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1.
A model reaction system was used to generate pure thiosulfinates (3) from S-alk(en)yl-L-cysteine sulfoxides (1) to facilitate studies on the intrinsic pH and thermal sensitivities of individual thiosulfinate species. Thiosulfinate decay could be characterized as first-order processes over the pH range of 1.2-9.0 and at 20-80 degrees C. The stability of thiosulfinates was greatest at pH 4.5-5.5, followed by pH 1.2, pH 6.5-7.5, and pH 8.0-9.0. Thiosulfinates with longer and saturated alk(en)yl groups were generally more stable than those with shorter and unsaturated alk(en)yl groups. Thiosulfinates underwent thioalkyl-exchange reactions at pH 8-9 without loss of total thiosulfinate levels within 60-90 min at 20 degrees C.  相似文献   

2.
In support of a new clinical trial designed to compare the effects of crushed fresh garlic and two types of garlic supplement tablets (enteric-coated dried fresh garlic and dried aged garlic extract) on serum lipids, the three garlic products have been characterized for (a) composition (14 sulfur and 2 non-sulfur compounds), (b) stability of suspected active compounds, and (c) availability of allyl thiosulfinates (mainly allicin) under both simulated gastrointestinal (tablet dissolution) conditions and in vivo. The allyl thiosulfinates of blended fresh garlic were stable for at least 2 years when stored at -80 degrees C. The dissolution release of thiosulfinates from the enteric-coated garlic tablets was found to be >95%. The bioavailability of allyl thiosulfinates from these tablets, measured as breath allyl methyl sulfide, was found to be complete and equivalent to that of crushed fresh garlic. S-Allylcysteine was stable for 12 months at ambient temperature. The stability of the suspected active compounds under the conditions of the study and the bioavailability of allyl thiosulfinates from the dried garlic supplement have validated the use of these preparations for comparison in a clinical trial.  相似文献   

3.
The dynamic changes in thiosulfinate profiles were studied in reaction systems containing a crude onion alliinase, S-alk(en)yl-L-cysteine sulfoxide substrates (1) and preformed thiosulfinates (4). Regioisomeric excesses of one of two possible heterologous 4 species (RS(O)SR', where R does not equal R') could be manipulated under conditions where alliinase, 1, and 4 levels were varied. Regioisomeric excesses could be explained by a thiosulfinate (4)/alkanesulfenic acid (2) trapping mechanism, with the greatest control over product profile governed by the rate of 2 generation in the system. The series of reactions existing in this dynamic reaction system was kinetically modeled with reasonable fits to the experimental data. The application of the 4/2 trapping strategy to manipulate thiosulfinate and related organosulfur product profiles in diluted onion homogenates was demonstrated using exogenous MeS(O)SMe (4a), PrS(O)SPr (4c), and AllS(O)SAll (4d) as the preformed thiosulfinate.  相似文献   

4.
This field study investigated the impact of various fertilization strategies with red clover ( Trifolium pratense L.) green manure on the levels of S-alk(en)yl- l-cysteine sulfoxides (ACSO) and l-ascorbic acid in leek. Two of the 12 treatments were controls, one without fertilizers and the other with a commercial mineral fertilizer. The remaining 10 treatments were different forms and quantities of green manure prepared from red clover. One treatment consisted of direct incorporation into soil of the preceding red clover crop. The other 9 treatments comprised three types of red clover green manure [anaerobically digested red clover biomass (biodigestate), composted red clover, fresh red clover as mulch] applied at three different doses. Yield was increased only at the highest dose of compost and the highest dose of mulch. High doses of green manure decreased dry matter content in leek. The fertilizer treatments increased the nitrogen uptake and the nitrogen content of leek. Sulfur uptake and sulfur levels were increased only by the mineral fertilizer and by the compost. Nonfertilized leek contained 20.4 +/- 5.8 g/kg of dry weight (dw) ACSOs as determined by LC-MS/MS and 1.57 +/- 0.01 g/kg of dw ascorbic acid as determined by HPLC. The ACSOs were to 92-96% isoalliin, the rest being methiin. Alliin was identified in only 1 of 72 samples. The ACSO level was increased by 37% by the mineral fertilizer. Whereas direct incorporation of red clover, mulch, and red clover biodigestate had no influence on the ACSO level, the highest dose of compost increased the ACSO level by 55%. Ascorbic acid levels were not influenced by the mineral treatment. Green manures increased ascorbic acid levels only on a dry weight basis. A high correlation between the content of sulfur and ACSO indicated that delivering capacity of sulfur from the manure to the plant strongly affected the ASCO content of the leek. In conclusion, the composted green manure was the most useful organic fertilizer in this study and reached at least the efficiency of the mineral fertilizer.  相似文献   

