41 results on '"phenylethanoid glycosides"'
Search Results
2. A review on the structure and pharmacological activity of phenylethanoid glycosides.
- Author
-
Tian XY, Li MX, Lin T, Qiu Y, Zhu YT, Li XL, Tao WD, Wang P, Ren XX, and Chen LP
- Subjects
- Animals, Asteraceae chemistry, Drug Discovery, Humans, Phenylethyl Alcohol chemistry, Phenylethyl Alcohol pharmacology, Plants chemistry, Scrophulariaceae chemistry, Glycosides chemistry, Glycosides pharmacology, Plant Extracts chemistry, Plant Extracts pharmacology
- Abstract
Phenylethanoid glycosides (PhGs) are compounds made of phenylethyl alcohol, caffeic acid and glycosyl moieties. The first published references about phenylethanoid glycosides concerned the isolation of echinacoside from Echinaceu ungustifolia (Asteraceae) in 1950 and verbascoside from Verbascum sinuatum (Scrophulariaceae) in 1963. Over the past 60 years, many compounds with these structural characteristics have been isolated from natural sources, and most of these compounds possess significant bioactivities, including antibacterial, antitumor, antiviral, anti-inflammatory, neuro-protective, antioxidant, hepatoprotective, and immunomodulatory activities, among others. In this review, we will summarize the phenylethanoid glycosides described in recent papers and list all the compounds that have been isolated over the past few decades. We will also attempt to present and assess recent studies about the separation, extraction, determination, and pharmacological activity of the excellent natural components, phenylethanoid glycosides., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Masson SAS. All rights reserved.)
- Published
- 2021
- Full Text
- View/download PDF
3. Minor acetylated metabolites from Euphrasia rostkoviana .
- Author
-
D'Ambrosio M, Ciocarlan A, and Aricu A
- Subjects
- Acetylation, Euphrasia metabolism, Flavonoids chemistry, Flavonoids isolation & purification, Molecular Structure, Rutin chemistry, Euphrasia chemistry, Plant Extracts chemistry
- Abstract
The phenylethanoids rostkovianoside, 6'- O -acetylcrassifolioside and the flavonoid rutin 3‴-acetate, were isolated from the methanolic extract of the aerial parts of Euphrasia rostkoviana Hayne. The structures of these previously undescribed compounds were elucidated by interpretation of spectroscopic data. The acetylation of rutin was also carried out and four ester derivatives were spectroscopically characterized. Finally, a chromatographic method was established to easily identify the acetylated position.
- Published
- 2020
- Full Text
- View/download PDF
4. Simultaneous Quantification of Four Phenylethanoid Glycosides in Rat Plasma by UPLC-MS/MS and Its Application to a Pharmacokinetic Study of Acanthus Ilicifolius Herb.
- Author
-
Zhang M, Ren X, Yue S, Zhao Q, Shao C, and Wang C
- Subjects
- Animals, Caffeic Acids blood, Caffeic Acids pharmacokinetics, Chromatography, Liquid, Glucosides blood, Glucosides pharmacokinetics, Glycosides pharmacokinetics, Male, Phenols blood, Phenols pharmacokinetics, Plant Extracts pharmacokinetics, Rats, Rats, Sprague-Dawley, Tandem Mass Spectrometry, Acanthaceae chemistry, Glycosides blood, Plant Extracts administration & dosage
- Abstract
Acanthus ilicifolius herb (AIH), the dry plant of Acanthus ilicifolius L., has long been used as a folk medicine for treating acute and chronic hepatitis. Phenylethanoid glycosides (PhGs) are one family of the main components in AIH with hepatoprotective, antioxidant, and anti-inflammatory activities. In this study, the pharmacokinetics of AIH was investigated preliminarily by ultra-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC-MS/MS). A simultaneously quantitative determination method for four PhGs (acteoside, isoacteoside, martynoside, and crenatoside) in rat plasma was first established by UPLC-MS/MS. These four PhGs were separated with an ACQUITY UPLC BEH C
18 column (2.1 × 50 mm, 1.7 μm) by gradient elution (mobile phase: MeCN and 0.1% formic acid in water, 0.4 mL/min). The mass spectrometry detection was performed using negative electrospray ionization (ESI- ) in multiple reaction monitoring (MRM) mode. By the established method, the preliminary pharmacokinetics of AIH was elucidated using the kinetic parameters of the four PhGs in rat plasma after intragastric administration of AIH ethanol extract. All four PhGs showed double peaks on concentration-time curves, approximately at 0.5 h and 6 h, respectively. Their elimination half-lives (t1/2 ) were different, ranging from 3.42 h to 8.99 h, although they shared similar molecular structures. This work may provide a basis for the elucidation of the pharmacokinetic characteristics of bioactive components from AIH.- Published
- 2019
- Full Text
- View/download PDF
5. Inhibition of Amyloid Beta Aggregation and Deposition of Cistanche tubulosa Aqueous Extract.
- Author
-
Chao CL, Huang HW, Huang HC, Chao HF, Yu SW, Su MH, Wang CJ, and Lin HC
- Subjects
- Alzheimer Disease drug therapy, Amyloid beta-Peptides chemistry, China, Humans, Plant Extracts chemistry, Water chemistry, Amyloid beta-Peptides antagonists & inhibitors, Cistanche chemistry, Plant Extracts pharmacology, Protein Aggregation, Pathological drug therapy
- Abstract
Cistanche tubulosa aqueous extract (CTE) is already used as a botanical prescription drug for treating dementia in China. Our previous studies reported that phenylethanoid glycosides of CTE have anti-Alzheimer's disease (AD) activity by inhibiting amyloid β peptide (Aβ) aggregation and deposition. However, recent studies considered that the phenylethanoid glycosides may be metabolized by intestinal bacteria, because all analysis results showed that the bioavailability of phenylethanoid glycosides is extremely low. In this study we demonstrate how iron chelation plays a crucial role in the Aβ aggregation and deposition inhibition mechanism of phenylethanoid glycosides of CTE. In addition, we further proved phenylethanoid glycosides ( 1 ⁻ 3 ) could reach brain. Active CTE component and action mechanism confirmation will be a great help for product quality control and bioavailability studies in the future. At the same time, we provide a new analysis method useful in determining phenylethanoid glycosides ( 1 ⁻ 3 ) in plants, foods, blood, and tissues for chemical fingerprint and pharmacokinetic research.
- Published
- 2019
- Full Text
- View/download PDF
6. Integrated approach for confidence-enhanced quantitative analysis of herbal medicines, Cistanche salsa as a case.
- Author
-
Liu W, Song Q, Yan Y, Liu Y, Li P, Wang Y, Tu P, Song Y, and Li J
- Subjects
- Plant Extracts chemistry, Chromatography, Reverse-Phase methods, Cistanche chemistry, Glycosides analysis, Herbal Medicine, Plant Extracts analysis, Tandem Mass Spectrometry methods
- Abstract
Although far away from perfect, it is practical to assess the quality of a given herbal medicine (HM) through simultaneous determination of a panel of components. However, the confidences of the quantitative outcomes from LC-MS/MS platform risk several technical barriers, such as chemical degradation, polarity range, concentration span, and identity misrecognition. Herein, we made an attempt to circumvent these obstacles by integrating several fit-for-purpose techniques, including online extraction (OLE), serially coupled reversed phase LC-hydrophilic interaction liquid chromatography (RPLC-HILIC), tailored multiple reaction monitoring (MRM), and relative response vs. collision energy curve (RRCEC) matching. Confidence-enhanced quantitative analysis of Cistanche salsa (Csa), a well-known psammophytic species and tonic herbal medicine, was conducted as a proof-of-concept. OLE module was deployed to prohibit chemical degradation, in particular E/Z-configuration transformation for phenylethanoid glycosides. Satisfactory retention took place for each analyte regardless of polarity because of successive passing through RPLC and HILIC columns. Optimum parameters for the minor components, at the meanwhile of inferior ones for the abundant ingredients, ensured the locations of all contents in the linear ranges. The unequivocal assignment of the captured signals was achieved by matching retention times, ion transitions, and more importantly, RRCECs between authentic compounds and suspect peaks. Diverse validation assays demonstrated the newly developed method to be reliable. Particularly, the distribution of mannitol rather than galactitol was disclosed although these isomers showed identical retention time and ion transitions. The contents of 21 compounds-of-interest were definitively determined in Csa as well as two analogous species, and the quantitative patterns exerted great variations among not only different species but different Csa samples. Together, the fortification of OLE-RPLC-HILIC-tailored MRM with RRCEC matching could fully address the demands from confidence-enhanced quantitative analysis of HMs., (Copyright © 2018 Elsevier B.V. All rights reserved.)
- Published
- 2018
- Full Text
- View/download PDF
7. Identification and Quantitation of the Bioactive Components in Osmanthus fragrans Fruits by HPLC-ESI-MS/MS.
- Author
-
Liao X, Hu F, and Chen Z
- Subjects
- Chromatography, High Pressure Liquid methods, Fruit chemistry, Oleaceae chemistry, Plant Extracts chemistry, Tandem Mass Spectrometry methods
- Abstract
Information on the chemical composition of Osmanthus fragrans fruits is still limited because there are many compounds present in low concentrations in the plant. In this work, the bioactive components in O. fragrans fruit extract were investigated by a new high-performance liquid chromatography electrospray ionization tandem mass spectrometry method, which allows sensitive analysis both in identification and quantitation. A total of 28 compounds were tentatively identified, and 16 components were discovered in O. fragrans fruits for the first time. The validated quantitative methods for the determination of the bioactive components were subsequently applied to analyze batches of O. fragrans fruits from different cultivars, which is beneficial for the comprehensive utilization of O. fragrans fruits.
