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1.
Dietary antioxidants that protect low-density lipoprotein (LDL) from oxidation may help to prevent atherosclerosis and coronary heart disease. The antioxidant activities of purified monomeric and dimeric hydroxycinnamates and of phenolic extracts from rye (whole grain, bran, and flour) were investigated using an in vitro copper-catalyzed human LDL oxidation assay. The most abundant ferulic acid dehydrodimer (diFA) found in rye, 8-O-4-diFA, was a slightly better antioxidant than ferulic acid and p-coumaric acid. The antioxidant activity of the 8-5-diFA was comparable to that of ferulic acid, but neither 5-5-diFA nor 8-5-benzofuran-diFA inhibited LDL oxidation when added at 10-40 microM. The antioxidant activity of the monomeric hydroxycinnamates decreased in the following order: caffeic acid > sinapic acid > ferulic acid > p-coumaric acid. The antioxidant activity of rye extracts was significantly correlated with their total content of monomeric and dimeric hydroxycinnamates, and the rye bran extract was the most potent. The data suggest that especially rye bran provides a source of dietary phenolic antioxidants that may have potential health effects.  相似文献   

2.
4-Hydroxycinnamate derivatives are known to be potent protectors against oxidation of low-density lipoproteins (LDL), via a combination of free radical scavenging and transition metal chelation. Through a series of 4-hydroxycinnamic ethyl ester derivatives and related 8-8 dehydrodimers, we have tried to bring out the structural requirements for radical scavenging and cupric ion chelation. We found that the monomeric compounds, except for highly lipophilic tert-butyl derivative 3, exhibited rather low radical scavenging properties. Furthermore, they did not chelate copper but, in contrast, reduced cupric ion to cuprous ion, affording the related 8-8 dehydrodimers, for which they could be considered as precursors in vitro. In the copper-dependent human LDL oxidation in vitro, the cyclic 8-8 dehydrodimer forms behaved essentially as efficient copper chelators, while related noncyclic 8-8 forms, which were found to be the best protectors, mainly acted as radical scavengers.  相似文献   

3.
Phenolics antioxidant phytochemicals have been recently implicated for the lower rates of cardiac disease mortality among people consuming a Mediterranean diet. Essential oils are natural products extracted from vegetable materials, which can be used as antibacterial, antifungal, antioxidants, and anti-carcinogenic agents or to preserve and give specific flavors to foods. The activities of 23 selected essential oils in inhibiting the copper-catalyzed oxidation of human-low-density lipoproteins (LDL) were determined in vitro. LDL oxidation was inhibited between 6, 2, and 83% by 2 microM (GAE) total phenolics. The relative inhibition of LDL oxidation was used to categorize the essential oils into four groups below 2% when they contained methylchavicol, anethol, p-cymen, apiole, cinnamic ether; 6-10% if they possessed a majority of carvacrol, thymol, p-cymene, or vanillin; 10-50% for moderate amounts of thymol, carvacrol, cuminol, or eugenol; and 50-100% when eugenol is the major component. Total phenol content of essential oils gave a correlation with LDL antioxidant activity of r = 0.75. The Activity of each phenolics compound could play a role in protecting LDL against oxidation if the substance is absorbed by the body.  相似文献   

4.
Dietary phenolic antioxidants have been shown to prevent LDL modifications mediated by several physiologic oxidants including peroxynitrite. However, more recent data demonstrated that CO(2) affected the fate of peroxynitrite in biological fluids and significantly reduced peroxynitrite scavenging by polyphenols, raising doubts concerning their antioxidant activity. We found that the oxidation of LDL lipids mediated by peroxynitrite decreased in the presence of bicarbonate, while Trp oxidation and 3-nitroTyr formation increased, suggesting a redirection of peroxynitrite reactivity toward the protein moiety. We therefore evaluated the protective activity of some phenolic antioxidants (quercetin, oleuropein, resveratrol, (+)-catechin, (-)-epicatechin, tyrosol, alpha- and gamma-tocopherol, ascorbate) on peroxynitrite-mediated oxidation of LDL aromatic residues. Some of these phenols protected LDL Trp from oxidation better than ascorbate or alpha-tocopherol, although protection at 100 microM did not exceed 30-40%. However, the same phenolic antioxidants were more active in inhibiting 3-nitroTyr formation and those with a catechin structure provided significant protection (IC(50%) 40-50 microM). Red wine, a polyphenol-rich beverage, showed a protective effect comparable to that of the most active phenolic antioxidants. Direct EPR studies showed that bicarbonate significantly increased the peroxynitrite-dependent formation of O-semiquinone radicals in red wine, supporting the hypothesis that polyphenols are efficient scavengers of radicals formed by peroxynitrite/CO(2). Ascorbate was a poor inhibitor of peroxynitrite/CO(2)-induced LDL tyrosine nitration, but the simultaneous addition to the most active polyphenols halved their IC(50%). In conclusion, although cooperation with other antioxidants can further decrease the IC(50%) of polyphenolics, as demonstrated for ascorbate, their antioxidant activity appears to occur at concentrations at least 1 order of magnitude higher than their bioavailability.  相似文献   

