Garbractin A (1), a structurally complicated polycyclic
polyprenylated acylphloroglucinol (PPAP) with an unprecedented 4,11-dioxatricyclo[4.4.2.01,5] dodecane skeleton, was isolated from the fruits of Garcinia bracteata, along with five new biosynthetic
analogues named garcibracteatones A–E (2–6). Their structures containing absolute configurations were
revealed using spectroscopic data, the residual dipolar coupling-enhanced
NMR approach, and quantum chemical calculations. The antihyperglycemic
effect of these PPAPs (1–6) was evaluated
using insulin-resistant HepG2 cells (IR-HepG2 cells) induced through
palmitic acid (PA). Compounds 1, 3, and 4 were found to significantly promote glucose consumption
in the IR-HepG2 cells and, therefore, may hold potential as candidates
for treating hyperglycemia.
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