Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals.
Cinnamoylphenethylamine (CNPA) derivatives including feruloylphenethylamine (FRPA), caffeoylphenethylamine (CFPA), cinnamoyltyramine (CNTA), feruloyltyramine (FRTA) and caffeoyltyramine (CFTA) were synthesized in order to investigate the influence of the number and position of hydroxyl group on Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. The radical-scavenging properties of these CNPA derivatives were also evaluated by trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonate) cationic radical (ABTS(+•)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) and galvinoxyl radical. In addition, these CNPA derivatives were tested by linoleic acid (LH)-β-carotene-bleaching experiment. The chemical kinetic was employed to treat the results from AAPH-induced oxidation of DNA and gave the order of antioxidant ability as CFTA > CFPA > FRTA > FRPA. CFTA and CFPA also possessed high abilities to inhibit Cu²(+)/GSH-mediated degradation of DNA, whereas FRPA and FRTA can protect LH against the auto-oxidation efficiently. Finally, CFPA and FRPA exhibited high activity in trapping ABTS(+•), DPPH and galvinoxyl radicals. Therefore, the cinnamoyl group bearing ortho-dihydroxyl or hydroxyl with ortho-methoxyl benefited for CNPA derivatives to protect DNA, while hydroxyl in tyramine cannot enhance the radical-scavenging abilities of CNPA derivatives.
Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, PR China.
Yang
Y
Yang
Zhi-Guang
ZG
Song
Zai-Qun
ZQ
Liu
D000578:Amidines / Q000378:metabolism; D000975:Antioxidants / Q000138:chemical synthesis / Q000378:metabolism*; D001559:Benzhydryl Compounds / Q000378:metabolism; D052160:Benzothiazoles / Q000378:metabolism; D001713:Biphenyl Compounds / Q000378:metabolism; D002934:Cinnamates / Q000138:chemical synthesis / Q000378:metabolism*; D003300:Copper / Q000737:chemistry / Q000378:metabolism; D004247:DNA / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000378:metabolism*; D005978:Glutathione / Q000378:metabolism; D006878:Hydroxides / Q000378:metabolism; D019787:Linoleic Acid / Q000378:metabolism; D010084:Oxidation-Reduction / Q000187:drug effects; D010627:Phenethylamines / Q000138:chemical synthesis / Q000378:metabolism*; D010851:Picrates / Q000378:metabolism; D012996:Solutions / Q000737:chemistry / Q000378:metabolism; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000378:metabolism; D019207:beta Carotene / Q000378:metabolism
D000578:Amidines; D000975:Antioxidants; D001559:Benzhydryl Compounds; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002934:Cinnamates; D016166:Free Radical Scavengers; D006878:Hydroxides; D010627:Phenethylamines; D010851:Picrates; D012996:Solutions; D013451:Sulfonic Acids; D019207:beta Carotene; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C046728:2,2'-azobis(2-amidinopropane); D003300:Copper; D004247:DNA; C031356:hydroxide ion; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D005978:Glutathione; C020338:galvinoxyl