Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics

C-prenyl coumarins (C-PYCs) are compounds with similar structures and various bioactivities, which are widely distributed in medicinal plants. Until now, the metabolic characterizations of C-PYCs and the relationship between metabolism and bioactivities remain unclear. In this study, ultra-performan...

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Autores principales:	Yan Cheng, Xiaofang Ma, Qi Zhao, Chunyan Wang, Dongmei Yan, Fei Li
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	C-prenyl coumarins metabolomics anti-inflammatory activity UPLC-ESI-QTOF-MS Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/b1bb1e0a10f041fcbe4d06b9d174b27c
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spelling	oai:doaj.org-article:b1bb1e0a10f041fcbe4d06b9d174b27c2021-11-11T18:32:34ZMetabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics10.3390/molecules262165581420-3049https://doaj.org/article/b1bb1e0a10f041fcbe4d06b9d174b27c2021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6558https://doaj.org/toc/1420-3049C-prenyl coumarins (C-PYCs) are compounds with similar structures and various bioactivities, which are widely distributed in medicinal plants. Until now, the metabolic characterizations of C-PYCs and the relationship between metabolism and bioactivities remain unclear. In this study, ultra-performance chromatography electrospray ionization quadrupole time-of-flight mass spectrometry-based metabolomics (UPLC-ESI-QTOF-MS) was firstly used to determine the metabolic characterizations of three C-PYCs, including meranzin hydrate (MH), isomeranzin (ISM), and meranzin (MER). In total, 52 metabolites were identified, and all of them were found to be novel metabolites. Among these metabolites, 10 were from MH, 22 were from ISM, and 20 were from MER. The major metabolic pathways of these C-PYCs were hydroxylation, dehydrogenation, demethylation, and conjugation with cysteine, <i>N</i>-acetylcysteine, and glucuronide. The metabolic rate of MH was much lower than ISM and MER, which was only 27.1% in MLM and 8.7% in HLM, respectively. Additionally, recombinant cytochrome P450 (CYP) screening showed that CYP1A1, 2B6, 3A4, and 3A5 were the major metabolic enzymes involved in the formation of metabolites. Further bioactivity assays indicated that all of these three C-PYCs exhibited anti-inflammatory activity, but the effects of ISM and MER were slightly higher than MH, accompanied by a significant decrease in inflammatory cytokines transcription induced by lipopolysaccharide (LPS) in macrophages RAW 264.7. Taken together, the metabolic characterizations of the three C-PYCs suggested that the side chain of the prenyl group may impact the metabolism and biological activity of C-PYCs.Yan ChengXiaofang MaQi ZhaoChunyan WangDongmei YanFei LiMDPI AGarticleC-prenyl coumarinsmetabolomicsanti-inflammatory activityUPLC-ESI-QTOF-MSOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6558, p 6558 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	C-prenyl coumarins metabolomics anti-inflammatory activity UPLC-ESI-QTOF-MS Organic chemistry QD241-441
spellingShingle	C-prenyl coumarins metabolomics anti-inflammatory activity UPLC-ESI-QTOF-MS Organic chemistry QD241-441 Yan Cheng Xiaofang Ma Qi Zhao Chunyan Wang Dongmei Yan Fei Li Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
description	C-prenyl coumarins (C-PYCs) are compounds with similar structures and various bioactivities, which are widely distributed in medicinal plants. Until now, the metabolic characterizations of C-PYCs and the relationship between metabolism and bioactivities remain unclear. In this study, ultra-performance chromatography electrospray ionization quadrupole time-of-flight mass spectrometry-based metabolomics (UPLC-ESI-QTOF-MS) was firstly used to determine the metabolic characterizations of three C-PYCs, including meranzin hydrate (MH), isomeranzin (ISM), and meranzin (MER). In total, 52 metabolites were identified, and all of them were found to be novel metabolites. Among these metabolites, 10 were from MH, 22 were from ISM, and 20 were from MER. The major metabolic pathways of these C-PYCs were hydroxylation, dehydrogenation, demethylation, and conjugation with cysteine, <i>N</i>-acetylcysteine, and glucuronide. The metabolic rate of MH was much lower than ISM and MER, which was only 27.1% in MLM and 8.7% in HLM, respectively. Additionally, recombinant cytochrome P450 (CYP) screening showed that CYP1A1, 2B6, 3A4, and 3A5 were the major metabolic enzymes involved in the formation of metabolites. Further bioactivity assays indicated that all of these three C-PYCs exhibited anti-inflammatory activity, but the effects of ISM and MER were slightly higher than MH, accompanied by a significant decrease in inflammatory cytokines transcription induced by lipopolysaccharide (LPS) in macrophages RAW 264.7. Taken together, the metabolic characterizations of the three C-PYCs suggested that the side chain of the prenyl group may impact the metabolism and biological activity of C-PYCs.
format	article
author	Yan Cheng Xiaofang Ma Qi Zhao Chunyan Wang Dongmei Yan Fei Li
author_facet	Yan Cheng Xiaofang Ma Qi Zhao Chunyan Wang Dongmei Yan Fei Li
author_sort	Yan Cheng
title	Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
title_short	Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
title_full	Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
title_fullStr	Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
title_full_unstemmed	Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
title_sort	metabolic profile of c-prenyl coumarins using mass spectrometry-based metabolomics
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/b1bb1e0a10f041fcbe4d06b9d174b27c
work_keys_str_mv	AT yancheng metabolicprofileofcprenylcoumarinsusingmassspectrometrybasedmetabolomics AT xiaofangma metabolicprofileofcprenylcoumarinsusingmassspectrometrybasedmetabolomics AT qizhao metabolicprofileofcprenylcoumarinsusingmassspectrometrybasedmetabolomics AT chunyanwang metabolicprofileofcprenylcoumarinsusingmassspectrometrybasedmetabolomics AT dongmeiyan metabolicprofileofcprenylcoumarinsusingmassspectrometrybasedmetabolomics AT feili metabolicprofileofcprenylcoumarinsusingmassspectrometrybasedmetabolomics
_version_	1718431781293654016

Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics

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