echinacoside and acteoside

To study the efficacy and mechanism of three phenylethanoid glycosides (PhGs) (verbascoside, echinacoside, and crenatoside) on altitude-induced fatigue in rats.. Altitude-induced fatigue model rats were established in a large hypobaric chamber. Swimming time, energy storage substances, metabolic enzymes, and metabolites were used to evaluate the anti-fatigue activities and mechanism of three PhGs (verbascoside, echinacoside, and crenatoside) (150 mg/kg, intragastric administration) in the hypoxic environment.. The three PhGs, especially verbascoside, could prolong the swimming time of rats, ameliorate the edema and inflammatory infiltration of liver and skeletal muscle, increase the level of energy storage substances, reduce the decomposition of proteins, and exhibit positive effects on the metabolism-related enzyme activity and metabolites.. The PhGs, especially verbascoside, are very potential with anti-fatigue activity in hypoxia. The mechanism may be explained with regulation of energy metabolism and reduction of oxidative stress.

Topics: Altitude; Animals; Glycosides; Hypoxia; Phenols; Rats

Topics: Animals; Antioxidants; Cell Line, Tumor; Chromatography, High Pressure Liquid; Flavonoids; Flowers; Gas Chromatography-Mass Spectrometry; Glucosides; Glycosides; HeLa Cells; Humans; Melanoma, Experimental; Mice; Oxidative Stress; Phenols; Phenylpropionates; Plant Extracts; Plant Leaves; Quercetin; Spectroscopy, Fourier Transform Infrared; Syringa

Plants of the Plantago genus are widely used in Turkish folk medicine especially for the treatment of wound, abscess, and inflammation. The aqueous extract and five phenylethanoid glycosides acteoside (1), arenarioside (2), echinacoside (3), isoacteoside (4), and leucosceptoside A (5) isolated from the aerial parts and roots of Plantago holosteum Scop. (Plantaginaceae) were tested for their possible inhibitory activity against hyaluronidase, elastase, and collagenase, related to wound pathogenesis. Even though the aqueous extract prepared from the aerial parts (36.26%) and roots (47.01%) and the isolated compounds acteoside (29.13%), echinacoside (28.73%), and isoacteoside (31.69%) exerted a notable inhibition, arenarioside and leucosceptoside A were found inactive in the hyaluronidase enzyme inhibition test. Similar results were obtained from the collagenase enzyme inhibition test. The aqueous extract prepared from the aerial parts (31.09%) and roots (35.17%), echinacoside (25.13%), and isoacteoside (23.85%) exerted a notable inhibition in this test. However, none of the extracts and isolated compounds displayed elastase enzyme inhibitory activity. The experimental data demonstrated that P. holosteum displayed a remarkable enzyme inhibitory activity against hyaluronidase and collagenase. This paper is the first report regarding the in vitro enzyme inhibitory activity of P. holosteum.

Topics: Collagenases; Enzyme Inhibitors; Glucosides; Glycosides; Humans; Hyaluronoglucosaminidase; Medicine, Traditional; Molecular Structure; Pancreatic Elastase; Phenols; Plant Components, Aerial; Plant Extracts; Plant Roots; Plantago; Turkey

Cistanche tubulosa is a precious traditional Chinese medicine that has been widely used in the treatment of osteoporosis and Alzheimer's disease. Echinacoside and acteoside are the main active constituents in Cistanche tubulosa that have the pharmacological activities with research value. It has been reported that echinacoside and acteoside could improve the learning and memory ability, promote the proliferation and differentiation of osteoblast.. Echinacoside and acteoside from Cistanche tubulosa have shown significant activities of anti-osteoporosis and anti-Alzheimer's disease, while these effects have not been studied concurrently in a rat model. The aim of this study was to establish and verify the model of osteoporosis combined with Alzheimer's disease in rat, and to investigate the double effects of echinacoside and acteoside on this concurrent model.. Compared with Sham group, OVX + D group could significantly reduce the learning and memory ability by causing oxidative damage, impairing neurons in hippocampus and affecting the hydrolysis and synthesis of acetylcholine. Meanwhile, the activities of BALP and TRAP in OVX + D group increased significantly (P < 0.001) as compared to Sham group. In addition, compared with Sham group, the mean bone mineral density obviously decreased (P < 0.05), the trabecular bone mass and microarchitecture were also destroyed significantly in OVX + D group. Furthermore, the maximum load and maximum stress significantly reduced (P < 0.01) and the energy absorption also decreased greatly as compared to Sham group. After administrated with echinacoside and acteoside, the typical pathological features of osteoporosis and Alzheimer's disease were ameliorated.. The model of osteoporosis combined with Alzheimer's disease in rat was feasible and successfully established. Echinacoside and acteoside also showed some significant effects on this concurrent model, and they could be potential candidates from Cistanche tubulosa with double effects for further study.

