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1.
Flavonoids of nine Australian monofloral Eucalyptus honeys have been analyzed and related to their botanical origins. The mean content of total flavonoids varied from 1.90 mg/100 g of honey for stringybark (E. globoidia) honey to 8.15 mg/100 g of honey for narrow-leaved ironbark (E. crebra) honey, suggesting that species-specific differences occur quantitatively among these Eucalyptus honeys. All of the honey samples analyzed in this study have a common flavonoid profile comprising tricetin (5,7,3',4',5'-pentahydroxyflavone), quercetin (3,5,7,3',4'-pentahydroxyflavone), and luteolin (5,7,3',4'-tetrahydroxyflavone), which, together with myricetin (3,5,7,3',4',5'-hexahydroxyflavone) and kaempferol (3,5,7,4'-tetrahydroxyflavone), were previously suggested as floral markers for European Eucalyptus honeys. Thus, flavonoid analysis could be used as an objective method for the authentication of the botanical origin of Eucalyptus honeys. Moreover, species-specific differences can also be found in the composition of honey flavonoid profiles. Among these honeys, bloodwood (E. intermedia) honey contains myricetin and tricetin as the main flavonoid compounds, whereas there is no myricetin detected in yapunyah (E. ochrophloia), narrow-leaved ironbark (E. crebra), and black box (E. largiflorens) honeys. Instead, these types of Eucalyptus honeys may contain tricetin, quercetin, and/or luteolin as their main flavonoid compounds. Compared to honeys from other geographical origins, the absence or minor presence of propolis-derived flavonoids such as pinobanksin, pinocembrin, and chrysin in Australian honeys is significant. In conclusion, these results demonstrate that a common flavonoid profile exists for all of the Eucalyptus honeys, regardless of their geographical origins; the individual species-specific floral types of Eucalyptus honey so common in Australia could be possibly differentiated by their flavonoid profile differences, either qualitatively or quantitatively or both.  相似文献   

2.
European Eucalyptus honeys showed a common and characteristic HPLC profile in which the flavonoids myricetin (3,5,7,3',4', 5'-hexahydroxyflavone), tricetin (5,7,3',4',5'-pentahydroxyflavone), quercetin (3,5,7,3',4'-pentahydroxyflavone), luteolin (5,7,3', 4'-tetrahydroxyflavone), and kaempferol (3,5,7, 4'-tetrahydroxyflavone) were identified. Their contents, and relative amounts, in the analyzed honey samples were quite constant and supported their floral origin. In addition, ellagic acid and the propolis-derived flavonoids pinobanksin, pinocembrin, and chrysin were detected in most samples. The contents of these nonfloral phenolics were much more variable as could be expected for their propolis origin. Myricetin, tricetin, and luteolin had not been identified as floral markers in any other honey sample previously analyzed in our laboratory (chestnut, citrus, rosemary, lavender, acacia, rapeseed, sunflower, heather, lime tree, etc.) or reported in the literature, suggesting that these could be useful markers. Only in some individual heather samples produced in Portugal has tricetin previously been detected in minor amounts. These samples, however, were contaminated with Eucalyptus as revealed by their pollen analysis and the lack of tricetin or their glycosides in heather floral nectar. It remains to be established if myricetin, tricetin, and luteolin originate from Eucalyptus floral nectar where the corresponding glycosides should be present.  相似文献   

