Journal article

Publication year: 2019

Pages: 13400-13411

Journal: Journal of Agricultural and Food Chemistry

Volume number: 67

Issue number: 49

DOI Link: https://doi.org/10.1021/acs.jafc.8b07263

Publisher: American Chemical Society

Abstract: 

The white-rot fungusPleurotus 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 (winelactone) (2). Submerged cultures grown in different media were analyzed by gas chromatography−mass spectrometry. Thestereochemistry of the formed isomers was elucidated by comparing their retention indices to those of reference compounds byenantioselective 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 thebiosynthesis of the bicyclic monoterpenoids correlated with the availability of the primary carbon source glucose. Spiking themedia with13C-labeled glucose demonstrated that the compounds were producedde novo. Supplementation studies i.a. withisotopically labeled substrates further identified limonene andp-menth-1-en-9-ol as intermediate compounds in the fungalpathways. PSA was able to biotransform all enantiomeric forms of the latter compounds to the respective isomers of dill etherand wine lactone.KEYWORDS:Pleurotus sapidus, submerged cultivation, dill ether, wine lactone, p-menth-1-en-9-ol, isotopic labeling studies,biotransformation

Harvard Citation style: Trapp, T., Kirchner, T., Birk, F., Fraatz, M. and Zorn, H. (2019) Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus, Journal of Agricultural and Food Chemistry, 67(49), pp. 13400-13411. https://doi.org/10.1021/acs.jafc.8b07263

APA Citation style: Trapp, T., Kirchner, T., Birk, F., Fraatz, M., & Zorn, H. (2019). Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus. Journal of Agricultural and Food Chemistry. 67(49), 13400-13411. https://doi.org/10.1021/acs.jafc.8b07263