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Radical-scavenging Activity and Mechanism of Resveratrol-oriented Analogues

Author: LiuXiaoDa
Tutor: ZhouBo
School: Lanzhou University
Course: Organic Chemistry
Keywords: Resveratrol Free radical scavenging activity Mechanism Reaction kinetics
CLC: R285
Type: Master's thesis
Year: 2009
Downloads: 88
Quote: 0
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Abstract


Resveratrol ( Resveratrol , 3,5,4 ' - trihydroxy - trans - stilbene ) as a phytoalexin widely present in grapes , peanuts and bilberry plants with antioxidant activity , including a variety of biological activity. We synthesized 9 resveratrol and its analogs : 3,5 - dihydroxy - trans - stilbene ( 3,5 - DHS) , 4 - hydroxy - trans - stilbene (4 -HS ) , 3 , 4 - dihydroxy - trans - stilbene (3,4-DHS), 4,4 '- dihydroxy - trans - stilbene ( 4,4 ??'- DHS) , 3 - methoxy -4 - hydroxy - trans - stilbene ( 3 -MeO - 4 -HS ) , 4 - hydroxy- 4'- methoxy - anti - stilbene ( 4' -MeO - 4 -HS ) , 4 - hydroxy-4'- methyl - trans - stilbene ( 4'- Me - 4- HS ) , 4 - hydroxy -4'-nitro - anti - stilbene ( 4'- NO 2 -4 - HS) and 4 - hydroxy-4' -trifluoromethyl - trans - stilbene ( 4'- CF 3 - 4- HS ) , studied their clear galvinoxyl radical in ethanol ( kinetics of GO · ) 's . By UV - visible spectrometer monitoring GO · decay kinetics , indicating four hydroxyl o on position push e - groups to help improve they cleared GO · activity , wherein having a the ortho dihydroxy structure of 3,4 - DHS highest activity . By studying the influence of acetic acid on the reaction rate was confirmed Kinetics of the first loss of the electron transfer mechanism (SPLET) by proton and hydrogen atom transfer mechanism , the mechanism (HAT) control . Moreover, they GO · in the oxidation product in ethanol is separated identification, dihydrofuran and dioxane structure dimer confirmed that resveratrol four hydroxyl groups are active site, whereas in the 3,4-DHS , dioxane structure dimer formation experienced o-quinone intermediates . The results of our study resveratrol the antioxidant drug molecules provide important information for designing based .

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