lignans and isolariciresinol

Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization step. To determine the stereochemistry of 1, we synthesized the natural product (±)-isolariciresinol (18) from alcohol 17. Comparison of the spectral data showed good agreement. Glycosylation was investigated using four different glycosyl donors. Only the Koenigs-Knorr condition using silver trifluoromethanesulfonate with 1,1,3,3-tetramethylurea provided the glycosylated product. Deprotection and purification using reverse-phase high-performance liquid chromatography gave schizandriside (1) and its diastereomer saracoside (2). Synthesized 1, 2 and 18 showed antioxidant activity with IC

Topics: Antioxidants; Glycosides; Lignans; Lignin; Naphthols; Plant Extracts

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

Small organic phenolic compounds from natural sources have attracted increasing attention due to their potential to ameliorate the serious consequences of acute and chronic traumata of the mammalian nervous system. In this contribution, it is reported that phenols from the knot zones of Siberian larch (Larix sibirica) wood, namely, the antioxidant flavonoid (+)-dihydroquercetin (1) and the lignans (-)-secoisolariciresinol (2) and (+)-isolariciresinol (3), affect migration and outgrowth of neurites/processes from cultured neurons and glial cells of embryonic and early postnatal mice. Compounds 1-3, which were available in preparative amounts, enhanced neurite outgrowth from cerebellar granule neurons, dorsal root ganglion neurons, and motoneurons, as well as process formation of Schwann cells in a dose-dependent manner in the low nanomolar range. Migration of cultured astrocytes was inhibited by 1-3, and migration of neurons out of cerebellar explants was enhanced by 1. These observations provide evidence for the neuroactive features of these phenolic compounds in enhancing the beneficial properties of neurons and reducing the inhibitory properties of activated astrocytes in an in vitro setting and encourage the further investigation of these effects in vivo, in animal models of acute and chronic neurological diseases.

Topics: Animals; Astrocytes; Butylene Glycols; Disease Models, Animal; Female; Larix; Lignans; Lignin; Male; Mice; Mice, Inbred C57BL; Models, Neurological; Molecular Structure; Naphthols; Neurites; Phenols; Quercetin; Schwann Cells; Stereoisomerism

A method for the characterization and quantitation of phyto-estrogenic lignans from pomegranate (Punica granatum L.) fruits and fruit-derived products by HPLC-DAD-MS(n) was developed. For this purpose, edible and nonedible parts of pomegranate (aril, peel, mesocarp, seed, and twigs), commercial juices, juices produced on pilot-plant scale, and encapsulated dietary supplements were analyzed. In addition to the peel, mesocarp, and twigs, lignans were detected in two juices obtained from entire fruits, four commercial juices, and three encapsulated pomegranate extracts. Isolariciresinol was the predominant lignan with contents of 5.0, 10.5, and 45.8 mg/kg dry matter in processed pomegranate mesocarp, peel, and twigs, respectively. In contrast, due to their low amounts, quantitation of lignans in pomegranate products was impossible. Therefore, contrary to previous assumptions, lignans were found to be less relevant in pomegranate-derived products. However, the byproduct from pomegranate processing may be used for lignan extraction. The method presented allows one to differentiate between pomegranate-derived products obtained from fruits without peels or by dejuicing applying low pressures, which were devoid of lignans, and those obtained from entire fruits applying high pressures, thus containing lignans. Consequently, this study helps to optimize process technology aiming at the recovery of preparations with well-desired compositions, which may reduce the risk of a wide range of diseases, such as certain types of cancer.

Topics: Beverages; Chromatography, High Pressure Liquid; Dietary Supplements; Fruit; Lignans; Lignin; Lythraceae; Naphthols; Plant Components, Aerial; Spectrometry, Mass, Electrospray Ionization

To study chemical constituents contained in ethanol extracts from roots of Machilus yaoshansis. Fifteen compounds were separated from the roots of M. yaoshansis by using various chromatographic techniques. Their structures were identified on the basis of their physicochemical properties and spectral data as twelve lignans(+)-guaiacin (1), kadsuralignan C (2), (+)-isolariciresinol (3), 5'-methoxy-(+)-isolariciresinol (4), (7'S, 8R, 8'R)-lyoniresinol (5), meso-secoisolariciresinol (6), isolariciresinol-9'-O-beta-D-xylopyranoside (7), 5'-methoxy-isolariciresinol-9'-O-beta-D-xylopyranoside (8), lyoniresinol-9'-O-beta-D-xylopyranoside (9), (2R, 3R) -2, 3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran (10), 3, 5'-dimethoxy-4', 7-epoxy-8, 3'-neolignan-4, 9, 9'-triol (11), nectandrin B (12), and three flavanes(+)-catechin (13), (-)-epicatechin (14), and bis-8, 8'-catechinylmethane (15). All of the compounds 1-15 were separated from M. yaoshansis for the first time.

