iridoids and geniposidic-acid

In the 1970s, Eucommia leaf tea, known as Tochu-cha in Japanese, was developed from roasted Eucommia leaves in Japan and is considered as a healthy tea. The antihypertensive, diuretic, anti-stress, insulin resistance improving, and anti-obesity effects of Eucommia leaf extract have been reported. However, the identification and properties of the active components as well as the underlying mechanism of action are largely unknown. In this review, we summarize studies involving the oral administration of geniposidic acid, a major iridoid component of Eucommia leaf extract which increases plasma atrial natriuretic peptide (ANP) on the atria of spontaneously hypertensive rats (SHR) by activating the glucagon-like peptide-1 receptor (GLP-1R). To achieve the antihypertensive effects of the Eucommia leaf extract through ANP secretion in humans, combining a potent cyclic adenosine monophosphate phosphodiesterase (cAMP-PDE) inhibitor, such as pinoresinol di-β-d-glucoside, with geniposidic acid may be necessary. Changes in the gut microbiota are an important aspect involved in the efficacy of asperuloside, another component of the Eucommia leaf extract, which improves obesity and related sequelae, such as insulin resistance and glucose intolerance. There are species differences of mechanisms associated with the antihypertensive and anti-obesity effects between rodents and humans, and not all animal test results are consistent with that of human studies. This review is focused on the mechanisms in antihypertensive and anti-obesity effects of the Eucommia leaf extract and summarizes the differences of mechanisms in their effects on rodents and humans based on our studies and those of others.

Topics: Animals; Antihypertensive Agents; Eucommiaceae; Humans; Insulin Resistance; Iridoids; Plant Extracts; Rats; Rats, Inbred SHR; Rodentia; Tea

The bark and leaves of Eucommia ulmoides Oliv (Eucommiaceae) and "Siberian ginseng" (Ezoukogi in Japanese) prepared from the root bark or stem bark of Eleutherococcus senticosus Maxim (Acanthopanax senticosus Harms) have been used as tonic and anti-stress drug. The extracts of Eucommia showed anti-hypertensive, anti-complementary, anti-oxidative, and anti-gastric ulcer effects, and promoting collagen synthesis, accelating granuloma formation, and other pharmacological effects. The Siberian ginseng exhibited anti-fatigue, anti-stress, immuno-enhancing effect, CNS activity, and anti-depressive effect. By now, 40, 28, and 10 compounds have been isolated from Eucommia ulmoides bark, Eucommia ulmoides leaves, and Siberian ginseng, respectively, and their structures were elucidated. Their pharmacological activities were mainly due to lignans and iridoid glycosides.

Topics: Adjuvants, Immunologic; Animals; Anti-Ulcer Agents; Antihypertensive Agents; Antioxidants; Collagen; Coumarins; Depression; Eleutherococcus; Eucommiaceae; Fatigue; Furans; Glucosides; Humans; Iridoid Glucosides; Iridoids; Lignans; Plant Extracts; Rats; Stress, Physiological

As a traditional Chinese medicine,

Topics: Eucommiaceae; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Seeds

Nowadays, the pharmacological effects of Plantaginis semen was getting more and more attention because of the great effect of treating diuresis, hypertension, hyperlipidemia, and hyperglycemia. According to the Chinese Pharmacopoeia, Plantaginis semen is the seed of Plantago asiatica L. or P. depressa Willd. This was verified by examining chemical composition differences in a preliminary experiment, predicting their differences in pharmacology.. In this study, we aimed to compared the the differences in main components and anti-obesity effects of Plantago asiatica L. seed extract (PASE) and P. depressa Willd. seed extract (PDSE).. The ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) analysis was used to characterize and compare the differences chemical constituents of PASE and PDSE. The difference therapeutic effects between PASE and PDSE on obesity and associated metabolic disorders was investigated by high-fat (HF) diet induced mice model.. The fingerprint of Plantaginis semen were established by screening and identified 15 main components, including iridoids, phenethanol glycosides, flavonoids, guanidines, and fatty acids. Pentahydroxy flavanone was observed only in PDSE but not in PASE. The quantitative analysis results indicated that the main bioactive components in PASE were geniposidic acid and acteoside; their concentrations were three times higher in PASE than in PDSE. In anti-obesity effects, the result show the levels of fasting blood glucose were improved in both PASE and PDSE when compared with the HF group, while the PASE is show a significant effect then the PDSE group and improved the glucose tolerance but not in PDSE. The results also displayed that the Plantaginis semen did not modify food intake or body weight but decreased abdominal white/brown adipocyte size, serum total cholesterol (TC), triglyceride (TG), low density lipoprotein cholesterol (LDL-c), hepatic TG and TC, fecal TG and TC concentrations when compared with the HF group. Among these indicators, serum TG, liver TG, fecal TC and TG levels were significantly improved in PASE compared with PDSE. The results indicated that PASE treatment more effectively improved lipid and glucose metabolism in HF diet-induced obese mice than did PDSE.. As Plantaginis semen sources, P. asiatica L. seeds demonstrated more bioactive components and favorable metabolic disorder treatment outcomes than did P. depressa Willd. seeds.

