ; Ribosomal DNA ; RNA polymerase ; Sequence Analysis, DNA ; Studies ; terpenoids ; VOCs ; Volatile organic compounds</subject><ispartof>Applied microbiology and biotechnology, 2015-04, Vol.99 (8), p.3715-3728</ispartof><rights>Springer-Verlag Berlin Heidelberg 2015</rights><rights>COPYRIGHT 2015 Springer</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c713t-e5d335a2f734d057c65f02650c5a212911428d4d77212c0140a40f98ecf832d63</citedby><cites>FETCH-LOGICAL-c713t-e5d335a2f734d057c65f02650c5a212911428d4d77212c0140a40f98ecf832d63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00253-014-6206-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00253-014-6206-5$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25672844$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shaw, Jeffery J</creatorcontrib><creatorcontrib>Spakowicz, Daniel J</creatorcontrib><creatorcontrib>Dalal, Rahul S</creatorcontrib><creatorcontrib>Davis, Jared H</creatorcontrib><creatorcontrib>Lehr, Nina A</creatorcontrib><creatorcontrib>Dunican, Brian F</creatorcontrib><creatorcontrib>Orellana, Esteban A</creatorcontrib><creatorcontrib>Narváez-Trujillo, Alexandra</creatorcontrib><creatorcontrib>Strobel, Scott A</creatorcontrib><title>Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H</title><title>Applied microbiology and biotechnology</title><addtitle>Appl Microbiol Biotechnol</addtitle><addtitle>Appl Microbiol Biotechnol</addtitle><description>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 incorporation¹³C 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.</description><subject>acetates</subject><subject>Analysis</subject><subject>Antibiotics</subject><subject>Ascomycota - classification</subject><subject>Ascomycota - genetics</subject><subject>Ascomycota - isolation & purification</subject><subject>Ascomycota - metabolism</subject><subject>biochemical pathways</subject><subject>Biodiesel fuels</subject><subject>Bioenergy and Biofuels</subject><subject>Biofuels</subject><subject>Biomedical and Life Sciences</subject><subject>Biosynthesis</subject><subject>Biotechnology</subject><subject>Chromatography</subject><subject>Cladistic analysis</subject><subject>decarboxylation</subject><subject>DNA, Fungal - chemistry</subject><subject>DNA, Fungal - genetics</subject><subject>endophytes</subject><subject>Endophytes - classification</subject><subject>Endophytes - genetics</subject><subject>Endophytes - isolation & purification</subject><subject>Endophytes - metabolism</subject><subject>Fungi</subject><subject>Gas chromatography</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Gasoline</subject><subject>Genes</subject><subject>genome</subject><subject>Genome, Fungal</subject><subject>Genomes</subject><subject>genomics</subject><subject>Hydrocarbons</subject><subject>Influence</subject><subject>Isotope Labeling</subject><subject>Life Sciences</subject><subject>loci</subject><subject>Metabolic Networks and Pathways - genetics</subject><subject>Metabolism</subject><subject>Metabolites</subject><subject>Microbial Genetics and Genomics</subject><subject>Microbiology</subject><subject>Molecular Sequence Data</subject><subject>Natural products</subject><subject>Phylogenetics</subject><subject>phylogeny</subject><subject>Physiological aspects</subject><subject>polyenes</subject><subject>Polyenes - metabolism</subject><subject>polyketide synthases</subject><subject>Ribosomal DNA</subject><subject>RNA polymerase</subject><subject>Sequence Analysis, DNA</subject><subject>Studies</subject><subject>terpenoids</subject><subject>VOCs</subject><subject>Volatile organic compounds</subject><issn>0175-7598</issn><issn>1432-0614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNqNks1u1DAUhSMEokPhAdhAJDawSPG_nWWpCq1UgUTp2vLYTsYlsYudSOQJeG3uMOVnEEJVFrFvvnN0782pqqcYHWGE5OuCEOG0QZg1giDR8HvVCjNKGiQwu1-tEJa8kbxVB9WjUq4RwkQJ8bA6IFxIohhbVd_ehFSWOG18CaU20dW9j2kMFs5mWLbF1NWjd2EeG7sxIdabxeVkTV6nWN_k5GY7BTiulxpcah9dutksEzh0c-zNUIeSBjP5-n3oc-oz-NajsZ9DjCmGUJ9ygsjZ4-pBZ4bin9y-D6urt6efTs6aiw_vzk-OLxorMZ0azx2l3JBOUuYQl1bwDhHBkYUiJi3GjCjHnJRws7AYZBjqWuVtpyhxgh5WL3e-0PmX2ZdJj6FYPwwm-jQXjYUSEnFK74QiRqUS5A6ogIaV4hLQF3-h12nOsOsflMLgythvChbodYhdmrKxW1N9zEgrEIy37fDoHxQ8zsMfTNF3Aep7gld7AmAm_3XqzVyKPr_8uM_iHWtzKiX7Tt_kMJq8aIz0Nn56Fz8NW9bb-GkOmme3w81ryMwvxc-8AUB2QIFPsff5j-n_4_p8J-pM0qbPoeirS4Iwh0ALKtuWfgf4Uep5</recordid><startdate>20150401</startdate><enddate>20150401</enddate><creator>Shaw, Jeffery J</creator><creator>Spakowicz, Daniel J</creator><creator>Dalal, Rahul S</creator><creator>Davis, Jared H</creator><creator>Lehr, Nina A</creator><creator>Dunican, Brian F</creator><creator>Orellana, Esteban A</creator><creator>Narváez-Trujillo, Alexandra</creator><creator>Strobel, Scott A</creator><general>Springer-Verlag</general><general>Springer Berlin Heidelberg</general><general>Springer</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope><scope>3V.