lignans and lyoniside

Saraca asoca Linn. (Caesalpiniaceae) is an important traditional remedy for gynaecological disorders and it contains lyoniside, an aryl tetralin lignan glycoside. The aglycone of lyoniside, lyoniresinol possesses structural similarity to enterolignan precursors which are established phytoestrogens.. This work illustrates biotransformation of lyoniside to lyoniresinol using Woodfordia fruticosa Kurz. (Lythraceae) flowers and simultaneous quantification of lyoniside and lyoniresinol using a validated HPTLC method.. The aqueous extract prepared from S. asoca bark was fermented using W. fruticosa flowers. The substrate and fermented product both were simultaneously analyzed using solvent system:toluene:ethyl acetate:formic acid (4:3:0.4) at 254 nm. The method was validated for specificity, accuracy, precision, linearity, sensitivity and robustness as per ICH guidelines.. The substrate showed the presence of lyoniside, however, it decreased as the fermentation proceeded. On 3rd day, lyoniresinol starts appearing in the medium. In 8 days duration most of the lyoniside converted to lyoniresinol. The developed method was specific for lyoniside and lyoniresinol. Lyoniside and lyoniresinol showed linearity in the range of 250-3000 and 500-2500 ng. The method was accurate as resulted in 99.84% and 99.83% recovery, respectively, for lyoniside and lyoniresinol.. Aryl tetralin lignan glycoside, lyoniside was successfully transformed into lyoniresinol using W. fruticosa flowers and their contents were simultaneously analyzed using developed validated HPTLC method.

Topics: Anisoles; Biotransformation; Calibration; Chromatography, High Pressure Liquid; Densitometry; Fermentation; Flowers; Glycosides; Lignans; Linear Models; Naphthalenes; Phytotherapy; Plant Bark; Plants, Medicinal; Reference Standards; Reproducibility of Results; Sitosterols; Woodfordia

Lyoniside is the major constituent of Saraca asoca Linn. (Caesalpiniaceae) bark. There is an immediate need to develop an efficient method to isolate its chemical constituents, since it is a therapeutically important plant.. A rapid extraction method for lyoniside based on microwave-assisted extraction of S. asoca bark was developed and optimized using response surface methodology (RSM).. Lyoniside was analyzed and quantified by high-performance liquid chromatography coupled with ultraviolet detection (HPLC-UV). The extraction solvent ratio (%), material solvent ratio (g/ml) and extraction time (min) were optimized using Box-Behnken design (BBD) to obtain the highest extraction efficiency. The optimal conditions were the use of 1:30 material solvent ratio with 70:30 mixture of methanol:water for 10 min duration.. The optimized microwave-assisted extraction yielded 9.4 mg/g of lyoniside content in comparison to reflux extraction under identical conditions which yielded 4.2 mg/g of lyoniside content. Under optimum conditions, the experimental values agreed closely with the predicted values. The analysis of variance (ANOVA) indicated a high goodness-of-fit model and the success of the RSM method for optimizing lyoniside extraction from the bark of S. asoca.. All the three variables significantly affected the lyoniside content. Increased polarity of solvent medium enhances the lyoniside yield.. The present study shows the applicability of microwave-assisted extraction in extraction of lyoniside from S. asoca bark.

Topics: Analysis of Variance; Chemical Fractionation; Chromatography, High Pressure Liquid; Fabaceae; Lignans; Microwaves; Models, Statistical; Nonlinear Dynamics; Phytotherapy; Plant Bark; Plant Extracts; Plants, Medicinal; Sitosterols; Solvents; Spectrophotometry, Ultraviolet

To separate and identify the chemical constituents from the stem of Schisandra chinensis.. Various chromatographic techniques were used to separate and purify the chemical constituents from 95% ethanol extraction of the stem of Schisandra chinensis. Their structures were elucidated based on the physico-chemical properties and spectral data.. Ten compounds were obtained and elucidated as (+)-deoxyschizandrin (1), γ-schizandrin (2), wuweizisu C (3), gomisin N (4), schizandrin (5), anwuweizic acid (6), (-)-dihydroguaiaretic acid (7), tetradecanoic acid (8), β-sitosterol (9) and daucosterol (10).. Compounds 6-8 are obtained from the stem of Schisandra chinensis for the first time.

Topics: Cyclooctanes; Guaiacol; Lignans; Phytochemicals; Plant Stems; Polycyclic Compounds; Schisandra; Sitosterols

To study the chemical constituents from the supercritical CO2 extraction of Schisandra chinensis.. The compounds were separated and purified by conventional column chromatography and their structures were identified by spectroscopic methods.. Nine compounds were isolated from the supercritical CO2 extraction of Schisandra chinensis, and their structures were identified as chrysophanol(1),schisandrin B(2), β-sitosterol(3), schisandrin C(4),schisandrol A(5), angeloylgomisin H(6), daucosterol(7) 1, 5-dimethyl citrate (8), and shikimic acid (9).. Compounds 1, 8 and 9 are isolated from Schisandra chinensis for the first time,and compound 1 as an anthraquinone is isolated from this genus for the first time.