Topics: Alzheimer Disease; Animals; Bone Density; Bone Remodeling; Cancellous Bone; Cistanche; Estradiol; Female; Glucosides; Glycosides; Hippocampus; Osteoporosis; Ovariectomy; Phenols; Plant Extracts; Rats; Rats, Wistar; Spatial Memory; Uterus

Cistanche deserticola Y.C. Ma has long been used for medical purposes in China. It mainly grows in the Chinese provinces of Inner Mongolia, Ningxia, Gansu, and Xinjiang, and the species in the Alxa region of northwest China, have the most distinct qualities. To explain the geoherbalism quality and geographical distribution of C. deserticola, we sampled 65 wild plants in Alxa, determined their echinacoside and acteoside content, and assessed the relationship between the ecological environment and quality of C. deserticola through maximum entropy modeling and geographic information system. We identified the areas suitable for the growth of high-quality C. deserticola species. The regionalization analysis of growth suitability showed that the most influential ecological factors for the growth of C. deserticola are soil type, annual sunshine duration, altitude, temperature seasonality (standard deviation ×100), vegetation type, sunshine duration in the growing season, mean precipitation in August and mean temperature in July. The most suitable areas for growing C. deserticola are southeast of Ejin Banner, central Alxa Right Banner, and north of Alxa Left Banner. The regionalization analysis of quality suitability showeds that the most influential ecological factors for glycosides in C. deserticola are sunshine duration in June, average precipitation in May, and average temperature in March, and the best-quality C. deserticola grows in Dalaihob Town, Ejin Banner. Upon inspection, the result of the experiment reached a high accuracy of 0.994, which indicates that these results are consistent with the actual distribution of C. deserticola in Alxa. The results of this study may serve as a scientific basis for site selection of artificial planting bases for C. deserticola.

Topics: Altitude; China; Cistanche; Ecological and Environmental Phenomena; Geography; Glucosides; Glycosides; Phenols; Plants, Medicinal; Rain; Seasons; Soil; Temperature

From two species of Sutera (S. foetida and S. cordata) (Scrophulariaceae tribe Limoselleae) were isolated three known secoiridoid glucosides (12-14) as well as four iridoid congeners (8-11), all biosynthetically derived from iridodial glucoside (and/or deoxyloganic acid). In addition, two previously unknown compounds were found, namely a terpenoid glucoside lactone (suterolide, 21) and the phenylethanoid glycoside 2''''-O-acetyl-angoroside A (19) as well as verbascoside, echinacoside and tubuloside A(15-17, respectively). Two other species, Jamesbrittenia dissecta and Lyperia antirrhinoides, previously considered to belong to the same genus (Sutera) were shown to be members of two different genera, respectively. Significantly, these two species contained iridoids derived from 8-epi-iridodial (and 8-epideoxyloganic acid), namely aucubin (2), melittoside (3) and acetylharpagide (4). In addition we investigated Melanospermum transvaalense, Lyperia tristis and Microdon dubius likewise from Limoselleae and all of these contained iridoid glucosides from the 8-epi-pathway. Thus, secoiridoid distribution confirms the DNA-based circumscription of Sutera and its sister-group relationship with Manulea. In addition, the results show that the clade including these two genera has a biosynthetic pathway to iridoids fundamentally different from the rest of the tribe and from the whole family Scrophulariaceae.

Topics: Glucosides; Glycosides; Iridoid Glucosides; Magnetic Resonance Spectroscopy; Molecular Structure; Phenols; Phylogeny; Pyrans; Scrophulariaceae; Spectrometry, Mass, Electrospray Ionization

Nuclear factor erythroid 2-related factor 2 (Nrf2) is a key transcription factor against oxidative stress and neurodegenerative disorders. Phenylethanoid glycosides (PhGs; salidroside, acteoside, isoacteoside, and echinacoside) exhibit antioxidant and neuroprotective bioactivities. This study was performed to investigate the neuroprotective effect and molecular mechanism of PhGs. PhGs pretreatment significantly suppressed H₂O₂-induced cytotoxicity in PC12 cells by triggering the nuclear translocation of Nrf2 and reversing the downregulated protein expression of heme oxygenase 1 (HO-1), NAD(P)H quinone oxidoreductase 1 (NQO1), glutamate cysteine ligase-catalytic subunit (GCLC), and glutamate-cysteine ligase modifier subunit (GCLM). Nrf2 siRNA or HO-1 inhibitor zinc protoporphyrin (ZnPP) reduced the neuroprotective effect. PhGs showed potential interaction with the Nrf2 binding site in Kelch-like ECH-association protein 1 (Keap1). This result may support the hypothesis that PhGs are activators of Nrf2. We demonstrated the potential binding between PhGs and the Keap1-activated Nrf2/ARE pathway, and that PhGs with more glycosides had enhanced effects.

Topics: Animals; Antioxidant Response Elements; Apoptosis; Glucosides; Glycosides; Hydrogen Peroxide; Neuroprotective Agents; NF-E2-Related Factor 2; PC12 Cells; Phenols; Protoporphyrins; Rats; Signal Transduction

