2-(2-Phenylethyl)chromone derivatives from Chinese agarwood induced by artificial holing
Graphical abstract
The structures of three new compounds and the sample of Chinese agarwood induced by artificial holing.
Introduction
Agarwood, the fragrant resinous wood obtained from certain trees of Aquilaria species (Thymelaeaceae), also called eaglewood, gaharu, kanankoh, kyara, jinkoh or chen xiang in different cultures, could be used as incense and traditional medicine [1]. According to the review of Naef R, agarwood possesses a panoply of effects such as aphrodisiac, sedative, cardiatonic and carminative, and to relieve gastric problems, coughs, rheumatism and high fever [2]. Agarwood cannot be generated in normal wood tissues, but might be formed when the Aquilaria plants were injured by natural or artificial effects, such as lighting striking, burning, microbial invasions, holing, cutting, and artificial fungus inoculation [1]. Phytochemical research showed that sesquiterpenoids and 2-(2-phenylethyl)chromone derivatives were identified from several sorts of agarwood [2], [3]. As agarwood has become more and more popular in the international market [4], [5], [6], [7], great efforts were under way to cultivate Aquilaria trees and to afford agarwood by artificial methods in recent years, to meet the demand for agarwood in the form of medicine, incense stick or oil.
Previous studies on Chinese agarwood originating from Aquilaria sinensis were mostly concentrated on the wild ones, and researchers have reported various sesquiterpenoids together with 2-(2-phenylethyl)chromone derivatives [2], [3]. To identify the chemical components of Chinese agarwood induced by artificial holing, as well as afford valuable information for understanding the bioorganic process of agarwood formation, the chemical constituents of Chinese agarwood induced by artificial holing from A. sinensis were investigated in this study. This paper described the isolation, the structure elucidation, the antibacterial activity and AChE inhibitory activity of three new 2-(2-phenylethy)chromone derivatives (1–3), together with thirteen known ones (4–16) from Chinese agarwood induced by artificial holing of A. sinensis.
Section snippets
General
1D and 2D NMR experiments were recorded on a Bruker AV III spectrometer (for 1H NMR at 500 MHz and 13C NMR at 125 MHz) using TMS as the internal standard. HRMS were acquired using an API Qstar Pulsar mass spectrometer (Bruker, Germany). Optical rotations were measured on a Rudolph Autopol III polarimeter (Rudolph, Flanders, America). IR spectra were performed on a Nicolet 380 FT-IR spectrometer (Thermo, America). UV spectra were recorded on a Shimadzu UV-2550 spectrometer (Beckman, America). HPLC
Results and discussion
Three new 2-(2-phenylethyl)chromone derivatives (1–3), together with thirteen known ones (4–16), were isolated from the EtOAc extract of Chinese agarwood induced by artificial holing originating from A. sinensis (Fig. 1). The thirteen known 2-(2-phenylethy)chromone derivatives were identified as rel-(1aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7H-oxireno[f][1]benzopyran-7-one (4) [11],
Acknowledgements
This work was financially supported by the National Support Science and Technology Subject (2013BAI11B04), Major Technology Project of Hainan Province (ZDZX2013013; ZDZX2013023-1) and Natural Science Foundation of Hainan Province (313080).
References (27)
- et al.
A new and rapid colorimetric determination of acetylcholinesterase activity
Biochem Pharmacol
(1961) - et al.
2-(2-Phenylethyl)chromones from Chinese eaglewood
Phytochemistry
(2012) - et al.
Three novel diepoxy tetrahydrochromones from agarwood artificially produced by intentional wounding
Tetrahedron Lett
(2005) - et al.
Two new chromones and a new flavone glycoside from Imperata cylindrica
Chin J Nat Med
(2013) - et al.
A new cytotoxic 2-(2-phenylethyl)chromones from Chinese eaglewood
Chin Chem Lett
(2008) - et al.
MS characterization and determination of 2-(2-phenylethyl) chromones in agarwood by GC–MS
Molecules
(2013) The volatile and semi-volatile constituents of agarwood, the infected heartwood of Aquilaria species: a review
Flav Fragr J
(2011)Review of the constituents isolated from Chen-Xiang
Nat Prod Res Dev
(1996)Studies on perilla, agarwood, and cinnamon through a combination of fieldwork and laboratory work
J Nat Med
(2008)- et al.
Smallholder tree growing for rural development and environmental services
(2008)
Heart of the matter: agarwood use and trade and CITES implementation for Aquilaria malaccensis
Wood for trees: a review of the agarwood (gaharu) trade in Malaysia
Antibacterial activity of the flavonoids from Dalbergia odorifera on Ralstonia solanacearum
Molecules
Cited by (93)
Structural, defense enzyme activity and chemical composition changes in the xylem of Aquilaria sinensis during fungus induction
2024, Industrial Crops and ProductsCharacteristic quality analysis for biologically induced agarwood columns in Aquilaria sinensis
2023, Environmental ResearchOccurrence, synthesis and biological activity of 2-(2-phenyethyl)chromones
2022, European Journal of Medicinal Chemistry
- 1
These authors contributed equally to this work.