Serrulatane diterpenoids with unusual side chain modifications from root bark of Eremophila longifolia
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Date
2022
Authors
Rasmussen, L.F.
Anton, J.
Kjaerulff, L.
Zhao, Y.
Semple, S.J.
Chi, N.
Buirchell, B.
Moller, B.L.
Staerk, D.
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Phytochemistry, 2022; 203(113408):1-14
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The plant genus Eremophila is endemic to Australia and widespread in arid regions. Root bark extract of Ere-mophila longifolia (R.Br.) F.Muell. (Scrophulariaceae) was investigated by LC-PDA-HRMS, and dereplication suggested the presence of a series of diterpenoids. Using a combination of preparative-and analytical-scale HPLC separation as well as extensive 1D and 2D NMR analysis, the structures of 12 hitherto unreported serrulatane diterpenoids, eremolongine A-L, were established. These structures included serrulatanes with unusual side chain modifications to form hitherto unseen skeletons with, e.g., cyclopentane, oxepane, and bicyclic hexahydro-1H- cyclopenta[c]furan moieties. Serrulatane diterpenoids in Eremophila have recently been shown to originate from a common biosynthetic precursor with conserved stereochemical configuration, and this was used for tentative assignment of the relative and absolute configuration of the isolated compounds. Triple high-resolution alpha-glucosidase/alpha-amylase/PTP1B inhibition profiling demonstrated that several of the eremolongines had weak inhibitory activity towards targets important for management of type 2 diabetes.
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Data source: Supplementary data, https://doi.org/10.1016/j.phytochem.2022.113408
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Copyright 2022 The author(s), published by Elsevier. Published by Elsevier Ltd. This is an open access article under the CC BY license. (http://creativecommons.org/licenses/by/4.0/)