syringin and rhodioloside

Three new lignan glycosides, akeqintoside A [(7S,8S)-7,8-dihydro-8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-benzofuranpropanol 2'-O-β-D-glucopyranoside] (1), akeqintoside B [(7R,8R)-7,8-dihydro-8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-(9'-methoxy-7'-propenyl) benzofuran 2'-O-β-D-glucopyranoside] (2), and akequintoside C [7R*,8R*-dihydroxy-7-(4-hydroxy-3-methoxyphenyl)-glycerol 9-O-β-D-(6'-O-caffeoyl)-glucopyranoside] (3) were isolated from Akebia quinata along with five known compounds, syringin (4), vanilloloside (5), salidroside (6), 3,4-dihydroxyphenylethyl alcohol 8-O-β-D-glucopyranoside (7), and calceolarioside B (8). The structures of the compounds were identified based on one dimensional (1D)- and 2D-NMR, including (1)H-(1)H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser effect spectroscopy (NOESY) spectroscopic analyses. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in tumor necrosis factor-alpha (TNF-α) stimulated MG-63 cells was also examined.

Topics: Caffeic Acids; Cells, Cultured; Drugs, Chinese Herbal; Glucosides; Glycosides; Humans; Interleukin-6; Lignans; Magnoliopsida; Molecular Structure; Phenols; Phenylpropionates; Tumor Necrosis Factor-alpha

An RRLC method capable of simultaneous identification and rapid quantification of six biologically active compounds (salidroside, tyrosol, rosarin, rosavin, rosin, rosiridin) in Rhodiola rosea L. and two active compounds (eleutheroside B and eleutheroside E) in Eleutherococcus senticosus Maxim. was developed. The chromatographic analyses were performed on a reversed phase Phenomenex C18 (2)-HST column at 40°C with a neutral mobile phase (purified water and acetonitrile) gradient system at a flow rate of 1.0ml/min and UV detection at 205 and 220nm simultaneously. Baseline separation of eight active compounds was achieved within 8min. This developed method provides good linearity (R>0.9997), precision (RSD<1.99%) and recovery of the bioactive compounds. The RRLC method developed is capable of controlling the quality of R. rosea and E. senticosus raw herbs, commercial extracts, as well as polyherbal formulations containing R. rosea and E. senticosus as ingredients. This RRLC method is accurate and sensitive; in addition, it greatly increases sample analysis throughput with reduced analysis time, which is suitable for routine quality control analysis.

Topics: Calibration; Chemistry Techniques, Analytical; Chemistry, Pharmaceutical; Chromatography; Chromatography, Liquid; Disaccharides; Eleutherococcus; Glucosides; Lignans; Phenols; Phenylethyl Alcohol; Phenylpropionates; Plant Extracts; Plant Preparations; Quality Control; Reproducibility of Results; Resins, Plant; Rhodiola

Three phenylpropanoid glycosides (salidroside, syringin and coniferin) and one lignan (phillyrin) isolated from the leaves of Phillyrea latifolia L. (Oleaceae) were tested for interactions with the cyclo-oxygenase and 5-lipoxygenase pathways of arachidonate metabolism in calcium-stimulated mouse peritoneal macrophages and human platelets, and for their effects on cell viability. These compounds are capable of exerting inhibitory actions on enzymes of the arachidonate cascade. Phillyrin, salidroside and syringin exert a preferential effect on the cyclo-oxygenase pathway, inhibiting release of the cyclo-oxygenase metabolites prostaglandin E2 (IC50 values 45.6 microM, 72.1 microM and 35.5 microM, respectively) and to a lesser extent reducing thromboxane B2 levels (IC50 values 168 microM, 154 microM and 29.3 microM, respectively). In contrast, coniferin can be classified as a "dual inhibitor", since it produces reduction in generation of both cyclo-oxygenase (IC50 values 75.2 microM for prostaglandin E2 and 619 microM for thromboxane B2) and 5-lipoxygenase metabolites, but the effects are greater against leukotriene C4 (IC50 value 63.6 microM). Structure-activity relationships of the three phenylpropanoid glycosides are discussed. Thus, like some other compounds found in medicinal herbs, our molecules possess an array of potentially beneficial anti-eicosanoid properties which may, alongside other constituents, contribute to the claimed therapeutic properties of the plant from which they are derived.

Topics: Animals; Anti-Infective Agents; Anti-Inflammatory Agents; Blood Platelets; Cells, Cultured; Cinnamates; Dinoprostone; Drug Interactions; Eicosanoids; Female; Glucosides; Glycosides; Humans; Ionophores; Leukotriene C4; Macrophages, Peritoneal; Magnoliopsida; Male; Mice; Phenols; Phenylpropionates; Plants, Medicinal; Thromboxane B2