Glycoside Composition Research Articles

Determination of flavonoids, polyphenols and antioxidant activity of Tephrosia purpurea: a seasonal study

ObjectiveTephrosia purpurea (Linn.) Pers. is widely used in traditional medicine to treat liver disorders, febrile attacks, enlargement and obstruction of liver, spleen, and kidney. In the present study, investigations were carried out to determine the seasonal impact on the content of flavonoid glycosides and on antioxidant activities so as to identify the optimal time of harvesting. MethodsThe plant materials were collected in different seasons during 2013–2014. Air-dried, powdered plant materials were extracted with 95% ethanol and ethanol:water (1:1) by ultrasound-assisted extraction process. Their chemical composition in terms of total polyphenol and flavonoid contents (TPCs and TFCs) was determined using modified colorimetric Folin-Ciocalteu method and aluminum chloride colorimetric assay respectively. To determine the in vitro antioxidant activity, diphenyl-picryl hydrazyl (DPPH) radical-scavenging assay and total antioxidant capacity by phosphomolybdate antioxidant assay were carried out. High-performance liquid chromatography (HPLC)/photo-diode array (PDA) analysis was used to quantify the flavonoid glycosides in the samples collected in different seasons. Correlation studies were also carried out between antioxidant activities and TPCs. ResultsThe highest TPC and TFC were found to be in the 95% ethanolic extract of the August sample and the lowest in the 50% hydro-alcoholic extract of the plant sample collected in winter season. It was observed that in both the assays used to determine the antioxidant activity, the 95% ethanolic extracts in all the seasons showed a higher activity than their respective 50% hydro-alcoholic extracts with an increase in activity as we go from cold to hot to rainy seasons. Based on correlation analysis, DPPH radical-scavenging activities as well as the spectrophotometrically measured phosphomolybdenum complex were also strongly correlated with TPC of the extracts. The most abundant flavonoid glycoside was quercetin-3-O-rhamnoglucoside in all the seasons. The content of all flavonoids was observed highest in the 95% ethanolic extract of the plant collected in August (TP-3). The 50% hydro-alcoholic extract of the plant collected in December (TP-6) showed the lowest amount of flavonoids and antioxidant activity. ConclusionThe findings of this study confirmed that the metabolism and production of flavonoids in T. purpurea are vigorously affected by seasonal factors. Significant differences were observed in the TPC, TFC and flavonoid glycoside composition in the 95% ethanolic as well as 50% hydro-alcoholic extracts of T. purpurea collected in different seasons. Since the 95% ethanolic extract of the August sample (TP-3), which also happens to be its flowering season, exhibited the highest TPC, TFC and antioxidant activities in both DPPH and phosphomolybdate assays as well as contained the highest content of all flavonoids, it could be recommended as the optimal season of harvesting T. purpurea with respect to its pharmaceutically important constituents, i.e., flavonoids.

Formation of protodioscin and deltoside isomers in suspension cultures of Nepal yam (Dioscorea deltoidea Wall.) cells

Changes in the content of the furostanol glycosides protodioscin and deltoside, particularly that of the (25S)-isomers of the glycosides, during suspension cultivation of different lines of Nepal yam (Dioscorea deltoidea Wall.) cells of the strain IFR-DM-0.5 has been investigated. The composition of furostanol glycosides has been characterized, and the dynamics of the accumulation of individual glycosides during lengthy subcultivation of cells maintained in flasks or in a barbotage bioreactor has been analyzed. A positive correlation between the growth and accumulation of substances that belonged to the class of furostanol glycosides has been demonstrated for cultured dioscorea cells, whereas the content of some of the individual glycosides varied considerably between the lines of the strain, cultures maintained under different conditions, and even between cells in different phases of the growth cycle. The increased content of (25R)-forms of the glycosides (protodioscin and deltoside) was correlated with a decrease in the cellular growth rate, whereas an increase in culture growth intensity occurred concomitantly to an increase of the amount of (25S)-isomers. This may be indicative of the specific stimulatory effect of (25S)-glycosides, but not the (25R)-forms, on cell proliferation in vitro. Thus, the concentration of (25S)-forms may increase due to the autoselection of cells capable of intensive division during prolonged cultivation.

Chemical composition, antibacterial, antioxidant and tyrosinase inhibitory activities of glycosides from aerial parts of Eryngium tricuspidatum L.

