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1.
A series of per-O-methylated flavonoid di- and tri-glycosides, linked with 1-2 and/or 1-6 glycosidic bonds between sugar rings that were isolated from different plant materials were analyzed. It was demonstrated that the fragmentation behavior of permethylated flavonoid glycosides is dependent on the glycosidic bond placement between sugars. Y(n) type fragment ions, created after glycosidic bond cleavage with oxygen retention on sugar at the reducing end for permethylated compounds, were observed in the normal and linked-scan mass spectra recorded for alpha(1-2) bonded conjugates of flavonoid di- and tri-glycosides. Moreover, for alpha (1-6) linked glycosides, Y fragments created after rearrangement and elimination of internal sugar residues were observed in addition to Y(n) type ions, but these fragment ions were not registered in normal desorption ionization spectra. This second type of fragmentation was also reported previously in collision-induced dissociation tandem mass spectrometry (CID MS/MS) spectra of some oligosaccharides and flavonoid glycosides, but their presence was independent of the glycosidic bonds placement between sugar rings.  相似文献   

2.
A bioguided isolation of an aqueous extract of fennel waste led to the isolation of 12 major phenolic compounds. Liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry (LC/UV/APCI-MS) combined with spectroscopic methods (NMR) was used for compound identification. Radical scavenging activity was tested using three methods: DPPH*, superoxide nitro-blue tetrazolium hypoxanthine/xanthine oxidase, and *OH/luminol chemiluminescence. In addition to products described in the literature, eight antioxidant compounds were isolated and identified for the first time in fennel: 3-caffeoylquinic acid, 4-caffeoylquinic acid, 1,5-O-dicaffeoylquinic acid, rosmarinic acid, eriodictyol-7-O-rutinoside, quercetin-3-O-galactoside, kaempferol-3-O-rutinoside, and kaempferol-3-O-glucoside. The structures of eriodictyol-7-O-rutinoside and quercetin-3-O-glucuronide were completely elucidated by two-dimensional NMR experiments. The isolated compounds exhibited a strong antiradical scavenging activity, which may contribute to the interpretation of the pharmacological effects of fennel.  相似文献   

3.
Fennel (Foeniculum vulgare Mill.) is a typical aromatic plant of the Mediterranean area, long used as a medicinal and spice herb. Fennel is also well-known for its essential oil, which has been extensively studied for many years owing to its commercial importance. In this work, the antioxidant activity and the total phenolic and flavonoid contents, as well as the quantitative determination of individual flavonoids and phenolic acids of wild, edible, and medicinal fennel from different Mediterranean countries, have been determined. The antioxidant activity was measured as the free radical (DPPH), hydroxyl radical, and superoxide anion scavenging activities. Wild fennel was found to exhibit a radical scavenging activity, as well as a total phenolic and total flavonoid content, higher than those of both medicinal and edible fennels.  相似文献   

4.
Volatile oil extracts of fennel seeds (Foeniculum vulgare Mill.) and thyme leaves (Thymus vulgaris L.) were obtained by simultaneous distillation-extraction (SDE) and supercritical fluid extraction (SFE) and analyzed by gas chromatography-mass spectrometry (GC-MS). In general, fennel oil extracted by SDE and SFE showed similar compositions, with trans-anethole, estragole, and fenchone as the main components. In contrast, thymol and p-cymene, the most abundant compounds in thyme leaves, showed big differences, with generally higher amounts of monoterpenes obtained by SDE. However, in this case, the differences between the extracts were higher. Key odorants of fennel seeds determined by gas chromatography-olfactometry (GC-O) showed similar patterns when applying SDE and SFE. trans-Anethole (anise, licorice), estragole (anise, licorice, sweet), fenchone (mint, camphor, warm), and 1-octen-3-ol (mushroom) were the most intense odor compounds detected in fennel extracts. Thymol and carvacrol, with oregano, thyme, and spicy notes, were identified as key compounds contributing to the aroma of thyme leaves.  相似文献   

