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UPLC-MS-guided isolation of single ether linkage dimeric 2-(2-phenylethyl)chromones from Aquilaria sinensis.

ABSTRACT: Eleven novel uncommon single ether linkage dimeric 2-(2-phenylethyl)chromones (aquilasinenones A-K) were isolated by a UPLC-MS guided method from artificial hole-induced agarwood originating from Aquilaria sinensis. Their structures were unambiguously deduced using HRESIMS data, detailed 1D and 2D NMR spectroscopic analysis, and experimental ECD spectra. All the compounds were tested for acetylcholinesterase (AChE) inhibitory activity by Ellman's colorimetric method, and compounds 9-11 displayed weak AChE inhibitory activity with the inhibition ranging from 15.6% to 16.8% at a concentration of 50 μg mL^-1.

SUBMITTER: Kuang T

PROVIDER: S-EPMC9064565 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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UPLC-MS-guided isolation of single ether linkage dimeric 2-(2-phenylethyl)chromones from <i>Aquilaria sinensis</i>.

Kuang Tongdong T Chen Hui-Qin HQ Wang Hao H Kong Fan-Dong FD Cai Cai-Hong CH Dong Wen-Hua WH Yuan Jing-Zhe JZ Mei Wen-Li WL Dai Hao-Fu HF

RSC advances 20190531 30

Eleven novel uncommon single ether linkage dimeric 2-(2-phenylethyl)chromones (aquilasinenones A-K) were isolated by a UPLC-MS guided method from artificial hole-induced agarwood originating from <i>Aquilaria sinensis</i>. Their structures were unambiguously deduced using HRESIMS data, detailed 1D and 2D NMR spectroscopic analysis, and experimental ECD spectra. All the compounds were tested for acetylcholinesterase (AChE) inhibitory activity by Ellman's colorimetric method, and compounds 9-11 di ...[more]

PMID: 35519867

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Project description:BackgroundAgarwood, is a resinous portion derived from Aquilaria sinensis, has been widely used in traditional medicine and incense. 2-(2-phenylethyl)chromones are principal components responsible for the quality of agarwood. However, the molecular basis of 2-(2-phenylethyl)chromones biosynthesis and regulation remains almost unknown. Our research indicated that salt stress induced production of several of 2-(2-phenylethyl)chromones in A. sinensis calli. Transcriptome analysis of A. sinensis calli treated with NaCl is required to further facilitate the multiple signal pathways in response to salt stress and to understand the mechanism of 2-(2-phenylethyl)chromones biosynthesis.ResultsForty one 2-(2-phenylethyl)chromones were identified from NaCl-treated A. sinensis calli. 93 041 unigenes with an average length of 1562 nt were generated from the control and salt-treated calli by Illmunina sequencing after assembly, and the unigenes were annotated by comparing with the public databases including NR, Swiss-Prot, KEGG, COG, and GO database. In total, 18 069 differentially expressed transcripts were identified by the transcriptome comparisons on the control calli and calli induced by 24 h or 120 h salinity stress. Numerous genes involved in signal transduction pathways including the genes responsible for hormone signal transduction, receptor-like kinases, MAPK cascades, Ca(2+) signal transduction, and transcription factors showed clear differences between the control calli and NaCl-treated calli. Furthermore, our data suggested that the genes annotated as chalcone synthases and O-methyltransferases may contribute to the biosynthesis of 2-(2-phenylethyl)chromones.ConclusionsSalinity stress could induce the production of 41 2-(2-phenylethyl)chromones in A. sinensis calli. We conducted the first deep-sequencing transcriptome profiling of A. sinensis under salt stress and observed a large number of differentially expressed genes in response to salinity stress. Moreover, salt stress induced dynamic changes in transcript abundance for novel classes of responsive genes involved in signal transduction, including the genes responsible for hormone signal transduction, receptor-like kinases, MAPK cascades, Ca(2+) signal transduction, and transcription factors. This study will aid in selecting the target genes to genetically regulate A. sinensis salt-stress signal transduction and elucidating the biosynthesis of 2-(2-phenylethyl)chromones under salinity stress.

Dataset Information

UPLC-MS-guided isolation of single ether linkage dimeric 2-(2-phenylethyl)chromones from Aquilaria sinensis.

Publications

UPLC-MS-guided isolation of single ether linkage dimeric 2-(2-phenylethyl)chromones from <i>Aquilaria sinensis</i>.

Similar Datasets

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