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1.
Cinnamon bark has been reported to be effective in the alleviation of diabetes through its antioxidant and insulin-potentiating activities. In this study, the inhibitory effect of cinnamon bark on the formation of advanced glycation endproducts (AGEs) was investigated in a bovine serum albumin (BSA)-glucose model. Several phenolic compounds, such as catechin, epicatechin, and procyanidin B2, and phenol polymers were identified from the subfractions of aqueous cinnamon extract. These compounds showed significant inhibitory effects on the formation of AGEs. Their antiglycation activities were not only brought about by their antioxidant activities but also related to their trapping abilities of reactive carbonyl species such as methylglyoxal (MGO), an intermediate reactive carbonyl of AGE formation. Preliminary study on the reaction between MGO and procyanidin B2 revealed that MGO-procyanidin B2 adducts are primary products which are supposed to be stereoisomers. This is the first report that proanthocyanidins can effectively scavenge reactive carbonyl species and thus inhibit the formation of AGEs. As proanthocyanidins behave in a similar fashion as aminoguanidine (AG), the first AGE inhibitor explored in clinical trials, they show great potential to be developed as agents to alleviate diabetic complications.  相似文献   

2.
Horseradish peroxidase (HRP; EC 1.11.1.7) catalyzed the H(2)O(2)-dependent oxidative coupling of (+)-catechin 1 to form three different biphenyl C-C dimers 2-4, whereas Rhus vernicifera laccase catalyzed the formation of two new catechin-hydroquinone adducts 5 and 6. Spectroscopic evidence showed that HRP dimers were linked through position 8 of the A-ring of one catechin moiety to C-5' of ring B in 2 and 4 and to C-2 of ring C in 3. The unusual catechin dicarboxylic acid dimer 4 was obtained by ortho cleavage of the E-ring. Hydroquinone served as both a shuttle oxidant and a reactant by coupling at C-2' and C-5' of the catechin B-ring during laccase oxidations. HRP and laccase oxidation products were compared to D,L-alpha-tocopherol and (+)-catechin for their abilities to inhibit iron-induced lipid peroxidation in rat brain homogenates and Fe(3+)-ADP/NADPH in rat liver microsomes, as measured by the intensity of thiobarbituric acid reactive substance. All metabolites exhibited anti-lipid peroxidation with IC(50) values approximately 2-8 times higher than those of standard compounds. Characteristic reaction products may prove to be novel markers for (+)-catechin antioxidant reactions in living systems.  相似文献   

3.
Oligomeric proanthocyanidins from mangosteen pericarps   总被引：2，自引：0，他引：2  
Oligomeric proanthocyanidins were extracted from mangosteen pericarps and fractionated by a Sephadex LH-20 column to give 0.66% yield (dry matter). (13)C and (1)H NMR signals showed the presence of predominantly procyanidins together with a few prodelphinidin units along with small amounts of stereoisomers of afzelechin/epiafzelechin, catechin/epicatechin, and gallocatechin/epigallocatechin. Depolymerization with benzylmercaptan resulted in epicatechin thioether as the major product, and the mean degree of polymerization was determined to be 6.6. The electron spray ionization-mass spectrometry and matrix-assisted laser desorption/ionization time-of-flight mass spectra revealed the dominant B type oligomers with mainly epicatechin units and with a small amount of A type oligomers. The isolated proanthocyanidins are potent peroxyl radical scavengers as evidenced by the high oxygen radical scavenging capacity at 1.7 x 10 (4) micromol TE/g, much higher than that of pine bark and grape seed extracts.  相似文献   

4.
The antitermitic activities of the essential oils from the leaves of two Cinnamomum osmophloeumclones (A and B) and their chemical ingredients against Coptotermes formosanus Shiraki were investigated according to direct contact application. Results from this experiment have demonstrated that the indigenous cinnamon B leaf essential oil has a more effective antitermitic activity than indigenous cinnamon A leaf essential oil. Furthermore, when cinnamaldehyde, eugenol, and alpha-terpineol are extracted from indigenous cinnamon leaf essential oil and used at the strength of 1 mg/g, their antitermitic effectiveness is much higher than that using indigenous cinnamon leaf essential oil. Among the congeners of cinnamaldehyde examined, cinnamaldehyde has exhibited the strongest termiticidal property.  相似文献   