Topics: Adipocytes; Animals; Anti-Obesity Agents; Body Weight; Cholesterol, LDL; Diet, High-Fat; Hyperlipidemias; Iridoid Glucosides; Iridoids; Male; Mice, Inbred C57BL; Obesity; Plant Extracts; Plantago; Seeds; Triglycerides

Nonalcoholic fatty liver disease (NAFLD) is a chronic liver disorder associated with features of metabolic syndrome and oxidative stress. We examined the mechanism by which the combined extracts of

Topics: AMP-Activated Protein Kinases; Animals; Antioxidants; Diet, High-Fat; Disease Models, Animal; Endoplasmic Reticulum Stress; Eucommiaceae; Fatty Liver; Iridoid Glucosides; Iridoids; Lipid Peroxidation; Male; Oxidative Stress; Phytotherapy; Plant Extracts; Rats, Sprague-Dawley; Reactive Oxygen Species

Topics: Anti-Bacterial Agents; Antioxidants; Bacteria; China; Chlorogenic Acid; Chromatography, High Pressure Liquid; Eucommiaceae; Flavonoids; Fungi; Gutta-Percha; Iridoid Glucosides; Iridoids; Kaempferols; Lignans; Metabolome; Phenols; Plant Bark; Plant Extracts; Plant Leaves; Plants, Medicinal; Quercetin; Rutin

1. Pinoresinol di-O-β-d-glucopyranoside (PDG), geniposide (GE), geniposidic acid (GA), aucubin (AN) and chlorogenic acid (CA) are the representative active ingredients in Eucommiae cortex (EC), which may be estrogenic. 2. The ultra high-performance liquid chromatography/tandem mass spectrometry (UHPLC-MS/MS) method for simultaneous determination of the five ingredients showed good linearity, low limits of quantification and high extraction recoveries, as well as acceptable precision, accuracy and stability in mice plasma and tissue samples (liver, spleen, kidney and uterus). It was successfully applied to the comparative study on pharmacokinetics and tissue distribution of PDG, GE, GA, AN and CA between normal and ovariectomized (OVX) mice. 3. The results indicated that except CA, the plasma and tissue concentrations of PDG, GE, GA in OVX mice were all greater than those in normal mice. AN could only be detected in the plasma and liver homogenate of normal mice, which was poorly absorbed in OVX mice and low in other measured tissues. PDG, GE and GA seem to be better absorbed in OVX mice than in normal mice proved by the remarkable increased value of AUC0-∞ and Cmax. It is beneficial that PDG, GE, GA have better plasma absorption and tissue distribution in pathological state.

Topics: Animals; Chlorogenic Acid; Drugs, Chinese Herbal; Estrogens; Glucosides; Iridoid Glucosides; Iridoids; Lignans; Mice; Ovariectomy; Tissue Distribution

Gardeniae fructus is one of the medicinal herbs that have been used in Far Eastern countries, such as Korea, China, and Japan. Gardeniae fructus is the dried ripe fruit of Gardenia jasminoides Ellis (Rubiaceae) and has been used as a yellow dye. It is widely used as traditional herbal medicine for reducing fever, cholagogue, diuretic and antiphlogistic effects. We established an analytical method that was useful to evaluate the quality control, and standardize quantification monitoring of 68 samples of Gardeniae fructus collected from Korea and China. While numerous previous studies have focused on the simultaneous analysis of geniposide, which constitutes the higher proportion of Gardeniae fructus, and crocin, which determines its color, no simultaneous analysis of gardenoside and geniposide, the major components of Gardeniae Fructus, has been performed. However, previously reported methods are not considered accurate enough because only geniposide or gardenoside was chosen to be the marker component for the quality control of Gardeniae fructus. Thus, we developed the method using simultaneous determination of four components including geniposide, gardenoside, geniposic acid and chlorogenic acid. Against this backdrop, this study aims to propose a new calculation for gardenoside and geniposide concentrations by analyzing their concentrations in Gardeniae fructus.