- Published
- 2018
- Full Text
- View/download PDF
8. Polar constituents, protection against reactive oxygen species, and nutritional value of Chinese artichoke (Stachys affinis Bunge).
- Author
-
Venditti A, Frezza C, Celona D, Bianco A, Serafini M, Cianfaglione K, Fiorini D, Ferraro S, Maggi F, Lizzi AR, and Celenza G
- Subjects
- Caco-2 Cells, Humans, Magnetic Resonance Spectroscopy, Nutritive Value, Iridoid Glycosides analysis, Plant Extracts chemistry, Reactive Oxygen Species analysis, Stachys chemistry, Succinic Acid analysis
- Abstract
In the present work, we studied the chemical composition of Chinese artichoke (S. affinis tubers) by analyzing its polar constituents and its macro- and micro- nutrients. A total of nine compounds were isolated from the tuber ethanolic extract and structurally elucidated by Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry (MS). The marker compounds identified were oligosaccharide stachyose and the organic acid, succinic acid, as well as phenylethanoid and iridoid glycosides. The macronutrient profile was dominated by carbohydrates (36.9% dw), whereas potassium (2.36%) was the most abundant micro-nutrient. The tuber ethanolic extract was able to efficiently protect human cells (Caco-2, SHSY-5Y and K562) against t-BHP-induced oxidative damage., (Copyright © 2016 Elsevier Ltd. All rights reserved.)
- Published
- 2017
- Full Text
- View/download PDF
9. Ultrasound-assisted aqueous two-phase extraction of phenylethanoid glycosides from Cistanche deserticola Y. C. Ma stems.
- Author
-
Dong B, Yuan X, Zhao Q, Feng Q, Liu B, Guo Y, and Zhao B
- Subjects
- Chromatography, High Pressure Liquid, Temperature, Water, Cistanche chemistry, Glycosides isolation & purification, Plant Extracts chemistry, Plant Stems chemistry, Ultrasonics
- Abstract
An efficient ultrasound-assisted aqueous two-phase extraction and enrichment process for phenylethanoid glycosides from Cistanche deserticola Y. C. Ma stems was developed in this work. An ethanol/ammonium sulfate system was chosen for the aqueous two-phase system due to its fine partitioning and recycling behaviors. Single-factor experiments and response surface methodology were used to optimize the process parameters of the ultrasound-assisted aqueous two-phase extraction. The optimal conditions were as follows: a salt concentration of 23.5%, an ethanol concentration of 20%, an extraction time of 37 min, an extraction temperature of 30°C, a liquid/solid ratio of 30:1 w/w, and an ultrasound power of 300 W. Under the above conditions, the extraction yields of echinacoside and acteoside (the main components of phenylethanoid glycosides) reached 5.35 and 6.22 mg/g dry material weight, respectively. The contents of echinacoside and acteoside in the extracts reached 27.56 and 30.23 mg/g, respectively, which were 2.46- and 2.58-fold higher than the amounts obtained in ultrasound-assisted extraction. In conclusion, ultrasound-assisted aqueous two-phase extraction was an efficient, ecofriendly, and economical method, and it may be a promising technique for extracting and enriching bioactive components from plants., (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Published
- 2015
- Full Text
- View/download PDF
10. Effect of chito-oligosaccharide on the intestinal absorptions of phenylethanoid glycosides in Fructus Forsythiae extract.
- Author
-
Zhou W, Tan X, Shan J, Liu T, Cai B, and Di L
- Subjects
- Animals, Antiviral Agents pharmacology, Caco-2 Cells, Caffeic Acids, Dogs, Fruit chemistry, Glucosides, Humans, Influenza A virus drug effects, Madin Darby Canine Kidney Cells, Male, Molecular Structure, Rats, Sprague-Dawley, Forsythia chemistry, Glycosides pharmacokinetics, Intestinal Absorption, Oligosaccharides pharmacology, Plant Extracts pharmacokinetics
- Abstract
Phenylethanoid glycosides, the main active ingredients in Fructus Forsythiae extract possesses strong antibacterial, antioxidant and antiviral effects, and their contents were higher largely than that of other ingredients such as lignans and flavones, but their absolute bioavailability orally was significantly low, which influenced clinical efficacies of its oral preparations seriously. In the present study, the absorption mechanism of phenylethanoid glycosides was studied using in vitro Caco-2 cell model. And the effect of chito-oligosaccharide (COS) on the intestinal absorption of phenylethanoid glycosides in Fructus Forsythiae extract was investigated using in vitro, in situ and in vivo models. The pharmacological effects such as antiviral activity improvement by COS were verified by MDCK cell damage inhibition rate after influenza virus propagation. The observations from in vitro Caco-2 cell showed that the absorption of phenylethanoid glycosides in Fructus Forsythiae extract so with that in monomers was mainly restricted by the tight junctions, and influenced by efflux transporters (P-gp and MRP2). Meanwhile, the absorption of phenylethanoid glycosides in Fructus Forsythiae extract could be improved by COS. Besides, COS at the same low, medium and high concentrations caused a significant, concentration-dependent increase in the Papp-value for phenylethanoid glycosides compared to the control group (p<0.05), and was all safe for the Caco-2 cells. The observations from single-pass intestinal perfusion in situ model showed that the intestinal absorption of phenylethanoid glycosides can be enhanced by COS. Meanwhile, the absorption enhancing effect of phenylethanoid glycosides might be saturable in different intestine sites. In pharmacokinetics study, COS at dosage of 25mg/kg improved the bioavailability of phenylethanoid glycosides in Fructus Forsythiae extract to the greatest extent, and was safe for gastrointestine from morphological observation. In addition, treatment with Fructus Forsythiae extract with COS at dosage of 25mg/kg prevented MDCK cell damage upon influenza virus propagation better than that of control. All findings above suggested that COS at dosage of 25mg/kg might be safe and effective absorption enhancer for improving the bioavailability of phenylethanoid glycosides and the antiviral activity in vitro in Fructus Forsythiae extract., (Copyright © 2014 Elsevier GmbH. All rights reserved.)
- Published
- 2014
- Full Text
- View/download PDF
11. Two-phase hollow fiber liquid phase microextraction based on magnetofluid for simultaneous determination of Echinacoside, Tubuloside B, Acteoside and Isoacteoside in rat plasma after oral administration of Cistanche salsa extract by high performance liquid chromatography.
- Author
-
Zhou J, Zhang Q, Sun JB, Sun XL, and Zeng P
- Subjects
- Administration, Oral, Animals, Calibration, Chromatography, High Pressure Liquid methods, Glucosides chemistry, Glycosides chemistry, Limit of Detection, Liquid Phase Microextraction methods, Male, Phenols chemistry, Rats, Rats, Sprague-Dawley, Solvents chemistry, Cistanche chemistry, Glucosides blood, Glycosides blood, Phenols blood, Plant Extracts administration & dosage, Plant Extracts chemistry
- Abstract
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., (Copyright © 2014 Elsevier B.V. All rights reserved.)
- Published
- 2014
- Full Text
- View/download PDF
12. Simultaneous separation and determination of four phenylethanoid glycosides in rat plasma sample after oral administration of Cistanche salsa extract by microemulsion liquid chromatography.
- Author
-
Zhou J, Zhang Q, Sun JB, Wang FQ, and Zeng P
- Subjects
- Administration, Oral, Animals, Chromatography, High Pressure Liquid, Drug Stability, Glycosides chemistry, Glycosides isolation & purification, Hydrogen-Ion Concentration, Male, Plant Extracts chemistry, Rats, Rats, Sprague-Dawley, Reproducibility of Results, Chromatography, Liquid methods, Cistanche chemistry, Glycosides blood, Plant Extracts administration & dosage
- Abstract
A simple, rapid and specific method was developed to separate as well as to determine the four phenylethanoid glycosides (PhGs) (echinacoside, tubuloside B, acteoside and isoacteoside) in rat plasma after oral administration of Cistanche salsa extract by reversed phase high performance liquid chromatography using a microemulsion as the mobile phase. The separations were performed on a Zorbax Extend-C18 column at 25°C. Photodiode-array detector was conducted at 322nm and with a flow rate of 0.8mLmin(-1). The optimized microemulsion mobile phase consisted of 0.3% triethylamine in 20mM phosphoric acid at pH 6.0, 0.8% (v/v) ethyl acetate as oil phase, 1.5% (v/v) Genapol X-080 as surfactant, 2.5% (v/v) n-propanol as co-surfactant. Under the optimal conditions, the calibration curve for four PhGs was linear in the range of 10-1000ngmL(-1) with the correlation coefficients greater than 0.9994. The intra-day and inter-day precision (RSD) were below 8.64% and the limits of detection (LOD) for the four PhGs were 0.4-1.3ngmL(-1) (S/N=3). The microemulsion liquid chromatography (MELC) method was successfully applied to separate and determine the four PhGs in rat plasma after oral administration of C. salsa extract., (Copyright © 2014 Elsevier B.V. All rights reserved.)