5.
A novel model of peroxyl radical initiated low-density lipoprotein (LDL) oxidation (LDL oxidation model for antioxidant capacity, or LOMAC) was developed to assess the free radical scavenging capacity of antioxidants and the extracts of natural products. A water-soluble free radical initiator, 2,2'-azobis(amidinopropane) dihydrochloride, was used at physiological temperature (37 degrees C) to generate peroxyl radicals to catalyze lipid oxidation of LDL isolated from human plasma samples. Headspace hexanal, a major decomposition product of LDL oxidation, was measured by a headspace gas chromatograph as an indicator of antioxidant capacity of different concentrations of pure antioxidants (vitamins C and E) and the extracts of natural products (fresh apple phytochemical extracts). All vitamin C and E and apple extract concentrations tested resulted in increasing partial suppression and delay of LDL oxidation. On the basis of the median effective dose (EC(50)) calculated for each compound or extract tested, the LOMAC value of 100 g of apple against LDL oxidation was equivalent to 1470 mg of vitamin E or to 402 mg of vitamin C. This study shows that the LOMAC assay can be routinely used to analyze or screen antioxidants or phytochemical extracts against LDL oxidation to prevent cardiovascular disease. The food-specific LOMAC values will be very useful as a new alternative biomarker for future epidemiological studies of cardiovascular disease.  相似文献   

6.
The fractions of monomeric catechins and the fractions of dimeric and trimeric procyanidins were extracted and concentrated from wild berries of Vaccinium species to study their antioxidant activities. The compositions of the fractions were analyzed using high-performance liquid chromatography combined with diode-array and electrospray ionization mass spectrometric detection. Rare A-type dimers and trimers were identified as the predominant procyanidins in wild lingonberry, cranberry, bilberry, and bog whortleberry. Lingonberry and cranberry catechin and procyanidin fractions as well as bog whortleberry catechin fraction were good scavengers of radicals in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test and more efficient than the respective bilberry fractions. Bog whortleberry procyanidin fraction was less active, this being mainly due to the lower content of these compounds. Fractions from lingonberry, cranberry, and bilberry were equally efficient in inhibiting the oxidation of methyl linoleate emulsion, but differences among the berries were found in their abilities to inhibit low-density lipoprotein (LDL) oxidation. Catechins, the monomers, exhibited comparable activity to the fractions containing dimers and trimers in inhibiting the oxidation of methyl linoleate emulsion and human LDL. Bog whortleberry catechins were excellent antioxidants toward the oxidation of human LDL. Radical scavenging and antioxidant activities of Vaccinium berry fractions were attributable to the their composition of catechins and procyanidins. In conclusion, Vaccinium catechins as well as dimeric and trimeric procyanidins provide substantial antioxidant protection.  相似文献   

7.
Guava (Psidium guajava L.) is a tropical fruit, widely consumed fresh and also processed (beverages, syrup, ice cream, and jams). Pulp and peel fractions were tested, and both showed high content of dietary fiber (48.55-49.42%) and extractable polyphenols (2.62-7.79%). The antioxidant activity of polyphenol compounds was studied, using three complementary methods: (i) free radical DPPH* scavenging, (ii) ferric reducing antioxidant power assay (FRAP), and (iii) inhibition of copper-catalyzed in vitro human low-density lipoprotein (LDL) oxidation. All fractions tested showed a remarkable antioxidant capacity, and this activity was correlated with the corresponding total phenolic content. A 1-g (dry matter) portion of peel contained DPPH* activity, FRAP activity, and inhibition of copper-induced in vitro LDL oxidation, equivalent to 43 mg, 116 mg, and 176 mg of Trolox, respectively. These results indicate that guava could be a suitable source of natural antioxidants. Peel and pulp could also be used to obtain antioxidant dietary fiber (AODF), a new item which combines in a single natural product the properties of dietary fiber and antioxidant compounds.  相似文献   

