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

doi:10.1021/acs.joc.0c02880

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	Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum
	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
	2021
发表期刊	JOURNAL OF ORGANIC CHEMISTRY
ISSN	0022-3263
卷号	86 期号:10 页码:7021-7027
摘要	Hypermonins A-D (1-4), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (5 and 6) were isolated and identified from the flowers of Hypericum monogynum. 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 (1-7). 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 (5) and hyperielliptone HA (7) 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.
关键词	MULTIDRUG-RESISTANCE DITERPENOIDS DERIVATIVES PLANT
DOI	10.1021/acs.joc.0c02880
WOS记录号	WOS:000656056500001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/73100
专题	中国科学院昆明植物研究所
作者单位	1.[Zeng, Yan-Rong 2.Li, Ya-Nan 3.Zhang, Zi-Zhen 4.Hu, Zhan-Xing 5.Gu, Wei 6.Huang, Lie-Jun 7.Li, Yan-Mei 8.Yuan, Chun-Mao 9.Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, Guiyang 550014, Peoples R China 10.Key Lab Chem Nat Prod Guizhou Prov, Guiyang 550014, Peoples R China 11.Chinese Acad Sci, Guiyang 550014, Peoples R China 12.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
推荐引用方式 GB/T 7714	Zeng,Yan-Rong,Li,Ya-Nan,Zhang,Zi-Zhen,et al. Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(10):7021-7027.
APA	Zeng,Yan-Rong.,Li,Ya-Nan.,Zhang,Zi-Zhen.,Hu,Zhan-Xing.,Gu,Wei.,...&Hao,Xiao-Jiang.(2021).Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum.JOURNAL OF ORGANIC CHEMISTRY,86(10),7021-7027.
MLA	Zeng,Yan-Rong,et al."Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum".JOURNAL OF ORGANIC CHEMISTRY 86.10(2021):7021-7027.

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