acteoside and harpagide

Topics: Chromatography, High Pressure Liquid; Epoxide Hydrolases; Glucosides; Inhibitory Concentration 50; Iridoid Glycosides; Liquid-Liquid Extraction; Methanol; Models, Statistical; Phenols; Phytochemicals; Plant Extracts; Pyrans; Solubility; Spectrometry, Mass, Electrospray Ionization; Stachys; Tandem Mass Spectrometry; Temperature; Tryptophan; Ultrasonic Waves

In this work, the phytochemical analysis of Teucrium chamaedrys L. collected in Italy was reported. Eight compounds were isolated and identified by means of classical column chromatography and spectroscopic techniques, such as NMR and MS. In detail, these compounds were: verbascoside (1), forsythoside b (2), samioside (3), alyssonoside (4), harpagide (5), 8-O-acetyl-harpagide (6), cirsiliol (7) and β-arbutin (8). The presence of these compounds, in particular iridoids and phenyl-ethanoid glycosides, has a chemotaxonomic relevance and results to be in perfect accordance with the current botanical classification of the species. In addition, it provides a phytochemical rationale for the use of this particular plant in the ethno-pharmacological field. Conversely, it is worth of mention the absence of potentially toxic components, unlike to what observed in other species of the genus which can no longer be used for ethno-medicinal purposes.

Topics: Arbutin; Caffeic Acids; Glucosides; Glycosides; Iridoid Glycosides; Italy; Magnetic Resonance Spectroscopy; Molecular Structure; Phenols; Plant Extracts; Polyphenols; Pyrans; Teucrium

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

An improved high-performance liquid chromatography with diode array detection combined with accelerated solvent extraction method was used to simultaneously determine six compounds in crude and processed Radix Scrophulariae samples. Accelerated solvent extraction parameters such as extraction solvent, temperature, number of cycles, and analysis procedure were systematically optimized. The results indicated that compared with crude Radix Scrophulariae samples, the processed samples had lower contents of harpagide and harpagoside but higher contents of catalpol, acteoside, angoroside C, and cinnamic acid. The established method was sufficiently rapid and reliable for the global quality evaluation of crude and processed herbal medicines.

Topics: Chromatography, High Pressure Liquid; Cinnamates; Coumaric Acids; Glucosides; Glycosides; Iridoid Glucosides; Iridoid Glycosides; Phenols; Pyrans; Quality Control; Scrophularia; Solvents; Trisaccharides

In this study, we report the isolation and identification of several compounds present in the polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, collected in the protected area of Majella National Park. In particular, we have isolated and identified harpagide, 7-β-hydroxy-harpagide, ajugol, 5-allosyloxy-aucubin, verbascoside and, for the first time in this genus, arbutin.

Topics: Arbutin; Glucosides; Glycosides; Iridoid Glucosides; Iridoid Glycosides; Italy; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Phenols; Plant Components, Aerial; Plant Extracts; Pyrans; Stachys

To develop an HPLC method for the simultaneous quantitation of five constituents in Scrophularia ningpoensis.. Samples were analyzed on an Agilent SB-C18 column(4.6 mm x 250 mm, 5 microm) eluted with acetonitrile and water containing 0.03% phosphate acid as mobile phases in a linear gradient mode. The flow rate was kept at 1.0 mL x min(-1), and the column temperature was set to 30 degrees C. The DAD detector wavelengths were 210, 280, 330 nm.. The linear ranges were 50-400 mg x L(-1) for harpagide, 1-40 mg x L(-1) for harpagoside, 1-20 mg x L(-1) for cinnamic acid, 0.5-4.5 mg x L(-1) for acteoside,1-60 mg x L(-1) for angoroside C, respectively. The average recoveries of the five constituents were 100.8% (RSD 0.62%), 101.7% (RSD 0.32%), 98.8% (RSD 0.48%), 99.9% (RSD 1.4%), 99.2% (RSD 1.1%), respectively.. Through the validation, the method was proved to be sensitive, accurate, repeatable, and can be used for quality control of the roots of S. ningpoensis.

Topics: Chromatography, High Pressure Liquid; Cinnamates; Coumaric Acids; Glucosides; Glycosides; Iridoid Glycosides; Phenols; Pyrans; Scrophularia; Trisaccharides

The current work compared the relative efficacies of six commercial formulations of H. procumbens. Each formulation was assayed for the content of harpagoside (1), harpagide (2), verbascoside (3) and 8-O-p-coumaroyl harpagide (4) and, based on the recommended dosages, the total daily amounts were determined and used to establish anti-/proinflammatory (A/P) factors. The formulations were compared using ex vivo porcine skin for their activities towards COX-2 by Western blotting. The results showed great variation in the amounts of compounds 1-4 within the six formulations examined. The relative proportions of 1-4 also varied widely between the products and this inconsistency was reflected in the A/P factors, which correlated with the COX-2 expression (R(2) = 0.9496). Although the data support the beneficial antiinflammatory effects from the use of some of the brands tested, others would appear potentially to exacerbate inflammation. To conclude, a ratio based upon the amount and relative proportions of anti- and proinflammatory compounds can be used to predict relative antiinflammatory properties. Also, with access to a diversity of ostensibly similar commercial products, the patient may experience varying therapeutic responses. Finally, current pharmacopoeia monographs, which are generally concerned with a minimum harpagoside content, are inadequate for ensuring the quality of products based on H. procumbens.

Topics: Administration, Cutaneous; Animals; Anti-Inflammatory Agents; Cyclooxygenase 2; Dose-Response Relationship, Drug; Glucosides; Glycosides; Harpagophytum; In Vitro Techniques; Iridoid Glycosides; Phenols; Phytotherapy; Plant Extracts; Pyrans; Skin; Skin Absorption; Swine

Harpagophytum procumbens, commonly known as Devil's Claw, is indigenous to southern Africa, and extracts of the tubers have been used for centuries in the treatment of a variety of inflammatory disorders. Its major active components, harpagoside (1), harpagide (2), 8-coumaroylharpagide (3), and verbascoside (4), are believed to interact either synergistically or antagonistically in modulating the enzymes responsible for inducing inflammation, although this has not been probed hitherto. In the current work, the ability of these compounds to inhibit the expression of COX-2 following administration to freshly excised porcine skin has been investigated. An ethanol-soluble extract of H. procumbens tubers and two of the pure compounds tested showed promising activity in Western blotting and immunocytochemical assays, with harpagoside (1) and 8-coumaroylharpagide (3) exhibiting greater reductions in COX-2 expression than verbascoside (4). Harpagide (2) caused a significant increase in the levels of COX-2 expression after 6 h of topical application. The data suggest that the efficacy of H. procumbens is dependent upon the ratios of compounds 1-4 present, which is inconsistent with some current official monograph specifications based solely on harpagoside (1) content.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Coumaric Acids; Cyclooxygenase 2 Inhibitors; Epidermis; Glucosides; Glycosides; Harpagophytum; Inflammation; Iridoid Glycosides; Molecular Structure; Phenols; Plants, Medicinal; Pyrans; Swine