8.
The potential of a laccase from the fungus Pycnoporus cinnabarinus to cross-link feruloylated soluble wheat arabinoxylans was investigated using capillary viscometry, size-exclusion HPLC, and reverse-phase HPLC of phenolic compounds. The laccase results were compared with those for a hydrogen peroxide/horseradish peroxidase system. The oxidants provoked an increase in viscosity of a 0.2% (w/v) arabinoxylan solution. A gel was formed after 30 min with laccase. Hydrogen peroxide was consumed rapidly before a gel could be formed. Free ferulic acid, methyl ferulate, and vanillic acid inhibited the gelation, whereas fumaric acid had no effect. This suggests that the aromatic ring, and not the propenoic chain of ferulic acid, was the initiating site for arabinoxylan cross-linking. Ferulic acid and its 8-O-4′, 8-5′, and 5-5′ dehydrodimers were present in nonoxidized arabinoxylans. Upon oxidation, the 8-8′ and 8-5′ benzofuran dehydrodimers appeared and the 8-O-4′ and 8-5′ dimers increased. The production of dimers was proportional to the consumption of ester-bound ferulic acid. In cross-linked arabinoxylans, the major dimers were 8-5′ benzofuran, 8-8′, and 8-O-4′, whereas the 5-5′ dehydrodimer remained at the same level as in the nonoxidized solution.  相似文献   

9.
Phenols present in olive oil may contribute to the health effects of the Mediterranean lifestyle. Olive oil antioxidants increase the resistance of low-density lipoproteins (LDL) against oxidation in vitro, but human intervention studies have failed to demonstrate similar consistent effects. To better mimic the in vivo situation, plasma was incubated with either individual olive oil phenols or olive oil extracts with different phenolic compositions, and LDL was subsequently isolated and challenged for its resistance to oxidation. The results show that the ortho-dihydroxy phenols (hydroxytyrosol and oleuropein-aglycone) are more efficient than their mono-hydroxy counterparts (tyrosol and ligstroside-aglycone) in increasing the resistance of LDL to oxidation. However, the concentration of antioxidants required to inhibit LDL oxidation when added to whole plasma was substantially higher as compared to previous data where antioxidants are directly added to isolated LDL. In conclusion, this study supports the hypothesis that extra virgin olive oil phenols protect LDL in plasma against oxidation. The explanation that in vitro studies show protective effects in contrast to the lack of effect in the majority of human studies may be that the dose of the phenols and thus their plasma concentration in humans was too low to influence ex vivo LDL oxidizability. Further studies are required to gain a better understanding of the potential health benefits that extra virgin olive oil may provide.  相似文献   

10.
Dietary phenolic compounds may act as antioxidants in vitro, but because of structural modifications during absorption, its role based on concentrations high enough to afford an antioxidant protection needs to be re-evaluated. We have explored the hypothesis that red wine procyanidins interact with low density lipoproteins (LDL) and that, at this location, the phenolic compounds efficiently protect LDL from oxidation and maintain LDL alpha-tocopherol at a high steady state concentration by recycling it back from the alpha-tocopheroxyl radical. To this end, human plasma was supplemented with wine procyanidins and isolated LDL were challenged with a constant flux of peroxyl radicals. As compared with LDL from plasma-free procyanidins, those LDL better resisted lipid oxidation and exhibited longer lag-phases of alpha-tocopherol consumption. The procyanidins, depending on their structure, were able to reduce the UV-induced alpha-tocopherol radical in a micellar system, as evidenced by electron paramagnetic ressonance. Mechanistically, the protection of LDL was interpreted in terms of quenching of peroxyl radicals and the recycling of alpha-tocopherol by the procyanidins bound to the lipoproteins. These results support the notion that, in human plasma, the procyanidins, via binding to LDL, may act as efficient local antioxidants.  相似文献   