5.
In this study we isolated crude thiosulfinates from Allium tuberosum L. using CH 2Cl 2 and then with silica gel column chromatography purified S-methyl methanthiosulfinate and S-methyl 2-propene-1-thiosulfinate from the crude thiosulfinates. Subsequently, in vitro cytotoxicities against human cancer cells and in vivo antitumor activities of the thiosulfinates were investigated. Their cytotoxicities were strong in human cancer cells, in the order of S-methyl 2-propene-1-thiosulfinate, crude thiosulfinates, and S-methyl methanthiosulfinate. When thiosulfinates were administered consecutively for 7 days at 10, 30, and 50 mg/kg ip, in mice, we found significant increases in the life spans of mice that had been inoculated with Sacorma-180 tumor cells. The crude thiosulfinates also induced apoptosis in MCF-7 cancer cells. These results suggest that thiosulfinates from Allium tuberosum L. inhibit the proliferation of cancer cells via apoptosis and have antitumor activities.  相似文献   

6.
Low-density lipoprotein (LDL) and plasma were isolated from patients with non-insulin-dependent diabetes. The protective effects of six organosulfur compounds (DAS, diallyl sulfide; DADS, diallyl disulfide; SAC, S-allylcysteine; SEC, S-ethylcysteine; SMC, S-methylcysteine; SPC, S-propylcysteine) against further oxidation and glycation in these already partially oxidized and glycated samples were studied. DAS and DADS showed significantly greater oxidative-delaying effects than four cysteine-containing compounds in both partially oxidized LDL and plasma samples (P < 0.05). However, cysteine-containing agents were superior to DAS and DADS in delaying glycative deterioration in already partially glycated LDL (P < 0.05). The observed delays of oxidative and glycative effects from each agent were significantly concentration-dependent (P < 0.05). Furthermore, six organosulfur agents significantly decreased the loss of catalase and glutathione peroxidase activities in plasma and increased alpha-tocopherol retention in LDL and plasma (P < 0.05). These results suggested that the use of these organosulfur agents derived from garlic at these concentrations could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases.  相似文献   

7.
The aim of the present study was to test whether variations in the root environment affect the content of health-related organosulfur compounds, total phenolic compounds, and flavonol glycoside concentrations in onions. For this purpose, greenhouse-grown onions ( Allium cepa L.) were either inoculated with a commercial arbuscular mycorrhizal inoculum or a sterile inoculum and were provided with two NH(4)(+):NO(3)(-) ratios as a nitrogen source. Onion growth, arbuscular mycorrhizal colonization rate, sugars, and nutrient element concentrations were also quantified. The plant antioxidant activity and quercetin monoglucoside and organosulfur compound concentrations increased with dominant nitrate supply. Furthermore, mycorrhizal colonization increased the antioxidant activity and also concentrations of the major quercetin glucosides. The present study provides clear evidence that antioxidant activity, quercetin glycosides, and organosulfur compounds can be increased in sufficiently supplied onion plants by dominant nitrate supply or application of arbuscular mycorrhizal fungi. This was probably due to increased precursor production and induced defense mechanisms.  相似文献   

8.
Sensitive and accurate testing for trace amounts of biotechnology-derived DNA from plant material requires pure, high-quality genomic DNA as template for subsequent amplification using the polymerase chain reaction (PCR). Six methodologies were evaluated for extracting DNA from ground corn kernels spiked with 0.1% (m/m) CBH351 (StarLink) corn. DNA preparations were evaluated for purity and fragment size. Extraction efficiency was determined. The alcohol dehydrogenase gene (adh1) and the CBH351 (cry9C, 35S promoter) genes in the genomic DNA were detected using PCR. DNA isolated by two of the methods proved unsuitable for performing PCR amplification. All other methods produced some DNA preparations that gave false negative PCR results. We observed that cornstarch, a primary component of corn kernels, was not an inhibitor of PCR, while acidic polysaccharides were. Our data suggest that amplification of an endogenous positive control gene, as an indicator for the absence of PCR inhibitors, is not always valid. This study points out aspects of DNA isolation that need to be considered when choosing a method for a particular plant/tissue type.  相似文献   

