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.

doi:10.1039/c9qo00245f

	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, Na 1; Shi, Zhengyi 1; Guo, Yi 1; Xie, Shuangshuang 1; Qiao, Yuben 1; Li, Xiao-Nian 2; Xue, Yongbo 1; Luo, Zengwei 1; Zhu, Hucheng 1; Chen, Chunmei 1; Hu, Linzhen 1,3; Zhang, Yonghui 1
通讯作者	Xue, Yongbo(yongboxue@mail.hust.edu.cn) ; Zhang, Yonghui(zhangyh@mails.tjmu.edu.cn)
	2019-05-07
发表期刊	ORGANIC CHEMISTRY FRONTIERS
ISSN	2052-4129
卷号	6 期号:9 页码:1491-1502
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.
DOI	10.1039/c9qo00245f
收录类别	SCI
语种	英语
WOS记录号	WOS:000466794900026
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/66778
专题	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.