Journal
FITOTERAPIA
Volume 134, Issue -, Pages 182-187Publisher
ELSEVIER
DOI: 10.1016/j.fitote.2019.02.031
Keywords
Agarwood; Artificial holing; Chiral tetrahydrochromone; TDDFT-ECD; AChE inhibitory activity
Categories
Funding
- Innovative Research Team Grant of the Natural Science Foundation of Hainan Province [2017CXTD020]
- Central Public-interest Scientific Institution Basal Research Fund for Innovative Research Team Program of CATAS [1630052017009, 17CXTD-15]
- China Agriculture Research System [CARS-21]
- National Research, Development and Innovation Office [NKFI K120181, K112951]
- EU
- European Regional Development Fund [GINOP-2.3.2-15-2016-00008]
- Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences
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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 IC50 value of 441.6, and 155.6 mu M, respectively.
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