Hyperpatone A, a polycyclic polyprenylated acylphloroglucinol with a rare 8/6/5/6/5 pentacyclic skeleton from Hypericum patulum

doi:10.1039/d2ob01851a

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	Hyperpatone A, a polycyclic polyprenylated acylphloroglucinol with a rare 8/6/5/6/5 pentacyclic skeleton from Hypericum patulum
	Zhang, Feng; Yang, Jue; Yi, Ping; Li, Ya-Nan; Hao, Xiao-Jiang; Yuan, Chun-Mao
	2022
发表期刊	ORGANIC & BIOMOLECULAR CHEMISTRY
卷号	21 期号:1 页码:140-146
摘要	Hyperpatone A (1), a highly oxidated polycyclic polyprenylated acylphloroglucinol (PPAP), along with a biosynthesized related PPAP (2) was isolated from Hypericum patulum under the guidance of LC-MS investigation. Architecturally, compound 1 represents the first PPAP with an unprecedented 8/6/5/6/5 pentacyclic skeleton and an intramolecular peroxy bridge, which might be derived from the [3.3.1]-type bicyclic polyprenylated acylphloroglucinol via the critical Baeyer-Villiger oxidation, decarboxylation, and intramolecular cyclization. The structures were established by extensive spectroscopic analysis, ACD software calculation, and quantum chemical computations. A plausible biogenetic pathway of 1 and 2 was also proposed. Importantly, both compounds exhibited moderate cytotoxic activities against the HEL cell line with the IC50 values ranging from 10.2 to 19.2 mu M. Moreover, compound 1 showed an inhibitory effect on NO production in lipopolysaccharide-stimulated RAW264.7 cells at a lower concentration of 5 or 1 mu M.
关键词	ASSISTED STRUCTURE ELUCIDATION
DOI	10.1039/d2ob01851a
收录类别	SCI
WOS记录号	WOS:000893216100001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74655
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Zhang, Feng,Yang, Jue,Yi, Ping,et al. Hyperpatone A, a polycyclic polyprenylated acylphloroglucinol with a rare 8/6/5/6/5 pentacyclic skeleton from Hypericum patulum[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2022,21(1):140-146.
APA	Zhang, Feng,Yang, Jue,Yi, Ping,Li, Ya-Nan,Hao, Xiao-Jiang,&Yuan, Chun-Mao.(2022).Hyperpatone A, a polycyclic polyprenylated acylphloroglucinol with a rare 8/6/5/6/5 pentacyclic skeleton from Hypericum patulum.ORGANIC & BIOMOLECULAR CHEMISTRY,21(1),140-146.
MLA	Zhang, Feng,et al."Hyperpatone A, a polycyclic polyprenylated acylphloroglucinol with a rare 8/6/5/6/5 pentacyclic skeleton from Hypericum patulum".ORGANIC & BIOMOLECULAR CHEMISTRY 21.1(2022):140-146.

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