Two new phenolic glucosides, together with six known compounds, were isolated from the aerial part of Eryngium tricuspidatum L. (Apiaceae). The structures of the new compounds were established as 2-hydroxy- 3,5-dimethyl-acetophenon-4-O-β-d-glucopyranoside (1) and 2,3-dimethyl-4-hydroxymethylphenyl-1-hydroxymethyl-O-β-d-glucopyranoside (2) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The antibacterial, tyrosinase inhibitory and DPPH radical scavenging activities of hydromethanolic extract, fractions, and the eight isolated compounds were evaluated. The antibacterial assay showed a moderate activity for magnolioside (4) against Staphylococcus aureus CIP 53.154. Compound 7 (quercetin 3-O-β-d-glucopyranosyl-(1→6)-O-β-d-galactopyranoside) had moderate DPPH radical scavenging activity whereas compounds 2 exhibited good inhibitory effect against mushroom tyrosinase.

In vitro and ex vitro propagation of Stevia rebaudiana Bertoni with high Rebaudioside-A content—A commercial scale application

Stevia rebaudiana Bertoni is a self-incompatible and the pollination is an entomophilous short-day plant. Rebaudioside A, as an individual steviol glycoside, is of particular interest in global sweetener market due to its most desirable flavour profile as compared to stevioside having aftertaste bitterness. In the present investigation, regenerant formation was performed for 6 weeks, in which randomly selected nodes excised from in vitro germinated seedlings were cultured on solid Murashige and Skoog medium (MS) with or without growth regulators (6-benzylaminopurine- BAP or kinetin- KIN) at various concentrations (ranging from 0.1 to 2.0mg/L). Irrespective of the medium composition, the results showed that all treatments were effective for shoot induction, producing an average of 2 shoots per explant after three weeks of culture. Following subsequent sub-culturing on MS medium at 3-week intervals, all the shoots regenerated from the nodes were transferred to MS medium with or without indole-3-acetic acid (IAA), indole-3-butyric acid (IBA) or naphthalene acetic acid (NAA) at two different concentrations (0.25 or 0.50mg/L) for root formation for 3 weeks. IAA was more effective for root formation, producing 7.6 roots per shoot with 100% rooting frequency. All the regenerants (∼13.5cm in length) were potted and successfully acclimatized in a greenhouse for 2 weeks, and then transferred to the field for 14 weeks with a high survival rate (>99%). Similarly, seedlings (8 weeks-old) derived from seed germination in pots were also transferred to the same field in a different plot. There was no significant difference in terms of morphological, yield performance and steviol glycoside compositions between regenerants and seedlings sampled from two developmental periods (late vegetative and flowering period). It was clearly shown that clonal propagation using nodal explants was effective for superior stock plant production with high Reb-A content (11.7% w/w).

Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur

Popular liqueurs made from apricot/cherry pits were evaluated in terms of their phenolic composition and occurrence of cyanogenic glycosides (CGG). Analyses consisted of detailed phenolic and cyanogenic profiles of cherry and apricot seeds as well as beverages prepared from crushed kernels. Phenolic groups and cyanogenic glycosides were analyzed with the aid of high-performance liquid chromatography (HPLC) and mass spectrophotometry (MS). Lower levels of cyanogenic glycosides and phenolics have been quantified in liqueurs compared to fruit kernels. During fruit pits steeping in the alcohol, the phenolics/cyanogenic glycosides ratio increased and at the end of beverage manufacturing process higher levels of total analyzed phenolics were detected compared to cyanogenic glycosides (apricot liqueur: 38.79μg CGG per ml and 50.57μg phenolics per ml; cherry liqueur 16.08μg CGG per ml and 27.73μg phenolics per ml). Although higher levels of phenolics are characteristic for liqueurs made from apricot and cherry pits these beverages nevertheless contain considerable amounts of cyanogenic glycosides.

