Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum

Hypermonins A-D ( - ), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs ( and ) were isolated and identified from the flowers of . Hypermoins A-D represented the first examples of highly modified...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2021-05, Vol.86 (10), p.7021-7027
Main Authors: Zeng, Yan-Rong, Li, Ya-Nan, Zhang, Zi-Zhen, Hu, Zhan-Xing, Gu, Wei, Huang, Lie-Jun, Li, Yan-Mei, Yuan, Chun-Mao, Hao, Xiao-Jiang
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Hypermonins A-D ( - ), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs ( and ) were isolated and identified from the flowers of . Hypermoins A-D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs ( - ). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E ( ) and hyperielliptone HA ( ) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02880