11.
Oxidative modification of low-density lipoprotein (LDL) particles is a key event in the development of atherosclerosis. Oxidized LDL induces oxidative stress and modifies gene expression in endothelial cells. Berries constitute a rich dietary source of phenolic antioxidants. We found that the endemic Chilean berry Aristotelia chilensis (ach) has higher phenol content and scores better for total radical-trapping potential and total antioxidant reactivity in in vitro antioxidant capacity tests, when compared to different commercial berries. The juice of ach is also effective in inhibiting copper-induced LDL oxidation. In human endothelial cell cultures, the addition of ach juice significantly protects from hydrogen peroxide-induced intracellular oxidative stress and is dose-dependent. The aqueous, anthocyanin-rich fraction of ach juice accounts for most of ach's antioxidant properties. These results show that ach is a rich source of phenolics with high antioxidant capacity and suggest that it may have antiatherogenic properties.  相似文献   

12.
The exposure of mammalian cells to UV light induces various deleterious responses. Some of the major harmful effects are DNA damage, cell membrane peroxidation, systemic immune suppression, and aging acceleration. Reactive oxygen species and free radicals are believed to be largely responsible for some of the deleterious effects of UV upon cells. Typical administration of antioxidants has recently proved to represent a successful strategy for protecting the cells against UV-mediated oxidative damage. The objective of this study was to investigate the inhibitory effect of phenolic acids (caffeic acid, ferulic acid, gallic acid, and protocatechuic acid) on oxidative damage in human erythrocytes and low-density lipoprotein (LDL) induced by UVB radiation. The results revealed that the thiobarbituric acids reactive substances induced by UVB were decreased from 2.78 to 0.12-0.89 nmol MDA/mg protein in erythrocyte ghost and from 0.72 to 0.14-0.43 nmol MDA/mg protein in LDL by the addition of phenolic acids (100 muM). Caffeic acid, ferulic acid, and gallic acid exhibited over 85 and 60% inhibitory effect toward UVB-induced oxidation in erythrocytes and LDL, respectively. Phenolic acids, especially gallic acid, could maintain the normal glutathione levels and glutathione peroxidase activity in hemolysate from erythrocytes that were exposed to UVB radiation in comparison with untreated control. The results indicate that the antioxidant activities of caffeic acid and ferulic acid play a potential role in protection against UVB oxidative damage to human erythrocytes and LDL.  相似文献   

13.
Carnosine is a beta-alanylhistidine dipeptide found in skeletal muscle and nervous tissue that has been reported to possess antioxidant activity. Carnosine is a potential dietary antioxidant because it is absorbed into plasma intact. This research investigated the ability of carnosine to inhibit the oxidation of low-density lipoprotein (LDL) in comparison to its constituent amino acid, histidine. Carnosine (3 microM) inhibited Cu2+-promoted LDL (20 of protein/mL) oxidation at carnosine/copper ratios as low as 1:1, as determined by loss of tryptophan fluorescence and formation of conjugated dienes. Carnosine (6 microM) lost its ability to inhibit conjugated diene formation and tryptophan oxidation after 2 and 4 h of incubation, respectively, of LDL with 3 microM Cu2+. Compared to controls, histidine (3 microM) inhibited tryptophan oxidation and conjugated diene formation 36 and 58%, respectively, compared to 21 and 0% for carnosine (3 microM) after 3 h of oxidation. Histidine was more effective at inhibiting copper-promoted formation of carbonyls on bovine serum albumin than carnosine, but carnosine was more effective at inhibiting copper-induced ascorbic acid oxidation than histidine. Neither carnosine nor histidine was a strong inhibitor of 2,2'-azobis(2-amidinopropane) dihydrochloride-promoted oxidation of LDL, indicating that their main antioxidant mechanism is through copper chelation.  相似文献   

