Abstract
Role of carotenoid end groups on their chainbreaking potency against lipid peroxidation was explored using density functional theory. Hydrogen abstraction and addition of the peroxide and O2 of the resultant radicals were investigated. The protective potency of CARs is exhibited by their faster reactions with the peroxide radical than fatty acid, and by the much reduced reactivity of the initiated radical toward O2. 3,3'-Dihydroxyisorenieratene (DHIR), which consists of hydroxyaryl (3-hydroxy-φ) end groups, is by far the most efficient chain-breaking antioxidant. The quinone form of DHIR is also an effective antioxidant. 4-Oxo functional group in β-ring enhances the antioxidative potency of carotenoids, while 3-hydroxyl functional group in β-ring does not have a noticeable effect.
| Original language | English |
|---|---|
| Pages (from-to) | 1-13 |
| Number of pages | 13 |
| Journal | Theoretical Chemistry Accounts |
| Volume | 132 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 2013 Mar 22 |
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All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
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A density functional theory study for the role of end groups on the antioxidative potency of carotenoids. / Liao, Fu Xing; Hu, Ching-Han.
In: Theoretical Chemistry Accounts, Vol. 132, No. 5, 22.03.2013, p. 1-13.Research output: Contribution to journal › Article
TY - JOUR
T1 - A density functional theory study for the role of end groups on the antioxidative potency of carotenoids
AU - Liao, Fu Xing
AU - Hu, Ching-Han
PY - 2013/3/22
Y1 - 2013/3/22
N2 - Role of carotenoid end groups on their chainbreaking potency against lipid peroxidation was explored using density functional theory. Hydrogen abstraction and addition of the peroxide and O2 of the resultant radicals were investigated. The protective potency of CARs is exhibited by their faster reactions with the peroxide radical than fatty acid, and by the much reduced reactivity of the initiated radical toward O2. 3,3'-Dihydroxyisorenieratene (DHIR), which consists of hydroxyaryl (3-hydroxy-φ) end groups, is by far the most efficient chain-breaking antioxidant. The quinone form of DHIR is also an effective antioxidant. 4-Oxo functional group in β-ring enhances the antioxidative potency of carotenoids, while 3-hydroxyl functional group in β-ring does not have a noticeable effect.
AB - Role of carotenoid end groups on their chainbreaking potency against lipid peroxidation was explored using density functional theory. Hydrogen abstraction and addition of the peroxide and O2 of the resultant radicals were investigated. The protective potency of CARs is exhibited by their faster reactions with the peroxide radical than fatty acid, and by the much reduced reactivity of the initiated radical toward O2. 3,3'-Dihydroxyisorenieratene (DHIR), which consists of hydroxyaryl (3-hydroxy-φ) end groups, is by far the most efficient chain-breaking antioxidant. The quinone form of DHIR is also an effective antioxidant. 4-Oxo functional group in β-ring enhances the antioxidative potency of carotenoids, while 3-hydroxyl functional group in β-ring does not have a noticeable effect.
UR - http://www.scopus.com/inward/record.url?scp=84875058481&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84875058481&partnerID=8YFLogxK
U2 - 10.1007/s00214-013-1357-5
DO - 10.1007/s00214-013-1357-5
M3 - Article
AN - SCOPUS:84875058481
VL - 132
SP - 1
EP - 13
JO - Theoretical Chemistry Accounts
JF - Theoretical Chemistry Accounts
SN - 1432-881X
IS - 5
ER -