Topics: Biomarkers; China; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Fruit; Gardenia; Iridoid Glucosides; Iridoids; Republic of Korea

We recently discovered that the activation of the spinal glucagon-like peptide-1 receptors (GLP-1Rs) by the peptidic agonist exenatide produced antinociception in chronic pain. We suggested that the spinal GLP-1Rs are a potential target molecule for the management of chronic pain. This study evaluated the antinociceptive activities of geniposide, a presumed small molecule GLP-1R agonist. Geniposide produced concentration-dependent, complete protection against hydrogen peroxide-induced oxidative damage in PC12 and HEK293 cells expressing rat and human GLP-1Rs, but not in HEK293T cells that do not express GLP-1Rs. The orthosteric GLP-1R antagonist exendin(9-39) right-shifted the concentration-response curve of geniposide without changing the maximal protection, with identical pA2 values in both cell lines. Subcutaneous and oral geniposide dose-dependently blocked the formalin-induced tonic response but not the acute flinching response. Subcutaneous and oral geniposide had maximum inhibition of 72% and 68%, and ED50s of 13.1 and 52.7 mg/kg, respectively. Seven days of multidaily subcutaneous geniposide and exenatide injections did not induce antinociceptive tolerance. Intrathecal geniposide induced dose-dependent antinociception, which was completely prevented by spinal exendin(9-39), siRNA/GLP-1R and cyclic AMP/PKA pathway inhibitors. The geniposide iridoid analogs geniposidic acid, genipin methyl ether, 1,10-anhydrogenipin, loganin and catalpol effectively inhibited hydrogen peroxide-induced oxidative damage and formalin pain in an exendin(9-39)-reversible manner. Our results suggest that geniposide and its iridoid analogs produce antinociception during persistent pain by activating the spinal GLP-1Rs and that the iridoids represented by geniposide are orthosteric agonists of GLP-1Rs that function similarly in humans and rats and presumably act at the same binding site as exendin(9-39).

Topics: Analgesics; Animals; Central Nervous System Agents; Exenatide; Formaldehyde; Glucagon-Like Peptide-1 Receptor; HEK293 Cells; Heterocyclic Compounds, 3-Ring; Humans; Iridoid Glucosides; Iridoids; Male; Mice; Nociception; PC12 Cells; Peptide Fragments; Peptides; Rats; Rats, Wistar; Receptors, Glucagon; Spinal Cord; Venoms

Cortex Eucommia has been used as a kidney-tonifying herbal medicine with a long history of compatibility with Fructus Psoraleae. Geniposide (GP) and geniposidic acid (GPA) are the two main chemical components in Cortex Eucommia. In the present study, the effects of Fructus Psoraleae extract (FPE) on intestinal absorption kinetics of GP and GPA in rat were investigated. Twenty four male Sprague-Dawley rats were randomly assigned into four groups which were treated with GP, GPA, GP mixed with FPE and GPA mixed with FPE, respectively, by in situ intestinal perfusion for 3 h. The samples of intestinal perfusion solutions were collected every 30 min, and analyzed by ultra high performance liquid chromatography (UPLC). The curves of time and residual quantities of GP and GPA (lnx) in the intestinal perfusion solution and the cumulative absorption rate were obtained. The results showed that FPE exhibited different effects on the intestinal absorption of GP and GPA in rat: it increased the intestinal absorption of GP (p<0.05), while demonstrated no significant effect on the absorption of GPA.