Chronic hyperalgesia and allodynia associated with progressive damage of peripheral neurons are the most prevalent complications of diabetes mellitus. Plants belonging to the family of Oleaceae were traditionally used in folk medicine for the management of diabetes.. The aim of this study was to investigate whether an aqueous extract from the leaves of Ligustrum vulgare (common privet) could be useful to target neuropathic pain in a rat streptozotocin (STZ) model of diabetes.. The chemical composition of the aqueous extract from privet leaf was characterized with the UHPLC-DAD-MS method and the analytical quantification of its constituents was performed with HPLC-DAD. Mechanical hyperalgesia and allodynia were evaluated with the Randall-Selitto and von Frey tests.. Our investigation revealed the presence of secoiridoids: oleacein (23.48 ± 0.87 mg/g), oleocanthal (8.44 ± 0.08 mg/g), oleuropein (1.50 ± 0.01 mg/g), as well as phenylpropanoids: echinacoside (6.46 ± 0.07 mg/g), verbascoside (4.03 ± 0.04 mg/g) and p-coumaroyl glucarates in the dried aqueous extract of privet leaves. Behavioral data indicated that chronic intraperitoneal administration of the extract (50-200 mg/kg) for 21 days resulted in a decrease in diabetes-induced hyperalgesia and allodynia. Blood glucose levels remained unaltered, while body weight and water intake decreased significantly.. The aqueous privet leaf extract could serve useful in facilitating treatment of painful diabetic neuropathy. Additionally, the study showed that the antihyperalgesic activity of Ligustrum vulgare leaf extract is not likely related to its antihyperglycemic properties.

Topics: Aldehydes; Animals; Chromatography, High Pressure Liquid; Cyclopentane Monoterpenes; Diabetes Mellitus, Experimental; Diabetic Neuropathies; Glucosides; Glycosides; Hyperalgesia; Iridoid Glucosides; Iridoids; Ligustrum; Male; Neuralgia; Phenols; Plant Extracts; Plant Leaves; Rats; Streptozocin

To meet the demands from plant physiologists and pharmacognosists, sustainable efforts are being devoted by the analytical chemists from all over the world to search an approach being capable of simultaneously monitoring primary along with secondary metabolites. The key technical bottlenecks currently lie at affording satisfactory chromatographic and spectrometric performances for both hydrophilic and hydrophobic substances that span a great content range. Herein, reverse phase liquid chromatography was directly coupled with hydrophilic interaction chromatography, namely RPLC-HILIC, to integrate their merits, whereas dilution pumps were employed to tackle the mismatching for the mobile phase between them. On the other side, inferior parameters rather than the optimal ones were applied for those abundant ingredients to advance the upper limits of quantitation, such as echinacoside (1250.0μg/mL), mannitol (100.0μg/mL), and acteoside (125μg/mL), in mass spectrometer domain. As a desert parasitic plant as well as tonic materials, Cistanche tubulosa (CT) has drawn widely interests from plant physiologists and pharmacognosists regarding its quantitative metabolome. Simultaneous determination of 23 abundant and minor ingredients covering most chemical families in CT, i.e. amino acid, nucleoside, organic acid, phenylethanoid glycoside, lignan, and iridoid, was attempted to understand the physiologic patterns as well as pharmacological values of the crude materials. Although the analytes spanned wide polarity (-3.326≤cLogP≤1.421) and content (more than 5 orders of magnitude) ranges, satisfactory chromatographic and spectrometric behaviors were gained for all analytes. Reliable quantitation was demonstrated via various method validation assays, such as recovery, linearity, sensitivity, and precision. The contents of 23 hydrophilic and hydrophobic substances were quantified in 20 batches of CT. Significant variations occurred for the contents of those components. Echinacoside (1.35-387.50mg/g) was usually observed as the most abundant component, whereas ferulic acid (<0.0043mg/g) always exhibited trace distributions. Above all, the integrated equipment setup could serve as a fit-for-purpose tool for in-depth quality evaluation of CT and more importantly, for comprehensively understanding the metabolome of plants.

Topics: Chromatography, Liquid; Chromatography, Reverse-Phase; Cistanche; Glucosides; Glycosides; Hydrophobic and Hydrophilic Interactions; Metabolome; Nucleosides; Phenols; Plant Extracts; Tandem Mass Spectrometry

Quantitative determination of multiple effective components in a given plant usually requires a very large amount of authentic natural products. In this study, we proposed a rapid and non-destructive method for the simultaneous determination of echinacoside, verbascoside, mannitol, sucrose, glucose and fructose in Cistanche tubulosa by near infrared spectroscopy (NIRS). Near infrared diffuse reflectance spectroscopy (DRS) and high performance liquid chromatography (HPLC) were conducted on 116 batches of C. tubulosa samples. The DRS data were processed using standard normal variety (SNV) and multiplicative scatter correction (MSC) methods. Partial least squares regression (PLSR) was utilized to build calibration models for components-of-interest in C. tubulosa. All models were then assessed by calculating the root mean square error of calibration (RMSEC), correlation coefficient of calibration (r). The r values of all six calibration models were determined to be greater than 0.94, suggesting each model is reliable. Therefore, the quantitative NIR models reported in this study can be qualified to accurately quantify the contents of six medicinal components in C. tubulosa.

