Structural Revision of Garcinielliptin Oxide and Garcinielliptone E

Previously, Lin et al. reported the isolation and structural determination of two triterpenoids, garcinielliptin oxide (GO) and garcinielliptone E (GE). Their unusual structural features, which remained unparalleled in subsequent decades despite the intervening discovery of hundreds of other polycyc...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-06, Vol.83 (6), p.2041-2044
Main Authors: Grossman, Robert B, Yang, Xing-Wei
Format: Article
Language:English
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Summary:Previously, Lin et al. reported the isolation and structural determination of two triterpenoids, garcinielliptin oxide (GO) and garcinielliptone E (GE). Their unusual structural features, which remained unparalleled in subsequent decades despite the intervening discovery of hundreds of other polycyclic polyprenylated acylphloroglucinols (PPAPs), caused us to question the originally assigned structures, so GO was reisolated from Garcinia subelliptica, and its NMR spectra were reacquired. In this Note, we revise the structures of GO and the related GE via NMR analysis, biosynthetic considerations, and chemical conversion. Garcinielliptone T, a new PPAP, was also isolated and characterized. GO exhibited weak inhibitory activity against acetylcholinesterase with an IC50 value of 20.7 μM.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.0c00306