- Published
- 2014
- Full Text
- View/download PDF
13. Anti-hyperglycemic and hypolipidemic effects of Cistanche tubulosa in type 2 diabetic db/db mice.
- Author
-
Xiong WT, Gu L, Wang C, Sun HX, and Liu X
- Subjects
- Animals, Blood Glucose analysis, Diabetes Mellitus, Type 2 metabolism, Glycogen metabolism, Hypoglycemic Agents pharmacology, Hypolipidemic Agents pharmacology, Insulin Resistance, Lipids blood, Liver metabolism, Male, Mice, Mice, Mutant Strains, Muscle, Skeletal metabolism, Phytotherapy, Plant Extracts pharmacology, Plant Stems, Cistanche, Diabetes Mellitus, Type 2 drug therapy, Hypoglycemic Agents therapeutic use, Hypolipidemic Agents therapeutic use, Plant Extracts therapeutic use
- Abstract
Ethnopharmacological Relevance: The dried succulent stem of Cistanche tubulosa (Schenk) R. Wight is one component of traditional Chinese medicine prescriptions for diabetes. However, there have been no modern scientific reports to confirm this traditional claim for the Cistanche species until now. Thus, we investigated the effects of Cistanche tubulosa on glucose homeostasis and serum lipids in male BKS.Cg-Dock7(m) +/+ Lepr(db)/J (db/db) mice, a model of type 2 diabetes., Materials and Methods: The verbascoside and echinacoside contents of Cistanche tubulosa powder were evaluated using HPLC. The total phenolic content, polysaccharide content and antioxidant activity of Cistanche tubulosa powder were also evaluated. Then, different doses of Cistanche tubulosa (equivalent to 120.9, 72.6 or 24.2mg verbascoside/kg) were administered orally once daily for 45 days to male db/db mice. Age matched db/+ mice were used as normal controls. Body weight, fasting blood glucose, postprandial blood glucose and insulin tolerance test were measured during the experiment. At the time of sacrifice, blood was collected for measurement of insulin level, the homeostatic model assessment of insulin resistance (HOMA-IR), and total cholesterol, triglyceride, HDL-c, LDL-c and VLDL-c levels; liver and muscle were harvested for measurement of glycogen levels., Results: Cistanche tubulosa significantly suppressed the elevated fasting blood glucose and postprandial blood glucose levels, improved insulin resistance and dyslipidemia, and suppressed body weight loss in db/db mice. However, Cistanche tubulosa did not significantly affect serum insulin levels or hepatic and muscle glycogen levels., Conclusion: This study provides scientific evidence for the traditional use of Cistanche tubulosa to treat diabetes, suggesting that Cistanche tubulosa has the potential for development into a functional food ingredient or drug to prevent hyperglycemia and treat hyperlipidemia., (© 2013 Published by Elsevier Ireland Ltd.)
- Published
- 2013
- Full Text
- View/download PDF
14. In vivo anti-inflammatory and anti-ulcerogenic activities of extracts from wild growing and in vitro plants of Castilleja tenuiflora Benth. (Orobanchaceae).
- Author
-
Sanchez PM, Villarreal ML, Herrera-Ruiz M, Zamilpa A, Jiménez-Ferrer E, and Trejo-Tapia G
- Subjects
- Animals, Anti-Inflammatory Agents pharmacology, Cell Line, Tumor, Cell Survival drug effects, Ethanol, Female, Humans, Male, Mice, Mice, Inbred ICR, Phytotherapy, Plant Extracts pharmacology, Rats, Rats, Sprague-Dawley, Stomach drug effects, Stomach pathology, Stomach Ulcer chemically induced, Stomach Ulcer pathology, Anti-Inflammatory Agents therapeutic use, Edema drug therapy, Orobanchaceae, Plant Extracts therapeutic use, Stomach Ulcer drug therapy
- Abstract
Ethnopharmacological Relevance: Castilleja tenuiflora Benth. (Orobanchaceae) is a perennial shrub used since the 16(th) century in Mexican traditional medicine for the treatment of a number of health disorders including inflammation, stomach pain and tumors. The aim of the present study was to evaluate the cytotoxic, anti-inflammatory and anti-ulcerogenic activities of ethyl acetate (EaE), methanol (ME) and aqueous extracts (AE) of Castilleja tenuiflora wild grown (CtW) and in vitro plants (CtIv)., Material and Method: Phytochemical analysis of the phenylethanoid glycoside (PhG) and iridoid glycoside (IG) components was carried out by chromatographic methods. In vitro cytotoxic activity of the extracts was evaluated in the following four carcinoma cell lines: colon (HF-6), breast (MCF-7), prostate (PC-3), and nasopharyngeal (KB). The topical anti-inflammatory activity was evaluated in mouse ear edema induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Anti-ulcerogenic activity was evaluated in rats using an absolute ethanol-induced acute gastric ulcer model., Results: The main compounds in the extracts were isoverbascoside, verbascoside and aucubin and their concentration depended both on the solvent used and on the plant material origin. None of the extracts showed cytotoxicity against the tested cell lines. In contrast, CtWEaE, CtWAE and CtIvEaE (1.6 mg/ear) showed moderate anti-inflammatory activity similar to dexamethasone (1 mg/ear) with a 38.2, 39.3 and 49.1% decrease of inflammation, respectively. CtWEaE and CtIvEaE (100 mg/kg) showed high anti-ulcerogenic activity with 88.3 and 83.1% inhibition, respectively, compared to famotidine (20 mg/kg, 32.8% inhibition)., Conclusion: Castilleja tenuiflora extracts provided significant gastric protection in an acute ulcer induction model and topical anti-inflammatory activity in a mouse ear edema model. These activities are related to verbascoside and may explain the traditional use of Castilleja tenuiflora in the treatment of anti-inflammatory and gastrointestinal disorders. Cultured Castilleja tenuiflora plants (in vitro) exhibited pharmacological activities and also have the potential to produce bioactive compounds., (© 2013 Published by Elsevier Ireland Ltd.)
- Published
- 2013
- Full Text
- View/download PDF
15. Protective effect of total phenylethanoid glycosides from Monochasma savatieri Franch on myocardial ischemia injury.
- Author
-
Shi M, He W, Liu Y, Li X, Yang S, and Xu Q
- Subjects
- Animals, Cardiotonic Agents isolation & purification, Cardiotonic Agents pharmacology, Cell Survival drug effects, Glycosides isolation & purification, Glycosides pharmacology, Heart drug effects, Heart physiopathology, Humans, Hydrogen Peroxide, Isoproterenol, Myocardial Ischemia chemically induced, Myocardial Ischemia pathology, Myocardial Ischemia physiopathology, Myocardium pathology, Myocytes, Cardiac drug effects, Phenols isolation & purification, Phenols pharmacology, Plant Extracts chemistry, Plant Extracts pharmacology, Rats, Rats, Sprague-Dawley, Cardiotonic Agents therapeutic use, Glycosides therapeutic use, Myocardial Ischemia drug therapy, Orobanchaceae chemistry, Phenols therapeutic use, Phytotherapy, Plant Extracts therapeutic use
- Abstract
The present study was designed to investigate the cardioprotective effect of total phenylethanoid glycosides from Monochasma savatieri Franch (TPG). The data showed that there were mainly four phenylethanoid glycosides isolated and identified from TPG. TPG significantly increased cells viability and inhibited morphological changes on H9c2 cardiomyocytes induced by H2O2 or Na2S2O4. In addition, TPG significantly decreased T-wave elevation and histopathological changes of heart tissues in myocardial infracted rats induced by isoproterenol. It also significantly reduced the infarct size induced by ligating the coronary artery in rats, increased the activities of antioxidative enzymes superoxide dismutase (SOD), the content of glutathione (GSH), and decreased the leakage of lactic dehydrogenase (LDH), the activities of creatine kinase (CK) and the content of maleic dialdehyde (MDA). In conclusion, these results suggested that TPG from Monochasma savatieri Franch might be developed as new natural medicine or food additives with effects of prevention of coronary artery disease due to its significant antioxidant activity., (Copyright © 2013 Elsevier GmbH. All rights reserved.)
- Published
- 2013
- Full Text
- View/download PDF
16. Adsorption properties and preparative separation of phenylethanoid glycosides from Cistanche deserticola by use of macroporous resins.
- Author
-
Liu B, Ouyang J, Yuan X, Wang L, and Zhao B
- Subjects
- Adsorption, Chromatography, High Pressure Liquid instrumentation, Glucosides analysis, Glucosides chemistry, Glycosides analysis, Glycosides chemistry, Kinetics, Phenols analysis, Phenols chemistry, Temperature, Chromatography, High Pressure Liquid methods, Cistanche chemistry, Glucosides isolation & purification, Glycosides isolation & purification, Phenols isolation & purification, Plant Extracts chemistry
- Abstract
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%., (Copyright © 2013 Elsevier B.V. All rights reserved.)
- Published
- 2013
- Full Text
- View/download PDF
17. Anti-obesity effects of isoacteoside on 3T3-L1 adipocytes.
- Author
-
Choi, Chang Geun, Lee, Deok Jae, Chung, Namhyun, and Joo, Yong Hoon
- Subjects
STAINS & staining (Microscopy) ,FAT cells ,PLANT extracts ,WESTERN immunoblotting ,POISONS - Abstract
Isoacteoside is a caffeoyl phenylethanoide glycoside found in various plant parts, such as the flower of Magnolia denudata. In particular, magnolia has been studied for its anti-obesity, anticancer, and anti-inflammatory effects. However, isoacteoside has not been extensively studied, except for its anti-inflammatory effects. In this study, the anti-obesity effects of isoacteoside were investigated in 3T3-L1 mouse pre-adipocytes. Isoacteoside treatment did not induce cytotoxicity in 3T3-L1 cells up to a concentration of 1000 μM. The anti-obesity effects on 3T3-L1 cells were confirmed using oil red O staining. In addition, the expression of obesity-related proteins and genes, such as peroxisome proliferator-activated acceptor gamma (PPARγ), CCAAT/enhancer-binding protein alpha (C/EBPα), and perilipin (PLIN1), was determined by western blotting and qRT-PCR assays to confirm the anti-obesity effects of isoacteoside. The results of this study suggest that isoacteoside, a natural substance isolated from plant extracts, is not highly toxic to normal cells, such as pre-adipocytes, and displays anti-obesity effects in vitro. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
18. Studies on Bignoniaceae: Newbouldiosides D – F, Minor Phenylethanoid Glycosides from Newbouldia laevis , and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata#.
