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.
Zhang, Na1; Shi, Zhengyi1; Guo, Yi1; Xie, Shuangshuang1; Qiao, Yuben1; Li, Xiao-Nian2; Xue, Yongbo1; Luo, Zengwei1; Zhu, Hucheng1; Chen, Chunmei1; Hu, Linzhen1,3; Zhang, Yonghui1
Corresponding AuthorXue, Yongbo(yongboxue@mail.hust.edu.cn) ; Zhang, Yonghui(zhangyh@mails.tjmu.edu.cn)
2019-05-07
Source PublicationORGANIC CHEMISTRY FRONTIERS
ISSN2052-4129
Volume6Issue:9Pages:1491-1502
AbstractThree 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.
DOI10.1039/c9qo00245f
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000466794900026
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/66778
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorXue, Yongbo; Zhang, Yonghui
Affiliation1.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
Recommended Citation
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.
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