3.
Acacia confusa Merr. (Leguminosae) is traditionally used as a medicinal plant in Taiwan. In the present study, anti-inflammatory activity of extracts from the heartwood of A. confusa were investigated for the first time. Results demonstrated that ethanolic extracts of A. confusa heartwood strongly suppressed NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Among all fractions derived from ethanolic extracts, the EtOAc fraction exhibited the best inhibitory activity. Following column chromatography and reverse-phase high-performance liquid chromatography, 13 specific phytocompounds including 5 new flavonoids (i.e., 7,8,3',4'-tetrahydroxy-4-methoxyflavan-3-ol, 7,8,3',4'-tetrahydroxyflavone, 7,8,3'-trihydroxy-3,4'-dimethoxyflavone, 7,3',4'-trihydroxyflavone, and 7,3',4'-trihydroxy-3-methoxyflavone) were isolated and identified from the EtOAc fraction. In addition, melanoxetin (3,7,8,3',4'-pentahydroxyflavone), a major compound in the EtOAc fraction, markedly suppressed LPS-induced NO and prostaglandin E 2 (PGE 2) production. Moreover, melanoxetin completely suppressed gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) at 50 and 100 microM, respectively. This is the first report to identify the inhibitory bioactivities of melanoxetin on iNOS and COX-2.  相似文献   

4.
Honey as rich source of enzymatic and nonenzymatic antioxidants serves as health-promoting nutrient in the human body. Here, we present the first time a comparative study of nutritional profiles (e.g., acidities, sugar, organic acid profile, total polyphenolic, flavonoid content) for different unifloral, multifloral honeys and their fermented products, in correlation with their antioxidant activity. Additionally, an optimized method for HPLC separation of organic acids from honey was established. The total phenolic content of honey samples varied widely among the honey types compared to fermented products. High amounts of total flavonoids were quantified in heather honey, followed by raspberry, multifloral, black locust, and linden honey. A positive correlation between the content of polyphenols, flavonoids, and antioxidant activity was observed in honey samples. After fermentation, the flavonoid content of dark honey fermented products decreased significantly. Black locust and linden honeys are more suitable for fermentation because the decrease in antioxidant substances is less pronounced.  相似文献   

5.
To select and establish floral biomarkers of the botanical origin of Diplotaxis tenuifolia honeys, the flavonoids and glucosinolates present in bee-deposited nectar collected from hive combs (unripe honey) and mature honey from the same hives fron which the unripe honey samples were collected were analyzed by LC-UV-PAD-ESI-MS(n). Glycosidic conjugates of the flavonols quercetin, kaempferol, and isorhamnetin were detected and characterized in unripe honey. D. tenuifolia mature honeys contained the aglycones kaempferol, quercetin, and isorhamnetin. The differences between the phenolic profiles of mature honey and freshly deposited honey could be due to hydrolytic enzymatic activities. Aliphatic and indole glucososinolates were analyzed in unripe and mature honeys, this being the first report of the detection and characterization of glucosinolates as honey constituents. Moreover, these honey samples contained different amounts of propolis-derived flavonoid aglycones (1765-3171 μg/100 g) and hydroxycinnamic acid derivatives (29-1514 μg/100 g). Propolis flavonoids were already present in the freshly deposited nectar, showing that the incorporation of these compounds to honey occurs at the early steps of honey production. The flavonoids quercetin, kaempferol, and isorhamnetin and the glucosinolates detected in the samples could be used as complementary biomarkers for the determination of the floral origin of Argentinean Diplotaxis honeys.  相似文献   

6.
With the objective of finding floral markers for the determination of the botanical origin of acacia (robinia) honey, the phytochemicals present in nectar collected from Robinia pseudacacia flowers were analyzed by high-performance liquid chromatography-tandem mass spectrometry. Eight flavonoid glycosides were detected and characterized as kaempferol combinations with rhamnose and hexose. Acacia honey produced in the same location where the nectar was collected contained nectar-derived kaempferol rhamnosides. This is the first time that flavonoid glycosides have been found as honey constituents. Differences in the stability of nectar flavonoids during honey elaboration and ripening in the hive were shown to be due to hydrolytic enzymatic activity and to oxidation probably related to hydrogen peroxide (glucose-oxidase) activity. Acacia honeys contained propolis-derived flavonoid aglycones (468-4348 microg/100 g) and hydroxycinnamic acid derivatives (281-3249 microg/100 g). In addition, nectar-derived kaempferol glycosides were detected in all of the acacia honey samples analyzed (100-800 microg/100 g). These flavonoids were not detected in any of the different honey samples analyzed previously from different floral origins other than acacia. Finding flavonoid glycosides in honey related to floral origin is particularly relevant as it considerably enlarges the number of possible suitable markers to be used for the determination of the floral origin of honeys.  相似文献   