- Subjects
- *
FLAVONOIDS , *BIOLOGICAL products , *GLYCOSIDES , *BARK , *DESCRIPTIVE statistics , *PLANT extracts , *MOLECULAR structure , *SPECTRUM analysis , *METABOLITES - Abstract
Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β -(3,4-dihydroxyphenyl)ethyl 5- O -syringoyl- β - D -apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, and β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O - α -L-rhamnopyranosyl-(1 → 2)-6- O -E-sinapoyl- β - D -glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5- O - α -L-rhamnopyranosyl-7- O - β -D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7- O -(2″- O -formyl)- β -D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
19. Studies on Bignoniaceae: Newbouldiosides D – F, Minor Phenylethanoid Glycosides from Newbouldia laevis , and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata#.
- Subjects
- *
FOLIAR diagnosis , *FLAVONOIDS , *CARCINOGENS , *GLYCOSIDES , *BARK , *MASS spectrometry , *PLANT extracts , *MOLECULAR structure , *FLAVANONES - Abstract
Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β -(3,4-dihydroxyphenyl)ethyl 5- O -syringoyl- β - D -apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, and β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O - α -L-rhamnopyranosyl-(1 → 2)-6- O -E-sinapoyl- β - D -glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5- O - α -L-rhamnopyranosyl-7- O - β -D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7- O -(2″- O -formyl)- β -D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
20. Studies on Bignoniaceae: Newbouldiosides D – F, Minor Phenylethanoid Glycosides from Newbouldia laevis , and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata#.
- Subjects
FLAVONOIDS ,BIOLOGICAL products ,GLYCOSIDES ,BARK ,DESCRIPTIVE statistics ,PLANT extracts ,MOLECULAR structure ,SPECTRUM analysis ,METABOLITES - Abstract
Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β -(3,4-dihydroxyphenyl)ethyl 5- O -syringoyl- β - D -apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, and β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O - α -L-rhamnopyranosyl-(1 → 2)-6- O -E-sinapoyl- β - D -glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5- O - α -L-rhamnopyranosyl-7- O - β -D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7- O -(2″- O -formyl)- β -D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
21. Studies on Bignoniaceae: Newbouldiosides D – F, Minor Phenylethanoid Glycosides from Newbouldia laevis , and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata#.
- Subjects
FOLIAR diagnosis ,FLAVONOIDS ,CARCINOGENS ,GLYCOSIDES ,BARK ,MASS spectrometry ,PLANT extracts ,MOLECULAR structure ,FLAVANONES - Abstract
Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β -(3,4-dihydroxyphenyl)ethyl 5- O -syringoyl- β - D -apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O -[ α -L-rhamnopyranosyl-(1 → 3)]-6- O -E-sinapoyl- β -D-glucopyranoside, and β -(3,4-dihydroxyphenyl)ethyl β -D-apiofuranosyloxy-(1 → 2)- O - α -L-rhamnopyranosyl-(1 → 2)-6- O -E-sinapoyl- β - D -glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5- O - α -L-rhamnopyranosyl-7- O - β -D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7- O -(2″- O -formyl)- β -D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF
22. Cytotoxic phenylethanoid glycosides from Digitalis davisiana Heywood: Evaluation of structure activity relationships and chemotaxonomical significance of isolated compounds.
- Author
-
Kutluay, Vahap Murat, Ishiuchi, Kan'ichiro, Makino, Toshiaki, and Saracoglu, Iclal
- Subjects
- *
CARDIAC glycosides , *CELL lines , *CELL surface antigens , *CHROMATOGRAPHIC analysis , *HIGH performance liquid chromatography , *IMMUNODIAGNOSIS , *MOLECULAR structure , *PLANTS , *REGRESSION analysis , *PLANT extracts , *DATA analysis software , *CYTOTOXINS , *DESCRIPTIVE statistics - Abstract
The phytochemical studies on the aerial parts of Digitalis davisiana Heywood led to the isolation of three undescribed phenylethanoid glycosides named as digidavisoside A (5), digidavisoside B (7), and davisoside (8), along with 9 known compounds, ferruginoside B (1), isolugrandoside (2), lugrandoside (3), maxoside (4), 3″″- O -methylmaxoside (6), trans -lamiuside E (9), digiciliside B (10), p -hydroxyacetophenone (11), and chrysoeriol (12). For the first time compound 11 was reported for Digitalis genus. The chemotaxonomical significance of these compounds in Plantaginaceae family was evaluated and 3′- O -glucosyl substituted phenylethanoid glycosides 4–8 and 10 were found to be chemotaxonomically important for the family. Cytotoxic activity of the aqueous fraction of the methanolic extract was also tested against HEp-2 (human larynx epidermoid carcinoma) and HepG2 (human hepatocellular carcinoma) cancer cell lines. The aqueous fraction showed stronger cytotoxicity on HEp-2 cells than on HepG2. Therefore, the cytotoxic activity of 1 – 4, 6, 7 and 9 were tested against HEp-2 and L929 (mouse fibroblast cell) cell lines. Other isolated compounds could not be tested due to their insufficient amount. The results were evaluated in the point of structure-activity relationships. IC 50 values against HEp-2 cells were established in a range of 71.9–220 μM. Maxoside (4), isolugrandoside (2) and lugrandoside (3) showed higher cytotoxicity against HEp-2 cell line than other isolated compounds. Phytochemical investigation of the aerial parts of Digitalis davisiana Heywood (Plantaginaceae) led to the isolation of three new phenylethanoid glycosides (davisoside, digidavisosides A and B) and nine known compounds. Cytotoxic activity of the isolated compounds were tested against HEp-2 and L929 cell lines. The chemotaxonomical significance of the isolated compounds was evaluated. Unlabelled Image [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
23. Therapeutic potential of phenylethanoid glycosides: A systematic review
- Author
-
Jianbo Xiao, Lipeng Wu, Baiyi Lu, Hesham R. El-Seedi, Satyajit D. Sarker, Lutfun Nahar, Hui Cao, and Milen I. Georgiev
- Subjects
RM ,Anti-Inflammatory Agents ,Antioxidants ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Verbascoside ,Drug Discovery ,Humans ,Medicine ,Glycosides ,Medicinal plants ,030304 developmental biology ,Pharmacology ,chemistry.chemical_classification ,0303 health sciences ,Plants, Medicinal ,Phenylethanoid glycosides ,Bioavailability ,Salidroside ,Traditional medicine ,Plant Extracts ,business.industry ,Glycoside ,Phenylethanoid ,3. Good health ,chemistry ,030220 oncology & carcinogenesis ,Molecular Medicine ,business - Abstract
Phenylethanoid glycosides (PhGs) are generally water‐soluble phenolic compounds that occur in many medicinal plants. Until June 2020, more than 572 PhGs have been isolated and identified. PhGs possess antibacterial, anticancer, antidiabetic, anti‐inflammatory, antiobesity, antioxidant, antiviral, and neuroprotective properties. Despite these promising benefits, PhGs have failed to fulfill their therapeutic applications due to their poor bioavailability. The attempts to understand their metabolic pathways to improve their bioavailability are investigated. In this review article, we will first summarize the number of PhGs compounds which is not accurate in the literature. The latest information on the biological activities, structure–activity relationships, mechanisms, and especially the clinical applications of PhGs will be reviewed. The bioavailability of PhGs will be summarized and factors leading to the low bioavailability will be analyzed. Recent advances in methods such as bioenhancers and nanotechnology to improve the bioavailability of PhGs are also summarized. The existing scientific gaps of PhGs in knowledge are also discussed, highlighting research directions in the future.
- Published
- 2020
24. Phytochemical Analysis and Anti-Inflammatory and Anti-Osteoarthritic Bioactive Potential of Verbascum thapsus L. (Scrophulariaceae) Leaf Extract Evaluated in Two In Vitro Models of Inflammation and Osteoarthritis
- Author
-
Anna Dolcimascolo, Agata Zappalà, Rosalba Parenti, Giuseppe Antonio Malfa, Rosaria Acquaviva, and Giovanna Calabrese
- Subjects
medicine.drug_class ,inflammatory cytokines ,Phytochemicals ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Organic chemistry ,Inflammation ,Osteoarthritis ,Pharmacology ,verbascoside ,Anti-inflammatory ,Article ,Analytical Chemistry ,Proinflammatory cytokine ,chemistry.chemical_compound ,Verbascoside ,QD241-441 ,matrix metalloproteases ,Drug Discovery ,medicine ,Humans ,Physical and Theoretical Chemistry ,cartilage ,biology ,Plant Extracts ,Phenylethanoid ,COX-2 ,biology.organism_classification ,medicine.disease ,phenylethanoid glycosides ,iNOS ,human chondrocytes ,chemistry ,Phytochemical ,Chemistry (miscellaneous) ,Cartilage ,Human chondrocytes ,Inflammatory cytokines ,INOS ,Matrix metalloproteases ,Phenylethanoid glycosides ,Phenylpropanoids ,Verbascum thapsus ,Molecular Medicine ,medicine.symptom ,Scrophulariaceae ,phenylpropanoids - Abstract
Osteoarthritis (OA) is a complex disease, source of pain and disability that affects millions of people worldwide. OA etiology is complex, multifactorial and joint-specific, with genetic, biological and biomechanical components. Recently, several studies have suggested a potential adjuvant role for natural extracts on OA progression, in terms of moderating chondrocyte inflammation and following cartilage injury, thus resulting in an overall improvement of joint pain. In this study, we first analyzed the phenylethanoid glycosides profile and the total amount of polyphenols present in a leaf aqueous extract of Verbascum thapsus L. We then investigated the anti-inflammatory and anti-osteoarthritic bioactive potential of the extract in murine monocyte/macrophage-like cells (RAW 264.7) and in human chondrocyte cells (HC), by gene expression analysis of specifics inflammatory cytokines, pro-inflammatory enzymes and metalloproteases. Six phenylethanoid glycosides were identified and the total phenolic content was 124.0 ± 0.7 mg gallic acid equivalent (GAE)/g of extract. The biological investigation showed that the extract is able to significantly decrease most of the cellular inflammatory markers, compared to both control cells and cells treated with Harpagophytum procumbens (Burch.) DC. ex Meisn, used as a positive control. Verbascum thapsus leaf aqueous extract has the potential to moderate the inflammatory response, representing an innovative possible approach for the inflammatory joint disease treatment.