ИДЕНТИФИКАЦИЯ ТЕРПЕНОВЫХ ЛАКТОНОВ И ФЛАВОНОГЛИКОЗИДОВ В ПРЕПАРАТАХ НА ОСНОВЕ ЭКСТРАКТА ГИНКГО БИЛОБА И НОВЫЙ СПОСОБ ПОЛУКОЛИЧЕСТВЕННОЙ ОЦЕНКИ СОДЕРЖАНИЯ ФЛАВОНОГЛИКОЗИДОВ МЕТОДОМ СПЕКТРОСКОПИИ ЯМР 1Н

The composition of terpen lactones and flavonol glycosides of commercial preparation series based on ginkgo biloba extracts was explored by quantitative 1 H NMR spectroscopy. The content of individual terpen lactones was determined using DMSO-d6 and acetone-d6 solvents. The structure effect of flavonol glycosides on the signal of the hydroxyl proton at position 5 of ring A was examined. A new approach of semi quantitative determination of flavonol glycosides amount by this signal, which is superposition of the singlets of individual flavonoids on the area from 12,5 to 12,65 ppm in DMSO-d6 solvent, was offered. The offered method can be used for detection of counterfeit ginkgo biloba extracts by cheap individual aglicones or rutin, because the signals of individual aglicones have different from flavonol glycosides chemical shifts.

Optimization of the separation and purification process for iridoid glycosides from Lamioplomisrotata

Objective To obtain iridoid glycosides with relatively high purity by the optimization of the preparation process of iridoid glycosides from Lamioplomisrotata. Methods Used methanol-water mobile phase with gradient run to set up an HPLC method and achieved the best separation of each composition. Recorded and calculated statistics for its three-dimensional absorption spectrum combined with UV visible wavelength scanning to analyze the characteristics of the impurities, which have affected the purity of previous preparations of iridoid glycosides from Lamioplomisrotata. To optimize the process, a macroporous adsorptive resin chromatographic column and a polyamide chromatographic column were used on the basis of characteristics of the impurities. A real time UV visible wavelength scan was applied to monitor the effluent components of each column to remove the impurities. Merged the ethanol elution which had the characteristic absorption at 235 nm and smaller absorptions at other wavelengths. The target solutions were cryodesiccated. Compared the differences of the iridoid glycoside compositions at equal concentrations before and after the experiment by HPLC. Results The contents of iridoid glycosides from Lamioplomisrotata before and after the purification process were 69.06% and 90.60% respectively. The yield was 16.70% (use the quality of the water extract as a reference).The transfer rate of iridoid glycosides was 74.72% (relative to the quality of water extract of total iridoid glycosides). Compared with the previous preparation technology, the content was increased to 21.54%. Conclusion The optimization process was simple and practicable with high efficiency, which made a significant improvement in the purity of the iridoid glycosides from Lamioplomisrotata.

Assessment of phytochemicals, antioxidant, and anti-inflammatory potential of Boerhavia procumbens Banks ex Roxb

Boerhavia procumbens is traditionally used in the treatment of various disorders including jaundice and gonorrhea, is a refrigerant, and exhibits anti-inflammatory and antispasmodic activities. The purpose of this study was to determine the phytochemical classes, antioxidant and anti-inflammatory activities of methanol extract (BPME) and different fractions (n-hexane (BPHE), ethyl acetate (BPEE), n-butanol (BPBE), and residual aqueous fraction (BPAE)) of B. procumbens against carrageenan-induced paw edema in rats. To assess the anti-inflammatory effects of B. procumbens, 42 Sprague Dawley male rats (150-200 g) were randomly divided into seven groups. Group I received distilled water and group II was treated with diclofenac potassium (10 mg/kg) body weight (bw) orally. Groups III, IV, V, VI, and VII were administered BPME, BPHE, BPEE, BPBE, and BPAE (200 mg/kg bw) orally, 1 h before the treatment with carrageenan (10 mg/kg bw) in rats. Anti-inflammatory effects of B. procumbens were determined by estimating the inhibition of edema at 1st, 2nd, and 3rd hour after carrageenan injection. Qualitative analysis of methanol extract indicated the composition of diverse classes, namely, flavonoids, tannins, saponins, phlobatannins, cardiac glycosides, alkaloids, terpenoids, and anthraquinones. Quantitative determination illustrated that BPBE and BPEE possessed the highest concentration of total phenolic (60.45 ± 2.1 mg gallic acid equivalent per gram sample) and total flavonoid content (68.05 ± 2.3 mg rutin equivalent per gram sample), respectively. A dose-dependent response for antioxidant activity was exhibited by all the samples. The sample with the highest aptitude for antioxidant activity was the BPBE for 2,2-azobis,3-ethylbenzothiozoline-6-sulfonic acid radical scavenging and total antioxidant capacity. Carrageenan-induced paw edema was significantly (p < 0.05) inhibited by BPBE and BPME at the 1st, 2nd, and 3rd hour and was comparable to control drug diclofenac potassium. Results revealed that various fractions of B. procumbens manifested the antioxidant and anti-inflammatory potential and accredit the local use of B. procumbens in various disorders.

