iridoids and ethyl-acetate

The ethyl acetate fraction of ethanol extract of Eucommiae Cortex can effectively inhibit joint inflammation and bone destruction in rats with collagen-induced arthritis(CIA) and has a potential therapeutic effect on rheumatoid arthritis. The triterpenoid(EU-Tid) and iridoid(EU-Idd) of Eucommiae Cortex are derivatives isolated from the ethyl acetate fraction of the ethanol extract of Eucommiae Cortex, and it is not clear whether they have inhibitory effects on joint inflammation and bone erosion in CIA rats. Therefore, based on the CIA model, the effects of EU-Tid, EU-Idd, and their combination(EU-TP) on arthritis in rats were observed, and the material basis of Eucommiae Cortex against arthritis was further clarified. The samples were collected two and four weeks after administration to observe the pathological changes in different stages of arthritis in CIA rats. For the rats in the model control group, with the prolongation of the disease course, the paw volume and arthritis score increased and histopathological lesions aggravated. Compared with the model control group, the drug administration groups showed reduced paw volumes and arthritis scores, and improved joint lesions and cartilage destruction. Additionally, the mRNA expression levels of tumor necrosis factor-α(TNF-α), interleukin-17(IL-17), and interleukin-23(IL-23) in the spleen were down-regulated in the drug administration groups. EU-TP and EU-Tid at concentrations of 160 and 320 μg·mL~(-1) could significantly inhibit the proliferation of human fibroblast-like synoviocytes-RA(HFLS-RA) and nitric oxide(NO) release in the supernatant of RAW264.7 cells induced by lipopolysaccharide(LPS) at the concentration range of 10-80 μg·mL~(-1) in vitro. EU-Idd had no effect on the proliferation of HFLS-RA but could reduce the NO release at concentrations of 40 and 80 μg·mL~(-1). The results indicated that the terpenoids of Eucommiae Cortex had great potential in the treatment of rheumatoid arthritis.

Topics: Animals; Arthritis, Experimental; Arthritis, Rheumatoid; Cytokines; Ethanol; Humans; Inflammation; Iridoids; Plant Extracts; Rats; Triterpenes; Tumor Necrosis Factor-alpha

The separation and purification of hydroxytysol and oleuropein from Olea europaea L. (olive) using a macroporous resin with a novel solvent system was systematically investigated. Static adsorption experiments with BMKX-4 resin revealed that the experimental data of both hydroxytysol and oleuropein fitted best to the pseudo-second-order kinetic and Freundlich isotherm models. The thermodynamic parameters indicated spontaneous and exothermic adsorption processes. The novel solvent system, composed of n-hexane:ethyl acetate:methanol:water in a (v/v/v/v) ratio of 1:9:1:9, had two phases (upper and lower). The separation and purification parameters of hydroxytysol and oleuropein were optimized using dynamic adsorption/desorption on a column packed with BMKX-4 resin. The effects of flow rates and volumes of the upper and lower phases on the separation efficiency were systematically studied. Under optimal conditions, the fraction of hydroxytysol in the final product increased by 6.34-fold from 0.46 to 2.96%, with a yield rate of 88.58% w/w, while that of oleuropein increased 4.17-fold from 11.40 to 47.59%, with a 93.31% w/w yield rate. These results may be help in selecting a suitable eluent for improved separation of macroporous adsorption resins.

Topics: Acetates; Adsorption; Hexanes; Iridoid Glucosides; Iridoids; Methanol; Olea; Particle Size; Porosity; Resins, Plant; Solvents; Surface Properties; Thermodynamics; Water

Application of a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, macroporous adsorbent resin, and reversed-phase HPLC, led to the isolation of 173 compounds including irdidoids, monoterpenes, sesquiterpenes, triterpenes, lignans, flavonoids, and simple aromatic derivatives from the ethyl acetate-soluble fraction of the whole plants of Valeriana jatamansi(Valerianaceae), and their structures were elucidated by spectroscopic methods including 1D, 2D NMR UV, IR, and MS techniques. Among them, 77 compounds were new. In previous reports, we have described the isolation, structure elucidation, and bioactivities of 68 new and 25 known compounds. As a consequence, we herein reported the isolation and structure elucidation of the remaining 9 new and 71 known compounds, the structure revision of valeriotriate A(8a), as well as cytotoxicity of some compounds.

