An ab initio computational study on selected lycopene isomers

被引:82
作者
Chasse, GA
Mak, ML
Deretey, E
Farkas, I
Torday, LL
Papp, JG
Sarma, DSR
Agarwal, A
Chakravarthi, S
Agarwal, S
Rao, AV
机构
[1] Velocet Commun Inc, Toronto, ON M5G 2E8, Canada
[2] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
[3] Univ Szeged, Albert Szent Gyorgyi Med & Pharmaceut Ctr, Dept Pharmacol & Pharmacotherapy, H-6701 Szeged, Hungary
[4] Univ Toronto, Lab Med & Pathobiol, Toronto, ON M5S 1A8, Canada
[5] Univ Toronto, Dept Nutr Sci, Toronto, ON M5S 3E2, Canada
来源
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2001年 / 571卷
关键词
all trans-lycopene; selected cis-isomers of lycopene; thermodynamic stability of lycopene isomers; computations of lycopene isomers; ab initio MO theory;
D O I
10.1016/S0166-1280(01)00424-9
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Lycopene is an effective antioxidant in vivo. Although lycopene is present in its all-trans isomeric form in fruits and vegetables, serum and tissue samples show a predominance of various cis-isomers of lycopene. The present study was undertaken to investigate the molecular structure of several cis-isomers of lycopene using an ab initio molecular modeling procedure. The relative stability of selected cis-isomers of lycopene with respect to the all-trans isomer, was studied. The following sequence of stability was observed. 5-cis > all-trans > 9-cis > 13-cis > 15-cis > 7-cis > 11-cis The first four of these isomers had relative energies within +1 kcal mol(-1), but the fifth isomer (i.e. 15-cis) was within 3 kcal mol(-1). However, the last two isomers were less stable than the all-trans-isomer with more than 5 kcal mol(-1), difference in energy. The optimized molecular conformational study structures indicated that the central conjugated part of every lycopene isomer is planar. However, the two tail ends of the molecules, each containing three single C-C bonds, avoid coplanarity. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:27 / 37
页数:11
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