Polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Hypericum perforatum and absolute configurations assignment of previously reported analogues

doi:10.1016/j.bioorg.2021.105144

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	Polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Hypericum perforatum and absolute configurations assignment of previously reported analogues
	Guo,Yi ; Cao,Yunfang ; Qi,Changxing ; Tong,Qingyi ; Chen,Chunmei ; Yang,Jing; Zhu,Hucheng ; Zhang,Yonghui
	2021
Source Publication	BIOORGANIC CHEMISTRY
ISSN	0045-2068
Volume	114 Pages:105144
Abstract	Hyperformitins A-I (1-9), nine undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) with doublebond migration, along with four new isomers hyperformitins J-M (10-13), were isolated from Hypericum perforatum. Their structures and absolute configurations were determined by spectroscopic analyses including HRESIMS, IR, UV, NMR, and ECD, as well as optical rotation (OR) calculations. The absolute configurations of previously reported analogues, garsubellins D and C as well as garcinielliptones L and M, were assigned for the first time by NMR spectra and specific rotations analyses assisting with OR calculations. Selected compounds were tested for their immunosuppressive activities against lipopolysaccharide (LPS)-induced B lymphocyte proliferation. Compounds 1, 3, 4, 5, 7, and 11 showed inhibition activities against the proliferation of B lymphocyte with IC50 values ranging from 4.1 to 9.7 mu M. Furthermore, the neuropmtective activities of the isolates against corticostemne (CORT)-induced injury in PC12 cells were also tested, and compounds 1, 12, and 13 exhibited neuroprotective effects with cell viabilities of 68.0%, 71.3%, and 68.4%, respectively under the concentration of 10 mu M.
Keyword	Hypericum perforatum Polycyclic polyprenylated acylphloroglucinols Configuration assignment Immunosuppressive activity Neuroprotective activity ST-JOHNS-WORT PHLOROGLUCINOL DERIVATIVES HYPERFORIN INHIBITION DEPRESSION SKELETON L.
DOI	10.1016/j.bioorg.2021.105144
WOS ID	WOS:000689520600011
Citation statistics
Document Type	期刊论文
Identifier	http://ir.kib.ac.cn/handle/151853/73000
Collection	中国科学院昆明植物研究所
Affiliation	1.Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
Recommended Citation GB/T 7714	Guo,Yi,Cao,Yunfang,Qi,Changxing,et al. Polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Hypericum perforatum and absolute configurations assignment of previously reported analogues[J]. BIOORGANIC CHEMISTRY,2021,114:105144.
APA	Guo,Yi.,Cao,Yunfang.,Qi,Changxing.,Tong,Qingyi.,Chen,Chunmei.,...&Zhang,Yonghui.(2021).Polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Hypericum perforatum and absolute configurations assignment of previously reported analogues.BIOORGANIC CHEMISTRY,114,105144.
MLA	Guo,Yi,et al."Polycyclic polyprenylated acylphloroglucinols with immunosuppressive activity from Hypericum perforatum and absolute configurations assignment of previously reported analogues".BIOORGANIC CHEMISTRY 114(2021):105144.

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