Topics: Chromatography, High Pressure Liquid; Cistanche; Fructose; Glucose; Glucosides; Glycosides; Liquid-Liquid Extraction; Mannitol; Methanol; Phenols; Plant Extracts; Solvents; Spectroscopy, Near-Infrared; Sucrose; Time Factors

We report the first analysis in absolute, and in particular, concerning the phytochemical pattern, about an endemic Italian species, Ajuga tenorei C. Presl. The analysis, performed by means of techniques such as Column Chromatography and NMR spectroscopy and Mass spectrometry, led to the isolation and the identification of five compounds namely verbascoside (1), echinacoside (2), ajugoside (3), harpagide (4) and 8-O-acetylharpagide (5). The presence of these compounds is important from both chemotaxonomic and ethno-pharmacological point of view. For what concerns the first point is confirmed the correct botanical classification of the species. The isolated compounds are also known to exert peculiar pharmacological activities and their presence may give a rationale to the historical medicinal properties associated to the Ajuga genus in general, since these plants have a long traditional use in many parts of the world. Such fact might suggest the use of also this species in this sense.

Topics: Ajuga; Glucosides; Glycosides; Iridoid Glycosides; Iridoids; Italy; Mass Spectrometry; Phenols; Plant Components, Aerial; Plant Extracts; Plants, Medicinal; Pyrans

In this study, we report the first phytochemical analysis of polar fraction of Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Several iridoid glucosides were isolated, namely aucubin (1), monomelittoside (2), plantarenaloside (3), euphroside (4), mussaenosidic acid (5) and 8-epiloganic acid (6), showing a composition in accordance with previous study on this genus. The studied samples, collected from Dolomites, presented a chemotype already recognised in species from North America, characterised by euphroside (4) and aucubin (1) as main components, but the main character was the presence of monomelittoside (2) never reported in this genus. The identification of verbascoside (7), leucosceptoside A (9) and echinacoside (10) complete the systematic framing of this species since is ascertained the co-occurrence of phenylethanoid glycosides with iridoids in Lamiales species.

Topics: Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Italy; Molecular Structure; Pedicularis; Phenols; Plant Extracts

Cistanche tubulosa is a traditional Chinese herbal medicine widely used for regulating immunity and phenylethanol glycosides (CPhGs) are among the primary components responsible for this activity. Previous studies have indicated the preventive and therapeutic effects of CPhGs on bovine serum albumin (BSA)-induced hepatic fibrosis in rats. The aim of the study was to evaluate the anti-hepatic fibrosis effect of CPhGs and the monomers echinacoside and acteoside by inhibiting hepatic stellate cell (HSC) activation, blocking the conduction of signaling pathways in transforming growth factor-β1 (TGF-β1)/smad, and determine their in vitro hepatoprotective activity. HSC proliferation was obviously inhibited after treatment with CPhGs (100, 50 μg/mL)/echinacoside (500, 250, 125 μg/mL)/acteoside (6, 3 μg/mL), with IC50 values of 119.125, 520.345 and 6.999 μg/mL, respectively, in the MTT assay. Different concentrations of CPhGs/echinacoside/acteoside did not affect the cellular toxicity on HSC according to lactate dehydrogenase (LDH) measurements. Different concentrations of CPhGs/echinacoside/acteoside increased the mRNA level and protein expression of smad7, and decreased the mRNA levels of smad2, smad3 and the protein expression of smad2, phospho-smad2 (p-smad2), smad3, phospho-smad3 (p-smad3) in HSC. In summary, these results demonstrate that CPhGs/echinacoside/acteoside can block the conduction of the signaling pathways in TGF-β1/smad, and inhibit the activation of HSC, suggesting that C. tubulosa may thus be a potential herbal medicine for the treatment of liver fibrosis.

Topics: Animals; Cell Line; Cistanche; Gene Expression Regulation; Glucosides; Glycosides; Hepatic Stellate Cells; L-Lactate Dehydrogenase; Phenols; Plant Extracts; Protective Agents; Protein Isoforms; Rats; RNA, Messenger; Signal Transduction; Smad Proteins; Transforming Growth Factor beta1

The aim of the work was to determine the interactions of a set of anti-cancer compounds with bovine serum albumin (BSA) using a ProteOn XPR36 array biosensor and molecular docking studies. The results revealed that a total of six anti-cancer compounds: gallic acid, doxorubicin, acteoside, salvianolic acid B, echinacoside, and vincristine were able to reversibly bind to the immobilized BSA. The sensorgrams of these six compounds were globally fit to a Langmuir 1:1 interaction model for binding kinetics analysis. There were significant differences in their affinity for BSA, with doxorubicin, the weakest binding compound having 1000-fold less affinity than salvianolic acid B, the strongest binding compound. However, compounds with a similar KD often exhibited markedly different kinetics due to the differences in

Topics: Animals; Antineoplastic Agents; Benzofurans; Binding Sites; Biosensing Techniques; Cattle; Doxorubicin; Gallic Acid; Glucosides; Glycosides; Molecular Docking Simulation; Phenols; Protein Array Analysis; Protein Binding; Serum Albumin, Bovine; Surface Plasmon Resonance; Vincristine

In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa, it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7-epi-loganic acid named Picconioside A and B. In addition were found the two 7-O-E/Z-cinnamoyl esters of 7-epi-loganic acid named Picconioside C and D.

