Journal
CHINESE SCIENCE BULLETIN
Volume 55, Issue 25, Pages 2885-2890Publisher
SCIENCE PRESS
DOI: 10.1007/s11434-010-3064-0
Keywords
hydroxycinnamic acid derivatives; dehydrodimers; trimers; silver oxide; antioxidant; 2,2-diphenyl-1-picrylhydrazyl radical; structure-activity relationship
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Funding
- National Natural Science Foundation of China [20972063, 20621091]
- 111 Project
- Program for New Century Excellent Talents in University [NCET-06-0906]
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4-Hydroxycinnamic acid derivatives, including ferulic acid (FA) (1), sinapic acid (SA) (2) and caffeic acid (CA) (3), are widely distributed in the plant kingdom, and undergo oxidative cross-coupling leading to the corresponding dehydrodimers, trimers and even higher oligomers in plants. In order to evaluate the antioxidative ability of these 4-hydroxycinnamic acid derivatives and their oligomers, we synthesized 8-8'-bis-lactone-dimers (8-8'-DiFA (4), 8-8'-DiSA (5) and 8-8'-DiCA (6)), as well as a new trimer (7), by the reaction of the corresponding monomers (1-3) with Ag(2)O in methanol, and assayed their free radical-scavenging activity by the reaction with 2,2-diphenyl-1-picrylhydrazyl radical (DPPH center dot). It was found that CA (3) and 8-8'-DiCA (6) bearing o-dihydroxyl groups exhibited significantly higher radical-scavenging activity than those bearing no such groups, and oxidative coupling of CA (3) resulted in remarkable enhancement in the activity.
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