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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 PublicationCHINESE JOURNAL OF CHEMISTRY
ISSN1001-604X
Volume39Issue:9Pages:2422-2432
AbstractMain 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.
KeywordHypericum monogynum Phytochemistry Structure elucidation Biological activity Multidrug resistance reversal activity P-GLYCOPROTEIN MODULATORS CANCER
DOI10.1002/cjoc.202100210
WOS IDWOS:000676096000001
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/73492
Collection中国科学院昆明植物研究所
Affiliation1.[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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