Topics: Animals; Chromatography, High Pressure Liquid; Intestinal Absorption; Iridoid Glucosides; Iridoids; Kinetics; Male; Plant Extracts; Psoralea; Rats; Rats, Sprague-Dawley

To study the effect of geniposide-acid(GA) on the anti-inflammatory action for adjuvant-induced arthritis (AA) rats and the proliferation of synoviocytes in AA rats and the feasible mechanism of apoptosis in vitro.. Forty-eight health male Wistar rats were divided randomly into six groups and were administered respectively with 200, 100, 50 mg x kg(-1) GA and 0.75 mg x kg(-1) MTX and normal sodium (normal or model control group) for four weeks when right posterior paw pads of rats excluding normal control group were injected intrademally with complete Freund's adjuvant after 19 days. The left posterior paws swelling degree, swelling inhibition ratio and arthritis index of secondary inflamation were detected. The TNF-alpha and IL-1beta proteins in serum of rats were assayed by enzyme linked immunosorbent assay (ELISA) kits. The synovial fibroblasts of AA rats were exposed to 1-4 micromol x L(-1) GA or 4 micromol x L(-1) MTX. The effect of GA on the proliferation of synoviocytes was detected by MTT assay. The morphologic change of apoptosis cells was observed by Hoechst/PI double stainning and fluorescence microscope. The rate of apoptosis cells was analyzed by flow cytometry. The mRNA expresstion of Bcl-2 and Bax gene was detected by reverse transcription PCR (RT-PCR).. 200 mg kg(-1) or 100 mg kg(-1) GA could decrease significantly the paw swelling degree, arthritis index and the level of TNF-alpha and IL-1beta proteins in serum of AA rats (P < 0.05 or P < 0.01) with 25.4%, 21.37% of the swelling inhibition ratio respectivly, 34.61%, 28% of protein inhibition ratio of TNF-alpha and 29.05%, 21.65% of that of IL-1beta. GA(1-4 micromol x L(-1)) inhibitated significantly the proliferation of synoviocytes culcured for 5 days. Flow cytometry showed that 1, 2, 4 micromol x L(-1) GA increased obviously the rate of apoptosis cells, the apoptosis ratios were 15.8%, 24.3%, 40.7% respectivly (P < 0.01). RT-PCR showed GA could decrease the expression level of Bcl-2 gene but increase that of Bax gene (P < 0.05 or P < 0.01).. GA could inhibit the secondary inflamation of AA rats and decrease the level of TNF-alpha and IL-1beta protein in the AA rats serum. GA could inhibit the proliferation of AA rat synoviocytes in vitro and induce apoptosis which mechanism was concerned with down-regulating the mRNA expression of Bcl-2 and up-regulating that of Bax.

Topics: Animals; Anti-Inflammatory Agents; Apoptosis; Arthritis, Experimental; Cytokines; Disease Models, Animal; Freund's Adjuvant; Glucosides; Humans; Iridoid Glucosides; Iridoids; Male; Random Allocation; Rats; Rats, Wistar; Synovial Fluid

A natural compound, aglycone geniposidic acid (aGSA), originated from the fruits of Gardenia jasminoides ELLIS was used for the fixation of collagenous tissues. The presumed crosslinking reaction mechanism of collagenous tissues with aGSA was inferred by reacting aGSA with a bifunctional amine, 1,6-hexanediamine, using a series of (1)H NMR, FT-IR, and UV/Vis spectra analyses. aGSA reacted with 1,6-hexanediamine by a nucleophilic attack on the olefinic carbon atom at C-2 of deoxyloganin aglycone, followed by opening the dihydropyran ring to form heterocyclic amine compounds. It is inferred that aGSA may form intramolecular and intermolecular crosslinks with a heterocyclic structure within collagen fibers in tissues. The degrees of tissue fixation by aGSA at different pH values were investigated by examining the fixation indices and denaturation temperatures of test samples. It was found that the fixation indices and denaturation temperatures of test samples fixed at neutral or basic pH (pH 7.4 or pH 8.5) were significantly greater than at acidic pH (pH 4.0). The results obtained in this study may be used to elucidate the crosslinking mechanism and optimize the fixation process for developing bioprostheses fixed by aGSA.

Topics: Bioprosthesis; Collagen; Cross-Linking Reagents; Gardenia; Glucosides; Hydrogen-Ion Concentration; Iridoid Glucosides; Iridoids; Tissue Adhesives

