seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron

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	seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron
	Kong, Ling-Mei 1,2,3; Long, Xian-Wen 1,2; Yang, Xing-Wei1,2 ; Xia, Fan 1,2,4,5; Khan, Afsar 6; Yan, Hui 1,2; Deng, Jun 1,2; Li, Xian 4,5; Xu, Gang1,2
刊名	TETRAHEDRON LETTERS
	2017-05-31
卷号	58 期号:22 页码:2113-2117
关键词	Polyprenylated acylphloroglucinol Hypericum ascyron Ascyronones A-D Biomimetic transformation
英文摘要	Three new seco-polycyclic polyprenylated acylphloroglucinols (PPAPs), ascyronones A-C (1-3), and a new biosynthetic precursor, ascyronone D (4), were isolated from Hypericum ascyron together with three known analogues (5-7). Compounds 1 and 2, sharing an unusual seven-membered carbon core fused with a gamma-lactone ring, could be derived from 1,9-seco-PPAPs via further rearrangement. A biomimetic transformation from 5 to 1 was performed by using base-driven retro-Claisen and rearrangement cascade reaction, which further confirmed the structure of 1 and shed light to its possible biosynthetic pathway. Interestingly, all these compounds are decorated with a methyl group at C-5 instead of a prenyl or geranyl group in many other PPAPs. The isolates were evaluated for their inhibitory activities against five human tumor cell lines. (C) 2017 Elsevier Ltd. All rights reserved.
类目[WOS]	Chemistry, Organic
研究领域[WOS]	Chemistry
关键词[WOS]	A-H ; DERIVATIVES ; HYPERFORIN ; COHAERENS ; HYPERCOHIN ; CONGENERS ; SCABRUM ; HENRYI ; CORE ; RING
收录类别	SCI
语种	英语
WOS记录号	WOS:000401877200008
内容类型	期刊论文
源URL	[http://ir.kib.ac.cn/handle/151853/51248]
专题	昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Yunnan Key Lab Nat Med Chem, Kunming 650201, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 4.Kunming Med Univ, Sch Pharmaceut Sci, Kunming 650500, Peoples R China 5.Kunming Med Univ, Yunnan Key Lab Pharmacol Nat Prod, Kunming 650500, Peoples R China 6.COMSATS Inst Informat Technol, Dept Chem, Abbottabad 22060, Pakistan
推荐引用方式 GB/T 7714	Kong, Ling-Mei,Long, Xian-Wen,Yang, Xing-Wei,et al. seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron[J]. TETRAHEDRON LETTERS,2017,58(22):2113-2117.
APA	Kong, Ling-Mei.,Long, Xian-Wen.,Yang, Xing-Wei.,Xia, Fan.,Khan, Afsar.,...&Xu, Gang.(2017).seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron.TETRAHEDRON LETTERS,58(22),2113-2117.
MLA	Kong, Ling-Mei,et al."seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron".TETRAHEDRON LETTERS 58.22(2017):2113-2117.