Production of 3,4-cis- and 3,4-trans-Leucocyanidin and Their Distinct MS/MS Fragmentation Patterns
| dc.rights.license | open | en_US |
| dc.relation.isnodouble | 8b56323d-95cf-4a3d-b7e7-1578f0fcaafc | * |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | ZHANG, Jia-Rong | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | TOLCHARD, James | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | BATHANY, Katell | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | D'ESTAINTOT, Beatrice Langlois | |
| hal.structure.identifier | Chimie et Biologie des Membranes et des Nanoobjets [CBMN] | |
| dc.contributor.author | CHAUDIERE, Jean | |
| dc.date.accessioned | 2020-04-07T16:02:16Z | |
| dc.date.available | 2020-04-07T16:02:16Z | |
| dc.date.issued | 2018 | |
| dc.identifier.issn | 0021-8561 | en_US |
| dc.identifier.other | 10.1021/acs.jafc.7b04380 | en_US |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/4155 | |
| dc.description.abstractEn | (+)-2,3-trans-3,4-cis-Leucocyanidin was produced by acidic epimerization of (+)-2,3-trans-3,4-trans-leucocyanidin synthesized by reduction of (+)-dihydroquercetin with NaBH4, and structures of the two stereoisomers purified by C18- and phenyl-reverse-phase high-performance liquid chromatography (HPLC) were confirmed by NMR spectroscopy. We confirm that only 3,4-cis-leucocyanidin is used by leucoanthocyanidin reductase as substrate. The two stereoisomers are quite stable in aqueous solution at -20 degrees C. Characterization of the two stereoisomers was also performed using electrospray ionization tandem mass spectrometry (ESI-MS/MS), and we discuss here for the first time the corresponding MS/MS fragmentation pathways, which are clearly distinct. The main difference is that of the mode of dehydration of the 3,4-diol in positive ionization mode, which involves a loss of hydroxyl group at either C-3 or C-4 for the 3,4-cis isomer but only at C-3 for the 3,4-trans isomer. Tandem mass spectrometry therefore proves useful as a complementary methodology to NMR to identify each of the two stereoisomers. | |
| dc.language.iso | EN | en_US |
| dc.subject.en | Leucocyanidin | |
| dc.subject.en | NMR | |
| dc.subject.en | leucoanthocyanidin reductase | |
| dc.subject.en | reverse-phase HPLC | |
| dc.subject.en | tandem mass spectrometry | |
| dc.subject.en | fragmentation pathways | |
| dc.title.en | Production of 3,4-cis- and 3,4-trans-Leucocyanidin and Their Distinct MS/MS Fragmentation Patterns | |
| dc.title.alternative | J. Agric. Food Chem. | en_US |
| dc.type | Article de revue | en_US |
| dc.identifier.doi | 10.1021/acs.jafc.7b04380 | |
| dc.subject.hal | Chimie/Matériaux | en_US |
| bordeaux.journal | Journal of Agricultural and Food Chemistry | en_US |
| bordeaux.page | 351-358 | en_US |
| bordeaux.volume | 66 | en_US |
| bordeaux.hal.laboratories | Institut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248 | |
| bordeaux.issue | 1 | en_US |
| bordeaux.institution | Bordeaux INP | en_US |
| bordeaux.institution | Université de Bordeaux | en_US |
| bordeaux.peerReviewed | oui | en_US |
| bordeaux.inpress | non | en_US |
| hal.identifier | hal-03160315 | |
| hal.version | 1 | |
| hal.date.transferred | 2021-03-05T09:09:47Z | |
| hal.export | true | |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20Agricultural%20and%20Food%20Chemistry&rft.date=2018&rft.volume=66&rft.issue=1&rft.spage=351-358&rft.epage=351-358&rft.eissn=0021-8561&rft.issn=0021-8561&rft.au=ZHANG,%20Jia-Rong&TOLCHARD,%20James&BATHANY,%20Katell&D'ESTAINTOT,%20Beatrice%20Langlois&CHAUDIERE,%20Jean&rft.genre=article |
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