5.
The fruits of the date palm (Phoenix dactylifera) are consumed throughout the world and are an important part of the diet in the Middle East. Dates at the rutab and tamar maturity and ripening stages contain a wide array of phenolic antioxidants, but little is known about the composition of phenolic compounds in dates at the khalal stage of ripening. In the current study, the flavonoid glycoside and procyanidin compositions of dates of the cultivar Deglet Noor harvested at the khalal stage of maturity were characterized using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI/MS/MS). Procyanidin oligomers through decamers were identified in extracts of these dates. Higher molecular weight polymers, undecamers through heptadecamers, were also apparent from mass spectra. Thirteen flavonoid glycosides of luteolin, quercetin, and apigenin, 19 when considering isomeric forms, were also identified. Mass spectra indicate that both methylated and sulfated forms of luteolin and quercetin are present as mono-, di-, and triglycosylated conjugates whereas apigenin is present as only the diglycoside. LC-ESI/MS/MS spectra indicate that quercetin and luteolin formed primarily O-glycosidic linkages whereas apigenin is present as the C-glycoside.  相似文献   

6.
Rooibos tea originates from the leaves and stems of the indigenous South African plant Aspalathus linearis. It has gained much attention for clinical purposes in the case of nervous tension, allergies (dermatitis), and various indigestive problems. Recently, antioxidative activity was also attributed to the tea on the basis of its flavonoid content. Therefore, an HPLC method using a C(18) reversed phase column was developed for the assay of 10 flavonoids in aqueous and methanolic infusions. Main compounds determined were the dihydrochalcone aspalthin, rutin, and orientin, and their content was in the range of 1.0 to 1.3 mg/g. The identity of detected flavonoids was confirmed by comparing their retention times and UV and MS spectra with those of corresponding standards. In addition, the MS analysis showed evidence of the presence of other compounds such as nothofagin, dihydroisoorientin, and dihydroorientin.  相似文献   

7.
以9个民勤地方茴香品种为试验材料,研究了不同种植密度对不同茴香品种株高、茎粗、分枝数、结实花序数、千粒重和产量的影响,确定不同民勤地方茴香品种的最佳密度。结果表明,大粒高秆晚熟茴香和割茬茴香的最适种植密度均为13.35万株/hm2,产量分别为3 819.05、3 990.48 kg/hm2;东润大粒高秆晚熟茴香、大粒高秆早熟茴香、小粒高秆晚熟茴香和小粒高秆早熟茴香的最适种植密度均为14.85万株/hm2,产量分别为 4 361.90、5 238.10、4 695.24、3 980.95 kg/hm2;酒泉小粒高秆早熟茴香、东湖大粒高秆早熟茴香和大粒矮秆早熟茴香的最适种植密度为16.50万株/hm2,产量分别为5 228.57、4 180.95、4 352.38 kg/hm2。  相似文献   

8.
The phenolic composition of heartwood from Robinia pseudoacacia, commonly known as false acacia, before and after toasting in cooperage was studied by HPLC-DAD and HPLC-DAD/ESI-MS/MS. A total of 41 flavonoid and nonflavonoid compounds were identified, some tentatively, and quantified. Seasoned acacia wood showed high concentrations of flavonoid and low levels of nonflavonoid compounds, the main compounds being the dihydroflavonols dihydrorobinetin, fustin, tetrahydroxy, and trihydroxymethoxy dihydroflavonol, the flavonol robinetin, the flavanones robtin and butin, and a leucorobinetinidin, none of which are found in oak wood. The low molecular weight (LMW) phenolic compounds present also differed from those found in oak, since compounds with a β-resorcylic structure, gallic related compounds, protocatechuic aldehyde, and some hydroxycinnamic compounds are included, but only a little gallic and ellagic acid. Toasting changed the chromatographic profiles of extracts spectacularly. Thus, the toasted acacia wood contributed flavonoids and condensed tannins (prorobinetin type) in inverse proportion to toasting intensity, while LMW phenolic compounds were directly proportional to toasting intensity, except for gallic and ellagic acid and related compounds. Even though toasting reduced differences between oak and acacia, particular characteristics of this wood must be taken into account when considering its use in cooperage: the presence of flavonoids and compounds with β-resorcylic structure and the absence of hydrolyzable tannins.  相似文献   