Topics: Cyclooctanes; Lignans; Phytochemicals; Polycyclic Compounds; Schisandra; Sitosterols

Lignans are diphenyl propanoids with vast range of biological activities. The present study provides an important insight into the anti-leishmanial activities of two lignan glycosides, viz. lyoniside and saracoside. These compounds inhibit catalytic activities of topoisomerase IB (LdTopIB) of Leishmania donovani in non-competitive manner and stabilize the LdTopIB mediated cleavage complex formation both in vitro and in Leishmania promastigotes and subsequently inhibit the religation of cleaved strand. These two compounds not only poison LdTopIB but also can interact with the free enzyme LdTopIB. We have also shown that lyoniside and saracoside are cytotoxic to promastigotes and intracellular amastigotes. The protein-DNA complex formation leads to double strand breaks in DNA which ultimately triggers apoptosis-like cell death in the parasite. Along with their cytotoxicity towards sodium antimony gluconate (SAG) sensitive AG83 strain, their ability to kill SAG resistant GE1 strain makes these two compounds potential anti-leishmanial candidates. Not only they effectively kill L. donovani amastigotes inside macrophages in vitro, lyoniside and saracoside demonstrated strong anti-leishmanial efficacies in BALB/c mice model of leishmaniasis. Treatment with these lignan glycosides produce nitric oxide and reactive oxygen species which result in almost complete clearance of the liver and splenic parasite burden. These compounds do not inhibit human topoisomerase IB upto 200μM concentrations and had poor cytotoxic effect on uninfected cultured murine peritoneal macrophages upto 100μM concentrations. Taken together it can be concluded that these compounds can be developed into excellent therapeutic agent against deadly disease leishmaniasis.

Topics: Animals; Apoptosis; Base Sequence; DNA Primers; DNA Topoisomerases, Type I; Glycosides; Leishmania donovani; Lignans; Macrophages, Peritoneal; Mice; Mice, Inbred BALB C; Sitosterols; Topoisomerase I Inhibitors

To study the chemical constituents of the dichloromethane extracted from pine needles of Cedrus deodara.. Compounds were isolated and purified from the dichloromethane extract of pine needles by chromatography on silica gel and Sephadex LH-20. Their structures were identified on the basis of spectroscopic analysis and physicochemical property.. Nine compounds were isolated and purified. Their structures were identified as stigmasterol (1), oleanolic acid (2), parahydroxybenzaldehyde (3), beta-sitosterol (4), syringaresinol (5), daucosterol (6), p-hydroxybenzoic acid (7), gallicin (8) and gallic acid (9).. Compounds 1-3, 5 -9 are isolated from pine needles of this genus for the first time.

Topics: Cedrus; Furans; Lignans; Magnetic Resonance Spectroscopy; Methylene Chloride; Oleanolic Acid; Plant Extracts; Plant Leaves; Sitosterols; Solvents; Stigmasterol

To investigate the chemical constituents of Kalopanax septemlobus.. Chromatographic techniques including silica gel, gel, semi-preparative HPLC and PTLC as well as recrystallization were employed in the isolation and purification, and the structures were elucidated by spectral analysis and physical and chemical properties.. 6 compounds were identified as liriodendrin (1), (-) -syringarenol (2), trans-coniferyl aldehyde (3), trans-caffeic acid (4), beta-daucosterol (5), beta-sitosterol (6).. Compounds 2 -5 are obtained from this genus for the first time.

Topics: Acrolein; Aldehydes; Caffeic Acids; Furans; Kalopanax; Lignans; Molecular Structure; Plant Bark; Plant Roots; Plants, Medicinal; Sitosterols

From the methanolic extract of the roots of Clerodendrum philipinum, a new rearranged abietane diterpene (1) and eight known compounds were isolated by various chromatography methods. Their structures were identified by means of spectroscopic methods, including 1D- and 2D-NMR, as 17(15-->16),18(4-->3)-bisabeo-11,12,14,16-tetrahydroxy-3,5,8,11,13,15-abietahexaen-7-one (1), binankadsurin A, clerodenoside A, martynoside, acteoside, isoacteoside, astragalin, p3-sitosterol, and daucosterol. Binankadsurin A was found for the first time from a Clerodendrum species.

Topics: Abietanes; Chromatography; Clerodendrum; Glucosides; Kaempferols; Lignans; Magnetic Resonance Spectroscopy; Methanol; Molecular Structure; Phenols; Sitosterols

To study the chemical constituents of the fruit handles from Schizandra chinensis.. Compounds from the 85% ethanol extracts were isolated by silica gel, Sephadex LH-20, recrystal, etc., and their structures were identified by the spectral analysis and chemical evidence.. Eight compounds were isolated and identified as wuweizisu C (I), ganwuweizic acid(II), beta-sitosterol(III), gomisin A(IV), schizandrin(V), daucosterol(VI), wuweizisu A(VII), gamma-schizandrin (VIII).. Compounds I - VIII are isolated from the fruit handles of Schizandra chinensis for the first time.

