Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes
Lipid extracts of the fungus were found to contain various scarce fatty acids including dodec-11-enoic acid and di- and tri-unsaturated C isomers. A biotechnological approach using a heterologously expressed carboxylic acid reductase was developed to transform the fatty acids into the respective ald...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2021-01, Vol.69 (1), p.345-353 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Hammer, Andreas K Emrich, Nils O Ott, Janina Birk, Florian Fraatz, Marco A Ley, Jakob P Geissler, Torsten Bornscheuer, Uwe T Zorn, Holger |
| description | Lipid extracts of the fungus
were found to contain various scarce fatty acids including dodec-11-enoic acid and di- and tri-unsaturated C
isomers. A biotechnological approach using a heterologously expressed carboxylic acid reductase was developed to transform the fatty acids into the respective aldehydes, yielding
dodec-11-enal. Supplementation studies gave insights into the fungal biosynthesis of this rarely occurring acid and suggested a terminal desaturation of lauric acid being responsible for its formation. A systematic structure-odor relationship assessment of terminally unsaturated aldehydes (C
-C
) revealed odor thresholds in the range of 0.24-22 μg/L in aqueous solution and 0.039-29 ng/L in air. In both cases, non-8-enal was identified as the most potent compound. All aldehydes exhibited green odor qualities. Short-chained substances were additionally associated with grassy, melon-, and cucumber-like notes, while longer-chained homologs smelled soapy and coriander leaf-like with partly herbaceous nuances. Dodec-11-enal turned out to be of highly pleasant scent without off-notes. |
| doi_str_mv | 10.1021/acs.jafc.0c06872 |
| format | Article |
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were found to contain various scarce fatty acids including dodec-11-enoic acid and di- and tri-unsaturated C
isomers. A biotechnological approach using a heterologously expressed carboxylic acid reductase was developed to transform the fatty acids into the respective aldehydes, yielding
dodec-11-enal. Supplementation studies gave insights into the fungal biosynthesis of this rarely occurring acid and suggested a terminal desaturation of lauric acid being responsible for its formation. A systematic structure-odor relationship assessment of terminally unsaturated aldehydes (C
-C
) revealed odor thresholds in the range of 0.24-22 μg/L in aqueous solution and 0.039-29 ng/L in air. In both cases, non-8-enal was identified as the most potent compound. All aldehydes exhibited green odor qualities. Short-chained substances were additionally associated with grassy, melon-, and cucumber-like notes, while longer-chained homologs smelled soapy and coriander leaf-like with partly herbaceous nuances. Dodec-11-enal turned out to be of highly pleasant scent without off-notes.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.0c06872</identifier><identifier>PMID: 33350305</identifier><language>eng</language><publisher>United States</publisher><subject>Adult ; Aldehydes - chemistry ; Biocatalysis ; Biotechnology - methods ; Fatty Acids - chemistry ; Female ; Flammulina - chemistry ; Humans ; Male ; Oxidoreductases - chemistry ; Smell ; Young Adult</subject><ispartof>Journal of agricultural and food chemistry, 2021-01, Vol.69 (1), p.345-353</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c214t-8db37f0f7ae9452a55f8a877f2aaa08526dfbdce94e411f7a9a0ac6230623af3</citedby><cites>FETCH-LOGICAL-c214t-8db37f0f7ae9452a55f8a877f2aaa08526dfbdce94e411f7a9a0ac6230623af3</cites><orcidid>0000-0001-9226-1993 ; 0000-0002-5028-9653 ; 0000-0001-9388-4260 ; 0000-0002-8383-8196 ; 0000-0003-0685-2696</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,2752,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33350305$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hammer, Andreas K</creatorcontrib><creatorcontrib>Emrich, Nils O</creatorcontrib><creatorcontrib>Ott, Janina</creatorcontrib><creatorcontrib>Birk, Florian</creatorcontrib><creatorcontrib>Fraatz, Marco A</creatorcontrib><creatorcontrib>Ley, Jakob P</creatorcontrib><creatorcontrib>Geissler, Torsten</creatorcontrib><creatorcontrib>Bornscheuer, Uwe T</creatorcontrib><creatorcontrib>Zorn, Holger</creatorcontrib><title>Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes</title><title>Journal of agricultural and food chemistry</title><addtitle>J Agric Food Chem</addtitle><description>Lipid extracts of the fungus
were found to contain various scarce fatty acids including dodec-11-enoic acid and di- and tri-unsaturated C
isomers. A biotechnological approach using a heterologously expressed carboxylic acid reductase was developed to transform the fatty acids into the respective aldehydes, yielding
dodec-11-enal. Supplementation studies gave insights into the fungal biosynthesis of this rarely occurring acid and suggested a terminal desaturation of lauric acid being responsible for its formation. A systematic structure-odor relationship assessment of terminally unsaturated aldehydes (C
-C
