Kalparinol, a Salvialane (Isodaucane) Sesquiterpenoid Derived from Native Australian Dysphania Species That Suggests a Putative Biogenetic Link to Zerumbone

Dysphania is a genus of plants endemic to the Australian continent, occurring primarily in arid and temperate zones. Despite their prevalence, very little in the way of phytochemical and/or bioactivity investigation of native Dysphania has been performed. Herein reported is the isolation and elucida...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-05, Vol.83 (5), p.1473-1479
Main Authors: Tan, Yuen Ping, Savchenko, Andrei I, Agnew-Francis, Kylie A, Boyle, Glen M, Bernhardt, Paul V, Fraser, James A, Williams, Craig M
Format: Article
Language:English
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Summary:Dysphania is a genus of plants endemic to the Australian continent, occurring primarily in arid and temperate zones. Despite their prevalence, very little in the way of phytochemical and/or bioactivity investigation of native Dysphania has been performed. Herein reported is the isolation and elucidation of (6E,9E)-zerumbone epoxide and a hitherto unreported isomer, (6Z,9E)-zerumbone epoxide, from D. kalpari. In addition, a novel isodaucane sesquiterepene, kalparinol, was isolated from both D. kalpari and D. rhadinostachya. The coisolation of the humulene and isodaucane skeletons, combined with the lack of any cadalane systems, could suggest an alternate novel biogenetic pathway originating from zerumbone, which is unlike any other proposals for the isodaucene system.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.9b01039