Hypermonones A-I,New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resi

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Main observation and conclusionrnEleven biogenetically related polyprenylated acylphloroglucinols (PPAPs),including four novel skeletons (1-4) and five new com-pounds (5-9),were isolated from the flowers of Hypericum monogynum.Hypermonones A-D (1-4) represented the first example of a unique dilactone structure containing carbonyl bonded single δ-lactone and tricyclic γ-lactone moieties.Their structures were elucidated by NMR analysis,X-ray crystallography,and ECD calculations.Moreover,we revised the structure of hyperibrin B to hy-permonone Ⅰ (9) via NMR analysis,a quantum computational chemistry method,and hypothetic biosynthetic considerations.Three compounds (5,6,and 9) with significant MDR reversal activity (RF ranging from 61 to 223) were superior to the positive control vera-pamil (MCF-7/ADR,RF:53;HepG2/ADR,RF:124).Mechanism study for compound 5 indicated that this compound could inhibit the function of P-gp transport rather than its expression,and the possible recognition mechanism between compound 5 and P-gp was predicted by molecular docking.
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