Topics: Azores; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Molecular Structure; Oleaceae; Phenols; Pyrans

The objective of this study was to address the beneficial effects of Cistanche tubulosa extract on improving the low intestinal permeability of echinacoside (ECH) and acteoside (ACT).. Absorption of ECH and ACT in C. tubulosa extract was characterized using human intestinal Caco-2 cell monolayers with intact compounds. Glucose transporter-dependent absorption of ECH and ACT was confirmed by an in-situ intestinal perfusion technique.. The apparent permeability (Papp ) was not significantly different between intact ECH and intact ACT. In the presence of phloridzin, the Pap p of the ECH and ACT at a high dose was reduced to 20% of the respective non-treatment, but was not altered by phloretin and verapamil. C. tubulosa extract at low and high doses enhanced the Papp of ECH and ACT (both by threefold), resulting in their large participation in sodium-dependent glucose transporter-independent absorption. At a low concentration, concomitant ECH and ACT levels in portal blood were significantly suppressed by phloridzin.. The dietary and medicinal C. tubulosa extract enhancing the intestinal absorption of ECH and ACT may serve to better manage human health, although the involvement of phloridzin-sensitive transport should be reduced.

Topics: Animals; Caco-2 Cells; Cistanche; Dose-Response Relationship, Drug; Glucosides; Glycosides; Humans; Intestinal Absorption; Male; Phenols; Phloretin; Phlorhizin; Plant Extracts; Rats; Rats, Wistar; Sodium-Glucose Transport Proteins; Verapamil

Five samples of Cistanches Herba from different places were analyzed by HPLC-ESI-MS and FTIR methods. The effective compositions in Cistanches Herba including cistanoside A, echinacoside, acteoside , isoacteoside, 2'-actylacteoside, cistanoside C and tubluoside B were determined by HPLC-MS. The common peak ratio and variant peak ratio were calculated by FTIR spectroscopy of the five samples and the dual index sequence of common peak ratio and variant peak ratio were established. The results showed that the evaluation results of the samples by the two methods were the same. The general fake plant Cynomorii Herba could be identified by FTIR. HPLC-ESI-MS, which has high sensitivity and rapid determination procedure, can be used to evaluate quality of Cistanches Herba by quantitative analysis of the primary compositions. FTIR is a non-destructive analysis method. without complicated extraction and separation procedures to the samples. The absorption strength and the absorption shape were the synergistic effect of the functional groups and the nestification of the components in Cistanches Herba. The provided method has some advantages such as rapid analysis process, good reproducibility, non-destructive, small quantity of sample, simple treatment, good specificity, low-cost and environment-friendly. The method meets the trend of complex analysis and whole analysis for the Chinese medicines. Combination of FTIR and HPLC-ESI-MS was a good method for identification and evaluation of quality of Chinese medicines.

Topics: Catechols; Chromatography, High Pressure Liquid; Cistanche; Drugs, Chinese Herbal; Glucosides; Glycosides; Mass Spectrometry; Phenols; Reproducibility of Results; Spectroscopy, Fourier Transform Infrared

A new and fast sample preparation technique based on two-phase hollow fiber liquid phase microextraction (HF-LPME) with magnetofluid was developed to quantitate and determine the four phenylethanoid glycosides (PhGs) (Echinacoside, Tubuloside B, Acteoside and Isoacteoside) in plasma after oral administration of Cistanche salsa extract. Analysis was accomplished by reversed-phase high performance liquid chromatography (RP-HPLC) with ultraviolet detection. Parameters that affect the HF-LPME processes, such as the content of magnetic powder, the solvent type, salt content, stirring speed, extraction time and hollow fiber length, were investigated and optimized. Under the optimized conditions, the preconcentration factors for PhGs were higher than 625. The calibration curve for PhGs was linear in the range of 0.1-100ngmL(-1) with correlation coefficients greater than 0.9996. The intra-day and inter-day precision (RSD) were below 8.74% and the limits of detection (LOD) for the four PhGs were 8-15pgmL(-1) (S/N=3). The validated method was successfully applied to separate and determine the four PhGs in rat plasma after oral administration of C. salsa extract.

Topics: Administration, Oral; Animals; Calibration; Chromatography, High Pressure Liquid; Cistanche; Glucosides; Glycosides; Limit of Detection; Liquid Phase Microextraction; Male; Phenols; Plant Extracts; Rats; Rats, Sprague-Dawley; Solvents

A general strategy for the synthesis of phenylethanoid glycosides (PhG) including echinacoside 1, acteoside 2, calceolarioside-A 3 and calceolarioside-B 4 is reported. The strategy features the application of low substrate concentration glycosylation and N-formyl morpholine modulated glycosylation methods for the construction of 1,2-trans β- and α-glycosidic bonds. The reported strategy does not invoke the use of the participatory acyl protecting function, which is incompatible with the ester function present in target PhG compounds. A preliminary study of the anti-proliferation properties of the PhG compounds 1–4 was performed; the acteoside 2 exhibited the best inhibition on the prostatic cancer cell proliferation.

Topics: Caffeic Acids; Cell Line, Tumor; Cell Proliferation; Chemistry, Organic; Glucosides; Glycosides; Humans; Male; Phenols; Phenylethyl Alcohol; Prostatic Neoplasms

Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-500 mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2 weeks of continuous administration at doses of 125 and/or 250 mg/kg/day p.o. without producing significant changes in body weight or food intake. In addition, several constituents from C. tubulosa, including 1 (IC50 = 3.1 μM), 2 (1.2 μM), isoacteoside (3, 4.6 μM), 2'-acetylacteoside (4, 0.071 μM), tubulosides A (5, 8.8 μM) and B (9, 4.0 μM), syringalide A 3-O-α-L-rhamnopyranoside (10, 1.1 μM), campneoside I (13, 0.53 μM), and kankanoside J1 (14, 9.3 μM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 μM), a clinical aldose reductase inhibitor.