Anthocyanin composition of different wild and cultivated berry species

A broad range of anthocyanins (glycosides of cyanidin, pelargonidin, peonidin, delphinidin, malvidin, and petunidin) was identified and quantified in the fruit of 24 wild and cultivated berry species using HPLC-DAD-MS2. The anthocyanin composition in species of Ribes, Rubus, Vaccinium, and Fragaria genus as well as in less known species of Crataegus, Morus, Amelanchier, Sorbus, Sambucus and Aronia genus was determined. Cyanidin was the most commonly occurring anthocyanidin, meanwhile malvidin glycosides were only detected in blueberries. Glycosides of pelargonidin were detected in raspberries, strawberry, black mulberry and chokeberry. Peonidin glycosides were identified in hawthorn, black currant and gooseberry as well as in blueberry species. The richest species in the content of peonidin glycosides were blueberries. Delphinidin glycosides were the prevailing form of anthocyanins in black currant and bilberry. The highest total anthocyanin content was determined in dark colored fruit of cultivated elderberry and bilberry whereas light-colored dog rose and Chinese hawthorn fruit had the lowest anthocyanin content. The composition of anthocyanidin glycosides did not differ between the fruit of wild growing and cultivated species, but their contents were generally different.

The Component Composition of Steroid Glycosides Extracted from the Fruits of Allium Schoenoprasum L. and Assessment of Their Effects on the Growth of Transplanted Tumors in Mice

Administration of steroid glycosides of both the spirostanol type, where the active substance is deltonin, and the furostanol type, the main components of which are deltoside and protodioscine, before transplantation of Ehrlich carcinoma (EC) and during its growth had no effect on the body’s resistance to tumor cells, with no effect on the latent period of formation of tumor nodules or the rate of tumor growth. Testing in a therapeutic regimen demonstrated a tendency to stimulation of EC growth in response to spirostanol glycosides. At the same time, treatment with furostanol glycosides showed weak, statistically insignificant, inhibition of tumor growth, in terms of both tumor volume and tumor mass.

Stability of quercetin derivatives in vacuum impregnated apple slices after drying (microwave vacuum drying, air drying, freeze drying) and storage

Microwave vacuum drying (MVD) was investigated for apple slices enriched with quercetin derivatives by vacuum impregnation (VI). Additional freeze drying (FD) and air drying (AD) were conducted. Compared to native apples, the impregnated tissue resulted in higher moisture content, elevation of weight and significant browning, due to the incorporated VI solution. The total quercetin content and quercetin glycoside composition were not affected by MVD and FD. The vacuum conditions protect the polyphenols from oxygen dependent degradation and browning reactions. AD resulted in an average quercetin glycoside loss of 44% and undesirable changes, particularly discoloration. The degradation is caused by both non-enzymatic and enzymatic reactions. The pulsed microwave energy intake improved the drying result in structure and led to a faster drying process of 130 min. The bulk density of MVD apple chips (0.69 g/ml) ranged between 0.33 g/ml for FD and 0.75 g/ml for AD. The final moisture content was the lowest after FD (6.8 g/100 g), followed by 9.0 g/100 g after MVD and 12.7 g/100 g after AD. The shelf life was significantly influenced by storage temperature and time. After 12 month at 20 °C, the total quercetin content decreased by 21%.

Proximate and Cardiac Glycoside Composition of Thevetia (Thevetia neriifolia. JUSS) Seed as Affected by Soaking in Water, Brine and Ethanol