A simple and rapid high performance liquid chromatographic method has been developed for the determination of geniposidic acid and chlorogenic acid in the male flowers and related products of Eucommia ulmoides. Two components were separated by a Shim-pack VP-ODS column (150 mm x4.6 mm, 5 [microm) with a mobile phase of methanol-water-acetic acid (24 :75: 1, v/v) at a flow rate of 1 mL/min, column temperature of 30 93 and detection wavelength of 240 nm. Under the chromatographic conditions mentioned above, the method performance, such as the number of theoretical plate, resolution, trailing etc have all reached required level. The linear ranges were 0. 025 - 0. 400 g/L for geniposidic acid and 0. 075 - 1. 200 g/L for chlorogenic acid, with the correlation coefficients of 0. 999 7 and 0. 999 9, respectively. The average recoveries were 100. 2% and 100. 5%, and the relative standard deviations (RSDs) were 1. 47% and 1. 49% respectively. The minimum detection limits were 0. 02 microg/L for geniposidic acid, and 0. 06 microg/L for chlorogenic acid. The method developed has demonstrated the characteristics of simple mobile phase composition, short retention, good resolution, high repeatability and precision. It is suitable for the determination of the two compounds in the male flowers of E. ulmoides and related products.

Topics: Chlorogenic Acid; Chromatography, High Pressure Liquid; Eucommiaceae; Flowers; Glucosides; Iridoid Glucosides; Iridoids; Reproducibility of Results

The purpose of this study was to evaluate the characteristics of a chitosan film cross-linked by a naturally occurring compound, aglycone geniposidic acid (aGSA). This newly developed aGSA-cross-linked chitosan film may be used as an edible film. The chitosan film without cross-linking (fresh) and the glutaraldehyde-cross-linked chitosan film were used as controls. The characteristics of test chitosan films evaluated were their degree of cross-linking, swelling ratio, mechanical properties, water vapor permeability, antimicrobial capability, cytotoxicity, and enzymatic degradability. It was found that cross-linking of chitosan films by aGSA (at a concentration up to 0.8 mM) significantly increased its ultimate tensile strength but reduced its strain at fracture and swelling ratio. There was no significant difference in the antimicrobial capability between the cross-linked chitosan films and their fresh counterpart. However, the aGSA-cross-linked chitosan film had a lower cytotoxicity, a slower degradation rate, and a relatively lower water vapor permeability as compared to the glutaraldehyde-cross-linked film. These results suggested that the aGSA-cross-linked chitosan film may be a promising material as an edible film.

Topics: Anti-Infective Agents; Cell Death; Chemical Phenomena; Chemistry, Physical; Chitosan; Cross-Linking Reagents; Fibroblasts; Glucosides; Humans; Iridoid Glucosides; Iridoids; Mechanics; Muramidase; Permeability; Water

An iridoid glycoside, oldenlandoside III (5) was isolated from the n-butanol fraction of methanol extracts of the aerial parts of Oldenlandia diffusa Roxb. along with six others previously characterized iridoid glycosides; geniposidic acid (1), scandoside (2), feretoside (3), 10-omicron-benzoylscandoside methyl ester (4), asperulosidic acid (6) and deacetylasperulosidic acid (7). Compounds 1, 2, and 7 inhibited LDL-oxidation, and showed 63.3+/-2.0, 62.2+/-1.6, and 63.8+/-1.5% inhibition, respectively, at a concentration of 20 microg/mL.

Topics: Glucosides; Glycosides; Humans; Iridoid Glucosides; Iridoids; Lipoproteins, LDL; Molecular Structure; Oldenlandia; Oxidation-Reduction; Plant Extracts; Structure-Activity Relationship

The methods using silica column chromatography, reversed-phase high performance liquid chromatography, liquid chromatography-electrospray ionization mass spectrometry and nuclear magnetic resonance (RP-HPLC/LC-ESI-MS/NMR) for the isolation, purification and identification of geniposidic acid (GPA) in Eucommia ulmoides Oliv. were established. The crude extract of E. ulmoides was obtained after E. ulmoides was extracted with 70% ethanol and the extract was concentrated under reduced pressures. The obtained crude extract dissolved in methanol was injected to a silica gel column and eluted with chloroform-methanol. The eluted fractions were analyzed by RP-HPLC. The eluant from chloroform-methanol (8:1, v/v) was indicated to be a single component by HPLC with a retention time of 5.142 min. The HPLC analysis of the mixture of this fraction with a GPA standard resulted in a single peak. The ultraviolet and infrared spectra of the eluted solution were essentially the same to those of GPA. On the other hand, LC-ESI-MS, 1H- and 13C-NMR experiments also indicated that the fraction was identical to GPA.