Topics: Acetates; Chromatography, High Pressure Liquid; Flavonoids; Iridoids; Lignans; Molecular Structure; Monoterpenes; Phytochemicals; Plant Extracts; Sesquiterpenes; Triterpenes; Valerian

As a defense mechanism of the aerial parts of Calceolaria talcana (Calceolariaceae; formerly Scrophulariaceae) against herbivore offenses and insect pest attack, diterpenoids, triterpenoids, phenylethanoids, flavonoids, and iridoids are rapidly accumulated along the aerial parts, resulting in a unique natural biopesticide complex from this plant. In addition to verbascoside a series of known compounds were screened for their inhibitory activity against mushroom tyrosinase and protease enzymes. Ethyl acetate and n-hexane extracts, together with cyclopropyl-7,15-ent-pimaradiene (1), abietatriene (2), ursolic acid (3), α-lupeol (4), β-sitosterol (5), 2-hydroxy-3-(1,1-dimethylallyl)-1,4-naphthoquinone (6), α-dunnione (7), verbascoside (8), martynoside (9), and some known model compounds proved to be inhibitors of oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase (EC 1.14.18.1) with an IC50 between 10.0 and 200 ppm or μM, respectively, suggesting that phenolic moieties in the molecules assayed are important for the activity.

Topics: Acetates; Agaricales; Animals; Antioxidants; Biological Control Agents; Diterpenes; Flavonoids; Hexanes; Inhibitory Concentration 50; Insecta; Iridoids; Monophenol Monooxygenase; Pesticides; Plant Components, Aerial; Plant Extracts; Protease Inhibitors; Scrophulariaceae

A highly sensitive, specific and simple LC-MS/MS method was developed to investigate in vivo bio-transformation of oleuropein in rat. Rat urine samples collected after the intravenous administrations were determined using liquid chromatography coupled to tandem mass spectrometry with electrospray ionization in the negative-ion mode. The assay procedure involves a simple liquid-liquid extraction of parent oleuropein and the metabolite from rat urine with ethyl acetate. Chromatographic separation was operated with 0.1% formic acid aqueous and methanol in gradient program at a flow rate of 0.80 mL/min on an RP-C(18) column with a total run time of 30 min. This method has been successfully applied to simultaneous determination of oleuropein and its metabolite in rat urine. Oxygenation was found to be the major metabolic pathway of the oleuropein in rat after intravenous administration.

Topics: Acetates; Animals; Chromatography, Liquid; Formates; Injections, Intravenous; Iridoid Glucosides; Iridoids; Liquid-Liquid Extraction; Male; Methanol; Pyrans; Rats; Rats, Sprague-Dawley; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry

In this article, an efficient method was developed to screen, isolate and identify the major radical scavengers in the leaves of Olea europaea L. by DPPH-HPLC-DAD, HSCCC and NMR. The method of DPPH-HPLC-DAD was used to screen the major radical scavengers. It was found that three major constituents (A, B, C) in the extract of the leaves of O. europaea L. possessed potential antioxidant activities. In order to identify the chemical structures of those compounds, the HSCCC method with a two-phase solvent system composed of petroleum ether-ethyl acetate-water at an optimized volume ratio of 6:600:700 (v/v/v) together with column chromatography was developed to isolate and purify the active compounds. Pure compounds A (225 mg), B (10 mg) and C (12 mg) with purities 92.6, 95.1 and 96.4%, respectively, were obtained from the crude sample (500 mg). Their structures were identified as oleuropein (A), luteolin-7-O-glucoside (B) and verbascoside (C) by (1) H-NMR and (13) C-NMR.

Topics: Acetates; Chromatography, High Pressure Liquid; Flavones; Free Radical Scavengers; Glucosides; Iridoid Glucosides; Iridoids; Olea; Phenols; Plant Extracts; Plant Leaves; Pyrans