Polycyclic polyprenylated acylphloroglucinols with acetylcholinesterase inhibitory activities from Hypericum perforatum

Huayong Lou; Ping Yi; Zhanxing Hu; Yanan Li; Yanrong Zeng; Wei Gu; Liejun Huang; Chunmao Yuan; Xiaojiang Hao

doi:10.1016/j.fitote.2020.104550

Polycyclic polyprenylated acylphloroglucinols with acetylcholinesterase inhibitory activities from Hypericum perforatum

Fitoterapia. 2020 Jun:143:104550. doi: 10.1016/j.fitote.2020.104550. Epub 2020 Mar 12.

Authors

Huayong Lou¹, Ping Yi², Zhanxing Hu², Yanan Li², Yanrong Zeng¹, Wei Gu², Liejun Huang², Chunmao Yuan³, Xiaojiang Hao⁴

Affiliations

¹ School of Basic Medical Sciences, Guizhou Medical University, Guiyang 550025, China; State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China.
² State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China.
³ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China. Electronic address: yuanchunmao01@126.com.
⁴ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China; State Key laboratory of phytochemistry and Plant Resources in West China, Kunming Institute of Boanty, Chinese Academy of Science, Kunming 650201, China. Electronic address: haoxj@mail.kib.ac.cn.

PMID: 32173424
DOI: 10.1016/j.fitote.2020.104550

Abstract

Six new polycyclic polyprenylated acylphloroglucinols, hyperfols CH (1-6), along with seven known ones (7-13), were isolated from the aerial parts of Hypericum perforatum. The structures were identified on the basis of comprehensive spectroscopic data analysis including 1D and 2D NMR, and the absolute configurations of the new compounds were determined by quantum chemical electronic circular dichroism (ECD) calculations. In addition, compounds 4 and 12 exhibited moderate acetylcholinesterase (AChE) inhibitory activities, with IC₅₀ values of 20.32 and 27.37 μM, respectively.

Keywords: Acetylcholinesterase inhibitory activities; Hypericum; Hypericum perforatum; Polycyclic polyprenylated acylphloroglucinols.

MeSH terms

China
Cholinesterase Inhibitors / isolation & purification
Cholinesterase Inhibitors / pharmacology*
Circular Dichroism
Hypericum / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Phloroglucinol / isolation & purification
Phloroglucinol / pharmacology*
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Components, Aerial / chemistry

Substances

Cholinesterase Inhibitors
Phytochemicals
Phloroglucinol