Topics: Chromatography, Thin Layer; Cyclooctanes; Dioxoles; Fruit; Lignans; Magnetic Resonance Spectroscopy; Plants, Medicinal; Polycyclic Compounds; Schisandra; Sitosterols

To study the chemical constituents from Clematis brevicaudata.. The compounds were isolated by column chromatography and their structures were elucidated through spectroscopic analysis (NMR).. Eight compounds were isolated and identified as: palmitic acid (1), 1-docosanol (2), pentacosanoic acid-2', 3'-dihydroxypropyl ester (3), beta-sitosterol (4), daucosterol (5), a mixture of the trans-p-coumarate of the n-alkanols (6), 3,4-dihydroxy-trans coumatate ethyl ester (7), syringaresinol-O-D-glucopyranoside (8).. All these compounds are obtained from Clematis brevicaudata for the first time.

Topics: Clematis; Drugs, Chinese Herbal; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Palmitic Acid; Plants, Medicinal; Sitosterols

To study the chemical constituents in the aerial part of Reineckea carnea.. The compounds were isolated by extraction, silica gel, gel, and reversed-phase silica gel coloum chromatography, and high-performance liquid chromatography. The structures were identified by various spectroscopic methods including 1D and 2D NMR spectrum, MS, IR, etc.. Six compounds were isolated and identified as 1alpha, 3beta-dihydroxy-5beta-pregn-16-en-20-one-3-O-beta-D-glucopyranoside (1), syringaresinol-beta-D-glucoside (2), sophoraflavone B (3), stigmast-5, 22-dien-3-O-beta-D-glucopyranoside (4), daucosterol (5), a-D-glucose (6).. Compound 1 was a new compound, coumpounds 2-6 were obtained from the plant for the first time.

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavanones; Glucose; Glucosides; Hydroxyprogesterones; Lignans; Magnetic Resonance Spectroscopy; Magnoliopsida; Molecular Structure; Plant Components, Aerial; Sitosterols; Spectrometry, Mass, Electrospray Ionization

To investigate the chemical constituents from the root of Lasianthus acuminatissimus of Rubiaceae.. Normal, reverse phase silica gel, macroporous resin column and HPLC chromatography were used for isolation. Spectroscopic methods (13C-NMR, 1H-NMR, DEPT, EI-MS) were used for identification.. Six compounds were isolated and elucidated as isoscopletin(I), isoscopletin-6-O-beta-D-glucopyranoside (II), beta configuration of Mudanoside-A (Ill), asperuloside (IV), (-)-pinoresinol 4-O-beta-D-glucopyranoside (V), daucosterol (VI).. These compounds were obtained from this plant for the first time.

Topics: Cyclopentane Monoterpenes; Glucosides; Glycosides; Lignans; Plant Roots; Plants, Medicinal; Pyrans; Rubiaceae; Sitosterols

To study the chemical constituents from Serissa serissoides DC. roots.. Seven compounds were obtained from the 80% ethanol extract of Serissa serissoides roots by repeated column chromatography over silica gel, Sephadex LH-20 and Polyamide. Their structures were identified by analysis of their spectral data and physics character.. Seven compounds obtained from the plant leaves were identified as: (+)-pinoresinol(1), (-)-syringaresinol( 2), (+)-meduiresinol(3), (-)-olivil(4), beta-sitosterol(5), oleanolic acid(6) and daucosterol(7).. They are all known compounds. Compound 2 and 4 was obtained from this genus plants for the first time, and compounds 1,3 and 7 as known compounds were obtained from the root of the plant firstly.

Topics: Furans; Lignans; Molecular Structure; Oleanolic Acid; Plant Leaves; Plant Roots; Plants, Medicinal; Rubiaceae; Sitosterols

The chemical constituents of the herb of Cuscuta chinensis Lam. were investigated. Five compounds were isolated from petroleum ether and chloroform fraction. Their structures were identified as beta-sitosterol, d-sesamin, 9(R)-hydroxy-d-sesamin, d-pinoresinol and daucosterol by chemical and spectroscopical methods. All these compounds were isolated from the stem for the first time.

Topics: Chemical Fractionation; Cuscuta; Dioxoles; Drugs, Chinese Herbal; Furans; Lignans; Sitosterols; Spectrum Analysis

Six compounds were isolated from the seeds of Arctium lappa L. One of them is a new lignan named neoarctin B(VI). The structure has been elucidated on the basis of spectral (UV, IR, 1H-NMR, 13C-NMR, DEPT, 2D-NMR and MS) analysis. The other five compounds were identified as daucosterol (I), arctigenin (II), arctiin (III), matairesinol (IV) and lappaol F (V).

Topics: Drugs, Chinese Herbal; Furans; Glucosides; Lignans; Molecular Structure; Sitosterols