7.
Manuka honey from New Zealand is often considered to be a medicinal product of special value due to its high level of antimicrobial activity. Therefore, the distinct authentication of its botanical origin is of great importance. Aside from the common pollen analysis, it is in this respect particularly the analysis of the phenolic acids, flavonoids, and norisoprenoids that is described as useful. In the present study, numerous manuka honeys were analyzed by UPLC-PDA-MS/MS after solid-phase extraction and compared to other kinds of honey to define marker substances characteristic for manuka honeys. The PDA profiles obtained differed markedly from each other so that the individual honey samples could be assigned to three groups. For the honeys of group 1 the comparably high concentrations of 4-hydroxybenzoic acid, dehydrovomifoliol, and benzoic acid proved to be typical, whereas the profiles of group 2 showed high kojic acid and 2-methoxybenzoic acid intensities. The manuka honeys of group 3, on the other hand, yielded high amounts of syringic acid, 4-methoxyphenyllactic acid, and methyl syringate. Furthermore, the comprehensive comparison of manuka honeys to other unifloral honeys revealed that especially kojic acid, 5-methyl-3-furancarboxylic acid, leptosin, unedone, 2-methoxybenzoic acid, 4-methoxyphenyllactic acid, 3-hydroxy-1-(2-methoxyphenyl)penta-1,4-dione, and methyl syringate were useful for distinguishing manuka honeys from the other kinds of investigated honeys. Moreover, kojic acid, unedone, 5-methyl-3-furancarboxylic acid, 3-hydroxy-1-(2-methoxyphenyl)penta-1,4-dione, and lumichrome were identified in manuka honey for the first time.  相似文献   

8.
Phytochemical investigations of blue plumbago ( Plumbago auriculata Poir. syn. Plumbago capensis Thunb.) flowers have led to the isolation of six new anthocyanins based on three new anthocyanidins with 5,7-dimethoxylated A-rings. Their structures were identified by 2D nuclear magnetic resonance and high-resolution mass spectrometry as the 3-O-β-galactopyranosides (1,2,4) and 3-O-α-rhamnopyranosides (3,5,6) of 5,7-dimethyldelphinidin, 5,7-dimethylpetunidin, and 5,7-dimethylmalvidin. Identification of 1-6 implies new structures for the previously reported anthocyanidins pulchellidin, europinidin, and capensinidin to be 5,7-dimethoxy-3,3',4',5'-tetrahydroxyflavylium, 5,7,3'-trimethoxy-3,4',5'-trihydroxyflavylium, and 5,7,3',5'-tetramethoxy-3,4'-dihydroxyflavylium cations, respectively. The anthocyanins (0.4 mg/g flowers) were accompanied by the dihydroflavonol taxifolin 3'-O-β-glucopyranoside (1.4 mg/g) and the flavonols 5-methylquercetin 3-O-α-rhamnopyranoside (8.8 mg/g) and 5-methylquercetin (0.4 mg/g). The anthocyanins 1-6 are the first reported natural anthocyanins with no free hydroxyl groups in their 5- and 7-positions on their A-rings. They have thus no possibility of forming the tautomeric quinonoidal bases (anhydrobases), which are related to the free hydroxyl groups in the 5- and 7-positions of previously reported anthocyanins. The genes behind the 5,7-dimethoxylated anthocyanins might be useful for making anthocyanins with special properties (colors, etc.).  相似文献   

