Ferulic acid dehydrodimers from wheat bran: isolation, purification and antioxidant properties of 8-O-4-diferulic acid

被引:78
作者
Garcia-Conesa, MT
Plumb, GW
Waldron, KW
Ralph, J
Williamson, G
机构
[1] Inst Food Res, Dept Biochem, Norwich NR4 7UA, Norfolk, England
[2] Agr Res Serv, US Dairy Forage Res Ctr, USDA, Madison, WI USA
关键词
D O I
10.1080/13510002.1997.11747129
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
Wheat bran contains several ester-linked dehydrodimers of ferulic acid, which were detected and quantified after sequential alkaline hydrolysis. The major dime rs released were: trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid (5-8-BendiFA), (Z)-beta-{4-[(E)-2-carboxyvinyl]-2-methoxy-phenoxy}-4-hydroxy-3-methoxycinnamic acid (8-O-4-diFA) and (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid (5-5-diFA). trans-7-hydroxy-1-(4-hydroxy-3methoxyphenyl)-6-melhoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid (8-8-diFA cyclic form) and 4,4'-dihydroxy-3,3'-dimethoxy-beta,beta'-bicinnamic acid (8-8-diFA non cyclic form) were not detected. One of the most abundant dimers, 8-O-4-diFA, was purified from de-starched wheat bran after alkaline hydrolysis and preparative HPLC. The resultant product was identical to the chemically synthesised 8-O-4-dimer by TLC and HPLC as confirmed by H-1-NMR and mass spectrometry. The absorption maxima and absorption coefficients for the synthetic compound in ethanol were: lambda(max): 323 nm, lambda(min): 258 nm, epsilon(lambda min) (M(-1)cm(-1)): 24800 +/- 2100 and epsilon(280) (M(-1)cm(-1)): 19700 +/- 1100. The antioxidant properties of 8-O-4-diFA were assessed using: (a) inhibition of ascorbate/iron-induced peroxidation of phosphatidylcholine liposomes and; (b) scavenging of the radical cation of 2,2'-azinobis (3-ethyl-benzothiazoline-6-sulphonate) (ABTS) relative to the water-soluble vitamin E analogue, Trolox C. The 8-O-4-diFA was a better antioxidant than ferulic acid in both lipid and aqueous phases. This is the first report of the antioxidant activity of a natural diferulate obtained from a plant.
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页码:319 / 323
页数:5
相关论文
共 28 条
[1]  
ARUOMA OI, 1993, CHEM BRIT, V29, P210
[2]   Differential distribution of ferulic acid to the major plasma constituents in relation to its potential as an antioxidant [J].
Castelluccio, C ;
Bolwell, GP ;
Gerrish, C ;
RiceEvans, C .
BIOCHEMICAL JOURNAL, 1996, 316 :691-694
[3]  
FRY SC, 1986, ANNU REV PLANT PHYS, V37, P165, DOI 10.1146/annurev.arplant.37.1.165
[4]   Antioxidant properties of ferulic acid dimers [J].
GarciaConesa, MT ;
Plumb, GW ;
Kroon, PA ;
Wallace, G ;
Williamson, G .
REDOX REPORT, 1997, 3 (04) :239-244
[5]   ANTIOXIDANT POTENTIAL OF FERULIC ACID [J].
GRAF, E .
FREE RADICAL BIOLOGY AND MEDICINE, 1992, 13 (04) :435-448
[6]   LIGNIN-CARBOHYDRATE LINKAGES IN PLANT-CELL WALLS .4. DIFERULIC ACID AS A COMPONENT OF CELL-WALLS OF LOLIUM-MULTIFLORUM [J].
HARTLEY, RD ;
JONES, EC .
PHYTOCHEMISTRY, 1976, 15 (07) :1157-1160
[7]   ISOLATION AND CHARACTERIZATION OF A DIFERULOYL ARABINOXYLAN HEXASACCHARIDE FROM BAMBOO SHOOT CELL-WALLS [J].
ISHII, T .
CARBOHYDRATE RESEARCH, 1991, 219 :15-22
[8]   DIFERULIC ACID AS A POSSIBLE CROSSLINK IN HEMICELLULOSES FROM WHEAT-GERM [J].
MARKWALDER, HU ;
NEUKOM, H .
PHYTOCHEMISTRY, 1976, 15 (05) :836-837
[9]   Dehydrodiferulic acids from sugar-beet pulp [J].
Micard, V ;
Grabber, JH ;
Ralph, J ;
Renard, CMGC ;
Thibault, JF .
PHYTOCHEMISTRY, 1997, 44 (07) :1365-1368
[10]   Oxidative cross-linking of corn bran hemicellulose: Formation of ferulic acid dehydrodimers [J].
Ng, A ;
Greenshields, RN ;
Waldron, KW .
CARBOHYDRATE RESEARCH, 1997, 303 (04) :459-462