9.
Pure thiosulfinates, R-S(O)S-R (2), where R = Me (2a), Pr (2b), or All (2c), at levels up to 4 mM were not capable of scavenging hydrogen peroxide or superoxide anion. Relative to standard antioxidants (ascorbic acid, n-propyl gallate, butylated hydroxytoluene, Trolox, and reduced glutathione), these thiosulfinates were 1-3 orders of magnitude less efficient at reducing 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, 0.5-2 orders of magnitude less efficient at quenching singlet oxygen, and about equally effective at scavenging hydroxyl radical. Generally, AllS(O)SAll (2c) was the most effective and PrS(O)SPr (2b) was the least effective thiosulfinate in these assays, except that MeS(O)SMe (2a) exhibited no quenching effect toward singlet oxygen. These thiosulfinates were also incapable at levels up to 0.1 mM (where they were toxic) of in vitro induction of quinone reductase (QR) in murine hepatoma (hepa 1c1c7) cells. However, S-1-propenyl-L-cysteine sulfoxide (isoalliin, 1a) and cycloalliin (3) induced QR in this system at 2 mM and 1 mM, respectively, although doubling of QR required levels of 10-15 mM.  相似文献   

10.
The raw form of garlic and some of its preparations are widely recognized as antiplatelet agents that may contribute to the prevention of cardiovascular disease. Herein, we examined the in-vitro antiaggregatory activity (IVAA) of human blood platelets induced by extracts of garlic samples that were previously heated (in the form of crushed versus uncrushed cloves) using different cooking methods and intensities. The concentrations of allicin and pyruvate, two predictors of antiplatelet strength, were also monitored. Oven-heating at 200 degrees C or immersing in boiling water for 3 min or less did not affect the ability of garlic to inhibit platelet aggregation (as compared to raw garlic), whereas heating for 6 min completely suppressed IVAA in uncrushed, but not in previously crushed, samples. The latter samples had reduced, yet significant, antiplatelet activity. Prolonged incubation (more than 10 min) at these temperatures completely suppressed IVAA. Microwaved garlic had no effect on platelet aggregation. However, increasing the concentration of garlic juice in the aggregation reaction had a positive IVAA dose response in crushed, but not in uncrushed, microwaved samples. The addition of raw garlic juice to microwaved uncrushed garlic restored a full complement of antiplatelet activity that was completely lost without the garlic addition. Garlic-induced IVAA was always associated with allicin and pyruvate levels. Our results suggest that (1) allicin and thiosulfinates are responsible for the IVAA response, (2) crushing garlic before moderate cooking can reduce the loss of activity, and (3) the partial loss of antithrombotic effect in crushed-cooked garlic may be compensated by increasing the amount consumed.  相似文献   

11.
Reactions involved in blue-green discoloration in a mixture of onion (Allium cepa L.) and garlic (Allium sativum L.) were investigated. Vivid-blue color was successfully reproduced by using a defined model reaction system comprising only trans-(+)-S-(1-propenyl)-L-cysteine sulfoxide (1-PeCSO) from onion, S-allyl-L-cysteine sulfoxide (2-PeCSO) from garlic, purified alliinase (EC 4.4.1.4), and glycine (or some other amino acids). Four reaction steps identified and factors affecting the blue color formation were in good agreement with those suggested by earlier investigators. When crude onion alliinase was used in place of garlic alliinase, less pigment was formed. This result was explained by a difference in the amount of thiosulfinates, colorless intermediates termed color developers, yielded from 1-PeCSO by these enzymes.  相似文献   

12.
The content of organosulfur compounds was determined in selected garlic cultivars grown at four locations in Andalusia, Spain. The organosulfur compounds studied were three γ-glutamyl peptides, namely, γ-l-glutamyl-S-(2-propenyl)-l-cysteine (GSAC), γ-l-glutamyl-S-(trans-1-propenyl)-l-cysteine (GSPC), and γ-l-glutamyl-S-methyl-l-cysteine (GSMC), and four cysteine sulfoxides (alliin, isoalliin, methiin, and cycloalliin). There was a significant effect of the location, cultivar, and garlic ecotype on individual organosulfur compound contents. Purple-type cultivars showed on average the highest contents of GSMC, GSAC, alliin, and methiin but the lowest isoalliin content. The impact of genotype was relatively high for GSAC, whereas this factor hardly contributed to the total variability in alliin and isoalliin content. Planting date had a significant effect on the content of alliin and isoalliin. Discriminant analysis evidenced the ability of organosulfur compounds to distinguish among garlic bulbs from different locations or ecotypes with 81 or 86% accuracy, respectively.  相似文献   