14.
Postmenopausal women have an increased risk of coronary heart disease. Oxidation of low-density lipoprotein (LDL) has been implicated in atherogenesis, and the presence of modified LDL (LDL(-)) in plasma appears to represent LDL oxidation in vivo. Because previous studies have demonstrated a strong antiatherogenic effect of estrogen due to its antioxidant activity and similar antioxidant activity was found for specific isoflavones derived from soy extract, the antioxidant activity of a phytoestrogen extract derived from soy and alfalfa was studied. Copper-mediated LDL oxidation was inhibited in the presence of soy and alfalfa extracts, and this effect was further enhanced in the presence of acerola cherry extract, which is rich in ascorbic acid. Male rabbit aortic endothelial cells pretreated with soy extract were resistant to the toxic effects of high levels of LDL and LDL(-), and a lesser, but significant protection, was also afforded by alfalfa extract. Cell-mediated oxidation of LDL, measured by LDL(-) formation, was inhibited in the presence of soy extract but not alfalfa extract. However, in the presence of acerola cherry extract, both soy and alfalfa extracts potently inhibited the formation of LDL(-). These findings show that acerola cherry extract can enhance the antioxidant activity of soy and alfalfa extracts in a variety of LDL oxidation systems. The protective effect of these extracts is attributed to the presence of flavonoids in soy and alfalfa extracts and ascorbic acid in acerola cherry extract, which may act synergistically as antioxidants. It is postulated that this synergistic interaction among phytoestrogens, flavonoids, and ascorbic acid is due to the "peroxidolitic" action of ascorbic acid, which facilitates the copper-dependent decomposition of LDL peroxides to nonradical products; this synergy is complemented by a mechanism in which phytoestrogens stabilize the LDL structure and suppress the propagation of radical chain reactions. The combination of these extracts markedly lowers the concentrations of phytoestrogens required to achieve significant antioxidant activity toward LDL.  相似文献   

15.
Rapeseed and pine bark are rich sources of phenolic compounds that have in previous studies been shown to exhibit antioxidant and anti-inflammatory properties. In this study, the antioxidant effect of rapeseed and pine bark phenolics in inhibiting the oxidation of lipids and proteins in meat was tested as a possible functional food application. The cooked pork meat with added plant material was oxidized for 9 days at 5 degrees C under light. The suitable level of plant material addition was first screened by following lipid oxidation only. For further investigations plant materials were added at a level preventing lipid oxidation by >80%. The oxidation was followed by measuring the formation of hexanal by headspace gas chromatography and the formation of protein carbonyls by converting them to 2,4-dinitrophenylhydrazones and measured by spectrophotometer. It was shown that rapeseed and pine bark were excellent antioxidants toward protein oxidation (inhibitions between 42 and 64%). These results indicate that rapeseed and pine bark could be potential sources of antioxidants in meat products.  相似文献   

16.
Dietary intake of antioxidants has been associated with a reduced risk of cardiovascular diseases, which is very likely caused by their capability of prevent oxidation of low-density lipoproteins (LDL). During food processing and storage, substances with antioxidative properties are formed by Maillard reactions. In this study, the activity of Maillard products to inhibit copper-induced oxidation of human LDL in vitro was investigated. d-Glucose was heated with an equimolar amount of glycine, l-lysine, or l-arginine, for 1 h under reflux. The increase of the antioxidative activity (AOA) of the Maillard mixtures was highly significant compared to the control mixtures. Additionally, two defined Maillard products with amino reductone structure were tested. 3-Hydroxy-4-(morpholino)-3-buten-2-one (1) and amino hexose reductone (2) showed a significant and dose dependent AOA. Compound 1 was about half as active as ascorbic acid, which served as positive control. Thus, it can be concluded that Maillard products, particularly those with amino reductone structure, have the strong potential to inhibit LDL oxidation.  相似文献   

17.
Plant-derived polyphenols may exert beneficial effects on atherosclerosis and cardiovascular diseases, in part, because of their antioxidant properties. In this study we compared the effects of unbound (free) and lipoprotein-associated red wine components on in vitro antioxidant protection of human low-density lipoprotein (LDL). Preincubation of LDL (1 mg protein/mL) with 0-2.5% (v/v) red wine for 3 h at 37 degrees C followed by gel filtration to remove unbound red wine components resulted in a dose-dependent, up to 4-fold increase in LDL-associated antioxidant capacity (measured as Trolox equivalents). Similar results were obtained with high-density lipoprotein (HDL) and bovine serum albumin (BSA). Furthermore, LDL was subjected to oxidation by copper and aqueous peroxyl radicals (2,2'-azobis[2-amidinopropane] dihydrochloride, AAPH). Under both types of oxidative stress, LDL-associated and free red wine components significantly decreased oxidation of the lipoprotein's protein moiety (assessed by tryptophan fluorescence) and lipid moiety (assessed by thiobarbituric acid-reactive substances and conjugated dienes). Similar protective effects of red wine components were observed against HDL oxidation. In contrast, red wine exerted a pro-oxidant effect on copper-induced oxidation of BSA tryptophan residues, while protecting them from AAPH-induced oxidation. Ascorbate strongly enhanced the protective effect of red wine against copper-induced LDL oxidation, and had an additive effect against AAPH-induced oxidation. Our data indicate that red wine components bind to LDL and HDL and protect these lipoproteins from metal ion-dependent and -independent protein and lipid oxidation.  相似文献   