Topics: Chromatography, High Pressure Liquid; Chromatography, Liquid; Eucommiaceae; Glucosides; Iridoid Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Spectrometry, Mass, Electrospray Ionization

All ten compounds were isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as three iridoid glycosides, asperuloside, geniposidic acid and asperulosidic acid, a coumarin glycoside, scopolin, and six flavonoids, rutin, kaempferol-3-O-rutinoside, quercitrin, astragalin, isoquercitrin and quercetin by spectroscopic analysis.

Topics: Chemistry, Pharmaceutical; Chromatography, Liquid; Coumarins; Flavonoids; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Kaempferols; Methanol; Plant Extracts; Plant Structures; Plants, Medicinal; Rubiaceae

To study the optimum technology of extracting bioactive component named geniposidic acid in Eucommia Ulmiodes by orthogonal test.. An orthogonal test table L16(4(5)) was used with the factors of extracting time, temperature, times, ethanol consistency and the ratio of solid to liquid. The content of geniposideic acid was determined by RP-HPLC.. The optimum technology was: temperature 50 degrees C, time 1 h, once, consistency 80%, and the ratio of solid and liquid 1:12. Under the condition, the best material of Eucommia Ulmiodes for extracting geniposidic acid was chosen.. The technology can provide some theoretic advice for industry.

Topics: Chromatography, High Pressure Liquid; Ethanol; Eucommiaceae; Glucosides; Iridoid Glucosides; Iridoids; Plant Bark; Plants, Medicinal; Technology, Pharmaceutical; Temperature; Time

To determine 3 kinds of biologically active components (9 compounds) in Gardenia, namely geniposidic acid, gentiobioside, gardenoside, genipin geniposide, chlorogenic acid, crocin 1, crocin 2, crocin 3 and crocetin simultaneously and quantitatively.. An HPLC method detected by 3 different UV-vis waves--240 nm for geniposidic acid, geniposide, gardenoside, genipin gentiobioside, 330 nm for chlorogenic acid, 440 nm for crocin 1, crocin 2, crocin 3 and crocetin respectively, has been developed: Phenomenex Luna C18 column(250 mm x 4.6 mm ID, 5 microns) with linear gradient elution using methanol-acetotrile (9:1) and 0.3% aqueous formic acid.. This method successfully determined 9 compounds in Gardenia (from 5 different areas) simultaneously and quantitatively.. This is a more reasonable and credible quality control method for the Chinese traditional medicine.

Topics: Carotenoids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Fruit; Gardenia; Glucosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Quality Control

A fast and easy method was sought for determination of the iridoid glycosides catalpol, ketologanin, verbenalin, loganin, 8-epi-loganic acid, geniposidic acid and 10-cinnamoyl catalpol in plant samples. The method involved micellar electrokinetic capillary chromatography (MEKC) coupled on-line to mass spectrometry. The partial filling technique and electrospray ionization were used. Seven iridoid glycosides could be separated with use of MEKC under basic conditions. However, 8-epi-loganic acid and geniposidic acid could not be detected simultaneously with the five neutral iridoid glycosides by mass spectrometry. Therefore, only the neutral iridoid glycosides were screened from plant samples. Catalpol, verbenalin, loganin and possibly 10-cinnamoyl catalpol were found in an examination of seven plant species in the genera Plantago, Veronica, Melampyrum, Succisa, and Valeriana. Aucubin, which was not included in the sample mixture used in method development because of overlapping with catalpol in MEKC, was also detected. The limits of detection for the iridoid glycosides, both at the UV and at the mass spectrometer, are given.

Topics: Chromatography, Micellar Electrokinetic Capillary; Glucosides; Hydrogen-Ion Concentration; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Mass Spectrometry; Molecular Structure; Molecular Weight; Plantago; Plants, Medicinal; Pyrans; Scrophulariaceae; Species Specificity; Spectrophotometry, Ultraviolet; Valerianaceae

To investigate the chemical constituents of Cistanche tubulosa.. The chemical constituents were isolated by solvent extraction together with various chromatographic techniques including preparative HPLC. The structures were elucidated on the basis of chemical evidence and spectral data.. Four iridoid glycosides, one lignan glycoside and one monoterpenoid were isolated from the 95% ethanol extract from the stem of C. tubulosa and identified as adoxosidic acid(I), 8-epiloganic acid(II), geniposidic acid (III), mussaenosidic acid(IV), (+)-syringaresinol-O-beta-D-gluco pyranoside(V) and 8-hydroxygeraniol(VI).. Compounds I and VI were isolated from the genus of Cistanche for the first time. Compounds III, IV and V were isolated from this plant for the first time.