5.
The chemical characteristics of the purified procyanidin polymers of the flowers of the forage legume red clover (Trifolium pratense L.) were studied by (13)C NMR, acid-catalyzed degradation with benzyl mercaptan, and electrospray ionization mass spectrometry (ESI-MS). The (13)C NMR showed that the fraction consisted of predominantly procyanidin polymers. The thiolysis reaction products indicated a mean degree of polymerization (mDP) of 9.3 with epicatechin (81%) as the abundant flavan-3-ol extension unit and the terminating units dominated by catechin (95%). ESI-MS showed a range of oligomeric procyanidin ions (DP of 2-11). The white clover floral prodelphinidins consist of terminal units with nearly equal proportions of epigallocatechin (52%) and gallocatechin (48%) and extender units showing epigallocatechin (56%) and gallocatechin (39%). The dramatic difference in the stereochemistry of the terminal and extender units observed for the red clover floral procyanidins contrasts with the mixture of cis and trans stereochemistry observed for white clover floral prodelphinidins.  相似文献   

6.
The procyanidins of nonedible parts of lotus (Nelumbo nucifera Gaertn.) were determined for the first time. The procyanidins of lotus seedpod were extracted with Me(2)CO/H(2)O and purified by Sephadex LH-20 column chromatography, with a purity of >98%. ESI-MS analysis showed that the main molecular weight distribution of procyanidins ranged from 291 to 1155, with M + H peak values of 291.1, 579.2, 731.2, 867.2, 1019.4, and 1155.3, respectively. This indicates that the extract contains monomers, dimers, and tetramers of procyanidins, in which the amounts of dimers are greatest, and catechin and epicatechin are the base units. (1)H NMR and (13)C NMR spectra confirmed that two to four monomers are linked through C(4)-C(8) (or C(6)) bonds. The effects of the procyanidins on lipid autoxidation, lipoxygenase activities, and free radical scavenging were also studied. The results showed that 0.1% procyanidins have a strong antioxidant activity in a soybean oil system, better than BHT at the same concentration; inhibited lipoxygenase activity by >90% at a concentration of 62.5 mug/mL, with an IC(50) value of 21.6 mug/mL; and had IC(50) inhibitory values rate to (*)OH of 10.5 mg/L and a scavenging effect on O(2)(*)(-) of 17.6 mg/L.  相似文献   

7.
The polymeric procyanidins were fractionated from lowbush blueberry on a Sephadex LH-20 column. The degree of polymerization (DP) for the polymers was determined by thiolysis to be in a range of 19.9 to 114.1. Normal-phase HPLC analysis indicated that the polymeric procyanidins did not contain oligomeric procyanidins with DP < 10. The polymers eluted as a single peak at the end of the chromatogram. The normal-phase HPLC gradient was modified to improve the separation of procyanidin monomers through decamers and to elute all the polymers beyond those as a distinct peak. Monomers through decamers were quantified individually. All the polymers (DP > 10) were quantified using a mixture of purified polymers as an external standard. Polymers were found to be the dominant procyanidins in brown sorghum bran, cranberry, and blueberry. Thiolysis of the polymer peaks indicated that epicatechin was present as extension units in these foods, however, the composition of terminal units varied considerably between catechin and epicatechin, or an A-type dimer linkage in the case of cranberry.  相似文献   

8.
Cassia bark or cortex cinnamomi, the dried stem bark of Cinnamomum cassia Presl. (Lauraceae), is a popular natural spice and a commonly used herb in traditional Chinese medicine. However, adulterants are frequently found in the market. In this study, 44 samples of Cassia bark including bark from seven related Cinnamomum species were collected from fields and market. Four characteristic components, cinnamaldehyde, cinnamic acid, cinnamyl alcohol, and coumarin were determined by RP-HPLC, and a fingerprint comprised of five markers was established. These results showed that cassia barks contained high contents of cinnamaldehyde (13.01-56.93 mg/g). The highest content of cinnamaldehyde (up to 93.83 mg/g) was found in debarked cortex, which is traditionally regarded as having the best quality in local herb shops. In contrast, the adulterants from the other Cinnamomum species, C. wilsonii Camble, C. japonicum Sieb., C. mairei Levl. and C. burmanii (Nees) Blume, contained low contents of cinnamaldehyde (<2.00 mg/g). The content of cinnamaldehyde in C. loureirii Nees was comparable to that in C. cassia. It is suggested that five characteristic peaks by HPLC are suitable for distinguishing genuine cassia bark from the adulterants and could be applied in the quality control of this commodity.  相似文献   