9.
An UHPLC-PDA-ESI/HRMS/MS(n) profiling method was used for a comprehensive study of the phenolic components of red mustard greens ( Brassica juncea Coss variety) and identified 67 anthocyanins, 102 flavonol glycosides, and 40 hydroxycinnamic acid derivatives. The glycosylation patterns of the flavonoids were assigned on the basis of direct comparison of the parent flavonoid glycosides with reference compounds. The putative identifications were obtained from tandem mass data analysis and confirmed by the retention time, elution order, and UV-vis and high-resolution mass spectra. Further identifications were made by comparing the UHPLC-PDA-ESI/HRMS/MS(n) data with those of reference compounds in the polyphenol database and in the literature. Twenty-seven acylated cyanidin 3-sophoroside-5-diglucosides, 24 acylated cyanidin 3-sophoroside-5-glucosides, 3 acylated cyanidin triglucoside-5-glucosides, 37 flavonol glycosides, and 10 hydroxycinnamic acid derivatives were detected for the first time in brassica vegetables. At least 50 of them are reported for the first time in any plant materials.  相似文献   

10.
"Rocket" is a collective name used to term some species within the Eruca and Diplotaxis genera, whose leaves are characterized by a more or less pungent taste. Different approaches have been carried out to differentiate both genera that have similar leaf morphologies. Following our research in flavonoid profiling of the Brassicaceae family using high-performance liquid chromatography/ultraviolet-diode array detection/electrospray ionization mass spectroemtry, we have investigated Eruca vesicaria and Diplotaxis tenuifolia leaf samples as new ingredients of fresh salads. The MS/MS study allowed the identification of new naturally occurring quercetin mono- and diacyl-tri-O-glucosides and the elucidation of the flavonoid glycosylation and acylation patterns. Important differences between flavonoid profiles of E. vesicaria and D. tenuifolia were observed. E. vesicaria contained kaempferol derivatives as principal compounds whereas D. tenuifolia instead accumulated quercetin derivatives. The exhaustive study of the profiling of these species could help further studies concerning the bioavailability of these flavonoids for epidemiological or clinical intervention studies because these species have considerable potential as healthy leafy salads because of the bioactive phytochemicals.  相似文献   

11.
Abstract

In this study, the effect of different levels of nitrogen (N) and potassium (K) fertilizers on vegetative fresh bulb yield, quality and biochemical attributes of sweet fennel were investigated in spring 2017 and 2018. Treatments consisted of 0, 50, 100, or 150?kg ha?1 of N and K in a randomized complete block design with three replications. Results showed that, the bulb fresh yield increased with application of N and K in both years, while the higher level of K had significant adverse effect in first year. Results also showed that sweet fennel bulb treated by N and K exhibited higher vitamin C, total phenols and flavonoid contents, and antioxidant capacity, especially in first year. In both years, alone or combined application of N and K increased total soluble solids (TSS) content as compared to control, and this effect was more pronounced in 2017 season. Macronutrient contents of bulb including magnesium (Mg), phosphorus (P), K, N, and calcium (Ca) were significantly enhanced by NK fertilizer, however an alone application of K decreased Ca and Mg nutrient contents. Therefore, to improve fresh bulb yield, quality and antioxidant capacity in sweet fennel, 150?kg ha?1 K and 100?kg ha?1 N is recommended.  相似文献   

12.
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13.
Polyphenolic content, flavonoid content, and free flavonoid aglycon compounds were determined in 11 samples of Spanish honeybee-collected pollen. Adequate extraction was obtained with ethyl acetate in the determination of free flavonoid aglycon. Recovery (>83.6%), within-run repeatability (<6.67%), between-run reproducibility (<8.73%), and detection limits (1.4--1.9 mg/kg) were satisfactory. A total of 15 compounds were separated with gradient reversed phase HPLC, and 13 were identified and quantified using diode array detector. The most predominant compounds were flavonoid glycosides, mainly flavonols. Eighty-two percent of the samples contained at least 14 of the phenolic components, primarily rutin, quercetin, myricetin, and trans-cinnamic acid as free aglycons. Total phenols were present, at levels of >0.85 g/100 g in the form of non-tannins, and flavonoids of >0.35 g/100 g, using spectrophotometric procedures. Rutin is the best identifier of free flavonoid aglycon compounds. A minimum quantity of 200 mg/kg of rutin is suggested to guarantee the nutritional and biological properties required in the European market.  相似文献   

