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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 6
BKCSDE 29(6)
June 20, 2008

Title	Synthesis of Dihydroxylated Chalcone Derivatives with Diverse Substitution Patterns and Their Radical Scavenging Ability toward DPPH Free Radicals
Author	Beom-Tae Kim, Kwang-Joong O, Jae-Chul Chun, Ki-Jun Hwang*
Keywords	Chalcones, Antioxidant, DPPH free radical, Structure-activity relationship, Semiquinone radical
Abstract	A series of dihydroxylated chalcone derivatives with diverse substitution patterns on a phenyl ring B and the para-substituents on a phenyl ring A were prepared, and their radical scavenging activities were evaluated by simple DPPH test to determine quantitative structure-activity relationship in these series of compounds. The chalcone compounds with the ortho- (i.e. 2',3'- and 3',4'-) and para- (i.e. 2,5'-) substitution patterns show an excellent antioxidant activities (80-90% of control at the concentration of 50 μM) which are comparable to those of ascorbic acid and α-tocopherol as positive reference materials. On the contrary, the compounds with meta- (i.e. 2',4'-, 3',5'-) substitution pattern demonstrate very dramatic decrease in activities which are around 25% of the control even at the concentration of 200 μ M (IC50 > 200 μ M). These dramatic differences could be interpreted in terms of the ease formation of fairly stable semiquinone radicals from the ortho- and para-substituted chalcone molecules through facilitating electron delocalization. Our results indicate that the substitution patterns of two hydroxyl groups on ring B are very important structural factors for their radical scavenging activity enhancement. Meanwhile, the substituents at para-position of the phenyl ring A of chalcones have no influence on the activity.
Page	1125 - 1130
Full Text	PDF

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