The absolute configurations of hyperilongenols A-C: rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable beta,beta '-tricarbonyl systems from Hypericum longistylum Oliv.
文献类型：期刊论文
| 作者 | Zhang, Na1; Shi, Zhengyi1; Guo, Yi1; Xie, Shuangshuang1; Qiao, Yuben1; Li, Xiao-Nian2; Xue, Yongbo1; Luo, Zengwei1; Zhu, Hucheng1; Chen, Chunmei1 |
| 刊名 | ORGANIC CHEMISTRY FRONTIERS
 |
| 出版日期 | 2019-05-07 |
| 卷号 | 6期号:9页码:1491-1502 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/c9qo00245f |
| 通讯作者 | Xue, Yongbo(yongboxue@mail.hust.edu.cn) ; Zhang, Yonghui(zhangyh@mails.tjmu.edu.cn) |
| 英文摘要 | Three novel 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinol (PPAP) derivatives, named hyperilongenols A-C (1-3), were isolated from the stems and leaves of Hypericum longistylum Oliv. Their planar structures were established by a combination of 1D and 2D NMR, HRESIMS data, and chemical derivatization. Their absolute configurations were defined using electronic circular dichroism (ECD) spectroscopy and X-ray crystallography. Compounds 1-3 represent the first examples of naturally occurring 12,13-seco-spirocyclic PPAPs with an enolizable beta, beta'-tricarbonyl system. The O-methylation of compounds 1-3, coupled with comprehensive analyses of their X-ray diffraction data and variable-temperature 1H NMR spectra collected in different solvents, allowed us to propose a general mechanism underlying the formation of inseparable C-24 epimers of hyperilongenol A (1), decipher the solvent effects on the enolizable beta, beta'-tricarbonyl enol protons, and explore the possibilities of keto-enol interconversions of compounds 1-3. Moreover, a reasonable proposal for the structural determination of PPAPs with enolizable beta-dicarbonyl and beta, beta'-tricarbonyl systems was developed. In addition, an in vitro bioassay showed that 2 exhibited potent antibacterial activity against Staphylococcus aureus. |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000466794900026 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/66777]  |
| 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 |
| 通讯作者 | Xue, Yongbo; Zhang, Yonghui |
| 作者单位 | 1.Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Hubei, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China 3.Hubei Univ, Sch Life Sci, Natl & Local Joint Engn Res Ctr High Throughput D, Hubei Key Lab Biotechnol Chinese Tradit Med, Wuhan 430062, Hubei, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhang, Na,Shi, Zhengyi,Guo, Yi,et al. The absolute configurations of hyperilongenols A-C: rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable beta,beta '-tricarbonyl systems from Hypericum longistylum Oliv.[J]. ORGANIC CHEMISTRY FRONTIERS,2019,6(9):1491-1502. |
| APA | Zhang, Na.,Shi, Zhengyi.,Guo, Yi.,Xie, Shuangshuang.,Qiao, Yuben.,...&Zhang, Yonghui.(2019).The absolute configurations of hyperilongenols A-C: rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable beta,beta '-tricarbonyl systems from Hypericum longistylum Oliv..ORGANIC CHEMISTRY FRONTIERS,6(9),1491-1502. |
| MLA | Zhang, Na,et al."The absolute configurations of hyperilongenols A-C: rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable beta,beta '-tricarbonyl systems from Hypericum longistylum Oliv.".ORGANIC CHEMISTRY FRONTIERS 6.9(2019):1491-1502. |
入库方式： OAI收割
来源：昆明植物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。