9.
HPLC-DAD-MS/MS chromatograms of thistle (Galactites tomentosa Moench) unifloral honeys, previously selected by sensory evaluation and melissopalynological analysis, showed high levels of two compounds. One was characterized as phenyllactic acid, a common acid found in honeys, but the other compound was very unusual for honeys. This compound was extracted from honey with ethyl acetate and purified by SPE using C(18), SiOH, and NH(2) phases. Its structure was elucidated on the basis of extensive 1D and 2D NMR experiments as well as HPLC-MS/MS and Q-TOF analysis, and it was identified as lumichrome (7,8-dimethylalloxazine). Lumichrome is known to be the main product of degradation obtained in acid medium from riboflavin (vitamin B(2)), and this is the first report of the presence of lumichrome in honeys. Analysis of the G. tomentosa raw honey and flowers extracts confirmed the floral origin of this compound. The average amount of lumichrome in thistle honey was 29.4 ± 14.9 mg/kg, while phenyllactic acid was 418.6 ± 168.9 mg/kg. Lumichrome, along with the unusual high level of phenyllactic acid, could be used as a marker for the botanical classification of unifloral thistle (G. tomentosa) honey.  相似文献   

10.
5,7,3',4'-Tetramethoxyflavone (TMF), one of the major polymethoxyflavones (PMFs) isolated from Kaempferia parviflor , has been reported possessing various bioactivities, including antifungal, antimalarial, antimycobacterial, and anti-inflammatory activities. Although several studies on the TMF have been reported, the information about the metabolism of TMF and the structures of TMF metabolites is still not yet clear. In this study, an isotope-labeling method was developed for the identification of TMF metabolites. Three isotope-labeled TMFs (5,7,3',4'-tetramethoxy[3'-D(3)]flavone, 5,7,3',4'-tetramethoxy[4'-D(3)]flavone, and 5,7,3',4'-tetramethoxy[5,4'-D(6)]flavone) were synthesized and administered to rats. The urine samples were collected, and the main metabolites were monitored by ultrahigh-performance liquid chromatography-electrospray ionization-mass spectrometry. Five TMF metabolites were unambiguously identified as 3'-hydroxy-5,7,4'-trimethoxyflavone, 7-hydroxy-5,3',4'-trimethoxyflavone sulfate, 7-hydroxy-5,3',4'-trimethoxyflavone, 4'-hydroxy-5,7,3'-trimethoxyflavone, and 5-hydroxy-7,3',4'-trimethoxyflavone.  相似文献   

11.
The acid dissociation and ferric stability constants for complexation by the flavonoids 3-hydroxyflavone (flavonol), 5,7-dihydroxyflavone (chrysin), and 3',4'-dihydroxyflavone in 50:50 (v/v) ethanol/water are determined by pH potentiometric and spectrophotometric titrations and the linear least-squares curve-fitting program Hyperquad. Over the entire range of pH and reagent concentrations spanning the titration experiments, the stoichiometry for iron-flavonoid complex formation was 1:1 for all three flavonoids examined. The three flavonoids were chosen for their hydroxy substitution pattern, with each possessing one of the three most commonly suggested sites for metal binding by the flavonoids. On the basis of the calculated stability constants, the intraflavonoid-binding site competition is illustrated as a function of pH via speciation curves. The curves indicate that the binding site comprised of the 3',4'-hydroxy substitutions, the catecholic site, is most influential for ferric complexation at the physiological pH of 7.4. The possibility for antioxidant activity by flavonoid chelation of ferric iron in the presence of other competitive physiological complexing agents is demonstrated through additional speciation calculations.  相似文献   

12.
Analysis of organic acids in strawberry-tree (Arbutus unedo) honey showed the presence of an unknown acid as the main constituent. This compound was isolated and identified as homogentisic acid (2, 5-dihydroxyphenylacetic acid) by MS and NMR techniques. Its average content in honey was 378 +/- 92 mg/kg. Analysis of nectar confirmed the floral origin of the compound found in honey. Since this acid was not detected in any of the different monofloral honeys, it could be used as a marker of strawberry-tree (A. unedo) honey.  相似文献   