13.
Five compounds oxidizing canine erythrocytes were isolated from an aqueous ethanol garlic extract by silica gel column chromatography and preparative thin-layer chromatography. On the basis of nuclear magnetic resonance, infrared spectroscopy, and mass spectrometry, they were identified as three known compounds: bis-2-propenyl trisulfide (1), bis-2-propenyl tetrasulfide (2), and bis-2-propenyl pentasulfide (3) as well as two novel compounds, bis-2-propenyl thiosulfonate (4) and trans-sulfuric acid allyl ester 3-allylsulfanyl-allyl ester (5). A mixture of compounds 1-3 and compounds 4 and 5 induced methemoglobin formation in canine erythrocyte suspension in vitro resulting in the oxidation of canine erythrocytes. These groups of characteristic organosulfur compounds contained in garlic probably contribute to oxidations in blood. The constituents of garlic have the potential to oxidize erythrocytes and hemoglobin, suggesting that foods containing quantities of garlic should be avoided for feeding dogs.  相似文献   

14.
The shallot is considered an important genetic resource for Allium breeding programs because, compared to the bulb onion, the shallot contains higher levels of several functional chemical compounds. However, there may be differences in content, composition and beneficial activity among shallot landraces. This study was carried out to characterize the differences in phenolic, quercetin, sugar, S-alk(en)yl-l-cystein sulfoxide (ACSO), and saponin contents and antioxidant capacities of a shallot germplasm including 31 strains derived from different regions of Vietnam and six other countries. A wide variation was observed in the quantitative analyses of the chemical contents. Shallots with high contents of polyphenols, saponins, and quercetins were found in the south of Vietnam and other low-latitude countries. Meanwhile, those possessing fairly high ACSO and sugar contents were observed in the north of Vietnam. Qualitative analysis of saponins via thin layer chromatography did not show clear variation among shallot strains, but polymorphism was observed between the shallot and other Allium species, such as A. roylei. The principal component analysis could clearly discriminate shallot strains by their geographical origins. All shallot strains showed potent antioxidant activities in a DPPH assay. The highest antioxidant capacity was in the strains possessing relatively high contents of polyphenol, quercetin, and saponin. Significant correlations were found between antioxidant capacity (IC 50 ?1 ) and four groups of chemical compounds (polyphenols, quercetins, saponins, and ACSOs) (r = 0.40–0.59). A strong correlation was observed between IC 50 ?1 and quercetin contents (r = 0.59, p < 0.01). The six Fusarium-inoculated shallot strains seemed to be adequately resistant against disease, and the levels of resistance may be related to the saponin content in the bulb tissues.  相似文献   

15.
The denaturation and aggregation of reagent-grade (Sigmaalpha-La), ion-exchange chromatography purified (IEXalpha-La), and a commercial-grade (Calpha-La) alpha-lactalbumin were studied with differential scanning calorimetry (DSC), polyacrylamide gel electrophoresis, and turbidity measurement. All three preparations had similar thermal denaturation temperatures with an average of 63.7 degrees C. Heating pure preparations of alpha-lactalbumin produced three non-native monomer species and three distinct dimer species. This phenomenon was not observed in Calpha-La. Turbidity development at 95 degrees C (tau95 degrees C) indicated that pure preparations rapidly aggregate at pH 7.0, and evidence suggests that hydrophobic interactions drove this phenomenon. The Calpha-La required 4 times the phosphate or excess Ca2+ concentrations to develop a similar tau95 degrees C to the pure preparations and displayed a complex pH-dependent tau95 degrees C behavior. Turbidity development dramatically decreased when the heating temperature was below 95 degrees C. A mechanism is provided, and the interrelationship between specific electrostatic interactions and hydrophobic attraction, in relation to the formation of disulfide-bonded products, is discussed.  相似文献   

16.
Red pigments were isolated from wine and grape-skin extracts using preparative high-speed countercurrent chromatography (HSCCC) and identified by NMR and MS techniques. Four solvent systems were developed in order to separate anthocyanins with different polarities. Malvidin-3-glucoside was the major component present in young red wines, and up to 500 mg of pure malvidin-3-glucoside could be obtained from a single bottle of a red wine. Other isolated pigments were the malvidin- and peonidin-3,5-diglucosides, as well as acetyl-, coumaroyl-, and caffeoyl-derivatives of anthocyanins. Furthermore, condensed red wine pigments formed from malvidin-3-glucoside (vitisin A and acetylvitisin A) were isolated on a preparative scale. Isolated compounds were used as standards for quantification of anthocyanins in a range of red wines. The "color activity concept" was applied to red wine, and visual detection thresholds were determined for some of the isolated anthocyanins. Mono-glucosides were found to exhibit lower visual detection thresholds than di-glucosides and acylated anthocyanins.  相似文献   