- Published
- 2021
- Full Text
- View/download PDF
25. A targeted strategy to analyze untargeted mass spectral data: Rapid chemical profiling of Scutellaria baicalensis using ultra-high performance liquid chromatography coupled with hybrid quadrupole orbitrap mass spectrometry and key ion filtering.
- Author
-
Qiao, Xue, Li, Ru, Song, Wei, Miao, Wen-juan, Liu, Jia, Chen, Hu-biao, Guo, De-an, and Ye, Min
- Subjects
- *
CHINESE skullcap , *LIQUID chromatography , *CHROMATOGRAPHIC analysis , *IONS , *PLANT extracts - Abstract
Structural identification of natural products by tandem mass spectrometry requires laborious spectral analysis. Herein, we report a targeted post-acquisition data processing strategy, key ion filtering (KIF), to analyze untargeted mass spectral data. This strategy includes four steps: (1) untargeted data acquisition by ultra-high performance liquid chromatography coupled with hybrid quadrupole orbitrap mass spectrometry (UHPLC/orbitrap-MS); (2) construction of a key ion database according to diagnostic MS/MS fragmentations and conservative substructures of natural compounds; (3) high-resolution key ion filtering of the acquired data to recognize substructures; and (4) structural identification of target compounds by analyzing their MS/MS spectra. The herbal medicine Huang-Qin ( Scutellaria baicalensis Georgi) was used to illustrate this strategy. Its extract was separated within 20 min on a C 18 column (1.8 μm, 2.1 × 150 mm) eluted with acetonitrile, methanol, and water containing 0.1% formic acid. The compounds were detected in the (−)-ESI mode, and their MS/MS spectra were recorded in the untargeted manner. Key ions were then filtered from the LC/MS data to recognize flavones, flavanones, O -/ C -glycosides, and phenylethanoid glycosides. Finally, a total of 132 compounds were identified from Huang-Qin, and 59 of them were reported for the first time. This study provides an efficient data processing strategy to rapidly profile the chemical constituents of complicated herbal extracts. [ABSTRACT FROM AUTHOR]
- Published
- 2016
- Full Text
- View/download PDF
26. Chemical Fractionation Joint to In-Mixture NMR Analysis for Avoiding the Hepatotoxicity of Teucrium chamaedrys L. subsp. chamaedrys
- Author
-
Simona Piccolella, Antonio Fiorentino, Brigida D'Abrosca, Assunta Esposito, Monica Scognamiglio, Severina Pacifico, Piccolella, S., Scognamiglio, M., D'Abrosca, B., Esposito, A., Fiorentino, A., and Pacifico, S.
- Subjects
Teucrium chamaedrys L. subsp. chamaedry ,Magnetic Resonance Spectroscopy ,Antioxidant ,medicine.medical_treatment ,antioxidant activity ,Chemical Fractionation ,HeLa Cell ,01 natural sciences ,Biochemistry ,Teucrium ,chemistry.chemical_compound ,Glycosides ,Teucrium chamaedrys L. subsp. chamaedrys ,chemistry.chemical_classification ,neo-clerodanes ,Traditional medicine ,biology ,NMR-based metabolomic ,Hep G2 Cells ,Phenylethanoid ,QR1-502 ,Phytochemical ,cytotoxicity ,Chemical and Drug Induced Liver Injury ,Plant Leave ,Cosmeceutical ,Human ,Cell Survival ,Hep G2 Cell ,Metabolomic ,Fractionation ,Microbiology ,Article ,Diterpenes, Clerodane ,Plant Extract ,Nutraceutical ,Phenols ,medicine ,Humans ,Metabolomics ,A549 Cell ,Molecular Biology ,Cell Proliferation ,Phenol ,Plant Extracts ,010405 organic chemistry ,Glycoside ,biology.organism_classification ,phenylethanoid glycosides ,0104 chemical sciences ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,chemistry ,A549 Cells ,NMR-based metabolomics ,Neo-clerodane ,HeLa Cells ,Phenylethanoid glycoside - Abstract
Dietary supplements based on Teucrium chamaedrys L. subsp. chamaedrys aerial parts were banned, due to the hepatotoxicity of furan-containing neo-clerodane constituents. Indeed, the plant leaf content in phenolic compounds could be further exploited for their antioxidant capability. Accordingly, bio-guided fractionation strategies have been applied, obtaining seven partially purified extracts. These latter were chemically investigated through 1D and 2D NMR techniques and tested for their antiradical, reducing and cytotoxic capability. Data acquired highlighted that, through a simple phytochemical approach, a progressive neo-clerodane depletion occurred, while maximizing phenylethanoid glycosides in alcoholic fractions. Thus, although the plant cannot be used as a botanical remedy as such, it is suggested as a source of healthy compounds, pure or in mixture, to be handled in pharmaceutical, nutraceutical and/or cosmeceutical sectors.
- Published
- 2021
- Full Text
- View/download PDF
27. Antioxidant properties and phenolic composition of wood betony (Betonica officinalis L., syn. Stachys officinalis L.).
- Author
-
Šliumpaitė, I., Venskutonis, P.R., Murkovic, M., and Ragažinskienė, O.
- Subjects
- *
PLANT phenols , *ANTIOXIDANTS , *WOOD , *STACHYS , *METHANOL , *PLANT extracts - Abstract
Highlights: [•] Wood betony contains phenolic glycosides with strong antioxidant activity. [•] Amount of total phenolic compounds was higher in methanolic extract than acetone. [•] Phenylethanoid glycosides and chlorogenic acid are the main wood betony antioxidants. [•] Stachys officinalis is a promising source of bioactive compounds. [Copyright &y& Elsevier]
- Published
- 2013
- Full Text
- View/download PDF
28. Antimicrobial, anti-inflammatory activities and toxicology of phenylethanoid glycosides from Monochasma savatieri Franch. ex Maxim.
- Author
-
Liu, Yan-li, He, Wen-jun, Mo, Li, Shi, Meng-fan, Zhu, Ying-ying, Pan, Shu, Li, Xiao-ran, Xu, Qiong-ming, and Yang, Shi-lin
- Subjects
- *
PNEUMONIA treatment , *ALTERNATIVE medicine , *ANIMAL experimentation , *ANTI-inflammatory agents , *ANTIBIOTICS , *BIOPHYSICS , *DOSE-effect relationship in pharmacology , *DRUG toxicity , *ESCHERICHIA coli , *GLYCOSIDES , *RESEARCH methodology , *MEDICINAL plants , *MICE , *MICROBIAL sensitivity tests , *PSEUDOMONAS diseases , *SEPSIS , *STAPHYLOCOCCAL diseases , *SURVIVAL , *PLANT extracts , *DESCRIPTIVE statistics , *IN vitro studies , *DISEASE complications , *PHARMACODYNAMICS - Abstract
Abstract: Ethnopharmacological relevance: Monochasma savatieri Franch. ex Maxim is used for treating many diseases in Traditional Chinese Medicine. Aim of the study: The present study was designed to evaluate antibacterial, anti-inflammatory activities and toxicity of the total phenylethanoid glycosides from Monochasma savatieri Franch. ex Maxim (TPG). Materials and methods: The antibacterial activity of TPG was checked by MIC and MBC in vitro; survival of mice with Pseudomonas aeruginosa or Staphylococcus aureus infection-induced sepsis was investigated to evaluate antibacterial activity of TPG in vivo. Additionally, antibacterial activities of TPG were also investigated in a Pseudomonas aeruginosa infection-induced pneumonia in the mice model. Cotton pellet induced granuloma and xylene induced ear swelling in mice models were used to quantify the anti-inflammatory activity. Results: TPG showed a significant possess bacteriostatic properties against five bacteria strains at a concentration between 0.0625 and 16mg/ml. Moreover, TPG has bactericidal activity against Pseudomonas aeruginosa, Streptococcus pneumoniae or Escherichia coli. TPG (60, 120, and 180mg/kg) prolonged survival rate of mice with Pseudomonas aeruginosa or Staphylococcus aureus infection-induced sepsis. In addition, TPG (180mg/kg) could reduce the bacterial colony-forming units in lung tissue. Furthermore, TPG (60–180mg/kg) had significantly reduced xylene-induced ear edema and granulomat formation induced by cotton pellet at a dose-dependent manner. In addition, administration of TPG (1.5g/kg) for 15 days did not result in toxicities in liver, kidney, spleen and thymus tissue in rats. Conclusion: These results indicated that TPG might be useful for the development of a novel treatment for respiratory infections or pneumonia caused by Pseudomonas aeruginosa or Staphylococcus aureus. [Copyright &y& Elsevier]
- Published
- 2013
- Full Text
- View/download PDF
29. Phenylethanoid glycosides from the stems of Callicarpa peii (hemostatic drug)
- Author
-
Wu, Ai-Zhi, Zhai, Ya-Jing, Zhao, Zhong-Xiang, Zhang, Cui-Xian, Lin, Chao-Zhan, and Zhu, Chen-Chen
- Subjects
- *
ALTERNATIVE medicine , *PHYSICAL & theoretical chemistry , *GLYCOSIDES , *MEDICINAL plants , *NUCLEAR magnetic resonance spectroscopy , *SPECTRUM analysis , *PLANT stems , *PHYTOCHEMICALS , *PLANT extracts , *DESCRIPTIVE statistics - Abstract