Topics: Aldehyde Reductase; Animals; Blood Glucose; Cistanche; Enzyme Inhibitors; Glucosides; Glycosides; Hypoglycemic Agents; Intestine, Small; Mice; Phenols; Rats

A simple and efficient chromatographic method for large-scale preparative separation of phenylethanoid glycosides (mainly contain echinacoside and acteoside) from Cistanche deserticola was developed. The adsorption properties of eight macroporous resins were evaluated. Three selected resins were further screened depending on the adsorption kinetics curves, in which HPD300 resin showed the best separation efficiency. The adsorption isotherm data on HPD300 resin were fitted to the Freundlich equation in certain concentration range. The dynamic adsorption and desorption experiments were carried out on columns packed with HPD300 resin to optimize the separation process. The breakthrough curves showed that acteoside had a higher affinity to the resin than echinacoside. The contents of echinacoside and acteoside in the product increased from 1.79% and 1.43% in the crude extracts to 16.66% and 15.17%, with recovery yields of 80.41% and 90.17%, respectively. The purity of total phenylethanoid glycosides in the product was 76.58%.

Topics: Adsorption; Chromatography, High Pressure Liquid; Cistanche; Glucosides; Glycosides; Kinetics; Phenols; Plant Extracts; Temperature

2-Aminoindan-2-phosphonic acid (AIP), a specific competitive phenylalanine ammonia lyase (PAL) inhibitor was applied to a suspension cell culture of Cistanche deserticola. The effects of AIP treatment on cell growth, PAL activity, contents and yields of total phenolic compound, salidroside and four phenylethanoid glycosides (PheGs) are investigated. The results demonstrated that, 0.5 and 2.0 μM AIP treatments had similar effects on the measurements investigated in this study. AIP treatment resulted in significant decreases in PAL activity, total phenolic compounds content, and PheGs content. Linear regression analysis showed that PAL activity had a high correlation coefficient with the total phenolic compound content and the four PheGs contents. Total PAL activity-time area under curve (AUC) had a high correlation coefficient with the total phenolic compound yield and the yields of five tested compounds in untreated cell samples. In AIP-treated cells, total PAL activity-time AUC retained a high correlation with the total phenolic compound yield and the yields of three tested compounds, echinacoside, acteoside, and tubuloside A, but not salidroside and cistanoside A. The difference could be caused by the different biosynthetic origins of each of the tested compounds. These results demonstrate the important role of PAL in the biosynthesis of PheGs in the suspension cell culture of C. deserticola.

Topics: Catechols; Chromatography, High Pressure Liquid; Cistanche; Glucosides; Glycosides; Indans; Organophosphonates; Phenols

Acteoside and echinacoside are the major active components of Herba Cistanches. Facilitated β-glucosidation was investigated as a means of increasing harvest of acteoside from Cistanche tubulosa. Fresh Cistanche tubulosa was treated by microwave moisture processing to inactivate enzymes. β-Glucosidase is capable of hydrolyzing echinacoside for the production of acteoside, so six β-glucosidases were compared for their efficiency, specific activities and kinetic parameters for conversion to acteoside. The acteoside and echinacoside content was found to be higher after microwave processing than by other previously reported methods. The results showed that β-glucosidase isolated from microorganisms (Trichoderma sp.) had highly specific activity towards echinacoside, and there was a 4.83 fold increase in the concentration of acteoside after an incubation period of 2 h. This is the first report of the potential application of β-glucosidases for the facilitated conversion of echinacoside to acteoside in Herba Cistanches extract.

Topics: beta-Glucosidase; Cistanche; Glucosides; Glycosides; Phenols

The immediate-type allergic reaction is involved in many allergic diseases such as asthma, allergic rhinitis, and sinusitis. In this study, we investigated the effect of acteoside extracted from CISTANCHE TUBULOSA (Schrenk) R. Wight on the basophilic cell-mediated allergic reaction. The effect of acteoside on β-hexosaminidase release and intracellular [Ca (2+)] I level from rat basophilic leukemia (RBL-2H3) cells was determined. Also, ELISA was used to determine the level of histamine, tumor necrosis factor (TNF)- α, and interleukin (IL)-4 on human basophilic (KU812) cells. The effect of acteoside on basophilic cell viability was determined using the 3-[4,5-dimethylthiazolyl]-2,5-diphenyltetrazolium bromide (MTT) assay. These results indicated that 0.1-10.0 µg/mL acteoside inhibits the release of β-hexosaminidase and [Ca (2+)] I influx from IgE-mediated RBL-2H3 cells. Moreover, acteoside inhibited histamine release, TNF- α, and IL-4 production in a dose-dependent manner from calcium ionophore A23187 plus phorbol 12-myristate 13-acetate (PMA) or compound 48/80-stimulated KU812 cells. Our findings provide evidence that acteoside inhibits basophilic cell-derived immediate-type and delayed-type allergic reactions. This is the first report describing antiallergic activity of acteoside extracted from CISTANCHE TUBULOSA on basophilic cells.

