Journalartikel

Autorenliste: Brescia, FF; Koch, M; Wende, RC; Schreiner, PR; Zorn, H; Fraatz, MA

Jahr der Veröffentlichung: 2023

Seiten: 7744-7751

Zeitschrift: Journal of Agricultural and Food Chemistry

Bandnummer: 71

Heftnummer: 20

ISSN: 0021-8561

DOI Link: https://doi.org/10.1021/acs.jafc.3c01807

Verlag: American Chemical Society

Abstract: 

Among the monoterpenoid aroma compounds formed by the basidiomycete Cystostereum murrayi are highly potent bicyclic benzofuran derivatives. In addition to the dill ethers previously described in a few fungi, two stereoisomers of the rare 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one (1a and 2c), also known as dihydromenthofurolactones, and a C3-unsaturated analogue (3a) are formed by C. murrayi. The analysis of synthesized reference standards of the lactones allowed an unambiguous assignment of the stereoisomers formed by the fungus. Despite a similar structure, two key differences in the stereochemistry of the lactones and dill ethers emerged. The analysis of submerged cultures further revealed the formation of additional, so far unknown, fungal terpenoids, including limonen-10-ol (7) and the corresponding aldehyde limonen-10-al (8). Analysis of chiral terpenoids as well as supplementation studies, including stable isotope-labeled compounds, indicated independent biogenesis pathways for dill ethers and lactones.

Harvard-Zitierstil: Brescia, F., Koch, M., Wende, R., Schreiner, P., Zorn, H. and Fraatz, M. (2023) Structure Elucidation of Aroma-Active Bicyclic Benzofuran Derivatives Formed by Cystostereum murrayi, Journal of Agricultural and Food Chemistry, 71(20), pp. 7744-7751. https://doi.org/10.1021/acs.jafc.3c01807

APA-Zitierstil: Brescia, F., Koch, M., Wende, R., Schreiner, P., Zorn, H., & Fraatz, M. (2023). Structure Elucidation of Aroma-Active Bicyclic Benzofuran Derivatives Formed by Cystostereum murrayi. Journal of Agricultural and Food Chemistry. 71(20), 7744-7751. https://doi.org/10.1021/acs.jafc.3c01807