14.
This study investigated the phenolic composition and antioxidant activities of aqueous infusions from wild-grown caper (Capparis spinosa L.) and sea fennel (Crithmum maritimum L.) from the Dalmatia region (Croatia) before and after their submission to an in vitro digestion process. HPLC/UV-vis-DAD/ESI-MS analysis of the caper infusion identified rutin, kaempferol 3-O-rutinoside, and isorhamnetin 3-O-rutinoside as dominant flavonoids in the matrix together with a series of cinnamoylquinic acid derivatives, whereas in the sea fennel aqueous infusion chlorogenic acid (5-caffeoylquinic acid), its isomers, and higher derivatives were identified as almost the sole class of phenolics. Both infusions exhibited good and dose-dependent antioxidant activity before in vitro digestion by the DPPH method, the β-carotene bleaching method, and copper-induced oxidation of human LDL. The amount of total phenolics (Folin-Ciocalteu assay) strongly decreased in digested samples (from 3.0 and 2.2% in caper and sea fennel infusions, respectively, to <1.0%), as did their antioxidant activity as measured by the three aforesaid methods. The results showed that the majority of phenolic compounds detected in both infusions are not stable under applied simulated gastrointestinal conditions and that the stability of these secondary metabolites strongly depends on the nature of the corresponding matrix.  相似文献   

15.
The aim of this study was to evaluate the absorption of a citrus flavonoid, naringin, as its glycosylated form. Six healthy volunteers (three males and three females) were studied. After a single oral administeration of 500 mg of naringin, intact naringin was isolated from 2-4 h urine. Isolated naringin was identified by the LC/electrospray ionization mass spectrometry (ESI-MS), MS/MS, and MS/MS/MS techniques. The cumulative urinary excretion of naringin and its metabolites (naringenin and naringenin glucuronides) was determined by HPLC for 0-24 h. Approximately 0.02% of the administered dose was recovered in urine as unchanged naringin, whereas urinary recoveries of naringenin and naringenin glucuronides were approximately 0.4 and 3.6% of the administered dose, respectively. It was concluded that trace amounts of orally administered naringin can be absorbed as the glycoside. However, it is not clear whether the glycoside is cleaved before or after absorption to generate naringenin.  相似文献   

16.
Horse chestnut extracts are widely used in pharmacy and cosmetic industries. The main active constituents are saponins of oleane type, but seeds of horse chestnut also contain flavonoids, being glycosides of quercetin and kaempferol. Their contribution to the overall activity of the extracts was not clear. In the present work, the main flavonoids from horse chestnut seeds were isolated and their structures established with spectral methods. Seven glycosides were isolated, out of which six ( 2, 3, 4, 7, 11, 13) were previously reported and one ( 9) was identified as a new tamarixetin 3- O- [beta- d-glucopyranosyl(1-->3)]- O-beta- d-xylopyranosyl-(1-->2)- O-beta- d-glucopyranoside. The structures of three additional compounds 1, 10, and 12, not previously reported, were deduced on the basis of their LC-ESI/MS/MS fragmentation characteristics. A new ultraperformance liquid chromatographic (UPLC) method has been developed for profiling and quantitation of horse chestnut flavonoids. The method allowed good separation over 4.5 min. Thirteen compounds could be identified in the profile, out of which di- and triglycoisdes of quercetin and kaempferol were the dominant forms and their acylated forms occurred in just trace amounts. The total concentration of flavonoids in the powdered horse chestnut seed was 0.88% of dry matter. The alcohol extract contained 3.46%, and after purification on C18 solid phase, this concentration increased to 9.40% of dry matter. The flavonoid profile and their content were also measured in the horse chestnut wastewater obtained as byproduct in industrial processing of horse chestnut seeds. The total flavonoid concentration in the powder obtained after evaporation of water was 2.58%, while after purification on solid phase, this increased to 11.23% dry matter. It was concluded that flavonoids are present in a horse chestnut extract in a relatively high amount and have the potential to contribute to the overall activity of these extracts. Industrial horse chestnut wastewater can be used to obtain quercetine and kaempferol glycosides for cosmetic, nutraceutical, and food supplement industries.  相似文献   

