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Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones

Agarwood is highly valued for its uses as incense, perfume, and medicine. However, systematic analyses of dynamic changes of secondary metabolites during the process of agarwood formation have not yet been reported. In this study, agarwood was produced by transfusing the agarwood inducer into the tr...

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Autores principales: Liao, Ge, Dong, Wen-Hua, Yang, Jin-Ling, Li, Wei, Wang, Jun, Mei, Wen-Li, Dai, Hao-Fu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100365/
https://www.ncbi.nlm.nih.gov/pubmed/29799457
http://dx.doi.org/10.3390/molecules23061261
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author Liao, Ge
Dong, Wen-Hua
Yang, Jin-Ling
Li, Wei
Wang, Jun
Mei, Wen-Li
Dai, Hao-Fu
author_facet Liao, Ge
Dong, Wen-Hua
Yang, Jin-Ling
Li, Wei
Wang, Jun
Mei, Wen-Li
Dai, Hao-Fu
author_sort Liao, Ge
collection PubMed
description Agarwood is highly valued for its uses as incense, perfume, and medicine. However, systematic analyses of dynamic changes of secondary metabolites during the process of agarwood formation have not yet been reported. In this study, agarwood was produced by transfusing the agarwood inducer into the trunk of Aquilaria sinensis, and changing patterns of chemical constituents, especially 2-(2-phenylethyl)chromones (PECs), in wood samples collected from the 1st to 12th month, were analyzed by GC-EI-MS and UPLC-ESI-MS/MS methods. Aromatic compounds, steroids, fatty acids/esters, sesquiterpenoids, and PECs were detected by GC-MS, in which PECs were the major constituents. Following this, UPLC-MS was used for further comprehensive analysis of PECs, from which we found that 2-(2-phenylethyl)chromones of flindersia type (FTPECs) were the most abundant, while PECs with epoxidated chromone moiety were detected with limited numbers and relatively low content. Speculation on the formation of major FTPECs was fully elucidated in our context. The key step of FTPECs biosynthesis is possibly catalyzed by type III polyketide synthases (PKSs) which condensate dihydro-cinnamoyl-CoA analogues and malonyl-CoA with 2-hydroxy-benzoyl-CoA to produce 2-(2-phenyethyl)chromone scaffold, or with 2,5-dihydroxybenzoyl-CoA to form FTPECS with 6-hydroxy group, which may serve as precursors for further reactions catalyzed by hydroxylase or O-methyltransferase (OMT) to produce FTPECs with diverse substitution patterns. It is the first report that systematically analyzed dynamic changes of secondary metabolites during the process of agarwood formation and fully discussed the biosynthetic pathway of PECs.
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spelling pubmed-61003652018-11-13 Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones Liao, Ge Dong, Wen-Hua Yang, Jin-Ling Li, Wei Wang, Jun Mei, Wen-Li Dai, Hao-Fu Molecules Communication Agarwood is highly valued for its uses as incense, perfume, and medicine. However, systematic analyses of dynamic changes of secondary metabolites during the process of agarwood formation have not yet been reported. In this study, agarwood was produced by transfusing the agarwood inducer into the trunk of Aquilaria sinensis, and changing patterns of chemical constituents, especially 2-(2-phenylethyl)chromones (PECs), in wood samples collected from the 1st to 12th month, were analyzed by GC-EI-MS and UPLC-ESI-MS/MS methods. Aromatic compounds, steroids, fatty acids/esters, sesquiterpenoids, and PECs were detected by GC-MS, in which PECs were the major constituents. Following this, UPLC-MS was used for further comprehensive analysis of PECs, from which we found that 2-(2-phenylethyl)chromones of flindersia type (FTPECs) were the most abundant, while PECs with epoxidated chromone moiety were detected with limited numbers and relatively low content. Speculation on the formation of major FTPECs was fully elucidated in our context. The key step of FTPECs biosynthesis is possibly catalyzed by type III polyketide synthases (PKSs) which condensate dihydro-cinnamoyl-CoA analogues and malonyl-CoA with 2-hydroxy-benzoyl-CoA to produce 2-(2-phenyethyl)chromone scaffold, or with 2,5-dihydroxybenzoyl-CoA to form FTPECS with 6-hydroxy group, which may serve as precursors for further reactions catalyzed by hydroxylase or O-methyltransferase (OMT) to produce FTPECs with diverse substitution patterns. It is the first report that systematically analyzed dynamic changes of secondary metabolites during the process of agarwood formation and fully discussed the biosynthetic pathway of PECs. MDPI 2018-05-25 /pmc/articles/PMC6100365/ /pubmed/29799457 http://dx.doi.org/10.3390/molecules23061261 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Liao, Ge
Dong, Wen-Hua
Yang, Jin-Ling
Li, Wei
Wang, Jun
Mei, Wen-Li
Dai, Hao-Fu
Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones
title Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones
title_full Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones
title_fullStr Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones
title_full_unstemmed Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones
title_short Monitoring the Chemical Profile in Agarwood Formation within One Year and Speculating on the Biosynthesis of 2-(2-Phenylethyl)Chromones
title_sort monitoring the chemical profile in agarwood formation within one year and speculating on the biosynthesis of 2-(2-phenylethyl)chromones
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100365/
https://www.ncbi.nlm.nih.gov/pubmed/29799457
http://dx.doi.org/10.3390/molecules23061261
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