iridoids and harpagoside

To study the compatibility regularity of Simiao Yong'an decoction by determining the plasma protein binding rate with the constituents in Simiao Yong'an decoction and to preliminarily clarify the effects of the compatibility on the plasma protein binding rate of different components.. Based on the equilibrium dialysis method, high-performance liquid chromatography was used to determine the contents of six constituents, which were divided into a single group and combination groups, in Simiao Yong'an decoction in the internal and external dialysis solutions. The obtained plasma protein binding rate through calculations was an index to evaluate the binding of the above components to plasma protein in different conditions.. Harpagide, harpagoside, sweroside and loganin showed low plasma protein binding rates, ferulic acid exhibited a moderate plasma protein binding rate, and glycyrrhizic acid showed a high plasma protein binding rate. The compatibility study showed that glycyrrhizic acid promoted the binding of ferulic acid to plasma protein. Glycyrrhizic acid and ferulic acid were the key compounds to promote the binding of harpagide to plasma protein. Glycyrrhizic acid, harpagide, harpagoside and loganin had a significant inhibitory effects on the binding of sweroside to plasma protein. The plasma protein binding capacities of harpagoside and loganin were reduced by the other five constituents. Glycyrrhizic acid had the strongest plasma protein binding effect, and the binding effect was not affected by other components.. This study explores the effects of compound compatibility on effective components from the perspective of plasma protein binding by high-performance liquid chromatography combined with the equilibrium dialysis method, and lays a foundation for clarifying the compatibility rule of Simiao Yong'an decoction and also provides a new idea for the study of the compatibility of traditional Chinese medicine formulas.

Topics: Chromatography, High Pressure Liquid; Coumaric Acids; Glycosides; Glycyrrhizic Acid; Iridoids; Phytochemicals; Protein Binding; Pyrans; Serum Albumin, Bovine

The present study evaluates the effect of isolated fractions of Harpagophytum procumbens (devil's claw) on cyclooxygenase (COX-1 and COX-2) activities and NO production using a whole blood assay. The activity of COX-1 was quantified as platelet thromboxane B(2) production in blood clotting and COX-2 as prostaglandin E(2) production in LPS-stimulated whole blood. Total NO(2) (-)/NO(3) (-) concentration was determined by Griess reaction in LPS stimulated blood. Assays were performed by incubation of isolated fractions obtained by flash chromatography monitored with HPLC, TLC and identified by (1)HNMR, containing different amounts of harpagoside with blood from healthy donors. Indomethacin and etoricoxib were the positive controls of COX-1 and COX-2 Inhibition. Data shows that fraction containing the highest concentration of harpagoside inhibited indistinctively COX-1 and COX-2 (37.2 and 29.5% respectively) activity and greatly inhibited NO production (66%). In contrast the fraction including iridoid pool increased COX-2 and did not alter NO and COX-1 activities. The fraction containing cinnamic acid was able to reduce only NO production (67%). Our results demonstrated that the harpagoside fraction is the main responsible for the effect of devils claw on these enzyme activities. However, other components from devil's claw crude extract could antagonize or increase the synthesis of inflammatory mediators.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Blood Chemical Analysis; Blood Coagulation; Blood Platelets; Cinnamates; Cyclooxygenase 1; Cyclooxygenase 2; Cyclooxygenase Inhibitors; Dinoprostone; Etoricoxib; Female; Glycosides; Harpagophytum; Humans; Indomethacin; Inflammation Mediators; Iridoids; Lipopolysaccharides; Nitric Oxide; Plant Extracts; Pyrans; Pyridines; Sulfones; Thromboxane B2

Two saponins: scrokoelziside A (1), scrokoelziside B (2), one iridoid glycoside, eurostoside (3), and two flavonoids: nepitrin (4) and homoplantaginin (5), were isolated from the leaves of Scrophularia ningpoensis for the first time. Moreover, eight known compounds: cane sugar (6), harpagide (7), aucubin (8), 6-O-methylcatalpol (9), harpagoside (10), angoroside C (11), beta-sitosterol (12) and beta-sitosterol glucoside (13) were isolated from the roots of S. ningpoensis. Furthermore, the antimicrobial activity of the extracts of the leaves of S. ningpoensis and the 10 compounds (1, 2, 3, 4, 5, 7, 8, 9, 10, 11) was studied in vitro against eight reference strains of bacteria by using the disc-diffusion method and micro-well dilution assay. The extracts of leaves and scrokoelziside A are effective against beta-haemolytic streptococci but had no effect against other strains. The extract of roots and other compounds showed no activity against all bacterial strains at the test concentration.