Abstract: Two new trisaccharide intermediates of phenylethanoid glycosides, peiioside A1/A2 (1a/1b) and peiioside B (2), were isolated from the n-BuOH fraction of MeOH extract of the stems of Callicarpa peii H.T. Chang, together with five biogenetic relevant known compounds 3–7. The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques) and acid-catalyzed hydrolysis as O-α-l-rhamnopyranosyl-(1″→3′)-O-[β-d-apiofuranosyl-(1‴→6′)] -4′-O-[(E)-caffeoyl]-d-glucopyranoside] (1a/1b), 3,4-dihydroxy-β-phenylethoxy-O-[β-d-apiofuranosyl-(1‴→6′)-α-l-rhamnopyranosyl-(1″→3′)-O-β-d-glucopyranoside] (2), respectively. On the basis of the isolated compounds, a presumable biogenetic pathway of the biologically interesting phenylethanoid glycosides about forsythoside B (3) and acteoside (4) isolated from this species was proposed. Isolation of five related intermediates (1–2, 5–7) provided further support for the biogenetic path. This is the first report about phytochemical research on C. peii and the biogenetic hypothesis of forsythoside B and acteoside. [Copyright &y& Elsevier]
- Published
- 2013
- Full Text
- View/download PDF
30. Antioxidant activity of phenolic and phenylethanoid glycosides from Teucrium polium L
- Author
-
De Marino, Simona, Festa, Carmen, Zollo, Franco, Incollingo, Filomena, Raimo, Gennaro, Evangelista, Giovanna, and Iorizzi, Maria
- Subjects
- *
GERMANDER , *ANTIOXIDANTS , *PHENOLS , *GLYCOSIDES , *FLAVONOIDS , *BIOMOLECULES , *PLANT extracts - Abstract
Abstract: In the present study, the chemical composition and antioxidant activities of Teucrium polium L. (Lamiaceae) were assessed. Fractionation of methanol extract obtained from the aerial parts of T. polium yielded one new phenylethanoid glycoside, named poliumoside B, together with four known flavonoids, two iridoid glycosides and a known poliumoside. The structures of all of these compounds were elucidated on the basis of spectroscopic data from 1D and 2D NMR experiments and MS spectral analyses. The antioxidant activities of the crude extracts and of the isolated compounds were evaluated through tests such as DPPH radical-scavenging capability, reducing power, xanthine oxidase inhibitory effect and inhibition of linoleic acid peroxidation. The highest antioxidant activity was found in the n-butanol extract, which also contained active polyphenols, thus suggesting that this plant could be used as a source of natural molecules, to provide safe antioxidant additives and nutraceuticals. The structure–activity relationships of the isolated compounds are also discussed. [Copyright &y& Elsevier]
- Published
- 2012
- Full Text
- View/download PDF
31. Simultaneous Quantification of Four Phenylethanoid Glycosides in Rat Plasma by UPLC-MS/MS and Its Application to a Pharmacokinetic Study of Acanthus Ilicifolius Herb
- Author
-
Meng-Qi Zhang, Shi-Jun Yue, Chang-Lun Shao, Qing Zhao, Ren Xia, and Chang-Yun Wang
- Subjects
Male ,Electrospray ionization ,Pharmaceutical Science ,Mass spectrometry ,01 natural sciences ,High-performance liquid chromatography ,Article ,Analytical Chemistry ,acanthus ilicifolius herb ,lcsh:QD241-441 ,Rats, Sprague-Dawley ,chemistry.chemical_compound ,Caffeic Acids ,lcsh:Organic chemistry ,Glucosides ,Phenols ,Pharmacokinetics ,Tandem Mass Spectrometry ,Acanthaceae ,Drug Discovery ,Animals ,Glycosides ,Physical and Theoretical Chemistry ,chemistry.chemical_classification ,Chromatography ,biology ,Plant Extracts ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Selected reaction monitoring ,Glycoside ,Phenylethanoid ,Acanthus ilicifolius ,biology.organism_classification ,phenylethanoid glycosides ,Rats ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Chemistry (miscellaneous) ,UPLC-MS/MS ,Molecular Medicine ,pharmacokinetics ,Chromatography, Liquid - Abstract
Acanthus ilicifolius herb (AIH), the dry plant of Acanthus ilicifolius L., has long been used as a folk medicine for treating acute and chronic hepatitis. Phenylethanoid glycosides (PhGs) are one family of the main components in AIH with hepatoprotective, antioxidant, and anti-inflammatory activities. In this study, the pharmacokinetics of AIH was investigated preliminarily by ultra-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC-MS/MS). A simultaneously quantitative determination method for four PhGs (acteoside, isoacteoside, martynoside, and crenatoside) in rat plasma was first established by UPLC-MS/MS. These four PhGs were separated with an ACQUITY UPLC BEH C18 column (2.1 ×, 50 mm, 1.7 &mu, m) by gradient elution (mobile phase: MeCN and 0.1% formic acid in water, 0.4 mL/min). The mass spectrometry detection was performed using negative electrospray ionization (ESI&minus, ) in multiple reaction monitoring (MRM) mode. By the established method, the preliminary pharmacokinetics of AIH was elucidated using the kinetic parameters of the four PhGs in rat plasma after intragastric administration of AIH ethanol extract. All four PhGs showed double peaks on concentration-time curves, approximately at 0.5 h and 6 h, respectively. Their elimination half-lives (t1/2) were different, ranging from 3.42 h to 8.99 h, although they shared similar molecular structures. This work may provide a basis for the elucidation of the pharmacokinetic characteristics of bioactive components from AIH.
- Published
- 2019
- Full Text
- View/download PDF
32. Exploring the halophyte Cistanche phelypaea (L.) Cout as a source of health promoting products: In vitro antioxidant and enzyme inhibitory properties, metabolomic profile and computational studies
- Author
-
Gokhan Zengin, Adriano Mollica, Odeta Celaj, Brigida D'Abrosca, Azzurra Stefanucci, Catarina Pereira, Maria João Rodrigues, Luísa Custódio, Francesca Trampetti, Selçuk Üniversitesi, Fen Fakültesi, Biyoloji Bölümü, Zengin, Gökhan, Francesca, Trampetti, Catarina, Pereira, Maria João Rodrigues, Odeta, Celaj, D'Abrosca, Brigida, Gokhan, Zengin, Adriano, Mollica, Azzurra, Stefanucci, and Luísa, Custódio
- Subjects
Iridoid Glycosides ,Antioxidant ,Cistanche ,Magnetic Resonance Spectroscopy ,Tyrosinase ,medicine.medical_treatment ,Clinical Biochemistry ,Ethyl acetate ,Pharmaceutical Science ,01 natural sciences ,Plant Roots ,Antioxidants ,Analytical Chemistry ,chemistry.chemical_compound ,Drug Discovery ,Cholinesterases ,Enzyme Inhibitors ,Spectroscopy ,Butyrylcholinesterase ,2. Zero hunger ,chemistry.chemical_classification ,Plant Stems ,Chemistry ,Salt-Tolerant Plants ,Free Radical Scavengers ,3. Good health ,Molecular Docking Simulation ,Biochemistry ,Carbohydrate hydrolysing enzymes ,Skin hyperpigmentation ,Echinacoside ,Flowers ,Phenylethanoid glycosides ,medicine ,Metabolomics ,Computational approach ,Herba ,010405 organic chemistry ,Plant Extracts ,Tubulosa ,010401 analytical chemistry ,Chemical-constituents ,Glycoside ,Cholinesterase ,NMR ,0104 chemical sciences ,Oxidative stress ,Oxidative stre ,Carbohydrate hydrolysing enzyme - Abstract
WOS: 000456899500016, PubMed: 30529825, In this study, ethyl acetate, acetone, ethanol and water extracts from flowers, stems and roots of Cistanche phelypaea (L.) Cout were appraised for radical scavenging activity (RSA) towards 1,1-diphenyl-2-picrylhydrazyl,2,2-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) and superoxide free radicals, and for metal chelating activities on iron and copper ions. The water extracts had the highest antioxidant activity, especially those from roots and flowers, and were further appraised for in vitro inhibition of enzymes implicated on the onset of human ailments, namely acetyl- (AChE) and butyrylcholinesterase (BuChE) for Alzheimer's disease, alpha-glucosidase and alpha-amylase for diabetes, and tyrosinase for skin hyper-pigmentation disorders. The extracts had a higher activity towards BuChE, and the roots extract had the highest capacity to inhibit tyrosinase. Samples showed a low capacity to inhibit carbohydrate hydrolysing enzymes, except for the root extract with a good inhibition on glucosidase. Samples were then characterized by NMR (1D and 2D): the main metabolites identified in the flowers extract were iridoid glycosides, in particular gluroside and bartsioside. In stems, phenylehanoid glycosides (PhGs) and iri doids were detected, especially acteoside. In roots were detected essentially PhGs, mainly echinacoside and tubuloside A. Docking studies were performed on the identified compounds. A favorable binding energy of tubuloside A to tyrosinase was calculated, and indicated this compound as a possible competitive inhibitor of alpha-glucosidase and tyrosinase. Our results suggest that C. phelypeae is a promising source of biologically-active compounds with health promoting properties for pharmaceutical and biomedical applications. (C) 2018 Elsevier B.V. All rights reserved., Foundation for Science and Technology (FCT, Portugal)Portuguese Foundation for Science and Technology; Portuguese National Budget funding through the CCMAR project [CCMAR/Multi/04326/2013]; FCTPortuguese Foundation for Science and Technology [IF/00049/2012, SFRH/BD/94407/2013, SFRH/BD/116604/2016], This work was supported by the Foundation for Science and Technology (FCT, Portugal) and by the Portuguese National Budget funding through the CCMAR/Multi/04326/2013 project. Luisa Custodio was supported by FCT Investigator Programme (IF/00049/2012). Catarina Guerreiro Pereira and Maria Joao Rodrigues acknowledges FCT for the PhD grants SFRH/BD/94407/2013 and SFRH/BD/116604/2016, respectively.