Topics: Carboxylic Acids; Cistanche; Drugs, Chinese Herbal; Glucosides; Iridoid Glucosides; Iridoids; Magnoliopsida; Plant Stems; Terpenes

To determine the iridoid contents in Gardenia sootepensis.. Using RP-HPLC with geniposidic acid, geniposide and scandoside methyl ether as standards.. According to the selected chromatographic conditions, the linear ranges of geniposidic acid, geniposide and scandoside methyl ether were 0.097-0.606 microgram, 0.0638-3.990 micrograms and 0.198-1.239 micrograms, respectively. The average recoveries of these three compounds were 100.0%, 99.9% and 100.1%, and RSD 1.23%, 1.38% and 1.53% (n = 5) respectively.. The method is easy, rapid, and reproducible.

Topics: Chromatography, High Pressure Liquid; Fruit; Gardenia; Glucosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans

We earlier reported that collagen synthesis in false aged model rats was stimulated by the administration of a methanol extract from the leaves of Eucommia ulmoides OLIVER. When the methanol extract was fractionated to n-hexane, ethyl acetate, acetone and methanol fractions by silica gel chromatography, we discovered that geniposidic acid and aucubin, contained in the acetone fraction, were the active ingredients. In the current study, we set out to examine if active compounds found in the Eucommia ulmoides OLIVER leaf (EUOL) improved the low turnover rate in the stratum corneum of false aged model rats. The turnover rate in the stratum corneum in rats was measured as 50% dansyl chloride clearance day. In the first experiment, administration of a 2.4% water soluble methanol extract (WSME) of EUOL, along with an 11% protein diet, led to a 20% higher turnover rate in the stratum corneum (p<0.05, Mann-Whitney) than the control value. The WSME mainly contained iridoid mono-glycosides such as geniposidic acid. In the second experiment, treatment with geniposidic acid similarly caused a higher turnover rate in the stratum corneum, increasing turnover by 23% (p<0.05, Mann-Whitney) compared to the control value. In this paper we reveal that the WSME contains compounds effective against aging, and one of them is geniposidic acid.

Topics: Aging; Animals; Body Weight; Drugs, Chinese Herbal; Epidermis; Glucosides; Iridoid Glucosides; Iridoids; Male; Plant Extracts; Plants, Medicinal; Pyrans; Rats; Rats, Wistar

To demonstrate the chemical constituents of the fruits of Gardenia sootepensis.. Column chromatographic technology was employed to separate the water soluble part, and the compounds obtained were elucidated by spectral and chemical analysis.. Ten compounds have been isolated, seven of which elucidated respectively as D-mannitol, beta-sitosterol, deacetylasperulosidic acid methyl ester, geniposidic acid, geniposide, scandoside methyl ester and dimeric molecule of quinide.. All the compounds were obtained from this plant for the first time.

Topics: Drugs, Chinese Herbal; Fruit; Gardenia; Glucosides; Iridoid Glucosides; Iridoids; Mannitol; Plants, Medicinal; Pyrans; Sitosterols

We have reported that collagen synthesis was stimulated by the administration of a hot water extract from the leaves of Eucommia ulmoides OLIVER, Eucommiaceae (Du-Zhong leaves) in false aged model rats. In this paper, we set out to examine the compounds in Du-Zhong leaves that stimulated collagen synthesis in false aged model rats. In experiment 1, a methanol extract of Du-Zhong leaves also stimulated collagen synthesis in aged model rats. An acetone fraction was derived from the methanol extract by silica gel chromatography in experiment 2. The acetone fraction mainly contained iridoides mono-glycosides such as geniposidic acid and aucubin. The administration of geniposidic acid or aucubin stimulated collagen synthesis in aged model rats in experiments 3 and 4 (significance (p<0.05)). The reported pharmacological effects of Du-Zhong leaves, including healing organs and strengthening bone and muscle, are closely related to collagen metabolism. It appears that geniposidic acid and aucubin are the actual compounds in Du-Zhong which caused the effect in our experiments.

