Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus
| العنوان: | Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus |
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| المؤلفون: | Marco A. Fraatz, Tobias Trapp, Florian Birk, Tabea Kirchner, Holger Zorn |
| المصدر: | Journal of Agricultural and Food Chemistry. 67:13400-13411 |
| بيانات النشر: | American Chemical Society (ACS), 2019. |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | chemistry.chemical_compound, Limonene, chemistry, Bicyclic molecule, Biotransformation, Enantioselective synthesis, Organic chemistry, Ether, General Chemistry, Gas chromatography, Wine lactone, Enantiomer, General Agricultural and Biological Sciences |
| الوصف: | The white-rot fungus Pleurotus sapidus (PSA) biosynthesizes the bicyclic monoterpenoids 3,6-dimethyl-2,3,3a,4,5,7a-hexahydrobenzofuran (dill ether) (1) and 3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one (wine lactone) (2). Submerged cultures grown in different media were analyzed by gas chromatography-mass spectrometry. The stereochemistry of the formed isomers was elucidated by comparing their retention indices to those of reference compounds by enantioselective multidimensional gas chromatography. The basidiomycete produced the rare (3R,3aR,7aS) and (3S,3aR,7aS) stereoisomers of dill ether and wine lactone. Kinetic analyses of the volatilome and bioprocess parameters revealed that the biosynthesis of the bicyclic monoterpenoids correlated with the availability of the primary carbon source glucose. Spiking the media with 13C-labeled glucose demonstrated that the compounds were produced de novo. Supplementation studies i.a. with isotopically labeled substrates further identified limonene and p-menth-1-en-9-ol as intermediate compounds in the fungal pathways. PSA was able to biotransform all enantiomeric forms of the latter compounds to the respective isomers of dill ether and wine lactone. |
| تدمد: | 1520-5118 0021-8561 |
| DOI: | 10.1021/acs.jafc.8b07263 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::19fed83da516b2f7dd9b4f608bc48438 https://doi.org/10.1021/acs.jafc.8b07263 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi...........19fed83da516b2f7dd9b4f608bc48438 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15205118 00218561 |
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| DOI: | 10.1021/acs.jafc.8b07263 |