17.
Antioxidant prenylated flavonoids from propolis collected in Okinawa, Japan   总被引：2，自引：0，他引：2  
Propolis is a resinous substance collected by honeybees from various plant sources. The composition of propolis depends upon the vegetation at the site of collection. We previously isolated four prenylated flavonoids from propolis collected in Okinawa, Japan. In this study, further fractionation of the extracts of Okinawan propolis resulted in the isolation of a new prenylated flavonoid, prokinawan, and four known compounds. The structure of prokinawan was determined by MS and NMR spectroscopic methods. Furthermore, the antioxidant activity using 1,1-diphenyl-2-picryl-hydrazyl radical scavenging and beta-carotene bleaching systems was investigated. The present study proved that the position of the geranyl or prenyl groups on the flavonoid skeleton plays an important role in exhibiting antioxidant activity.  相似文献   

18.
Supercritical carbon dioxide extraction and fractionation of fennel oil   总被引：3，自引：0，他引：3  
Ground fennel seeds were extracted with supercritical carbon dioxide. Small-scale subsequent extractions of the same sample showed that the composition of volatile compounds was changed with the extension of extraction time and only principal volatile components (limonene, fenchone, methylchavicol, and anethole) were present in the last-extracted sample. Fennel oil was successfully fractionated into the essential oil rich and fatty oil rich products in pilot-scale apparatus using two separators in series. Designed experiments were carried out to map the effects of pressure and temperature in the first separator on the yields and compositions of the products. The minimum level of the total undesired components in both essential oil rich and fatty oil rich products appeared at a pressure of 80-84 bar and a temperature of 31-35 degrees C in the first separator. Supercritical CO(2) extraction of fennel seeds resulted in higher yield (10.0%) than steam distillation (3.0%), almost the same yield as hexane extraction (10.6%), and lower yield than alcohol extraction (15.4%). Analysis of the volatile compounds revealed the significant difference of the composition in distilled oil and oleoresins prepared by CO(2) and solvent extractions. Sensory evaluation showed that the CO(2) extraction product and distilled oil were more intense in odor and taste than alcohol and hexane extracts.  相似文献   

19.
Six flavonoids have been isolated and identified in buckwheat grain. These are rutin, orientin, vitexin, quercetin, isovitexin, and isoorientin. Rutin and isovitexin are the only flavonoid components of buckwheat seeds while hulls contain all six identified compounds. The total flavonoid concentration in the seeds was 18.8 and in the hulls 74 mg/100 g of dry matter. Dehulling the grain by using different temperature regimes resulted in drastic reductions of the total flavonoid concentration in the grain (by 75% of the control) and smaller but significant (15-20%) reduction in the hulls.  相似文献   

20.
Fennel, a seed of Foeniculum vulgare, is used as a culinary spice and traditional medicine. The methanolic extract of fennel showed a characteristic of mechanism-based inactivation on erythromycin N-demethylation mediated by human liver microsomal cytochrome P450 3A4 (CYP3A4). The present study was conducted to identify the fennel constituent having the inhibition. Thirteen compounds have been isolated from a methanol extract of fennel and tested for their inhibition on CYP3A4. Among them, 5-methoxypsoralen (5-MOP) showed the strongest inhibition with an IC50 value of 18.3 microM and a mixed type of inhibition. In addition, with the preincubation time of 20 min only 5-MOP showed preincubation time dependency; the IC50 value decreased from 18.3 microM with a preincubation time of 0 min to 4.6 microM with a preincubation time of 20 min. Further investigation on 5-MOP showed the characteristics of time-dependent inhibition, requirement of NADPH, lack of protecting effect of nucleophiles, and recovery of CYP3A4 activity by the competitive inhibitor. This result suggests that the inhibitory activity of CYP3A4 by 5-MOP was a mechanism-based inactivation. The kinetic parameter for mechanism-based inactivation was characterized by a KI value of 15.0 microM and a kinact value of 0.098 min(-1).  相似文献   

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