Topics: Butylene Glycols; Catechin; Lauraceae; Lignans; Lignin; Naphthols; Plant Roots

To separate and identify chemical constituents from Coptis chinensis.. The compounds were separated and purified by various chromatographic techniques. Their structures were identified on the basis of their physicochemical properties using spectral techniques such as NMR and MS.. Thirteen compounds were separated from ethanol extracts of C. chinensis, including seven lignans, three simple phenylpropanoids, two flavones and one phenolic acid, and identified as erythro-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (1), threo-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (2), (+)-pinoresinol (3), (+)-medioresinol (4), (+)-lariciresinol (5), (+)-5'-methoxylariciresinol (6), (+)-isolariciresinol (7), chlorogenic acid (8), ferulic acid (9), Z-octadecyl caffeate (10), rhamnetin (11), wogonin (12), and vanillic acid (13).. Compounds 1, 2, 4, 6, 10-13 were separated from the genus Coptis for the first time.

Topics: Caffeic Acids; Chlorogenic Acid; Coptis; Coumaric Acids; Ethanol; Flavanones; Flavones; Furans; Hydroxybenzoates; Lignans; Lignin; Naphthols; Quercetin; Vanillic Acid

To study the chemical constitutents of the 60% ethanol extract of the stems of Sambucus williamsii.. Compounds were isolated and purified by Diaion D101, silica gel,Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were identified by spectroscopic methods.. Seven lignans were isolated and identified as erythro-guaiacylglycerol-beta-O-4'-sinapyl ether (1), 1-( 4'-hydroxy-3'-methoxyphenyl) -2- [4"-( 3-hydroxypropyl) -2", 6"-dimethoxyphenoxy] propane-1,3-diol (2), isolariciresinol (3), burselignan (4), lyoniresinol (5), 5-methoxy-isolariciresinol (6), cycloolivil (7).. All these compounds were obtained from this genus for the first time.

Topics: Anisoles; Antineoplastic Agents, Phytogenic; Chromatography, High Pressure Liquid; Lignans; Lignin; Microscopy; Naphthalenes; Naphthols; Plant Stems; Sambucus

To study the chemical constituents in the root of Isatis indigotica.. The constituents root were separated through various chromatographic techniques and their structures were elucidated by means of physicochemical properties and the analysis of their spectral data.. Eleven compounds were isolated and identified as (+) -isolariciresinol (1), lariciresinol (2), lariciresinol-9-O-beta-D-glucopyranoside (3), lariciresinol-4'-O-beta-D-glucopyranoside (4), lariciresinol-4,4'-bis-O-beta-D-glucopyranoside (5), 3-formylindole (6), 1-methoxy-3-indolecarbaldehyde (7), 1-methoxy-3-indoleacetonitrile (8), deoxyvasicinone (9), epigoitrin (10), adenosine (11).. Compounds 4-8 were isolated from I. indigotica for the first time.

Topics: Furans; Glucosides; Indoles; Isatis; Lignans; Lignin; Naphthols; Plant Extracts; Plant Roots; Plants, Medicinal; Spectrometry, Mass, Electrospray Ionization

The paper describes a method for the determination of selected lignans in plant foods. First, samples were submitted to methanolysis resulting in cleavage of ester bonds between lignan glycosides and organic acids. Glycosidic linkages were then broken by enzymatic hydrolysis using cellulase. The released aglycones were separated isocratically (acetonitrile/10 mM sodium acetate buffer, pH 4.8, 225:775, v:v) by reversed phase high performance liquid chromatography (RP-HPLC) and the compounds were detected coulometrically at four electrodes set on potentials between +260 and +330 mV against palladium reference electrodes. The selectivity and sensitivity of the method allowed quantitation of the lignans secoisolariciresinol, lariciresinol and isolariciresinol in various foodstuffs down to the upper ppb-range with recoveries between 44.7 and 97.0%. Unidentified peaks displaying similar current-voltage curves (CVCs) as the investigated lignans indicated the presence of further possible lignan representatives. In addition, investigation of various foodstuffs involving enzymatic hydrolysis with and without preceding methanolysis showed that the degree of esterification of lignans in plant foods is species dependent.