18.
The antioxidant activity of berry phenolics (at concentrations of 1.4, 4.2, and 8.4 mug of purified extracts/mL of liposome sample) such as anthocyanins, ellagitannins, and proanthocyanidins from raspberry (Rubus idaeus), bilberry (Vaccinium myrtillus), lingonberry (Vaccinium vitis-idaea), and black currant (Ribes nigrum) was investigated in a lactalbumin-liposome system. The extent of protein oxidation was measured by determining the loss of tryptophan fluorescence and formation of protein carbonyl compounds and that of lipid oxidation by conjugated diene hydroperoxides and hexanal analyses. The antioxidant protection toward lipid oxidation was best provided by lingonberry and bilberry phenolics followed by black currant and raspberry phenolics. Bilberry and raspberry phenolics exhibited the best overall antioxidant activity toward protein oxidation. Proanthocyanidins, especially the dimeric and trimeric forms, in lingonberries were among the most active phenolic constituents toward both lipid and protein oxidation. In bilberries and black currants, anthocyanins contributed the most to the antioxidant effect by inhibiting the formation of both hexanal and protein carbonyls. In raspberries, ellagitannins were responsible for the antioxidant activity. While the antioxidant effect of berry proanthocyanidins and anthocyanins was dose-dependent, ellagitannins appeared to be equally active at all concentrations. In conclusion, berries are rich in monomeric and polymeric phenolic compounds providing protection toward both lipid and protein oxidation.  相似文献   

19.
In the present study, the antioxidant profile of olive oil antioxidants was investigated. Hydroxytyrosol and oleuropein are potent scavengers of hydroxyl radicals (OH*), peroxynitrite (ONOOH), and superoxide radicals (O(2)*(-)). Homovanillic alcohol, one of the main metabolites of hydroxytyrosol, and tyrosol are less potent scavengers of these reactive species. None of the olive oil antioxidants are good hypochlorous acid (HOCl) or hydrogen peroxide (H(2)O(2)) scavengers. Hydroxytyrosol efficiently protects against LDL oxidation in vitro and in vivo. However, no protective effect of hydroxytyrosol is usually demonstrated ex vivo against the oxidation of LDL isolated from humans after hydroxytyrosol consumption. The present study shows that this controversy is due to the isolation of LDL, which greatly reduces the protective effect of hydroxytyrosol against LDL oxidation. Hydroxytyrosol is an efficient scavenger of several free radicals. The physiological relevance of the high intrinsic antioxidant activity of hydroxytyrosol is illustrated by its protection against LDL oxidation.  相似文献   

20.
Lipid oxidation is a major deteriorative factor in meats. Sources of natural antioxidants that are as effective as commercially available antioxidants are desired. The objective of this research was to investigate honey as an inhibitor of lipid oxidation in ground poultry. The antioxidant content of different varieties of honey was investigated spectrophotometrically and honey's effectiveness in reducing oxidation of ground poultry determined by monitoring thiobarbituric acid reactive substances (TBARS). Buckwheat honey had the highest antioxidant content and acacia honey the lowest. Honeys of different floral sources differed in their protection against lipid oxidation. Buckwheat honey (5%, w/w) reduced TBARS approximately 70%, whereas acacia honey reduced TBARS approximately 34% at 3 days of storage at 4 degrees C. In comparison to butylated hydroxytoluene and tocopherol (0.02% of total fat), honey (at 5% of the weight of the meat) was much more effective at preventing oxidation. Honey has great potential as an antioxidant source and may result in greater acceptability of meat products and prevent negative health implications of oxidized meats.  相似文献   

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