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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
发表期刊CHINESE JOURNAL OF CHEMISTRY
ISSN1001-604X
卷号39期号:9页码:2422-2432
摘要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.
关键词Hypericum monogynum Phytochemistry Structure elucidation Biological activity Multidrug resistance reversal activity P-GLYCOPROTEIN MODULATORS CANCER
DOI10.1002/cjoc.202100210
WOS记录号WOS:000676096000001
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文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/73492
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.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
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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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