Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity

doi:10.1016/j.phytochem.2023.113727

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	Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity
	Hu,Ya-Li; Yue,Grace Gar-Lee; Li,Xing-Ren; Xu,Gang; Lau,Clara Bik-San
	2023
发表期刊	PHYTOCHEMISTRY
ISSN	1873-3700
卷号	212 页码:113727
摘要	Ten spirocyclic polycyclic polyprenylated acylphloroglucinols (PPAP), hunascynols A-J (1-10), and 12 known analogs were isolated from the aerial parts of Hypericum ascyron Linn. Compounds 1 and 2, which share a 1,2seco-spirocyclic PPAP skeleton, could be derived from spirocyclic PPAP, with a common octahydrospiro[cyclohexan-1,5 '-indene]-2,4,6-trione core, through a cascade of Retro-Claisen, keto-enol tautomerism, and esterification reactions. Aldolization of normal spirocyclic PPAP yielded 3, which has a caged framework with a 6/5/6/ 5/6 ring system. The structures of these compounds were determined using spectroscopy and X-ray diffraction. The inhibitory activities of all isolates were tested in three human cancer cell lines and a zebrafish model. Compounds 1 and 2 displayed moderate cytotoxicity against HCT116 cells (IC50 6.87 and 9.86 mu M, respectively). The mechanisms of these compounds were evaluated using Western blot assays. Compounds 3 and 5 inhibited the growth of sub-intestinal vessels in zebrafish embryos. Further, the target genes were screened using real-time PCR.
关键词	Hypericaceae Polycyclic polyprenylated acylphloroglucinols Spirocyclic polyprenylated acylphloroglucinols HCT116 cells Zebrafish model Hypericum ascyron Linn NATURAL-PRODUCTS A-H DERIVATIVES FLOWERS VEGF
学科领域	Biochemistry & Molecular Biology ; Plant Sciences
DOI	10.1016/j.phytochem.2023.113727
收录类别	SCI
WOS记录号	WOS:001009319600001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/75528
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Hu,Ya-Li,Yue,Grace Gar-Lee,Li,Xing-Ren,et al. Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity[J]. PHYTOCHEMISTRY,2023,212:113727.
APA	Hu,Ya-Li,Yue,Grace Gar-Lee,Li,Xing-Ren,Xu,Gang,&Lau,Clara Bik-San.(2023).Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity.PHYTOCHEMISTRY,212,113727.
MLA	Hu,Ya-Li,et al."Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity".PHYTOCHEMISTRY 212(2023):113727.

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