Cyclooxygenase Inhibitory and Antioxidant Compounds from Crabapple Fruits
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- 作者：Navindra P. Seeram ; Robert H. Cichewicz ; Amitabh Chandra ; and Muraleedharan G. Nair
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2003
- 出版时间：March 26, 2003
- 年：2003
- 卷：51
- 期：7
- 页码：1948 - 1951
- 全文大小：73K
- 年卷期：v.51,no.7(March 26, 2003)
- ISSN：1520-5118
文摘
Crabapple trees belong to the Malus genus (Rosaceae) and bear fruits that are sparingly consumedand used in the preparation of fruit beverages. Cyclooxygenase (COX) enzyme inhibitory andantioxidant bioassay-guided fractionation of the aqueous and methanol extracts of Malus × kornicensisand Malus × Indian Summer yielded (+)-catechin (1), (-)-epicatechin (2), cyanidin-3-O-
-galactopyranoside (3), and amygdalin (4). Pure compounds 1-4 were obtained by HPLC, identified by LC-ES/MS, CD, and NMR spectroscopic methods and evaluated for their COX enzyme inhibitory andantioxidant activities. In COX-1 and -2 enzyme inhibitory assays, compounds 1-3 (all at 80 
M)showed activities of 20.4, 46.3%; 57.6, 47.9%; and 8.2, 13.7%, respectively, compared to naproxen(54.3, 41.3%; 10 M), ibuprofen (47.5, 39.8%; 10 M), Celebrex (46.2, 66.3%; 1.67 ppm), and Vioxx(23.8, 88.1%, 1.67 ppm). In the antioxidant assay, the catechins (1-2) and anthocyanin (3) (all at 40M) showed activities of 61.3, 62.5, and 60.1%, respectively. The synthetic antioxidants, tert-butylhydroquinone (TBHQ), butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), andvitamin E (all tested at 10 M), gave 75.2, 80.1, 70.0, and 10.2% activities, respectively. Thecyanogenic glycoside, amygdalin (4), and its hydrolysis products, mandelonitrile (5) and benzaldehyde(6), were not active in the antioxidant or COX enzyme inhibitory assays at 80 M concentrations.Keywords: Malus; Rosaceae; crabapple; catechin; anthocyanin; cyanogenic; antioxidant; cyclooxygenase
-galactopyranoside (3), and amygdalin (4). Pure compounds 1-4 were obtained by HPLC, identified by LC-ES/MS, CD, and NMR spectroscopic methods and evaluated for their COX enzyme inhibitory andantioxidant activities. In COX-1 and -2 enzyme inhibitory assays, compounds 1-3 (all at 80 M)showed activities of 20.4, 46.3%; 57.6, 47.9%; and 8.2, 13.7%, respectively, compared to naproxen(54.3, 41.3%; 10 M), ibuprofen (47.5, 39.8%; 10 M), Celebrex (46.2, 66.3%; 1.67 ppm), and Vioxx(23.8, 88.1%, 1.67 ppm). In the antioxidant assay, the catechins (1-2) and anthocyanin (3) (all at 40M) showed activities of 61.3, 62.5, and 60.1%, respectively. The synthetic antioxidants, tert-butylhydroquinone (TBHQ), butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), andvitamin E (all tested at 10 M), gave 75.2, 80.1, 70.0, and 10.2% activities, respectively. Thecyanogenic glycoside, amygdalin (4), and its hydrolysis products, mandelonitrile (5) and benzaldehyde(6), were not active in the antioxidant or COX enzyme inhibitory assays at 80 M concentrations.Keywords: Malus; Rosaceae; crabapple; catechin; anthocyanin; cyanogenic; antioxidant; cyclooxygenase