9.
trans-Cinnamaldehyde, the principal component of cinnamon flavor, is a potent antimicrobial compound present in essential oils such as cinnamon. In the course of studies designed to discover its maximum microbial lethality under food-processing conditions, a gas chromatographic-mass spectrophotometric procedure was developed for the extraction and analysis of essential oil components such as cinnamaldehyde from commercial cinnamon-containing foods (several brands of cinnamon breads, cereals, cookies, puddings, applesauces, and fruit juices). The cinnamaldehyde content ranged from trace amounts in orange juice to 12.2 mg/100 g (122 ppm) in apple cinnamon cereals and 31.1 mg/100 g (311 ppm) for cinnamon swirl bread (highest value). To ascertain the heat stability of cinnamaldehyde, pure cinnamaldehyde, pure eugenol, cinnamon oil, and mixtures consisting of cinnamaldehyde plus eugenol or cinnamon oil were heated at graded temperatures up to 210 degrees C and 60 min, and then possible compositional changes were examined. Eugenol was stable to heat, as were the components of cinnamon oil: carvone, eugenol, and linalool. In contrast, starting at approximately 60 degrees C, pure cinnamaldehyde undergoes a temperature-dependent transformation to benzaldehyde under the influence of heat. Eugenol, both pure and in cinnamon oil, when added to pure cinnamaldehyde protected the aldehyde against heat destruction. The protection may due to an antioxidative action of eugenol. The possible mechanism of this effect and the significance of these findings for food chemistry and microbiology are discussed.  相似文献   

10.
Recently we reported that the release profile of cinnamaldehyde from a sugar-free chewing gum was correlated to the release of the sugar alcohol phase or was not in agreement with the log P model. The objective of this study was therefore to investigate mechanisms of cinnamaldehyde release from a sugar-free chewing gum; p-cresol (similar log P value) was also analyzed for comparison. Breath analysis of the chewing gum samples over an 8 min consumption period reported that the maximum concentration of cinnamaldehyde was 2- to 3-fold higher during the initial phase of mastication in comparison to the later phase, whereas the concentration of p-cresol was relatively constant over these two time periods. By contrast the release profile of cinnamaldehyde from a flavored gum base (no sugar alcohol phase) was constant over the 8 min consumption period and similar to the release of cresol from the flavored gum base. On the basis of tandem mass spectrometry, cinnamaldehyde was reported to react with sorbitol and generate hemiacetal reaction products that were not stable under slight alkaline conditions; it was suggested to revert back to free cinnamaldehyde and sugar alcohol in the oral cavity. The increased polarity of these transient cinnamaldehyde-sorbitol hemiacetal reaction products would result in a more rapid release rate of cinnamaldehyde than would be typically predicted based on the affinity of cinnamaldehyde for the gum base.  相似文献   

11.
The breakdown of collagenous networks with aging results in hypoactive changes in the skin. Accordingly, reviving stagnant collagen synthesis can help protect dermal homeostasis against aging. We searched for type I collagen biosynthesis-inducing substances in various foods using human dermal fibroblasts and found that cinnamon extract facilitates collagen biosynthesis. Cinnamon extract potently up-regulated both mRNA and protein expression levels of type I collagen without cytotoxicity. We identified cinnamaldehyde as a major active component promoting the expression of collagen by HPLC and NMR analysis. Since insulin-like growth factor-I (IGF-I) is the most potent stimulator of collagen biosynthesis in fibroblasts, we examined the effect of cinnamaldehyde on IGF-I signaling. Treatment with cinnamaldehyde significantly increased the phosphorylation levels of the IGF-I receptor and its downstream signaling molecules such as insulin receptor substrate-1 and Erk1/2 in an IGF-I-independent manner. These results suggested that cinnamon extract is useful in antiaging treatment of skin.  相似文献   

12.
Fresh and 3-day-old coffee pulp of the Arabica variety were analyzed for polyphenol composition followed by characterization by two different methods. The first method consisted in subjecting coffee pulp powder to direct thiolysis. For the second method, coffee pulp was subjected to successive solvent extractions, followed by thiolysis. Quantification of phenolic compounds was then achieved by high-performance liquid chromatography (HPLC) analysis of thiolysis products. Four major classes of polyphenols were identified: flavan-3-ols (monomers and procyanidins), hydroxycinnamic acids, flavonols, and anthocyanidins. Differences in concentration of procyanidins were observed between fresh and 3-day-old coffee pulp. Constitutive units were mainly epicatechin, representing more than 90% of the proanthocyanidin units, with average degrees of polymerization in the range of 3.8-9.1. Monomer to hexamer units of flavan-3-ols from fresh coffee pulp were separated by normal-phase HPLC. Molecular size of oligomeric proanthocyanidins was obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). Results obtained confirm the presence of oligomers of the flavan-3-ol (-)-epicatechin.  相似文献   