Topics: Animals; Anti-Allergic Agents; beta-N-Acetylhexosaminidases; Calcimycin; Calcium; Catechols; Cell Line; Cistanche; Enzyme-Linked Immunosorbent Assay; Glucosides; Glycosides; Histamine; Humans; Interleukin-4; Phenols; Rats; Tetradecanoylphorbol Acetate; Tumor Necrosis Factor-alpha

Through analyze of shape, structure and content of effective components of Cistanche deserticola, the variation of "you cong rong" is discussed.. The color surface, texture, the size of pith and the arrange of vascular bundle was observed with freshed, dried drugs and the transverse section, the effective component of echinacoside and acteoside was analyzed with hplc and the amylose was analyzed with ultraviolet spectrophotometry.. The variation of "you cong rong" is obvious different with the common drug in shape and structure, the content of echinacoside is 2.5 times, acteoside is 3.8 times, amylose yield is 1.6 times and the content is 2 times of the common drugs.. "you cong rong" is an independent variation pattern of C. deserticola, it has no relationship with the ecological and geographical conditions.

Topics: Amylose; Chromatography, High Pressure Liquid; Cistanche; Drugs, Chinese Herbal; Glucosides; Glycosides; Phenols

To establish the processing method of Cistanche tubulosa decoction pieces.. The orthogonal test of four factors and three levels was used to optimize the main factors in the process of fresh C. tubulosa decoction pieces processing, including the thickness, temperature, and the time for inactivation of the enzyme in the plant. The result showed that the optimized condition was that fresh C. tubulosa was cut into 4 mm thickness, and heated at 70 degrees C for inactivation the enzyme in the plant for 6 min. Moreover, the optimized method was compared with the method of insolation and traditional dried method.. The content of echinacoside in the C. tubulosa decoction piece by the optimized method was 7.3 times of that dried by insolation, and 12.8 times of that by traditional dry method; the content of verbascoside was 6. 5 and 14. 9 times of that dried by insolation and by traditional dry method, respectively; the content of galactitol was 7.1 and 13.2 times of that dried by insolation and by traditional dry method, respectively.. The quality of C. tubulosa decoction pieces could be improved by this method, and its crud drug could be saved, which would protect the source of the mild Herba Cistanche, and produced the better economic and ecological benefits.

Topics: Cistanche; Desiccation; Drugs, Chinese Herbal; Galactitol; Glucosides; Glycosides; Hot Temperature; Phenols; Plants, Medicinal; Quality Control; Technology, Pharmaceutical

To analyse the echinacoside and acteoside content of Cistanche tubulosa, collected from different hosts and different size of the cultivated, which is compared to the wilding by RP-HPLC method.. An Agilent Eclipse XDB-C18(4.6 mm x 250 mm, 5 microm) column was used and a mixture of methanol-acetonitrile-1% acetic acid (15:10:75) was used as the mobile phase at a flow rate of 0.6 mL x min(-1). The column temperature was 30 degrees C and the UV detection wavelength was 334 nm.. The calibration curves of echinacoside and acteoside were in good linearity over the range of 0.904-9.04 microg (r = 0.999 9), and 1.27-12.7 microg (r = 0.999 9) respectively and the average recoveries of echinacoside (and acteoside) were 98.9% (n = 5, RSD 1.9%), and 97.0% (n = 5, RSD 0.97%).. The method is simple, quick, acurate. In all of the samples, the contents of echinacoside is markedly more than that of acteoside, the content of the two active component in the wilding is higher than that in the planting. The content of sample in the different sizes gradually increase from the big to the small, and the contents of samples collected from the different hosts vary markedly. These results are useful for the quality evaluation of medicinal materials of C. tubulosa.

Topics: Breeding; Chromatography, High Pressure Liquid; Cistanche; Glucosides; Glycosides; Host-Parasite Interactions; Phenols; Plants, Medicinal; Tamaricaceae

To have a contrast study on phenylethanoid glycosides from Cistanche deserticola Y. C. Ma collected in different seasons.. LC/MS method has been applied for the analysis of four kinds of phenylethanoid glycosides compunds (echinacoside, acteoside, cistanoside A and 2'-acetylacteoside) from Cistanche deserticola Y. C. Ma in spring and autumn.. According to the special MS spectra and HPLC chromatogram, this four kinds of phenylethanoid glycosides compounds were detected in each Cistanche deserticola Y. C. Ma, but the content is considerable different except the acteoside.. The content of phenylethanoid glycosides from Cistanche deserticola Y. C. Ma in different seasons has a difference from each other, the quality of Cistanche deserticola Y. C. Ma is also different.

Topics: Chromatography, Liquid; Cistanche; Gas Chromatography-Mass Spectrometry; Glucosides; Glycosides; Phenols; Plant Stems; Plants, Medicinal; Seasons

When, on the 15th day of growth, an elicitor from Fusarium solani was added at 40 mg l(-1) to Cistanche deserticola cell suspension cultures, the contents of echinacoside, acteoside and total phenylethanoid glycosides (PeGs) in cultured cells all increased over the next 27 d by over 100% to 15 mg g(-1) dry wt, 9 mg g(-1) dry wt and 57 mg g(-1) dry wt, respectively. The final biomass (1.3 mg dry wt ml(-1)) was not affected.