Topics: Aging; Animals; Body Weight; Collagen; Drugs, Chinese Herbal; Glucosides; Granuloma; Iridoid Glucosides; Iridoids; Magnoliopsida; Male; Organ Size; Plant Leaves; Pyrans; Rats; Rats, Wistar

The suppressing effect of crude extracts of Tochu tea, an aqueous extract of Eucommia ulmoides leaves and a popular beverage in Japan, on the induction of chromosome aberrations in CHO cells and mice was studied. When CHO cells were treated with Tochu tea crude extract after MMC treatment, the frequency of chromosome aberrations was reduced. Out of 17 Tochu tea components, 5 irridoids (geniposidic acid, geniposide, asperulosidic acid, deacetyl asperulosidic acid, and asperuloside) and 3 phenols (pyrogallol, protocatechuic acid, and p-trans-coumaric acid) were found to have anticlastogenic activity. Since the anticlastogenic irridoids had an alpha-unsaturated carbonyl group, this structure was considered to play an important role in the anticlastogenicity. The anticlastogenic effect of Tochu tea extracts was examined in mice using a micronucleus assay. When mice received 1.0 ml 4% Tochu tea extract by oral gavage 6 h before intraperitoneal injection of MMC, a decrease in the frequency of micronuclei was observed. This decrease was not due to a delay in the maturation of micronucleated reticulocytes.

Topics: Animals; Antimutagenic Agents; Beverages; CHO Cells; Chromatids; Chromosome Aberrations; Cricetinae; Cyclopentane Monoterpenes; Glucosides; Iridoid Glucosides; Iridoids; Japan; Male; Mice; Mice, Inbred ICR; Micronucleus Tests; Mitomycin; Mutagens; Phenols; Plant Extracts; Pyrans

The antitumor effects of two iridoid compounds, geniposidic acid (GA) and geniposide (GP), were investigated in mice along with their possible effects on radioprotection after sublethal X-irradiation. Decreases in the growth of the implanted tumor by ascitic cells were a result of intraperitoneal administration of GA and GP at high concentrated levels. This result was achieved by exerting the levels of dosage in a dose-dependent manner. Except on the 12th day after treatment by the dosage of 500 mg/kg, reduced radiation effects of mice treated with the drugs in the 30 min preirradiated period by GA and GP on peripheral leukocytes were not observed significantly by the sublethal whole-body X-irradiation. And except on the 7th day after treatment, when these two compounds were administered i.p. to mice 30 min before 4 Gy irradiation, neither GA nor GP enhanced significantly the postirradiation responses of splenic blastogenesis by PHA. In addition, GA might be a more potent tumor growth inhibitor than GP when combined with the X-irradiation, though there was no significant synergetic effect on their combined antitumor activity. The preliminary results of GA and GP on hematological and blastogenic observations in this study suggested that they may very well, partially, play a role in an effective anticancer product with the ability to decrease undesirable radiation damage to the hematologic tissue after high dose irradiation.

Topics: Animals; Antineoplastic Agents; Carcinoma, Ehrlich Tumor; Dose-Response Relationship, Drug; Drugs, Chinese Herbal; Glucosides; Iridoid Glucosides; Iridoids; Leukocyte Count; Lymphocyte Activation; Male; Mice; Mice, Inbred ICR; Pyrans; Radiation-Protective Agents; Time Factors; Whole-Body Irradiation

The isolation and identification of two cardioactive compounds from two Eremophila species (Myoporaceae) considered important in the pharmacopoeia of the Australian Aboriginal people is described. Verbascoside, isolated from the methanol and water extracts of E. alternifolia leaves, mediated significant increases in chronotropism, inotropism and coronary perfusion rate (CPR) in the Langendorff rat heart. Geniposidic acid, isolated from the methanol extract of E. longifolia leaves, mediated an inhibitory effect with significant negative chronotropism, negative inotropism and CPR.

Topics: Animals; Antioxidants; Australia; Coronary Circulation; Drugs, Chinese Herbal; Female; Glucosides; Heart Rate; Iridoid Glucosides; Iridoids; Medicine, Traditional; Methanol; Myocardial Contraction; Phenols; Plant Extracts; Plant Leaves; Pyrans; Rats; Rats, Wistar; Structure-Activity Relationship

Four iridoid constituents: geniposide, gardenoside, geniposidic acid and genipin-1-beta-gentiobioside, have been separated by using an ODS (7 microns) column with gradient elution. The iridoid contents of the crude drug were quantified by peak height ratio. Thirty-one specimens from various sources were analyzed.

Topics: Drugs, Chinese Herbal; Glucosides; Iridoid Glucosides; Iridoids; Pyrans

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Pyrans