UPLC-Q-TOF-MS and NMR identification of structurally different A-type procyanidins from peanut skin and their inhibitory effect on acrylamide.

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Tytuł:: UPLC-Q-TOF-MS and NMR identification of structurally different A-type procyanidins from peanut skin and their inhibitory effect on acrylamide.
Autorzy:: Zhao L; College of Food Science and Technology, Huazhong Agricultural University, Wuhan, China.
Yan F; College of Food Science and Technology, Huazhong Agricultural University, Wuhan, China.
Lu Q; College of Food Science and Technology, Huazhong Agricultural University, Wuhan, China.; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, Wuhan, China.; Wuhan Engineering Research Center of Bee Products on Quality and Safety Control, Wuhan, China.
Tang C; College of Food Science and Technology, Huazhong Agricultural University, Wuhan, China.; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, Wuhan, China.
Wang X; College of Food Science and Technology, Huazhong Agricultural University, Wuhan, China.; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, Wuhan, China.
Liu R; College of Food Science and Technology, Huazhong Agricultural University, Wuhan, China.; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, Wuhan, China.; Wuhan Engineering Research Center of Bee Products on Quality and Safety Control, Wuhan, China.
Źródło:: Journal of the science of food and agriculture [J Sci Food Agric] 2022 Dec; Vol. 102 (15), pp. 7062-7071. Date of Electronic Publication: 2022 Jul 02.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Publication: <2005-> : Chichester, West Sussex : John Wiley & Sons
Original Publication: London, Society of Chemical Industry.
MeSH Terms:: Proanthocyanidins*/chemistry
Catechin*/chemistry
Humans ; Arachis/chemistry ; Polyphenols ; Acrylamide
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Contributed Indexing:: Keywords: acrylamide; identification; inhibition; procyanidins; structure
Substance Nomenclature:: 4852-22-6 (procyanidin)
0 (Proanthocyanidins)
8R1V1STN48 (Catechin)
0 (Polyphenols)
20R035KLCI (Acrylamide)
Entry Date(s):: Date Created: 20220612 Date Completed: 20221103 Latest Revision: 20221103
Update Code:: 20240105
DOI:: 10.1002/jsfa.12067
PMID:: 35690888
: Czasopismo naukowe

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Background: Flavan-3-ol polyphenols have been shown to have great advantages in inhibiting acrylamide formation. However, flavan-3-ol polyphenols have structures that vary significantly, and existing research has been focused mainly on the effects of B-type procyanidins and structural units of procyanidins. This study aims to separate structurally different A-type procyanidins from peanut skin and compare their inhibitory effects on acrylamide in an asparagine-glucose simulation system.
Results: Five compounds were separated and identified from peanut skin, including epicatechin-(2β → O → 7, 4β → 8)-ent-epicatechin, epicatechin-(2β → O → 7, 4β → 8)-epicatechin, epicatechin-(2β → O → 7, 4β → 8)-epicatechin-(4β → 6)-catechin, epicatechin-(2β → O → 7, 4β → 8)-epicatechin-(4β → 8)-catechin, and epicatechin-(4β → 6)-epicatechin-(4β → 8, 2β → O → 7)-catechin. All the procyanidins could reduce the acrylamide content within a certain range of concentrations. The highest inhibition rates followed the order of compound 5 (A-type trimer) > compound 1 (A-type dimer) > compound 2 (A-type dimer) > compound 3 (A-type trimer) > compound 4 (A-type trimer). Comparison analysis showed that structurally different A-type procyanidins have various inhibitory effects on acrylamide production, which may be related to their spatial configuration and bond connection mode.
Conclusion: Overall, our findings help us to gain a better understanding of the relationship between the structure of procyanidins and their inhibitory effects on acrylamide, particularly the inhibitory effect of A-type. There are potential practical implications if people use A-type procyanidins as acrylamide inhibitors in hot processed foods in the future. © 2022 Society of Chemical Industry.
(© 2022 Society of Chemical Industry.)

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