- Published
- 2019
33. Inhibition of Amyloid Beta Aggregation and Deposition of Cistanche tubulosa Aqueous Extract
- Author
-
Muh-Hwan Su, Chao-Jih Wang, Chien-Liang Chao, Hang-Ching Lin, Hsin-Fan Chao, Hsin-Wen Huang, Hui-Chi Huang, and Shuen-Wen Yu
- Subjects
China ,Cistanche ,Amyloid beta ,Pharmaceutical Science ,Protein Aggregation, Pathological ,Article ,Analytical Chemistry ,Iron chelation ,lcsh:QD241-441 ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Cistanche tubulosa ,lcsh:Organic chemistry ,Pharmacokinetics ,Alzheimer Disease ,Drug Discovery ,Humans ,Physical and Theoretical Chemistry ,030304 developmental biology ,Aqueous extract ,chemistry.chemical_classification ,0303 health sciences ,iron chelation ,Amyloid beta-Peptides ,biology ,Chemistry ,Plant Extracts ,Organic Chemistry ,Glycoside ,Water ,Phenylethanoid ,phenylethanoid glycosides ,Bioavailability ,Biochemistry ,Chemistry (miscellaneous) ,biology.protein ,Molecular Medicine ,Alzheimer’s disease ,030217 neurology & neurosurgery - Abstract
Cistanche tubulosa aqueous extract (CTE) is already used as a botanical prescription drug for treating dementia in China. Our previous studies reported that phenylethanoid glycosides of CTE have anti-Alzheimer&rsquo, s disease (AD) activity by inhibiting amyloid &beta, peptide (A&beta, ) aggregation and deposition. However, recent studies considered that the phenylethanoid glycosides may be metabolized by intestinal bacteria, because all analysis results showed that the bioavailability of phenylethanoid glycosides is extremely low. In this study we demonstrate how iron chelation plays a crucial role in the A&beta, aggregation and deposition inhibition mechanism of phenylethanoid glycosides of CTE. In addition, we further proved phenylethanoid glycosides (1&ndash, 3) could reach brain. Active CTE component and action mechanism confirmation will be a great help for product quality control and bioavailability studies in the future. At the same time, we provide a new analysis method useful in determining phenylethanoid glycosides (1&ndash, 3) in plants, foods, blood, and tissues for chemical fingerprint and pharmacokinetic research.
- Published
- 2019
34. Echinacoside Isolated from
- Author
-
Chieh-Ju, Wu, Mei-Yin, Chien, Nan-Hei, Lin, Yi-Chiao, Lin, Wen-Ying, Chen, Chao-Hsiang, Chen, and Jason T C, Tzen
- Subjects
Male ,Models, Molecular ,Cistanche ,Molecular Structure ,Plant Extracts ,Molecular Conformation ,phenylethanoid glycosides ,Mass Spectrometry ,Article ,Rats ,growth hormone secretion ,Growth Hormone ,ghrelin ,Animals ,Glycosides ,Receptors, Ghrelin ,Chromatography, High Pressure Liquid ,echinacoside ,Chromatography, Liquid ,cistanche tubulosa - Abstract
Cistanche species, the ginseng of the desert, has been recorded to possess many biological activities in traditional Chinese pharmacopoeia and has been used as an anti-aging medicine. Three phenylethanoid glycosides—echinacoside, tubuloside A, and acteoside—were detected in the water extract of Cistanche tubulosa (Schenk) R. Wight and the major constituent, echinacoside, was further purified. Echinacoside of a concentration higher than 10−6 M displayed significant activity to stimulate growth hormone secretion of rat pituitary cells. Similar to growth hormone-releasing hormone-6, a synthetic analog of ghrelin, the stimulation of growth hormone secretion by echinacoside was inhibited by [D-Arg1, D-Phe5, D-Trp7,9, Leu11]-substance P, an inverse agonist of the ghrelin receptor. Molecular modeling showed that all the three phenylethanoid glycosides adequately interacted with the binding pocket of the ghrelin receptor, and echinacoside displayed a slightly better interaction with the receptor than tubuloside A and acteoside. The results suggest that phenylethanoid glycosides, particularly echinacoside, are active constituents putatively responsible for the anti-aging effects of C. tubulosa and may be considered to develop as non-peptidyl analogues of ghrelin.
- Published
- 2019
35. Phenylethanoid Glycosides from Monochasma savatieri and Their Anticomplement Activity through the Classical Pathway.
- Author
-
Min Li, Meng-Fan Shi, Yan-Li Liu, Qiong-Ming Xu, and Shi-Lin Yang
- Subjects
- *
MASS spectrometry methodology , *COMPLEMENT (Immunology) , *GAS chromatography , *GLYCOSIDES , *HEPARIN , *HIGH performance liquid chromatography , *MOLECULAR structure , *NUCLEAR magnetic resonance spectroscopy , *PHARMACEUTICAL chemistry , *RESEARCH funding , *PLANT extracts , *DESCRIPTIVE statistics - Abstract
Five new phenylethanoid glycosides, savasides A-E (1-5), along with 6 known ones were isolated from the whole plant of Monochasma savatieri Franch. The structures of 1-5 were elucidated on the basis of spectroscopic data analysis. Moreover, all isolated compounds were evaluated for anticomplement activity through the classical pathway. [ABSTRACT FROM AUTHOR]
- Published
- 2012
- Full Text
- View/download PDF
36. Cistanche tubulosa phenylethanoid glycosides induce apoptosis in H22 hepatocellular carcinoma cells through both extrinsic and intrinsic signaling pathways
- Author
-
Xinhui Wang, Yi Yang, Lijie Xia, Yijie Li, Pengfei Yuan, Adila Aipire, Jinyao Li, and Jinyu Li
- Subjects
0301 basic medicine ,Male ,Cell cycle checkpoint ,Cistanche ,DNA Repair ,Apoptosis ,03 medical and health sciences ,Mice ,Cell Line, Tumor ,Phenylethanoid glycosides ,Animals ,Humans ,MTT assay ,Glycosides ,Membrane Potential, Mitochondrial ,Cistanche tubulosa ,Chemistry ,Cell growth ,Plant Extracts ,Signaling pathway ,Intrinsic apoptosis ,Cell Cycle ,Liver Neoplasms ,General Medicine ,lcsh:Other systems of medicine ,Cell cycle ,lcsh:RZ201-999 ,Xenograft Model Antitumor Assays ,Cell biology ,Tumor mouse model ,030104 developmental biology ,Complementary and alternative medicine ,Signal transduction ,Signal Transduction ,Research Article - Abstract
Background Cistanche tubulosa (Schenk) R. Wight is a traditional Chinese medicine that parasitizes the roots of the Tamarix plant and has been used to treat male impotence, sterility, body weakness, and as a tonic. However, its antitumor effect on hepatocellular carcinoma is still elusive. Here, we investigated the antitumor effect of C. tubulosa phenylethanoid glycosides (CTPG) on H22 hepatocellular carcinoma cells both in vitro and in vivo and its mechanisms. Methods The morphology, viability, apoptosis, cell cycle and mitochondrial membrane potential (Δψm) of H22 cells were analyzed by inverted microscopy, MTT assay and flow cytometry, respectively. The expression and activation of proteins in apoptosis pathway were detected by Western blot. The in vivo antitumor effect was evaluated in tumor mouse model established using male Kunming mice. Results CTPG treatment significantly suppressed H22 cell growth in a dose- and time-dependent manner, which was correlated with the increased apoptosis and cell cycle arrest at G0/G1 and G2/M phases. Moreover, the chromosomal condensation was observed in CTPG-treated H22 cells. CTPG treatment significantly increased Bax/Bcl-2 ratio, reduced Δψm and enhanced the release of cytochrome c. The levels of cleaved caspase-8 and caspase-9 in both extrinsic and intrinsic signaling pathways were significantly increased that sequentially activated caspase-7 and -3 to cleave PARP. Finally, CTPG inhibited the growth of H22 cells in mice and improved the survival rate of tumor mice. Conclusions These results suggested that CTPG suppressed H22 cell growth through both extrinsic and intrinsic apoptosis pathways.
