Five new epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones from Chinese agarwood by artificial holing

Wei Li, Ge Liao, Hao Wang, Wen Hua Dong, Li Yang, Fan Dong Kong, Cai Hong Cai, Jun Wang, Attila Mándi, T. Kurtán, Wen Li Mei, Hao Fu Dai

Research output: Contribution to journalArticle

Abstract

Five optically active epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone derivatives (1–5) with four chirality centers in the condensed cyclohexene ring were isolated from artificial holing agarwood originating from Aquilaria sinensis (Lour.) Gilg. Their structures were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analyses. The absolute configuration of 2 was elucidated by TDDFT-ECD calculations and ECD spectra of 1, 3–5 allowed their configurational assignment as well. All of the new compounds contained a condensed oxirane ring, and compound 1 was the only 6,7-epoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone derivative that has ever been found in agarwood. AChE inhibitory activity was tested for the first time of these new compounds by using modified Ellman's colorimetric method. Compounds 3 and 5 exhibited inhibitory activity against AChE with IC 50 value of 441.6, and 155.6 μM, respectively.

Original languageEnglish
Pages (from-to)182-187
Number of pages6
JournalFitoterapia
Volume134
DOIs
Publication statusPublished - Apr 1 2019

Fingerprint

Thymelaeaceae
Ethylene Oxide
2-(2-phenylethyl)chromone
cyclohexene

Keywords

  • AChE inhibitory activity
  • Agarwood
  • Artificial holing
  • Chiral tetrahydrochromone
  • TDDFT-ECD

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Five new epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones from Chinese agarwood by artificial holing. / Li, Wei; Liao, Ge; Wang, Hao; Dong, Wen Hua; Yang, Li; Kong, Fan Dong; Cai, Cai Hong; Wang, Jun; Mándi, Attila; Kurtán, T.; Mei, Wen Li; Dai, Hao Fu.

In: Fitoterapia, Vol. 134, 01.04.2019, p. 182-187.

Research output: Contribution to journalArticle

Li, W, Liao, G, Wang, H, Dong, WH, Yang, L, Kong, FD, Cai, CH, Wang, J, Mándi, A, Kurtán, T, Mei, WL & Dai, HF 2019, 'Five new epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones from Chinese agarwood by artificial holing', Fitoterapia, vol. 134, pp. 182-187. https://doi.org/10.1016/j.fitote.2019.02.031
Li, Wei ; Liao, Ge ; Wang, Hao ; Dong, Wen Hua ; Yang, Li ; Kong, Fan Dong ; Cai, Cai Hong ; Wang, Jun ; Mándi, Attila ; Kurtán, T. ; Mei, Wen Li ; Dai, Hao Fu. / Five new epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones from Chinese agarwood by artificial holing. In: Fitoterapia. 2019 ; Vol. 134. pp. 182-187.
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