lignans and olivil

A new unsaturated fatty acid (

Topics: alpha-Glucosidases; Glycoside Hydrolase Inhibitors; Lignans; Mass Spectrometry; Phytochemicals; Plant Extracts; Plant Stems; Stearic Acids; Urticaceae

The lignan 4'-

Topics: Hypnotics and Sedatives; Lignans; Plant Extracts; Plant Roots; Valerian

For the first time, we describe the stereocontrolled total syntheses of olivil, cephafortin A, 4-des-

Topics: Lignans; Phenols; Stereoisomerism

To study the chemical constituents of water extracted fraction from Oldenlandia diffusa.. The compounds were isolated and purified by column chromatography on macroporous resin,silica gel,MCI gel,Sephadex LH-20,ODS medium pressure liquid chromatography and RP-semi-preparative HPLC. The structures of compounds were elucidated on the basis of physicochemical and spectral analysis.. 16 compounds were isolated from the water extract of Oldenlandia diffusa,and their structures were identified as asperuloside( 1),deacetyl asperuloside( 2),geniposide( 3),10-dehydrogeniposide( 4),daphylloside( 5),diffusoside A( 6),diffusoside B( 7),coniferin( 8),scandoside methyl ester( 9),acetyl scandoside methyl ester( 10),deacetylasperulosidic acid methyl ester( 11),gardenoside( 12),galioside( 13),galioside 10-acetate( 14),loliolide( 15) and( +)-neo-olivil( 16),respectively.. Compounds 3,8 and 14 ~ 16 are obtained from Oldenlandia diffusa for the first time.

Topics: Chromatography, High Pressure Liquid; Cyclopentane Monoterpenes; Glucosides; Iridoids; Lignans; Oldenlandia; Pyrans

Chemical examination of the ethanol extract of rhizomes of Iris tectorum led to the isolation and characterization of three new lignans, (7R,7'R,8S,8'S)-5'-methoxy-neo-olivil (1a), (7S,7'S,8R,8'R) -5'-methoxy-neo-olivil (1b), (7S,7'R,8S,8'S)-neo-olivil (2a), (7R,7'S,8R,8'R)-neo-olivil (2b), (7R,7'R,8S,8'S,7''S,8''S)-threo-neo-olivil-4'-O-8-guaiacylglycerol ether (3), together with six known ones (4-9). Among them, compounds 1 and 2 were found to be racemic mixtures, respectively, which were verified by chiral HPLC analysis, compound 3 was a new sesquineolignan. The structures were elucidated on the basis of extensive spectroscopic analysis. To our knowledge, this is the first report of lignan constituents isolated from I. tectorum. All compounds were evaluated for their cytotoxicity against five human tumor cell lines and none of them displayed significant toxicity in tested cell lines at a concentration of 10 μM.

Topics: Cell Line, Tumor; Humans; Iris Plant; Lignans; Molecular Structure; Plant Extracts; Rhizome

To study the chemical constituents in the stem bark of Styrax perkinsiae.. The chemical constituents were separated and purified by chromatographic methods after solvent extraction and identified by spectroscopic analyses.. Ten lignans were isolated from the stem bark of Styrax perkinsiae and identified as following: pinoresinol 4-O-β-D-glucopyranoside (1), matairesinoside (2), styraxlignolide B (3), 3- (β-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl )-7-methoxy-(2R , 3S) -dihydrobenzofuran (4), burselignan (5), (+) -neo-olivil (6), threo-1-(4-hydroxy-3-methoxyphenyl )-2-[ 4-(3-hydroxypropyl)-2-methoxyphenoxy]-1, 3-propanediol (7), erythro-1-(4-hydroxy-3-methoxyphenyl )-2-[ 4-(3-hydroxypropyl )-2-methoxyphenoxy ] -1 ,3-propanediol (8), isolariciresinol(9) and (+) -lariciresinol (10).. Compounds 5 - 10 are isolated from the plants of Styrax genus for the first time.

Topics: Furans; Lignans; Lignin; Naphthols; Plant Bark; Plant Extracts; Styrax

In this study, we isolated (-)-olivil-9'-O-β-d-glucopyranoside (OLI9G), a phytochemical from the stem bark of Sambucus williamsii, and investigated the antifungal mechanism of OLI9G against Candida albicans. First of all, the antifungal susceptibility testing and hemolysis assay showed that OLI9G exerted a potent activity without hemolysis compared to the activity of amphotericin B. To investigate the mechanism of action of OLI9G, we first examined membrane depolarization using cyanine dye, 3,3'-dipropylthiacarbocyanine iodide (diSC35). The results showed that OLI9G significantly changed the fungal membrane potential. To further understand this activity on the membrane, we did the propidium iodide (PI) influx assay. From the results, OLI9G caused membrane permeabilization in the fungal membrane, and the three dimensional (3D) flow cytometric contour plot from the PI influx assay further showed that the cells had shrunk due to the membrane damage. Finally, the membrane-active mechanism of OLI9G was confirmed by synthesizing a model membrane, calcein-encapsulating large unilamellar vesicles (LUVs). The calcein leakage showed the membrane-disruptive effects caused by direct action of OLI9G. In conclusion, the current study suggests that OLI9G exerts its antifungal activity through a membrane-disruptive action.

Topics: Antifungal Agents; Cell Membrane; Cells, Cultured; Erythrocytes; Flow Cytometry; Fluoresceins; Fungi; Hemolysis; Humans; Lignans; Membrane Potentials; Microbial Sensitivity Tests; Sambucus; Unilamellar Liposomes

Olivil-type lignans, an enantiomeric type of natural olivil, were synthesized for the first time to evaluate the relationship between the structure of olivil and its antioxidant activity. A comparison of the antioxidant activity with that of other synthesized tetrahydrofuran lignans indicated reduced activity with the tertiary hydroxy group. A different effect of the two phenolic groups of olivil on the antioxidant activity was also observed.

Topics: Antioxidants; Lignans; Molecular Structure

Guided by a feeding stimulant activity test on the olive weevil (Dyscerus perforatus), two compounds that showed potent feeding stimulant activity were isolated from the olive tree (Olea europaea). Based on their spectral data and a literature survey, they were identified as (-)-olivil (1) and (+ )-1-acetoxypinoresinol (2). The activities of these minor lignans were significantly higher for the female than for the male weevil.

Topics: Animals; Coleoptera; Dose-Response Relationship, Drug; Feeding Behavior; Female; Lignans; Male; Nuclear Magnetic Resonance, Biomolecular; Oleaceae; Stereoisomerism; Stimulation, Chemical