13.
A new active paper package based on the incorporation of cinnamon essential oil to solid wax paraffin as an active coating is proposed, developed, and evaluated. The antifungal activity of the active paper is tested against Rhizopusstolonifer, and the results demonstrate that 6% (w/w) of the essential oil in the active coating formulation completely inhibits the growth of R. stolonifer, whereas 4% still has strong antimicrobial activity in in vitro conditions. Then, active paper is evaluated with actual food, sliced bread, using different storage times. After 3 days of storage, almost complete inhibition is obtained with 6% cinnamon essential oil. Qualitative analysis by solid-phase microextraction and determination of cinnamaldehyde in the sliced bread were also performed and confirmed the strong correspondence between the inhibition of the mold and the amount of cinnamaldehyde in the bread.  相似文献   

14.
Chemical compositions of leaf essential oils from eight provenances of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) were compared. According to GC-MS and cluster analyses, the leaf essential oils of the eight provenances and their relative contents were classified into five chemotypes-cinnamaldehyde type, linalool type, camphor type, cinnamaldehyde/cinnamyl acetate type, and mixed type. The larvicidal activities of leaf essential oils and their constituents from the five chemotypes of indigenous cinnamon trees were evaluated by mosquito larvicidal assay. Results of larvicidal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against the fourth-instar larvae of Aedes aegypti. The LC(50) values for cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type against A. aegypti larvae in 24 h were 36 ppm (LC(90) = 79 ppm) and 44 ppm (LC(90) = 85 ppm), respectively. Results of the 24-h mosquito larvicidal assays also showed that the effective constituents in leaf essential oils were cinnamaldehyde, eugenol, anethole, and cinnamyl acetate and that the LC(50) values of these constituents against A. aegypti larvae were <50 ppm. Cinnamaldehyde had the best mosquito larvicidal activity, with an LC(50) of 29 ppm (LC(90) = 48 ppm) against A. aegypti. Comparisons of mosquito larvicidal activity of cinnamaldehyde congeners revealed that cinnamaldehyde exhibited the strongest mosquito larvicidal activity.  相似文献   

15.
The adsorption of procyanidins (condensed tannins) on cell-wall material was quantified by bringing into contact solutions of procyanidins and suspensions of cell-wall material. A model was developed on the basis of the Langmuir isotherm formulation and a factorial experimental design. The parameters that influenced the adsorption were the concentration and molecular weight of the procyanidins, the ionic strength of the solution, the temperature, and the apple cell-wall concentration. The model was applied to partitioning of procyanidins from apple between juice and mash. The parameters to be taken into account are the composition of the apples and, specifically, (i) the concentration and molecular weight of the procyanidins, (ii) their acidity and pH as a determinant of the ionic strength, and (iii) their cell-wall content and the temperature at pressing. To estimate the ability of the model to relate procyanidin concentrations in the juice to their concentration in the apple, apples of three varieties of widely different procyanidin compositions were pressed in conditions that prevent oxidation. In these conditions, yields in the juice were >80% for phenolic acids or catechin monomers but <50% for procyanidins, with the lowest rates obtained for the higher polymers in accordance with the model.  相似文献   

16.
The skin penetrating antioxidant cysteamine derivative of (-)-epicatechin as well as other thio conjugates were efficiently obtained with high yields from pine (Pinus pinaster) bark by simultaneous one pot extraction and depolymerization using water and cysteamine hydrochloride. The influence of the concentration of bark, acid, and cysteamine, as well as the reaction time on the total conversion, was studied. The total conversion into the epicatechin and catechin conjugates was as high as 47 g/kg pine bark with 1666 g cysteamine/kg bark and 28 g/kg with 166 g cysteamine/kg bark. A fast cleanup step by absorption/desorption on XAD-16 greatly facilitated further purification of the active major component. At a pilot scale, 4beta-(2-aminoethylthio)epicatechin (1) (conversion 263 g, purity 35% by reversed phase high-performance liquid chromatography/weight) was obtained from 17 kg of pine bark after simultaneous extraction/depolymerization followed by cleanup with the polymeric resin in approximately 10 h. The results show that pine (P. pinaster) bark is a suitable source of flavanols for the preparation of active thio derivatives. Conditions are given for the fast and efficient preparation of the conjugates.  相似文献   

