Natural polyphenols as direct trapping agents of lipid peroxidation-derived acrolein and 4-hydroxy-trans-2-nonenal.
Acrolein (ACR) and 4-hydroxy-trans-2-nonenal (HNE) are two cytotoxic lipid-derived alpha,beta-unsaturated aldehydes which have been implicated as causative agents in the development of carbonyl stress-associated pathologies. In this study, 21 natural polyphenols were screened to identify effective scavenging agents of ACR and/or HNE in simulated physiological conditions. It was found that flavan-3-ols, theaflavins, cyanomaclurin, and dihydrochalcones effectively trapped ACR and HNE by working as sacrificial nucleophiles. The most effective one was phloretin, which quenched up to 99.6% ACR in 90 min and 90.1% HNE in 24 h. Subsequent LC-MS/MS analysis showed that these effective polyphenols formed adducts with ACR and HNE. A major adduct formed from phloretin and ACR was purified, and its structure was characterized by LC-MS and NMR spectroscopy as diACR-conjugated phloretin. The chemical nature of interactions between ACR and polyphenols was proposed as the Michael addition reaction of phloretin to the C horizontal lineC double bond of ACR, followed by the formation of hemiacetal between the hydroxyl group in the A ring of phloretin and the C horizontal lineO carbonyl group in ACR, thus yielding more stable products. Findings of the present study highlighted certain classes of polyphenols as promising sequestering agents of alpha,beta-unsaturated aldehydes to inhibit or restrain carbonyl stress-associated diseases.
Zhu
Qin
Q
State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, PR China.
Zheng
Zong-Ping
ZP
Cheng
Ka-Wing
KW
Wu
Jia-Jun
JJ
Zhang
Shuo
S
Tang
Yun Sang
YS
Sze
Kong-Hung
KH
Chen
Jie
J
Chen
Feng
F
Wang
Mingfu
M
D000171:Acrolein / Q000737:chemistry* / Q000633:toxicity; D000447:Aldehydes / Q000737:chemistry* / Q000633:toxicity; D002853:Chromatography, Liquid; D003432:Cross-Linking Reagents / Q000737:chemistry* / Q000633:toxicity; D005419:Flavonoids / Q000737:chemistry*; D015227:Lipid Peroxidation; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry*; D010693:Phloretin / Q000737:chemistry; D059808:Polyphenols; D053719:Tandem Mass Spectrometry
D000447:Aldehydes; D003432:Cross-Linking Reagents; D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols; D000171:Acrolein; C027576:4-hydroxy-2-nonenal; D010693:Phloretin