13.
Tomatoes ( Lycopersicon esculentum Mill.) have been recognized as an important source of dietary flavonoids because of a high consumption worldwide. The qualitative and quantitative flavonoid compositions of assorted tomato cultivars including individual quantitative contributions of the five most significant flavonoids have been determined in this work. The dihydrochalcone phloretin 3',5'-di-C-beta-glucopyranoside and the flavonol quercetin 3-O-(2'-O-beta-apiofuranosyl-6'-O-alpha-rhamnopyranosyl-beta-glucopyranoside) were identified for the first time in Solanaceae spp. and found to be among the main flavonoids in all cultivars. Phloretin 3',5'-di-C-glc is the first C-glycoside identified in tomatoes and also the first dihydrochalcone from this species. In addition, chalconaringenin, kaempferol 3-rutinoside, and quercetin 3-rutinoside (rutin), though previously reported to occur in tomato, were fully characterized by extensive use of 2D NMR techniques and high-resolution LCMS. The total flavonoid content of different tomato types varied from 4 to 26 mg 100 (-1) g FW with chalconaringenin as the predominant compound comprising 35 to 71% of the total flavonoid content. The individual quantities of quercetin 3-O-(2'- O-beta-apiofuranosyl-6'- O-alpha-rhamnopyranosyl-beta-glucopyranoside) and phloretin 3',5'-di-C-beta-glucopyranoside was similar to that of rutin in several cultivars.  相似文献   

14.
In the present study, the ethanolic extracts from the heartwood of Acacia confusa, a species indigenous to Taiwan, exhibit strong antioxidant effects. Among all the fractions from ethanolic extracts of heartwood, the EtOAc soluble fraction exhibits the best antioxidant activity. The 80% 1,1-diphenyl-2-picrylhydrazyl radical inhibitory activity by the EtOAc extract was observed at a concentration of 5 mug/mL, and at the same dosage there was a similar free radical scavenging activity for (-)-ascorbic acid and (+)-catechin, both of which are well-known antioxidants. In addition, the EtOAc extract also protects PhiX174 supercoiled DNA against strand scission induced by hydroxyl radical. Furthermore, following by column chromatography and reverse-phase high-performance liquid chromatorgrapy, 10 pure phenolic compounds, including three major antioxidants (3,7,8,3',4'-pentahydroxyflavone, 7,8,3',4'-tetrahydroxy-3-methoxyflavone, and 3,4,2',3',4'-pentahydroxy-trans-chalcone) and a new flavonoid (3,7,8,3'-tetrahydroxy-4'-methoxyflavone), were isolated from the ethanolic extracts of A. confusa heartwood.  相似文献   

15.
Honey adulterations can be carried out by addition of inexpensive sugar syrups, such as high fructose corn syrup (HFCS) and inverted syrup (IS). Carbohydrate composition of 20 honey samples (16 nectar and 4 honeydew honeys) and 6 syrups has been studied by GC and GC-MS in order to detect differences between both sample groups. The presence of difructose anhydrides (DFAs) in these syrups is described for the first time in this paper; their proportions were dependent on the syrup type considered. As these compounds were not detected in any of the 20 honey samples analyzed, their presence in honey is proposed as a marker of adulteration. Detection of honey adulteration with HFCS and IS requires a previous enrichment step to remove major sugars (monosaccharides) and to preconcentrate DFAs. A new methodology based on yeast (Saccharomyces cerevisiae) treatment has been developed to allow the detection of DFAs in adulterated honeys in concentrations as low as 5% (w/w).  相似文献   

16.
Cholinesterases are key enzymes that play important roles in cholinergic transmission. Nine flavonoids displaying cholinesterase inhibitory activity were isolated from the root bark of Morus lhou L., a cultivated edible plant. The isolated compounds were identified as a new flavone (1), 5'-geranyl-5,7,2',4'-tetrahydroxyflavone (2), kuwanon U (3), kuwanon E (4), morusin (5), morusinol (6), cyclomorusin (7), neocyclomorusin (8), and kuwanon C (9). All compounds apart from compound 6 inhibited cholinesterase enzyme in a dose-dependent manner with K(i) values ranging between 3.1 and 37.5 μM and between 1.7 and 19.1 μM against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes, respectively. The new compound was charactierized as 5'-geranyl-4'-methoxy-5,7,2'-trihydroxyflavone (1). It showed the most potent inhibitory activity (K(i) = 3.1 μM for AChE, K(i) = 1.74 μM for BChE). Lineweaver-Burk and Dixon plots and their secondary replots indicated that flavones (5-9) with prenyl substitution on C-3 were noncompetitive inhibitors, whereas those unsubstituted (1-4) at C-3 were mixed inhibitors of both AChE and BChE. In conclusion, this is the first study to demonstrate that alkylated flavonoids of M. lhou have potent inhibitory activities against AChE and BChE.  相似文献   