17.
Procyanidins can bind cell wall material in raw product, and it could be supposed that the same mechanism of retention of procyanidins by apple cell walls takes place in cooked products. To evaluate the influence of cell wall composition and disassembly during cooking on the cell walls' capacity to interact with procyanidins, four cell wall materials differing in their protein contents and physical characteristics were prepared: cell wall with proteins, cell wall devoid of protein, and two processed cell walls differing by their drying method. Protein contents varied from 23 to 99 mg/g and surface areas from 1.26 to 3.16 m(2)/g. Apple procyanidins with an average polymerization degree of 8.7 were used. The adsorption of apple procyanidins on solid cell wall material was quantified using the Langmuir isotherm formulation. The protein contents in cell wall material had no effect on procyanidin/cell wall interactions, whereas modification of the cell wall material by boiling, which reduces pectin content, and drying decreased the apparent affinity and increased the apparent saturation levels when constants were expressed relative to cell wall weight. However, boiling and drying increased apparent saturation levels and had no effect on apparent affinity when the same data were expressed per surface units. Isothermal titration calorimetry indicated strong affinity (K(a) = 1.4 × 10(4) M(-1)) between pectins solubilized by boiling and procyanidins. This study higllights the impact of highly methylated pectins and drying, that is, composition and structure of cell wall in the cell wall/procyanidin interactions.  相似文献   

18.
Intake of flavanols, a subgroup of dietary polyphenols present in many fruits and vegetables, may be associated with health benefits, particularly with reducing the risk of coronary diseases. Cocoa and chocolate products are rich in flavanol monomers, oligomers, and polymers (procyanidins). This study used normal phase HPLC to detect, identify, and quantify epicatechin, catechin, total monomers, procyanidin oligomers and polymers in 14 commercially available chocolate bars. In addition, methylxanthines (theobromine and caffeine) were also quantified. Nonfat cocoa solids (NFCS) were determined both gravimetrically and by calculation from theobromine contents. The flavanol levels of 12 commonly consumed brands of dark chocolate have been quantified and correlated with % theobromine and % NFCS. Epicatechin comprised the largest fraction of total chocolate flavonoids, with the remainder being catechin and procyanidins. Calculated NFCS did not reflect epicatechin (R(2) = 0.41) or total flavanol contents (R(2) = 0.49). Epicatechin (R(2) = 0.96) was a reliable marker of total flavanols, catechin (R(2) = 0.67) to a lesser extent. All dark chocolate tested contained higher levels of total flavanols (93.5-651.1 mg of epicatechin equiv/100 g of product) than a milk or a white "chocolate" (40.6 and 0.0 mg of epicatechin equiv/100 g, respectively). The amount and integrity of procyanidins often suffer in the manufacturing of chocolate, chiefly due to oxidation and alkalinization. In this study, the labeled cocoa content of the chocolate did not always reflect analyzed levels of flavonoids. Increasingly, high % NFCS is being used commercially to reflect chocolate quality. If the flavanol content of chocolate is accepted to be a key determinant of health benefits, then continued monitoring of flavanol levels in commercially available chocolate products may be essential for consumer assurance.  相似文献   

19.
Sorghum procyanidins were characterized and quantified from two brown sorghum varieties and their processed products by normal phase HPLC with fluorescence detection. The DP of the procyanidins was determined by thiolysis. Quantification was done by using purified oligomeric and polymeric cocoa procyanidins as external standards. Sorghum procyanidins were composed mostly of high MW (DP > 10) polymers. Significant differences were observed in levels as well as distribution of the different MW procyanidins between the sorghums. Processing of the sorghum brans into cookies and bread significantly reduced the levels of procyanidins; this effect was more pronounced in the higher MW polymers. Cookies had a higher retention of procyanidins (42-84%) than bread (13-69%). Extrusion of sorghum grain resulted in an increase in the levels of procyanidin oligomers with DP /= 6. This suggests a possible breakdown of the high MW polymers to the lower MW constituents during extrusion. Processing changes not only the content of procyanidins in sorghum products but also the relative ratio of the different molecular weights.  相似文献   

20.
Blueberries and cranberries were analyzed for procyanidins using normal-phase HPLC/MS. Monomers, identified as (+)-catechin and (-)-epicatechin, and a series of oligomers were detected in blueberries, and MS data confirmed that the oligomers consisted of (epi)catechin units that were exclusively singly linked (B-type). The procyanidin "fingerprints" were similar for Tifblue and Rubel but higher than that for lowbush blueberries. In whole cranberries, (-)-epicatechin was present, along with a complex series of oligomers. Both A-type (contained only one double linkage per oligomer) and B-type oligomers were present. Two commercial cranberry juices exhibited similar procyanidin profiles, except that one contained increased quantities. There were processing effects on the procyanidin content of cranberry extract and juices when compared to those of the unprocessed fruits. Monomer, dimers, and A-type trimers were the primary procyanidins, with only trace levels of the B-type trimers and A-type tetramers and with an absence of the higher oligomers in cranberry extract and juices.  相似文献   

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