Topics: Cell Division; Cell Survival; Cistanche; Culture Techniques; Dose-Response Relationship, Drug; Fungal Proteins; Fusarium; Glucosides; Glycosides; Phenols; Quality Control

To study the metabolic process of phenylethanoid glycosides (PhGs) in the gastrointestine of beagle dogs that were administered intragastrially process, and develop some new methods of biopharmacology on the effective position of traditional Chinese medicine.. High-performance liquid chromatography was used to purify constituents from faeces and analyze relative contents of the three main compounds in the gastrointestinal tract at different times and in the faeces of dogs. Every sample was collected, extracted with methanol and analyzed with integration.. Four compounds, based on reference substances, were identified as echinacoside, acteoside, isoacteoside, and 2'-acetylacteoside from extraction of faces of dogs. Quantitative "with HPLC" analysis reveals that variation of ratios of the three main compounds is not distinct when moving in the gastrointestinal tract 7 h, that is quite different from those in faeces, in which the content of echinacoside fell from 48.0% to 16.0%, and acteoside increased from 11.0% to 34.7%.. PhGs are mainly metabolized in large intestine. Among them, a portion of echinacoside is transformed into aceteoside.

Topics: Animals; Cistanche; Dogs; Feces; Gastric Mucosa; Glucosides; Glycosides; Intestine, Large; Phenols; Phenylethyl Alcohol; Plants, Medicinal

To establish the quality standard for Herba Cistanches.. A qualitative identification method by TLC was established for five kinds of active components(acteoside, echinacoside, cistanoside A, betaine and mannitol) and RP-HPLC was used to quantify the acteoside contents.. Qualitative and quantitative analyses were carried out for fourteen kinds of Herba Cistanches and eleven kinds of Yinpian. This method is accurate, reliable and of good separability and reproducibility.. This method can be applied as standard for the quality control of cistanche deserticola.

Topics: Betaine; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Glucosides; Glycosides; Magnoliopsida; Mannitol; Phenols; Plants, Medicinal; Quality Control

There are few reports about marker substances for the identification of Cistanchis Herba in formulations. First, constituent analysis was performed by HPLC for screening of a marker substance, using several lots of Cistanchis Herba and its fluid extract. As a result, two components were clearly detected, which were thought to be good marker substances and identified to be echinacoside and acteoside by structural analysis. Stability testing of these two marker substances in various pH and temperature conditions was carried out, which suggested that they are stable and suitable enough for the identification. Therefore, the identification methods of Cistanchis Herba and its fluid extract in formulations were investigated using five different kinds of commercial drinkable preparations with authentic standard of echinacoside and acteoside as marker substances. Consequently, echinacoside and acteoside were clearly detected in all formulations investigated, using an HPLC-photodiode array detector system. Echinacoside and acteoside will be successfully used as marker substances for the identification of Cistanchis Herba and its fluid extract in formulations.

Topics: Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Drug Stability; Drugs, Chinese Herbal; Glucosides; Glycosides; Hydrogen-Ion Concentration; Pharmaceutical Solutions; Phenols; Temperature

Four phenylethanoid glucosides were isolated from the flower of Buddleja officinalis. On the basis of specteral data, they were identified as salidroside(1), verbascoside(2), isoverbascoside(3) and echinacoside(4). Compounds 1, 3 and 4 were obtained from the plant for the first time. Compound 2 showed antibacterial and anticancer activities.

Topics: Drugs, Chinese Herbal; Glucosides; Glycosides; Magnoliopsida; Molecular Structure; Phenols; Plants, Medicinal

The Chinese drug "Rou Cong-rong" (Herba Cistanchis) is one of the commonly used drugs in Chinese traditional medicine. It is used to reinforce the vital function of kidney, especially that of the sexual organs and induce laxation, for the treatment of impotence, premature ejaculation in men, infertility, morbid leukorrhea, profuse metrorrhagia in women, and chronic constipation in the aged. This paper deals with the qualitative and quantitative analysis of phenylethanoid glycosides of four species and one variety of Genus Cistanche and 23 lots of commercial crude drugs of Herba Cistanchis by RP-HPLC. The results were as follows: the chemical constituents of Cistanche deserticola Ma, C. salsa (C. A. Mey) G. Beck, C. salsa var. albiflora P. F. Tu et Z. C. Lou and C. tubulosa were similar while those of C. sinensis were different from the others; the contents of echinacoside and acteoside of C. salsa, which were 2.13% and 1.51%, were the highest of the genus Cistanche. An ODS column (Alltima C18, 5 microns, 250 x 4.6 mm) was employed. Linear gradient elution of acetonitrile--1.5% acetic acid was used as mobile phase, and concentration of acetontrile was from 8% to 20% (0-60 min) in the qualitative analysis, and from 11.5 to 20% (0-35 min) in the quantitative analysis. The flow rate was 1.2 ml.min-1. The detection wavelength was set at 335 nm.

Topics: Chromatography, High Pressure Liquid; Drug Contamination; Drugs, Chinese Herbal; Glucosides; Glycosides; Immunosuppressive Agents; Magnoliopsida; Phenols; Plants, Medicinal; Quality Control