Topics: Anti-Infective Agents; Bacteria; Flavonoids; Glucosides; Glycosides; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Luteolin; Microbial Sensitivity Tests; Molecular Structure; Plant Extracts; Plant Leaves; Plant Roots; Pyrans; Scrophularia; Sitosterols; Triterpenes

The cognitive-enhancing activities of E-harpagoside and 8-O-E-p-methoxycinnamoylharpagide (MCA-Hg) isolated from Scrophularia buergeriana were evaluated in scopolamine-induced amnesic mice by the Morris water maze and by passive avoidance tests. E-harpagoside and MCA-Hg significantly improved the impairment of reference memory induced by scopolamine in the Morris water maze test. The mean escape latency, the mean path length and swimming movement were also improved by both compounds. In passive avoidance test, E-harpagoside and MCA-Hg (2 mg/kg body weight, p.o.) significantly ameliorated scopolamine-induced amnesia by as much as 70% of the level found in normal control mice. Donepezil, an acetylcholinesterase inhibitor and the most widely used drug for AD treatment was employed as a positive control. The activity of acetylcholinesterase was inhibited significantly by E-harpagoside or MCA-Hg within the cortex and hippocampus to a level similar to that observed in mice treated with donepezil (2 mg/kg body weight, p.o.). Moreover, treatment with E-harpagoside or MCA-Hg to scopolamine-induced amnesic mice significantly decreased TBARS level which was accompanied by an increase in the activities or contents of glutathione reductase, SOD and reduced GSH. We believe these data demonstrate that E-harpagoside or MCA-Hg exerted potent cognitive-enhancing activity through both anti-acetylcholinesterase and antioxidant mechanisms.

Topics: Acetylcholinesterase; Animals; Antioxidants; Avoidance Learning; Cerebral Cortex; Cognition; Glutathione Peroxidase; Glutathione Reductase; Glycosides; Hippocampus; Iridoids; Male; Maze Learning; Mice; Mice, Inbred ICR; Muscarinic Antagonists; Neuroprotective Agents; Nootropic Agents; Pyrans; Scopolamine; Scrophularia; Superoxide Dismutase; Thiobarbituric Acid Reactive Substances

Five iridoid glycosides, including the two new compounds scropolioside-D(2) (1) and harpagoside-B (2), were isolated from the aerial parts of Scrophularia deserti DEL (Scrophulariaceae). Their structures were elucidated on the basis of spectral data to be 6-O-[2",4"-di-O-acetyl-3"-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-8 alpha-hydroxymethyl-1 alpha,5 beta,6 alpha,7 alpha,9 beta-pentahydro-7(8)-epoxy-2-oxaind-3-ene-1-O-beta-D-glucopyranoside-6'-O-acetate (1) and 5-O-beta-hydroxy-8-O-beta-trans-cinnamoyl-8 alpha-methyl-1,6,7,9-tetrahydro-2-oxaind-3-ene-1-O-beta-D-glucopyranoside (2), respectively. In addition, three more iridoid glycosides, scropolioside-D (3), koelzioside (4), and 8-O-acetyl-harpagide (5), were also isolated and characterized from this source. The biological activity and the structure activity relationship of the compounds were also studied, and scropolioside-D (3) and harpagoside-B (2) were found to possess significant antidiabetic and antiinflammatory activity, respectively.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Diabetes Mellitus, Experimental; Edema; Female; Glycosides; Hypoglycemic Agents; Iridoid Glucosides; Iridoids; Male; Mice; Plant Components, Aerial; Plant Extracts; Pyrans; Rats; Rats, Wistar; Scrophularia

A protocol for de novo regeneration and rapid micropropagation of Scrophularia yoshimurae (Scrophulariaceae) has been developed. Multiple shoot development was achieved by culturing the shoot-tip, leaf-base, stem-node and stem-internode explants on Murashige and Skoog (MS) medium supplemented with 4.44 microM N6-benzyladenine (BA) and 1.07 microM alpha-naphthaleneacetic acid (NAA). Stem-node and shoot-tip explants showed the highest response (100%) followed by stem-internode (74.4%) and leaf-base (7.7%) explants. The shoots were multiplied by subculturing on the same medium used for shoot induction. Shoots were rooted on growth regulator-free MS basal medium and the plantlets were transplanted to soil and acclimatized in the growth chamber. The content of harpagoside, a quantitatively predominant iridoid glycoside, in different plant material was determined by high performance liquid chromatography (HPLC). The analysis revealed that the content of harpagoside in the aerial and underground parts of S. yoshimurae was significantly higher than the marketed crude drug (underground parts of Scrophularia ningpoensis).

Topics: Chromatography, High Pressure Liquid; Culture Techniques; Glucosides; Glycosides; Iridoids; Plant Extracts; Plant Roots; Plant Shoots; Pyrans; Regeneration; Scrophulariaceae