Humulene Diepoxides from the Australian Arid Zone Herb Dysphania: Assignment of Aged Hops Constituents |
| |
| Authors: | Yuen Ping Tan Kylie A Agnew-Francis Julian Hofmann Dr Andrei I Savchenko Dr Scott R Lafontaine Prof Glen M Boyle Prof Paul V Bernhardt Prof James A Fraser Prof Thomas H Shellhammer Prof Craig M Williams |
| |
| Institution: | 1. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072 Australia;2. Institute of Organic Chemistry, Karlsruhe Institute for Technology, 76131 Karlsruhe, Germany;3. Department of Food Science and Technology, Oregon State University, Corvallis, OR, 97331-6602 USA;4. QIMR Berghofer Medical Research Institute, PO Royal Brisbane Hospital, Brisbane, 4029 Queensland, Australia |
| |
| Abstract: | Dysphania is an abundant genus of plants, many of which are endemic to the Australian continent, occurring primarily in arid and temperate zones. Despite their prevalence, very few investigations into the phytochemistry of native Dysphania have been undertaken. Described herein, is the isolation and elucidation of two enantiomeric diastereomers of humulene diepoxide C from D. kalpari and D. rhadinostachya, of which unassigned diastereomers of humulene diepoxide C have been previously reported as components in beer brewed from aged hops. In addition, two (+)-humulene diepoxiols (humulene diepoxiol C-I and C-II) were isolated from D. rhadinostachya. Analysis of Chinook hops oil confirmed the presence of both humulene diepoxide C-I and C-II as trace components, and in turn enabled GC-MS peak assignment to the relative stereochemistry. Anticancer assays did not reveal any significant activity for the (+)-humulene diepoxides. Antifungal assays showed good activity against a drug-resistant strain of C. auris, with MIC50 values of 8.53 and 4.91 μm obtained for (+)-humulene diepoxide C-I and C-II, respectively. |
| |
| Keywords: | diepoxides epoxides hops humulenes natural products |
|
|