) revealed odor thresholds in the range of 0.24-22 μg/L in aqueous solution and 0.039-29 ng/L in air. In both cases, non-8-enal was identified as the most potent compound. All aldehydes exhibited green odor qualities. Short-chained substances were additionally associated with grassy, melon-, and cucumber-like notes, while longer-chained homologs smelled soapy and coriander leaf-like with partly herbaceous nuances. Dodec-11-enal turned out to be of highly pleasant scent without off-notes.</description><subject>Adult</subject><subject>Aldehydes - chemistry</subject><subject>Biocatalysis</subject><subject>Biotechnology - methods</subject><subject>Fatty Acids - chemistry</subject><subject>Female</subject><subject>Flammulina - chemistry</subject><subject>Humans</subject><subject>Male</subject><subject>Oxidoreductases - chemistry</subject><subject>Smell</subject><subject>Young Adult</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kE1LAzEQhoMotlbvnmSPXrZOks3u9lhL_YBCBes5TPNht2w3NdkV-hP8df4lU1s9DAMzzzsMDyHXFIYUGL1DFYZrtGoICvKyYCekTwWDVFBanpI-RCYtRU575CKENQCUooBz0uOcC-Ag-mR-X7nWqFXjavdeKayTF-90p9rKNQk2Onk1TXB-l0w_se7wd-xs8v1F07cmYNt5bI1OxrU2q5024ZKcWayDuTr2AVk8TBeTp3Q2f3yejGepYjRr01IveWHBFmhGmWAohC2xLArLEDF-yXJtl1rFpckojdgIAVXOOMRCywfk9nB2691HZ0IrN1VQpq6xMa4LkmUFo5DnWRZROKDKuxC8sXLrqw36naQg9xZltCj3FuXRYozcHK93y43R_4E_bfwHztZw3Q</recordid><startdate>20210113</startdate><enddate>20210113</enddate><creator>Hammer, Andreas K</creator><creator>Emrich, Nils O</creator><creator>Ott, Janina</creator><creator>Birk, Florian</creator><creator>Fraatz, Marco A</creator><creator>Ley, Jakob P</creator><creator>Geissler, Torsten</creator><creator>Bornscheuer, Uwe T</creator><creator>Zorn, Holger</creator><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>7X8</scope><orcidid>https://orcid.org/0000-0001-9226-1993</orcidid><orcidid>https://orcid.org/0000-0002-5028-9653</orcidid><orcidid>https://orcid.org/0000-0001-9388-4260</orcidid><orcidid>https://orcid.org/0000-0002-8383-8196</orcidid><orcidid>https://orcid.org/0000-0003-0685-2696</orcidid></search><sort><creationdate>20210113</creationdate><title>Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes</title><author>Hammer, Andreas K ; Emrich, Nils O ; Ott, Janina ; Birk, Florian ; Fraatz, Marco A ; Ley, Jakob P ; Geissler, Torsten ; Bornscheuer, Uwe T ; Zorn, Holger</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c214t-8db37f0f7ae9452a55f8a877f2aaa08526dfbdce94e411f7a9a0ac6230623af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Adult</topic><topic>Aldehydes - chemistry</topic><topic>Biocatalysis</topic><topic>Biotechnology - methods</topic><topic>Fatty Acids - chemistry</topic><topic>Female</topic><topic>Flammulina - chemistry</topic><topic>Humans</topic><topic>Male</topic><topic>Oxidoreductases - chemistry</topic><topic>Smell</topic><topic>Young Adult</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hammer, Andreas K</creatorcontrib><creatorcontrib>Emrich, Nils O</creatorcontrib><creatorcontrib>Ott, Janina</creatorcontrib><creatorcontrib>Birk, Florian</creatorcontrib><creatorcontrib>Fraatz, Marco A</creatorcontrib><creatorcontrib>Ley, Jakob P</creatorcontrib><creatorcontrib>Geissler, Torsten</creatorcontrib><creatorcontrib>Bornscheuer, Uwe T</creatorcontrib><creatorcontrib>Zorn, Holger</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hammer, Andreas K</au><au>Emrich, Nils O</au><au>Ott, Janina</au><au>Birk, Florian</au><au>Fraatz, Marco A</au><au>Ley, Jakob P</au><au>Geissler, Torsten</au><au>Bornscheuer, Uwe T</au><au>Zorn, Holger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J Agric Food Chem</addtitle><date>2021-01-13</date><risdate>2021</risdate><volume>69</volume><issue>1</issue><spage>345</spage><epage>353</epage><pages>345-353</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>Lipid extracts of the fungus
were found to contain various scarce fatty acids including dodec-11-enoic acid and di- and tri-unsaturated C
isomers. A biotechnological approach using a heterologously expressed carboxylic acid reductase was developed to transform the fatty acids into the respective aldehydes, yielding
dodec-11-enal. Supplementation studies gave insights into the fungal biosynthesis of this rarely occurring acid and suggested a terminal desaturation of lauric acid being responsible for its formation. A systematic structure-odor relationship assessment of terminally unsaturated aldehydes (C
-C
) revealed odor thresholds in the range of 0.24-22 μg/L in aqueous solution and 0.039-29 ng/L in air. In both cases, non-8-enal was identified as the most potent compound. All aldehydes exhibited green odor qualities. Short-chained substances were additionally associated with grassy, melon-, and cucumber-like notes, while longer-chained homologs smelled soapy and coriander leaf-like with partly herbaceous nuances. Dodec-11-enal turned out to be of highly pleasant scent without off-notes.</abstract><cop>United States</cop><pmid>33350305</pmid><doi>10.1021/acs.jafc.0c06872</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-9226-1993</orcidid><orcidid>https://orcid.org/0000-0002-5028-9653</orcidid><orcidid>https://orcid.org/0000-0001-9388-4260</orcidid><orcidid>https://orcid.org/0000-0002-8383-8196</orcidid><orcidid>https://orcid.org/0000-0003-0685-2696</orcidid></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Adult Aldehydes - chemistry Biocatalysis Biotechnology - methods Fatty Acids - chemistry Female Flammulina - chemistry Humans Male Oxidoreductases - chemistry Smell Young Adult |
| title | Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes |
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