- Published
- 2018
37. New phenylethanoid glycosides from Cistanche phelypaea and their activity as inhibitors of monoacylglycerol lipase (MAGL)
- Author
-
Marinella De Leo, Giulia Bononi, Djemaa Berrehal, Khadidja Aya Beladjila, Alessandra Braca, Nunziatina De Tommasi, and Carlotta Granchi
- Subjects
Cistanche ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Cistanche phelypaea, Orobanchaceae, phenylethanoid glycosides, cancer, monoacylglycerol lipase, lactate dehydrogenase ,Cistanche phelypaea ,Pharmaceutical Science ,01 natural sciences ,Analytical Chemistry ,chemistry.chemical_compound ,monoacylglycerol lipase ,Orobanchaceae ,Lactate dehydrogenase ,Neoplasms ,Drug Discovery ,Humans ,cancer ,Glycosides ,IC50 ,Pharmacology ,chemistry.chemical_classification ,biology ,L-Lactate Dehydrogenase ,Molecular Structure ,010405 organic chemistry ,Plant Extracts ,Organic Chemistry ,Glycoside ,Active site ,Monoacylglycerol Lipases ,Phenylethyl Alcohol ,lactate dehydrogenase ,Phenylethanoid ,biology.organism_classification ,phenylethanoid glycosides ,0104 chemical sciences ,Monoacylglycerol lipase ,010404 medicinal & biomolecular chemistry ,Enzyme ,Complementary and alternative medicine ,chemistry ,biology.protein ,Molecular Medicine - Abstract
Four new phenylethanoid glycosides (1–4), 1-β-p-hydroxyphenyl-ethyl-2-O-acetyl-3,6-di-α-l-rhamnopyranosyl-β-d-glucopyranoside (1), 1-β-p-hydroxyphenyl-ethyl-3,6-O-di-α-l-rhamnopyranosyl-β-d-glucopyranoside (2), 1-β-p-hydroxyphenyl-ethyl-2-O-acetyl-3,6-di-α-l-rhamnopyranosyl-4-p-coumaroyl-β-d-glucopyranoside (3), and 1-β-p-hydroxyphenyl-ethyl-3,6-di-α-l-rhamnopyranosyl-4-p-coumaroyl-β-d-glucopyranoside (4), together with three known compounds, were isolated from the n-butanol extract of Cistanche phelypaea aerial parts. The structural characterization of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The isolated compounds were assayed for their inhibitory activity on two enzymes involved in the peculiar glycolytic or lipidic metabolism of cancer cells, human lactate dehydrogenase (LDH), and monoacylglycerol lipase (MAGL), respectively. All the compounds showed negligible activity on LDH, whereas some of them displayed a certain inhibition activity on MAGL. In particular, compound 1 was the most active on MAGL, showing an IC50 value of 88.0 µM, and modeling studies rationalized the supposed binding mode of 1 in the MAGL active site.
- Published
- 2018
38. Polar constituents, protection against reactive oxygen species, and nutritional value of Chinese artichoke (Stachys affinis Bunge)
- Author
-
Alessandro Venditti, Claudio Frezza, Giuseppe Celenza, Kevin Cianfaglione, Diana Celona, Stefano Ferraro, Anna Rita Lizzi, Armandodoriano Bianco, Filippo Maggi, Dennis Fiorini, Mauro Serafini, and Università degli Studi di Camerino (UNICAM)
- Subjects
Iridoid Glycosides ,Magnetic Resonance Spectroscopy ,food.ingredient ,Potassium ,[SDV]Life Sciences [q-bio] ,Succinic Acid ,chemistry.chemical_element ,01 natural sciences ,Anti-reactive oxygen species activity ,Chinese artichoke ,Iridoids ,Nutrients ,Phenylethanoid glycosides ,Secondary metabolites ,Stachys affinis ,Analytical Chemistry ,Food Science ,Medicine (all) ,Stachyose ,chemistry.chemical_compound ,food ,Botany ,Humans ,Food science ,chemistry.chemical_classification ,Plant Extracts ,010405 organic chemistry ,secondary metabolites ,phenylethanoid glycosides ,iridoids ,nutrients ,anti-reactive oxygen species activity ,food and beverages ,General Medicine ,Phenylethanoid ,Oligosaccharide ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Succinic acid ,Stachys ,Caco-2 Cells ,Reactive Oxygen Species ,Nutritive Value ,Organic acid - Abstract
In the present work, we studied the chemical composition of Chinese artichoke (S. affinis tubers) by analyzing its polar constituents and its macro- and micro- nutrients. A total of nine compounds were isolated from the tuber ethanolic extract and structurally elucidated by Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry (MS). The marker compounds identified were oligosaccharide stachyose and the organic acid, succinic acid, as well as phenylethanoid and iridoid glycosides. The macronutrient profile was dominated by carbohydrates (36.9% dw), whereas potassium (2.36%) was the most abundant micro-nutrient. The tuber ethanolic extract was able to efficiently protect human cells (Caco-2, SHSY-5Y and K562) against t-BHP-induced oxidative damage.
- Published
- 2017
39. Elicited Teucrium chamaedrys cell cultures produce high amounts of teucrioside, but not the hepatotoxic neo-clerodane diterpenoids
- Author
-
Ferruccio Poli, Fabiana Antognoni, Manuela Mandrone, Antonio Fiorentino, Pier Paolo Giovannini, Carmelina Iannello, Monica Scognamiglio, Antognoni, F, Iannello, C, Mandrone, M, Scognamiglio, M, Fiorentino, Antonio, Giovannini, P. P., Poli, F., F. Antognoni, C. Iannello, M. Mandrone, M. Scognamiglio, A. Fiorentino, P.P. Giovannini, and F. Poli
- Subjects
Clerodane ,neo-Clerodane diterpenoids ,Time Factors ,Cell Culture Techniques ,Plant Science ,Acetates ,Biochemistry ,Teucrium ,chemistry.chemical_compound ,Fusarium ,Glycosides ,Trichoderma ,Methyl jasmonate ,biology ,Phenylpropanoid ,food and beverages ,Free Radical Scavengers ,General Medicine ,Phenylethanoid ,neo-Clerodane diterpenoid ,Hydroxyproline ,NMR analysis ,Metabolome ,Cell cultures ,Elicitation ,Lamiaceae ,Phenylethanoid glycosides ,Teucrium chamaedrys ,Caffeic Acids ,Chitosan ,Cyclopentanes ,Diterpenes, Clerodane ,Metabolomics ,Mycelium ,Oxylipins ,Plant Cells ,Plant Extracts ,Plant Leaves ,Proline ,Molecular Biology ,Horticulture ,Diterpenes ,NO ,NMR analysi ,biology.organism_classification ,chemistry ,Cell culture ,Callus ,Teucrium chamaedry ,Phenylethanoid glycoside ,Explant culture - Abstract
Teucrium chamaedrys, one of the most common and investigated species of the genus Teucrium, has been used for centuries in traditional medicine for many purposes. Its phytochemical components comprise, among others, phenylethanoid glycosides (PGs) and neo-clerodane diterpenoids. Several reports have demonstrated a wide range of beneficial biological and pharmacological activities of the phenylethanoid components, while the diterpenes were shown to be strongly hepatotoxic. In this work, in vitro cultures were established from leaf explants of T. chamaedrys. Both solid (callus) and liquid (cell suspension) cultures maintained the capacity to produce PGs, with teucrioside (TS) representing the most abundant one. Cell suspensions had a lower TS content than that found in leaf extracts, but higher than that of calli. An NMR-based metabolomics approach was used to compare the product profile of intact plants vs. cell suspension cultures, and results showed that neo-clerodane diterpenes, present in the intact plant, were not detected in cell cultures. Several elicitors were supplied to cell cultures with the aim of increasing TS production, and elicitation was tested at different growth phases and by exposing cells for different periods. Methyl jasmonate and fungal mycelia from Trichoderma viridae and Fusarium moniliforme were able to significantly increase TS production if supplied at the early-exponential growth phase for 24 h. Based on the proposed link between proline and the phenylpropanoid pathways, proline accumulation in cell cultures was followed throughout a 14-day culture period, showing that it strictly reflected that of TS production. Moreover, exogenously supplied proline, and its analogue hydroxyproline, turned out to be very effective in increasing teucrioside production. © 2012 Elsevier Ltd. All rights reserved.
- Published
- 2012
40. Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in Dolomites, Italy
- Author
-
Alessandro Venditti, Claudio Frezza, Mauro Serafini, and Armandodoriano Bianco
- Subjects
hemiparasitic plant ,iridoids ,monomelittoside ,orobanchaceae ,pedicularis kerneri Dalla Torre ,phenylethanoid glycosides ,glucosides ,glycosides ,iridoid glucosides ,molecular structure ,pedicularis ,phenols ,plant extracts ,Iridoid Glucosides ,Lamiales ,Plant Science ,01 natural sciences ,Biochemistry ,Analytical Chemistry ,chemistry.chemical_compound ,Verbascoside ,Glucosides ,Phenols ,Botany ,Iridoids ,Glycosides ,Pedicularis ,Aucubin ,Traditional medicine ,biology ,Chemotype ,Molecular Structure ,010405 organic chemistry ,Plant Extracts ,Organic Chemistry ,Phenylethanoid ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Orobanchaceae ,Italy - Abstract
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.
- Published
- 2015
41. Phenylethanoid and iridoid glycosides in the New Zealand snow hebes (Veronica, Plantaginaceae)
- Author
-
Phil J. Garnock-Jones, Tetsuo Kokubun, Rilka M. Taskova, Ken G. Ryan, and Søren Rosendal Jensen
- Subjects
Iridoid Glycosides ,Iridoid ,medicine.drug_class ,Chionohebe ,Iridoid glucosides ,chemistry.chemical_compound ,Genus ,Drug Discovery ,Botany ,Phenylethanoid glycosides ,medicine ,Plantaginaceae ,Iridoids ,Glycosides ,Plantago ,Chromatography, High Pressure Liquid ,Phylogeny ,chemistry.chemical_classification ,biology ,Ethanol ,Molecular Structure ,Plant Extracts ,Glycoside ,Water ,General Chemistry ,General Medicine ,Phenylethanoid ,biology.organism_classification ,Snow ,Veronica ,Chemotaxonomy ,chemistry ,Solubility ,Veronica pulvinaris ,New Zealand - Abstract
Snow hebes are the alpine cushion-forming plants of New Zealand Veronica, formerly classified as Chionohebe. The chemical compositions of Veronica pulvinaris and Veronica thomsonii were studied and 33 water-soluble compounds were isolated. The structures of 14 previously unknown esters of phenylethanoid glycosides were elucidated by spectroscopic analyses. Further, eight known phenylethanoids, nine iridoids, 6'-feruloyl-sucrose and mannitol are also reported. It was found that the iridoid profile of the snow hebes was different from the other species of Veronica in New Zealand but similar to the alpine Northern Hemisphere representatives of the genus.
- Published
- 2010
Catalog
Discovery Service for Jio Institute Digital Library
For full access to our library's resources, please sign in.