17.
In normal onion (Allium cepa), trans-S-1-propenyl-L-cysteine sulfoxide is transformed via 1-propenesulfenic acid into propanethial S-oxide, a lachrymatory factor, through successive reactions catalyzed by alliinase and lachrymatory factor synthase (LFS). A recent report showed that suppression of the LFS activity caused a dramatic increase in thiosulfinates previously reported as "zwiebelane isomers". After purification by recycle high-performance liquid chromatography and subsequent analyses, we established the planar structure of the putative "zwiebelane isomers" as S-3,4-dimethyl-5-hydroxythiolane-2-yl 1-propenethiosulfinate, in which two of the three molecules of 1-propenesulfenic acid involved in the formation gave the thiolane backbone, and the third molecule gave the thiosulfinate structure. Of at least three stereoisomers observed, one in the (2'R,3'R,4'R,5'R)-configuration was collected as an isolated fraction, and the other isomers were collected as a combined fraction because spontaneous tautomerization prevented further purification. Both fractions showed inhibitory activities against cyclooxygenase-1 and α-glucosidase in vitro.  相似文献   

18.
alpha-(1-6) and alpha-(1-3)-linked oligosaccharides were obtained from the reaction between sucrose and maltose, catalyzed by an alternansucrase isolated from Leuconostoc mesenteroides NRRL B-21297 and separated using a Bio-Gel P2 column in six fractions. Fractions 1, 2, and 3 were mainly composed of DP3, DP4, and DP5, respectively. However, fractions 4, 5, and 6 consisted of mixtures from DP5 to DP9, and they are identified here as DP5.7, DP6.7, and DP7.4, respectively. Potential prebiotic properties of these oligosaccharides were tested using pure and mixed cultures. Generally, in pure studies, most of the tested bacteria failed to grow or grew poorly using the DP6.7 and DP7.4 fractions and showed the greatest growth on DP3. Growth of fecal bacteria on the maltose-acceptor products was tested following an in vitro fermentation method. DP3 showed the highest prebiotic effect, followed by DP4 and DP6.7, whereas DP7.4 did not present any prebiotic activity.  相似文献   

19.
Two novel, structurally unusual cysteine derivatives were isolated from the bulbs of Allium stipitatum (Allium subg. Melanocrommyum) and shown to be S-(2-pyridyl)cysteine N-oxide and S-(2-pyridyl)glutathione N-oxide. The former compound is the first example of a naturally occurring alliinase substrate that contains an N-oxide functionality instead of the S-oxide group. In addition, S-methylcysteine S-oxide (methiin) and S-(methylthiomethyl)cysteine 4-oxide (marasmin) were found in the bulbs. Presented data suggest that the previously reported identification of S-(2-pyridyl)cysteine S-oxide was most likely erroneous. The alliinase-mediated formation of pyridyl-containing compounds following disruption of A. stipitatum bulbs was studied by a combination of HPLC-MS, HPLC-PDA, DART-MS, and NMR techniques. It was found that no pyridyl-containing thiosulfinates are present in homogenized bulbs in detectable quantities. Instead, various pyridine N-oxide derivatives are formed, including N-hydroxypyridine-2(1H)-thione (pyrithione), 2-(methyldithio)pyridine N-oxide, 2-[(methylthio)methyldithio]pyridine N-oxide, di(2-pyridyl) disulfide N-oxide, and di(2-pyridyl) disulfide N,N'-dioxide. This represents the first report of pyrithione formation as a natural product.  相似文献   

20.
Bioassay-guided fractionation of the EtOAc crude extract from Sicilian almond hulls, a waste material from Prunus dulcis crop, allowed identification of 10 constituents, isolated as pure compounds (1-5, 7, and 10) or unseparable mixtures (5 + 6 and 8 + 9). All compounds were subjected to spectroscopic analysis and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide bioassay on MCF-7 human breast cancer cells. In addition to the main components oleanolic (1), ursolic (2), and betulinic (3) acids, the 2-hydroxy analogues alphitolic (4), corosolic (5), and maslinic (6) acids, as well as the related aldehydes, namely, betulinic (7), oleanolic (8), and ursolic (9), were identified. From a more polar fraction, the beta-sitosterol 3-O-glucoside (10) was also identified. A sample of commercially available betulin (11) was also included in bioassays as further support to a structure-activity relationship study. Betulinic acid showed antiproliferative activity toward MCF-7 cells (GI50 = 0.27 microM), higher than the anticancer drug 5-fluorouracil.  相似文献   

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