A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity

被引：21
作者：
Bernini, Roberta [1 ]
Gualandi, Giampiero [1 ]
Crestini, Claudia [2 ]
Barontini, Maurizio [1 ]
Belfiore, Maria Cristina [1 ]
Willfor, Stefan [3 ]
Eklund, Patrik [3 ]
Saladino, Raffaele [1 ]
机构：
[1] Univ Tuscia, Dipartimento Agrobiol & Agrochim, I-01100 Viterbo, Italy
[2] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy
[3] Abo Akad Univ, Abo Akad Proc Chem Ctr, FI-20500 Turku, Finland
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 15期
基金：
芬兰科学院;
关键词：
Lignans; Oxidation; Methyltrioxorhenium; Antioxidant activity; Apoptogenic activity; HYDROGEN-PEROXIDE; (H2O2)/METHYLTRIOXORHENIUM CH3REO3; SELECTIVE OXIDATION; (MTO)/H2O2 SYSTEMS; ANTIVIRAL ACTIVITY; BENZYLIC OXYGEN; DIMETHYLDIOXIRANE; DERIVATIVES; LIGNIN; HYDROXYMATAIRESINOL;
D O I：
10.1016/j.bmc.2009.06.010
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Highly oxidized lignans produced during the cytochrome P-450 metabolism in the cells show biological activities significantly different from those of their parent natural compounds. Lignans precursors of mammalian enterolignans were treated with a methyltrioxorhenium/hydrogen peroxide catalytic system to afford new compounds oxidized at benzylic as well as in arylic positions. The evaluation of the antioxidant and apoptogenic activity by in vivo protocols of these compounds showed some interesting structure-activity relationships related to the oxidation degree of the molecules. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5676 / 5682
页数：7
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