Direct antioxidant activity of purified glucoerucin, the dietary secondary metabolite contained in rocket (Eruca sativa Mill.) seeds and sprouts

被引:166
作者
Barillari, J
Canistro, D
Paolini, M
Ferroni, F
Pedulli, GF
Iori, R
Valgimigli, L
机构
[1] Ist Sperimentale Colture Ind, Consiglio Ric & Sperimentaz Agricoltura CRA, I-40129 Bologna, Italy
[2] Univ Bologna, Dept Pharmacol, Biochem Toxicol Unit, I-40126 Bologna, Italy
[3] Univ Bologna, Dept Organ Chem A Mangini, I-40126 Bologna, Italy
关键词
antioxidant; rocket; Eruca sativa (Mill.); Eruca vesicaria (L.); glucosinolate; isothlocyanate; glucoerucin; erucin;
D O I
10.1021/jf047945a
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Rocket (Eruca sativa Mill. or Eruca vesicaria L.) is widely distributed all over the world and is usually consumed fresh (leafs or sprouts) for its typical spicy taste. Nevertheless, it is mentioned in traditional pharmacopoeia and ancient literature for several therapeutic properties, and it does contain a number of health promoting agents including carotenoids, vitamin C, fibers, flavonoids, and glucosinolates (GLs). The latter phytochemicals have recently gained attention as being the precursors of isothiocyanates (ITCs), which are released by myrosinase hydrolysis during cutting, chewing, or processing of the vegetable. ITCs are recognized as potent inducers of phase II enzymes (e.g., glutathione transferases, NAD(P)H:quinone reductase, epoxide hydrolase, etc.), which are important in the detoxification of electrophiles and protection against oxidative stress. The major GL found in rocket seeds is glucoerucin, GER (108 +/- 5 mu mol g(-1) d.w.) that represents 95% of total GLs. The content is largely conserved in sprouts (79% of total GLs), and GER is still present to some extent in adult leaves. Unlike other GLs (e.g., glucoraphanin, the bio-precursor of sulforaphane), GER possesses good direct as well as indirect antioxidant activity. GER (and its metabolite erucin, ERN) effectively decomposes hydrogen peroxide and alkyl hydroperoxides with second-order rate constants of k(2) = 6.9 +/- 0.1 x 10(-2) M-1 s(-1) and 4.5 +/- 0.2 x 10(-3) M-1 s(-), respectively, in water at 37 degrees C, thereby acting as a peroxide-scavenging preventive antioxidant. Interestingly, upon removal of H2O2 or hydroperoxides, ERN is converted into sulforaphane, the most effective inducer of phase 11 enzymes among ITCs. On the other hand, ERN (and conceivably GER), like other ITCs, does not possess any chain-breaking antioxidant activity, being unable to protect styrene from its thermally (37 degrees C) initiated autoxidation in the presence of AMVN. The mechanism and relevance of the antioxidant activity of GER and ERN are discussed.
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页码:2475 / 2482
页数:8
相关论文
共 54 条
[1]   Modeling the co-antioxidant behavior of monofunctional phenols. Applications to some relevant compounds [J].
Amorati, R ;
Ferroni, F ;
Pedulli, GF ;
Valgimigli, L .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9654-9658
[2]   A quantitative approach to the recycling of α-tocopherol by coantioxidants [J].
Amorati, R ;
Ferroni, F ;
Lucarini, M ;
Pedulli, GF ;
Valgimigli, L .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9295-9303
[3]   Absolute rate constants for the reaction of peroxyl radicals with cardanol derivatives [J].
Amorati, R ;
Pedulli, GF ;
Valgimigli, L ;
Attanasi, OA ;
Filippone, P ;
Fiorucci, C ;
Saladino, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (11) :2142-2146
[4]  
[Anonymous], 1968, The Greek Herbal Dioscordes
[5]  
ARIETTI N, 1965, FLORA MED ERBORISTIC, P460
[6]   Stereoselective synthesis of (+/-)-alpha-kainic acid using free radical key reactions [J].
Bachi, MD ;
BarNer, N ;
Melman, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7116-7124
[7]  
BALME F, 1978, PLANTAS MED, P398
[8]   Barbarea verna as a source of 2-phenylethyl glucosinolate, precursor of cancer chemopreventive phenylethyl isothiocyanate [J].
Barillari, J ;
Gueyrard, D ;
Rollin, P ;
Iori, R .
FITOTERAPIA, 2001, 72 (07) :760-764
[9]   THE INVENTION OF RADICAL REACTIONS .23. NEW REACTIONS - NITRILE AND THIOCYANATE TRANSFER TO CARBON RADICALS FROM SULFONYL CYANIDES AND SULFONYL ISOTHIOCYANATES [J].
BARTON, DHR ;
JASZBERENYI, JC ;
THEODORAKIS, EA .
TETRAHEDRON, 1992, 48 (13) :2613-2626
[10]   Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket) [J].
Bennett, RN ;
Mellon, FA ;
Botting, NP ;
Eagles, J ;
Rosa, EAS ;
Williamson, G .
PHYTOCHEMISTRY, 2002, 61 (01) :25-30