Unusual adamantane type polyprenylated acylphloroglucinols with an oxirane unit and their structural transformation from Hypericum hookerianum

被引：27
作者：
Ye, Ye [1 ,2 ]
Yang, Xing-Wei [1 ]
Xu, Gang [1 ]
机构：
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
TETRAHEDRON | 2016年 / 72卷 / 22期
基金：
中国科学院西部之光基金;
关键词：
Polyprenylated acylphloroglucinol; Hypericum hookerianum; Hookeriones A-H; Adamantane; Oxirane; ANTITUMOR-ACTIVITY; DERIVATIVES; HYPERFORIN; SAMPSONII; SKELETON; HENRYI; CORES; TUMOR; MICE; STEM;
D O I：
10.1016/j.tet.2016.04.025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hookeriones A-D (1-4), adamantane type polycyclic polyprenylated acylphloroglucinols (PPAPs), and hookeriones E-H (5-8), 1,9-seco-adamantane type PPAPs, were isolated from Hypericum hookerianum, along with six known analogues. The structures of 1-8, sharing a common 28,29-epoxide moiety, were determined on the basis of comprehensive NMR and MS spectroscopic data. The biomimetic synthesis of 5-7 from the biogenetically precursors 1-3 was performed, respectively. Absolute configurations of these new PPAPs were further defined by electronic circular dichroism (ECD) and biomimetic synthesis methods. (C) 2016 Published by Elsevier Ltd.
引用
收藏
页码：3057 / 3062
页数：6
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