Effects of soaking using water, ethanol and brine on proximate and cardiac glycoside composition of Thevetia neriifolia seed (TS) were undertaken. Each 100g portion of TS was soaked in either water or ethanol for 24 hours or in 2.5, 5.0 and 7.5% brine solution for 2, 3 or 4 hours. The samples were then either sun-dried for 3 days or toasted after soaking and thereafter analyzed for chemical and residual glycoside composition. There were significant (P<0.05) variations in the composition of ash which ranged from 13.0% in the raw meal (TR) to 11.04% in T4 (TS soaked in fine-grade ethanol and sun-dried). Obtained values for nitrogen free extracts was between 12.56% in T1 (TS soaked in water and toasted) and 28.31% in T4. These values varied significantly (P<0.05) among the groups except in T2 (TS soaked in water and sun-dried) (19.47%) and T3 (TS soaked in fine-grade ethanol and toasted) (20.09%) where the values were similar (P>0.05). Toasting significantly (P<0.05) reduced the crude protein (CP) in water and ethanol treated samples from19.35% in raw sample to 18.14 and 18.43%, respectively. The CP increased significantly in sun-dried water (22.1%) and brine treated (23.1%) samples. Soaking in 7.5% brine for 3 hours significantly (P<0.05) reduced glycoside content from 4.7% to 0.07% (98.51% reduction of glycoside).

Effects of Salt Stress on the Growth, Physiological Responses, and Glycoside Contents of Stevia rebaudiana Bertoni

This study examined the effects of three different NaCl concentrations (60, 90, and 120 mM) on the growth, physiological responses, and steviol glycoside composition of Stevia rebaudiana Bertoni for 4 weeks. The results showed that the total dry weight decreased by 40% at 120 mM NaCl but remained the same at 60 and 90 mM NaCl. As salt concentration increased, chlorophyll contents decreased markedly by 10-70%, whereas the increments of the antioxidant enzyme activities were 1.0-1.6, 1.2-1.3, and 2.0-4.0 times, respectively, for superoxide dismutase, peroxidase, and catalase. The proline contents in salt-treated plants were 17-42 times higher than that in control. Moreover, leaf possessed significantly higher K⁺ content and K⁺/Na⁺ ratio than stem and root for all salt treatments. In addition, 90-120 mM NaCl treatment notably decreased the content of rebaudioside A (RA) and stevioside (ST) by 16.2-38.2%, whereas the increment of the ratio of RA/ST of salt-treated plants was 1.1-1.4 times. These results indicate that S. rebaudiana is moderately tolerant to salt stress. Hypohaline soil can be utilized in the plantation of S. rebaudiana and may be profitable for optimizing the steviol glycoside composition.

BIOCHEMICAL STUDIES ON NIGERIAN &lt;i&gt;MONODORA TENUIFOLIA&lt;/i&gt; SEED

The nutritive constituents of the seeds of Monodora tenuifolia were analyzed to augment the available information on Monodora tenuifolia research. Blood glucose and lipid profile were investigated on the flavonoid rich fraction of M. tenuifolia in rats. The composition (gkg-1) of alkaloids, cyanogenic glycosides, tannins and flavonoids were 13.3±0.1, 21.2×10-2±0.6, 1.3±0.1, 1.7±0.1 and 11.7±1.1 respectively. The proximate composition (gkg-1) of M. tenuifolia seed were crude fibre (262.3±1.2), crude protein (82.6±1.0), crude fat (349.9±1.9), ash (49.9±0.6), moisture (190.0±0.00) and carbohydrate (65.5±4.7). Analysis of the minerals content (gkg-1) yielded calcium (864.0±29.38), sodium (2752.0±140.35), iron (3.34±0.06), zinc (5.26±0.08), potassium (326.4±13.06), magnesium (342.9±13.71) and phosphorus (9.52±0.17), while vitamin analysis yielded vitamin A (10.05±0.17 iu/100 g), C (56.40±0.14 gkg-1) and E (11.71±0.87 iu /100 g), thiamine (0.11±0.01 gkg-1), niacin (0.46±0.32 gkg-1) and riboflavin (0.04±0.01 gkg-1). The results of amino acid analysis showed the total amino acid of M. tenuifolia seed was 71.78 of crude protein. The total essential amino acid with Histidine was calculated to be 29.24 of the crude protein. The antinutrient analysis of M. tenuifolia shows it contained total phenol (0.8±0.0 gkg-1), oxalates (4.09±1.17 gkg-1), phytates (0.012±0.42 gkg-1) and trypsin inhibitor (0.230±0.42 iu/g). The main fatty acids of the seed oil are linoleic acid (401.7 g kg-1), oleic acid (346.1 g kg-1) and palmitic acid (122.61 g kg-1). The LD50 of the flavonoid-rich fraction was found to be above 5000 mg kg-1 b.w. After the day 14 study, biochemical markers such as triacylglycerol, very low density lipoprotein increased significantly (p

ИССЛЕДОВАНИЕ СОДЕРЖАНИЯ ФЛАВОНОИДОВ И АНТОЦИАНОВ В СПЕЛЫХ ПЛОДАХ БУЗИНЫ

Using liquid chromatography studied fruit elderberry ( Sambucus nigra L), ubiquitous in the highlands of Georgia for the presence of phenolic compounds. The quantitative and qualitative composition of flavonoid glycosides and anthocyanins. Found that ripe fruit of elderberry contains flavonoid glycosides - 289 mg/kg and anthocyanins - 1110 mg/kg.

