| seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron | |
Kong, Ling-Mei1,2,3; Long, Xian-Wen1,2; Yang, Xing-Wei1,2 ; Xia, Fan1,2,4,5; Khan, Afsar6; Yan, Hui1,2; Deng, Jun1,2; Li, Xian4,5; Xu, Gang1,2
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| 2017-05-31 | |
| Source Publication | TETRAHEDRON LETTERS
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| Volume | 58Issue:22Pages:2113-2117 |
| Abstract | 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. |
| Keyword | Polyprenylated Acylphloroglucinol Hypericum Ascyron Ascyronones A-d Biomimetic Transformation |
| DOI | 10.1016/j.tetlet.2017.04.044 |
| Indexed By | SCI |
| Language | 英语 |
| WOS ID | WOS:000401877200008 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.kib.ac.cn/handle/151853/51248 |
| Collection | 植物化学与西部植物资源持续利用国家重点实验室 |
| Affiliation | 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 |
| Recommended Citation 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. |
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| 1-s2.0-S004040391730（599KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Download | |
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