Topics: Butylene Glycols; Calibration; Chromatography, High Pressure Liquid; Electrochemistry; Electrodes; Furans; Hydrolysis; Lignans; Lignin; Molecular Structure; Naphthols; Plants, Edible; Reproducibility of Results

To study the chemical constituents of the leaves of Isatis indigotica.. The leaves of I. indigotica were extracted with 80% ethanol. The EtOH extract was dispersed in H20 and extracted with petroleum, EtOAc and BuOH successively. The EtOAc fraction was isolated and purified by column chromatography on silica gel, Sephadex LH -20 and Rp-8, Rp-18. All the compounds were identified on the basis of spectral analyses (including MS, 1H-NMR, 13 C-NMR) , RESULT: Eleven compounds were isolated from the leaves of I. indigotica, and structures were characterized as 10H-indolo [3, 2-b] quinoline (1), indirubin (2), 4 (3H)-quinazo-linone (3), (E)-3-(3', 5'-dimethoxy-4'-hydroxybenzylidene) -2-indolinone (4), 2, 3-dihydropyrrolo [2, 1-b] quinazolin-9(1H) -one (5) , benzoic acid (6) , o-droxy-benzoic acid (7), ( - ) -lariciresinol (8) , ( + ) -isolariciresinol (9), isovitexin (10), 6-f-D-glucopyranosyldiosmetin (11).. 1, 4, 5, 8, 9, 11 were obtained from the leaves of I. indigotica for the first time.

Topics: Furans; Indole Alkaloids; Isatis; Lignans; Lignin; Naphthols; Plant Leaves; Plants, Medicinal; Quinolines

Total extract of resin from Araucaria angustifolia was analyzed by gas chromatography/mass spectrometry and 32 lignans were identified. Lignan acetates are present in the resin and consist of four secoisolariciresinol acetates, six lariciresinol acetates, two 7'-hydroxylariciresinol acetates and an isolariciresinol acetate, which have hitherto not been reported in the plant kingdom. Shonanin and 7'-hydroxylariciresinol type lignans are also present in A. angustifolia resin. Lignans containing syringyl moieties, characteristic for angiosperms, occur in the resin and consist of 5-methoxylariciresinol-9-acetate, 5'-methoxylariciresinol-9-acetate, 5-methoxypinoresinol dimethyl ether and 5-methoxypinoresinol. This is noteworthy because syringyl moieties have only been reported for Thuja species (Cupressaceae) among the gymnosperms. The mass spectra of the various lignan trimethylsilyl derivatives are discussed with the interpretations of the fragmentation patterns.

Topics: Butylene Glycols; Furans; Gas Chromatography-Mass Spectrometry; Lignans; Lignin; Naphthols; Phenols; Pinus; Resins, Plant; Trimethylsilyl Compounds

To study the chemical constituents of the pine needles from Pinus massoniana Lamb... Various chromatographic techniques were used for the separation and purification. The physicochemical properties and spectral data were used to elucidate the structures.. Three compounds were isolated from the n-BuOH fraction of water-extracts. The structures were identified as (7S,8R)-4,9'-dihydroxyl-3, 3'-dimethyoxyl-7, 8-dihydrobenzofunan-1'-propanolneolignan-9-O-alpha- L-rhamnopyranoside (massonianoside D, 7), 4,4',9,9'-tetrahydroxyl-3,3'-dimethyoxyl-tetrahydrocyclolignan ((+)-isolariciresinol, 8) and 4,4',9'-trihydroxyl-3,3'-dimethyoxyl-tetrahydrocyclolignan-9-O-beta-D- xylopyranoside (isolariciresinol-9-O-xyloside, 9) on the basis of spectral data (ORD, UV, IR, MS, 1HNMR, 13CNMR, 1H-1HCOSY, HMQC and HMBC etc.).. Compound 7 is a new compound, while compounds 8 and 9 were isolated from this plant for the first time.

Topics: Drugs, Chinese Herbal; Lignans; Lignin; Molecular Structure; Monosaccharides; Naphthols; Pinus; Plant Leaves; Plants, Medicinal

Bioassay-guided fractionation of the neutral extract of the bark of Sarcomelicope megistophylla resulted in the isolation of the new nor-neolignan sarcomeginal ( 1), together with the known ailanthoidol ( 2) and (+/-)-seco-isolariciresinol ( 3). The structure of 1 was determined by spectroscopic means. Estrogenic activity of the isolated compounds was tested using estrogen receptor-positive MCF7 and estrogen receptor-negative MDA-MB-231 human mammary adenocarcinoma cell lines. Compound 3 displayed significant estrogenic activity.