ФЛАВОНОИДЫ НЕКОТОРЫХ ВИДОВ РОДА RHODODENDRON L. ФЛОРЫ СИБИРИ И ДАЛЬНЕГО ВОСТОКА

The composition and content of flavonoids glycosides and aglycones in the leaves of Rhododendron adamsii, Rh. parvifolium, Rh. impeditum, and the closely related species of the subsection Rhodorastra (Rh. dauricum, Rh. ledebourii, Rh. sichotense, Rh. mucronulatum) from populations of the Altai, Yakutia, Tuva, the Amur region and Primorsky Krai, Buryatia, China were studied by HPLC. The aglycones content in hydrolysates of the majority of the species is about 1%, and quercetin and dihydroquercetin prevail in aglycones composition. In Rh. adamsii and Rh. parvifolium aglycones are found predominantly in the free state, and in the species of the subsection Rhodorastra – in a bound one. Values of paired affinity of the investigated species on composition of phenolic compounds of extracts and hydrolysates vary from 30 to 90%, maximums are in pairs Rh. sichotense-Rh. dauricum, Rh. adamsii-Rh. ledebourii. As a result of the analysis of affinity of flavonoids composition of the species relation with D. Chamberlain’s anatomo-morphological classification is not exposed. Significant value of affinity Rh. adamsii and Rh. parvifolium is revealed. The minimum value of group affinity on flavonoids composition of extracts and hydrolysates of Rh. impeditum casts doubt on his position equally with Rh. parvifolium in the subsection Lapponica.

The molecular and enzymatic basis of bitter/non‐bitter flavor of citrus fruit: evolution of branch‐forming rhamnosyltransferases under domestication

Domestication and breeding of citrus species/varieties for flavor and other characteristics, based on the ancestral species pummelo, mandarin and citron, has been an ongoing process for thousands of years. Bitterness, a desirable flavor characteristic in the fruit of some citrus species (pummelo and grapefruit) and undesirable in others (oranges and mandarins), has been under positive or negative selection during the breeding process of new species/varieties. Bitterness in citrus fruit is determined by the composition of branched-chain flavanone glycosides, the predominant flavonoids in citrus. The flavor-determining biosynthetic step is catalyzed by two branch-forming rhamnosyltransferases that utilize flavanone-7-O-glucose as substrate. The 1,2-rhamnosytransferase (encoded by Cm1,2RhaT) leads to the bitter flavanone-7-O-neohesperidosides whereas the 1,6-rhamnosytransferase leads to the tastelessflavanone-7-O-rutinosides. Here, we describe the functional characterization of Cs1,6RhaT, a 1,6-rhamnosyltransferase-encoding gene directing biosynthesis of the tasteless flavanone rutinosides common to the non-bitter citrus species. Cs1,6RhaT was found to be a substrate-promiscuous enzyme catalyzing branched-chain rhamnosylation of flavonoids glucosylated at positions 3 or 7. In vivo substrates include flavanones, flavones, flavonols and anthocyanins. Cs1,6RhaT enzyme levels were shown to peak in young fruit and leaves, and gradually subside during development. Phylogenetic analysis of Cm1,2RhaT and Cs1,6RhaT demonstrated that they both belong to the branch-forming glycosyltransferase cluster, but are distantly related and probably originated separately before speciation of the citrus genome. Genomic data from citrus, supported by a study of Cs1,6RhaT protein levels in various citrus species, suggest that inheritance, expression levels and mutations of branch-forming rhamnosyltransferases underlie the development of bitter or non-bitter species/varieties under domestication.

