Hypermonones A-I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity

doi:10.1002/cjoc.202100210

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	Hypermonones A-I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity
	Zeng,Yan-Rong ; Li,Ya-Nan ; Yang,Jue ; Yi,Ping ; Huang,Lei ; Huang,Lie-Jun ; Gu,Wei; Hu,Zhan-Xing ; Li,Yan-Mei ; Yuan,Chun-Mao ; Hao,Xiao-Jiang
	2021
Source Publication	CHINESE JOURNAL OF CHEMISTRY
ISSN	1001-604X
Volume	39 Issue:9 Pages:2422-2432
Abstract	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 delta-lactone and tricyclic gamma-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.
Keyword	Hypericum monogynum Phytochemistry Structure elucidation Biological activity Multidrug resistance reversal activity P-GLYCOPROTEIN MODULATORS CANCER
DOI	10.1002/cjoc.202100210
WOS ID	WOS:000676096000001
Citation statistics
Document Type	期刊论文
Identifier	http://ir.kib.ac.cn/handle/151853/73492
Collection	中国科学院昆明植物研究所
Affiliation	1.[Zeng, Yan-Rong 2.Li, Ya-Nan 3.Yang, Jue 4.Yi, Ping 5.Huang, Lei 6.Huang, Lie-Jun 7.Gu, Wei 8.Hu, Zhan-Xing 9.Li, Yan-Mei 10.Yuan, Chun-Mao 11.Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, Guiyang 550014, Guizhou, Peoples R China 12.Key Lab Chem & Nat Prod Guizhou Prov, Guiyang 550014, Guizhou, Peoples R China 13.Chinese Acad Sci, Guiyang 550014, Guizhou, Peoples R China 14.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
Recommended Citation GB/T 7714	Zeng,Yan-Rong,Li,Ya-Nan,Yang,Jue,et al. Hypermonones A-I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity[J]. CHINESE JOURNAL OF CHEMISTRY,2021,39(9):2422-2432.
APA	Zeng,Yan-Rong.,Li,Ya-Nan.,Yang,Jue.,Yi,Ping.,Huang,Lei.,...&Hao,Xiao-Jiang.(2021).Hypermonones A-I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity.CHINESE JOURNAL OF CHEMISTRY,39(9),2422-2432.
MLA	Zeng,Yan-Rong,et al."Hypermonones A-I, New Polyprenylated Acylphloroglucinols from Hypericum monogynum with Multidrug Resistance Reversal Activity".CHINESE JOURNAL OF CHEMISTRY 39.9(2021):2422-2432.

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