</scope><scope>7QL</scope><scope>7T7</scope><scope>7WY</scope><scope>7WZ</scope><scope>7X7</scope><scope>7XB</scope><scope>87Z</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8FL</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BEZIV</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FRNLG</scope><scope>FYUFA</scope><scope>F~G</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K60</scope><scope>K6~</scope><scope>K9.</scope><scope>L.-</scope><scope>LK8</scope><scope>M0C</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PQBIZ</scope><scope>PQBZA</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><scope>7QO</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20150401</creationdate><title>Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H</title><author>Shaw, Jeffery J ; Spakowicz, Daniel J ; Dalal, Rahul S ; Davis, Jared H ; Lehr, Nina A ; Dunican, Brian F ; Orellana, Esteban A ; Narváez-Trujillo, Alexandra ; Strobel, Scott A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c713t-e5d335a2f734d057c65f02650c5a212911428d4d77212c0140a40f98ecf832d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>acetates</topic><topic>Analysis</topic><topic>Antibiotics</topic><topic>Ascomycota - classification</topic><topic>Ascomycota - genetics</topic><topic>Ascomycota - isolation & purification</topic><topic>Ascomycota - metabolism</topic><topic>biochemical pathways</topic><topic>Biodiesel fuels</topic><topic>Bioenergy and Biofuels</topic><topic>Biofuels</topic><topic>Biomedical and Life Sciences</topic><topic>Biosynthesis</topic><topic>Biotechnology</topic><topic>Chromatography</topic><topic>Cladistic analysis</topic><topic>decarboxylation</topic><topic>DNA, Fungal - chemistry</topic><topic>DNA, Fungal - genetics</topic><topic>endophytes</topic><topic>Endophytes - classification</topic><topic>Endophytes - genetics</topic><topic>Endophytes - isolation & purification</topic><topic>Endophytes - metabolism</topic><topic>Fungi</topic><topic>Gas chromatography</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Gasoline</topic><topic>Genes</topic><topic>genome</topic><topic>Genome, Fungal</topic><topic>Genomes</topic><topic>genomics</topic><topic>Hydrocarbons</topic><topic>Influence</topic><topic>Isotope Labeling</topic><topic>Life Sciences</topic><topic>loci</topic><topic>Metabolic Networks and Pathways - 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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 incorporation¹³C 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.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><pmid>25672844</pmid><doi>10.1007/s00253-014-6206-5</doi><tpages>14</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0175-7598 |
| ispartof | Applied microbiology and biotechnology, 2015-04, Vol.99 (8), p.3715-3728 |
| issn | 0175-7598 1432-0614 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1686705336 |
| source | MEDLINE; SpringerLink Journals |
| subjects | acetates Analysis Antibiotics Ascomycota - classification Ascomycota - genetics Ascomycota - isolation & purification Ascomycota - metabolism biochemical pathways Biodiesel fuels Bioenergy and Biofuels Biofuels Biomedical and Life Sciences Biosynthesis Biotechnology Chromatography Cladistic analysis decarboxylation DNA, Fungal - chemistry DNA, Fungal - genetics endophytes Endophytes - classification Endophytes - genetics Endophytes - isolation & purification Endophytes - metabolism Fungi Gas chromatography Gas Chromatography-Mass Spectrometry Gasoline Genes genome Genome, Fungal Genomes genomics Hydrocarbons Influence Isotope Labeling Life Sciences loci Metabolic Networks and Pathways - genetics Metabolism Metabolites Microbial Genetics and Genomics Microbiology Molecular Sequence Data Natural products Phylogenetics phylogeny Physiological aspects polyenes Polyenes - metabolism polyketide synthases Ribosomal DNA RNA polymerase Sequence Analysis, DNA Studies terpenoids VOCs Volatile organic compounds |
| title | Biosynthesis and genomic analysis of medium-chain hydrocarbon production by the endophytic fungal isolate Nigrograna mackinnonii E5202H |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T19%3A02%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_proqu&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Biosynthesis%20and%20genomic%20analysis%20of%20medium-chain%20hydrocarbon%20production%20by%20the%20endophytic%20fungal%20isolate%20Nigrograna%20mackinnonii%20E5202H&rft.jtitle=Applied%20microbiology%20and%20biotechnology&rft.au=Shaw,%20Jeffery%20J&rft.date=2015-04-01&rft.volume=99&rft.issue=8&rft.spage=3715&rft.epage=3728&rft.pages=3715-3728&rft.issn=0175-7598&rft.eissn=1432-0614&rft_id=info:doi/10.1007/s00253-014-6206-5&rft_dat=%3Cgale_proqu%3EA429602126%3C/gale_proqu%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1668116844&rft_id=info:pmid/25672844&rft_galeid=A429602126&rfr_iscdi=true |