HPLC에 의한 뽀리뱅이 플라본 배당체 화합물의 동시정량

This research was attempted to determine the composition of flavone glycosides (luteolin 7-O-glucoside, luteolin 7-O-glucuronide, linarin) in addition to luteolin simultaneously in aerial part of Youngia japonica (Compositae) by high-performance liquid chromatography. The MeOH extract was further fractionated into the three parts, <TEX>$CHCl_3$</TEX> fraction, EtOAc fraction and BuOH fraction, to investigate the contents of the four flavones in the three fractions. The content of luteolin 7-O-glucuronide (10.07 mg/g) was highest in the MeOH extract among those of the flavones. These four compounds were observed to be less than 1.0 mg/g in <TEX>$CHCl_3$</TEX>- and EtOAc fractions but relatively high in BuOH fraction.

UHPLC-(ESI)QTOF MS/MS Profiling of Quercetin Metabolites in Human Plasma Postconsumption of Applesauce Enriched with Apple Peel and Onion

An ultrahigh pressure liquid chromatography accurate mass quadrupole time-of-flight mass spectrometry with electrospray ionization (UHPLC-(ESI)QTOF MS/MS) method was developed for measuring individual quercetin metabolites in human plasma with high sensitivity and high selectivity. Quercetin (3,3',4',5,7-pentahydroxyflavone) occurs as glycosides in foods. The composition of glycosides is species and cultivar specific. In humans, quercetin undergoes extensive biotransformation, resulting in a range of metabolites. The bioactivity of quercetin metabolites will depend on the type and position of the conjugates. Herein, individual quercetin metabolites (i.e., sulfate, glucuronide or methyl conjugates) were identified by accurate mass MS in human plasma (females = 8 and males = 8) over 24 h after consumption of applesauce enriched with either micronized apple peel (AP) or onion powder (OP). The AP and OP contained ~180 μmol of quercetin glycosides. The relative amounts of quercetin metabolites were quantified in plasma. The complement of identified quercetin metabolites was similar after consumption of AP and OP. Primary metabolites included the following: quercetin sulfate, quercetin glucuronide, and quercetin diglucuronide. A quercetin glutathione adduct was identified in negative ion mode but not apparent in positive ion mode. The pharmacokinetic parameters for AUC0-24 h and Cmax were significantly different for AP and OP. For example, consumption of the AP resulted in Cmax of quercetin sulfate, 4.6 ng/mL; quercetin glucuronide, 15.5 ng/mL; quercetin diglucuronide, 9.3 ng/mL; quercetin glucuronide sulfate, 1.3 ng/mL; methyl quercetin glucuronide, 7.5 ng/mL; and methyl quercetin diglucuronide, 3.6 ng/mL, whereas the OP resulted in Cmax of quercetin sulfate, 37.3 ng/mL; quercetin glucuronide, 212.8 ng/mL; quercetin diglucuronide, 168.8 ng/mL; quercetin glucuronide sulfate, 43.0 ng/mL; methyl quercetin glucuronide, 90.1 ng/mL; methyl quercetin diglucuronide, 65.4 ng/mL. Gender-related differences in the AUC0-24 h for quercetin sulfate and quercetin sulfate glucuronide metabolites were also observed.

A novel strategy for target profiling analysis of bioactive phenylethanoid glycosides in Plantago medicinal plants using ultra‐performance liquid chromatography coupled with tandem quadrupole mass spectrometry

Phenylethanoid glycosides are a group of phenolic compounds with diverse biological activities such as hypotensive, diuretic, and hypoglycemic effects. In this study, a target profiling analysis approach using ultra-performance liquid chromatography coupled with tandem quadrupole mass spectrometry (MS) was established on the basis of parent ion scanning for m/z 161, the characteristic product ion for phenylethanoid glycosides. It was successfully employed to discriminate the chemical composition of phenylethanoid glycosides between Plantaginis Herba and Plantaginis Semen, two medicinal parts of Plantago plants, which are widely used as herbal medicine in China. Totally, 34 phenylethanoid glycosides were characterized and tentatively identified by their retention times, MS, and tandem quadrupole MS (MS/MS) data. Combined with chemometrics analysis of principal component analysis and orthogonal projection to latent structural discriminate analysis, eight of them, especially acteoside and plantamajoside, were picked out and contributed to the chemical distinction between Plantaginis Herba and Plantaginis Semen, which might be responsible for the differences in diuretic and hypotensive effects between the two medicinal parts. This new approach for target profiling provides not only a novel idea for specific analysis of active chemical constituents in the same type, but also a promising and reference method for quality evaluation of traditional Chinese medicines.