Topics: Adenocarcinoma; Antineoplastic Agents, Hormonal; Benzofurans; Breast Neoplasms; Dose-Response Relationship, Drug; Female; Humans; Inhibitory Concentration 50; Lignans; Lignin; Naphthols; Phytotherapy; Plant Bark; Plant Extracts; Receptors, Estrogen; Rutaceae; Tumor Cells, Cultured

To study the lignans from Patrinia scabra Bunge.. The constituents were separated and purified by column chromatography with silical gel, RP-silical gel and Sephadex LH-20. Their structures were identified on the basis of spectral data (IR, MS, 1HNMR, 13CNMR, HMQC and HMBC).. A new lignan was obtained and its structure was elucidated as 4-[1-ethoxyl-1-(4-hydroxy-3-methoxy)benzyl]methyl- 2-(4-hydroxy-3-methoxy)benzyl-3-hydroxymethyl-tetrahydro-furan (2), along with three known lignans, lariciresinol (1), isolariciresinol (3) and nortracheloside (4).

Topics: Furans; Guaiacol; Lignans; Lignin; Molecular Structure; Naphthols; Patrinia; Plant Roots; Plants, Medicinal

Coptis japonica Makino (Ranunculaceae) is known to possess several biological activities such as anti-inflammatory effects. In this study, five lignans, isolariciresinol (1), lariciresinol glycoside (2), pinoresinol (3), pinoresinol glycoside (4) and syringaresinol glycoside (5), isolated from the rhizomes of C. japonica were tested to evaluate their in vitro anti-inflammatory effects. Pinoresinol and isolariciresinol showed higher inhibitory effects on TNF-alpha production, whereas syringaresinol glycoside strongly suppressed lymphocyte proliferation. The results indicate that the lignans may differentially modulate inflammatory cell responses, suggesting that these compounds may participate in anti-inflammatory processes by C. japonica.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; CD4-Positive T-Lymphocytes; Cells, Cultured; Furans; Glucosides; Glycosides; Interferon-gamma; Interleukin-2; Lignans; Lignin; Lipopolysaccharides; Macrophages; Male; Medicine, Traditional; Mice; Mice, Inbred BALB C; Molecular Structure; Naphthols; Nitric Oxide; Plants, Medicinal; Spleen; Tumor Necrosis Factor-alpha

The isolation and characterization of the lignans, isolariciresinol, pinoresinol, secoisolariciresinol, and matairesinol, potent phytoestrogens, from flaxseed meal are described. This is the first report of isolariciresinol and pinoresinol being detected in a food. The extraction method selected combined the removal of the lignan glycosides from the plant matrix with an alcoholic solvent system, followed by acid hydrolysis to release the aglycons. A reversed-phase high-performance liquid chromatography with diode array detection system was used for initial separation and detection of the lignans at 280 nm in the acid-hydrolyzed methanolic extract. Lignan trimethylsilyl ether derivatives were characterized by gas chromatography/mass spectrometry. Secoisolariciresinol is the major lignan in flaxseed; isolariciresinol, pinoresinol, and matairesinol were identified as minor lignan components.

Topics: Chromatography, High Pressure Liquid; Flax; Flour; Furans; Gas Chromatography-Mass Spectrometry; Lignans; Lignin; Naphthols; Seeds

The mammalian lignans enterolactone and enterodiol are regular constituents of human urine and are excreted daily in mumol amounts. They are produced by metabolic action of intestinal bacteria from natural plant lignan precursors which are constituents of various food plants. However, natural plant lignans seem to occur very seldom in detectable amounts in human urine. The present investigation shows that only in 5% of the 150 diphenolic fractions extracted from the urine of women plant lignans other than the previously identified matairesinol could be found. The lignans lariciresinol, isolariciresinol and secoisolariciresinol were identified for the first time by comparison of their GC characteristics and mass spectra with the corresponding results of authentic synthesized reference compounds. Secoisolariciresinol is one natural precursor of the mammalian lignan enterodiol. Of the two other plant lignans, no animal or human metabolic products are known. The occurrence of chemically unchanged plant lignans in some cases in human urine could be a result of an insufficient metabolic capacity of intestinal bacteria, resulting in a decreased detoxification of phenolic plant products.

Topics: Adult; Butylene Glycols; Chemical Phenomena; Chemistry; Female; Furans; Gas Chromatography-Mass Spectrometry; Humans; Lignans; Lignin; Naphthols; Plant Extracts