17.
As a preliminary study, we have found that honey from manuka (Leptospermum scoparium) in New Zealand inhibits myeloperoxidase (MPO) activity. In this study, using a chromatographic technique, we isolated two active compounds for MPO-inhibition from manuka honey. One is methyl syringate (MSYR), and the other was identified as a novel glycoside of MSYR, methyl syringate 4-O-β-D-gentiobiose, which has been named "leptosin" after the genus Leptospermum . The amount of the glycoside ranged from 0.2 to 1.2 μmol/g honey. Leptosin was only found in honeys from the Oceania region, and abundantly in manuka honey including jelly bush honey from Leptospermum polygalifolium in Australia. Therefore, leptosin may be a good chemical marker for manuka honey. Interestingly, the concentration of leptosin in manuka honey was positively correlated with the unique manuka factor (UMF) value, which is expressed as phenol equivalents of its bactericidal activity.  相似文献   

18.
The free amino acid content of 61 honey samples from Estonia has been determined by HPLC-UV with precolumn derivatization with diethyl ethoxymethylenemalonate. Analyzed samples were seven types of unifloral honeys and polyfloral honeys. The main amino acids found in Estonian honeys were proline and phenylalanine. The resulting data have been analyzed by t test and principal component analysis (PCA). t Test revealed that some amino acids (alpha-alanine, beta-alanine, asparagine, gamma-aminobutyric acid, glutamine, glycine, histidine, ornithine, phenylalanine, proline, serine, and tryptophan) are more potent for assigning honey botanical origin than others. PCA enabled differentiation of some honey types by their botanical origin. In the space of the two first principal components, heather honeys form a cluster that is clearly separable from, for example, polyfloral honeys. It is concluded that analysis of the free amino acid profile may serve as a useful tool to assess the botanical origin of Estonian honeys.  相似文献   

19.
An ethyl acetate-soluble extract of Chorizanthe diffusa was found to exhibit significant antioxidant activity, as judged by scavenging stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals and inhibition of 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced free radical formation with cultured HL-60 cells. Bioassay-directed fractionation of this extract using the DPPH antioxidant assay as a monitor led to the isolation of five structurally related flavonoids (1-5), including the novel compound 5,8,3',4',5'-pentahydroxy-3, 7-dimethoxyflavone (1). Isolates 1-5 demonstrated varying degrees of antioxidant or antimutagenic activity. Two of the compounds, 5,7,3', 4'-tetrahydroxy-3-methoxyflavone (2) and quercetin (4), were subsequently found to inhibit carcinogen-induced preneoplastic lesions in a mouse mammary organ culture model. Inhibitory activity of this type is known to correlate with cancer chemopreventive effects in full-term models of tumorigenesis.  相似文献   

20.
High-performance liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, approximately 20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6' '-O-malonate (39), formononetin 7-O-beta-D-glucoside 6' '-O-malonate (40), biochanin A 7-O-beta-D-glucoside 6' '-O-malonate (41), trifoside 6' '-O-malonate (42), irilone 4'-O-beta-D-glucoside 6' '-O-malonate (43), pratensein 7-O-beta-D-glucoside 6' '-O-malonate (44), isoquercitrin 6' '-O-malonate (45), and 3-methylquercetin 7-O-beta-D-glucoside 6' '-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42-46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.  相似文献   

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