Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro

被引:325
作者
Miranda, CL
Stevens, JF
Ivanov, V
McCall, M
Frei, B
Deinzer, ML
Buhler, DR [1 ]
机构
[1] Oregon State Univ, Dept Environm & Mol Toxicol, Corvallis, OR 97331 USA
[2] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA
[3] Oregon State Univ, Linus Pauling Inst, Corvallis, OR 97331 USA
[4] Oregon State Univ, Dept Biochem & Biophys, Corvallis, OR 97331 USA
关键词
antioxidants; flavonoids; prenylated chalcones; prenylated flavanones; low-density lipoprotein;
D O I
10.1021/jf0002995
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Prenylated flavonoids found in hops and beer, i.e., prenylchalcones and prenylflavanones, were examined for their ability to inhibit in vitro oxidation of human low-density lipoprotein (LDL). The oxidation of LDL was assessed by the formation of conjugated dienes and thiobarbituric acid-reactive substances (TBARS) and the loss of tryptophan fluorescence. At concentrations of 5 and 25 mu M, all of the prenylchalcones tested inhibited the oxidation of LDL (50 mu g protein/ml) induced by 2 mu M copper sulfate. The prenylflavanones showed less antioxidant activity than the prenylchalcones, both at 5 and 25 mu M. At 25 mu M, the nonprenylated chalcone, chalconaringenin (CN), and the nonprenylated flavanone, naringenin (NG), exerted prooxidant effects on LDL oxidation, based on TEARS formation. Xanthohumol (XN), the major prenylchalcone in hops and beer, showed high antioxidant activity in inhibiting LDL oxidation, higher than alpha-tocopherol and the isoflavone genistein but lower than the flavonol quercetin. When combined, XN and alpha-tocopherol completely inhibited copper-mediated LDL oxidation. These findings suggest that prenylchalcones and prenylflavanones found in hops and beer protect human LDL from oxidation and that prenylation antagonizes the prooxidant effects of the chalcone, CN, and the flavanone, NG.
引用
收藏
页码:3876 / 3884
页数:9
相关论文
共 47 条
  • [1] CHELATING AND FREE-RADICAL SCAVENGING MECHANISMS OF INHIBITORY-ACTION OF RUTIN AND QUERCETIN IN LIPID-PEROXIDATION
    AFANASEV, IB
    DOROZHKO, AI
    BRODSKII, AV
    KOSTYUK, VA
    POTAPOVITCH, AI
    [J]. BIOCHEMICAL PHARMACOLOGY, 1989, 38 (11) : 1763 - 1769
  • [2] ANTICANCER AND ANTIOXIDANT ACTIVITY OF SYNTHETIC CHALCONES AND RELATED-COMPOUNDS
    ANTO, RJ
    SUKUMARAN, K
    KUTTAN, G
    RAO, MNA
    SUBBARAJU, V
    KUTTAN, R
    [J]. CANCER LETTERS, 1995, 97 (01) : 33 - 37
  • [3] Antioxidant effects of flavonoids
    Bors, W
    Michel, C
    Stettmaier, K
    [J]. BIOFACTORS, 1997, 6 (04) : 399 - 402
  • [4] TOCOPHEROL-MEDIATED PEROXIDATION - THE PROOXIDANT EFFECT OF VITAMIN-E ON THE RADICAL-INITIATED OXIDATION OF HUMAN LOW-DENSITY-LIPOPROTEIN
    BOWRY, VW
    STOCKER, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6029 - 6044
  • [5] Brown JE, 1998, BIOCHEM J, V330, P1173
  • [6] Buege J A, 1978, Methods Enzymol, V52, P302
  • [7] Camejo G, 1998, Methods Mol Biol, V108, P377
  • [8] Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships
    Cao, GH
    Sofic, E
    Prior, RL
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 1997, 22 (05) : 749 - 760
  • [9] Oxygen activation during peroxidase catalysed metabolism of flavones or flavanones
    Chan, T
    Galati, G
    O'Brien, PJ
    [J]. CHEMICO-BIOLOGICAL INTERACTIONS, 1999, 122 (01) : 15 - 25
  • [10] Antioxidant properties of butein isolated from Dalbergia odorifera
    Cheng, ZJ
    Kuo, SC
    Chan, SC
    Ko, FN
    Teng, CM
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-LIPIDS AND LIPID METABOLISM, 1998, 1392 (2-3): : 291 - 299