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Hypermonones A—I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity
Author(s) -
Zeng YanRong,
Li YaNan,
Yang Jue,
Yi Ping,
Huang Lei,
Huang LieJun,
Gu Wei,
Hu ZhanXing,
Li YanMei,
Yuan ChunMao,
Hao XiaoJiang
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202100210
Subject(s) - chemistry , stereochemistry , tricyclic , lactone , docking (animal) , hypericum , computational chemistry , traditional medicine , medicine , nursing
Main observation and conclusion Eleven biogenetically related polyprenylated acylphloroglucinols (PPAPs), including four novel skeletons (1—4) and five new compounds (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 hypermonone 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 verapamil (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.