stigmasterol and lyoniside

Charantin, a steroidal glycoside, exists as a mixture of stigmasterol glucoside (STG) and β-sitosterol glucoside (BSG) in the fruits of Momordica charantia. Charantin has anti-diabetic activity comparable to insulin. The present work discusses a method for separation of components of charantin namely STG and BSG by simple extraction technique followed by preparative HPLC. The identity of separated components was established by chromatographic as well as spectral techniques. Also reversed phase HPLC-DAD method was developed and validated for estimation of STG and BSG present in fruits of Momordica charantia. The method used C18 column (75 mm × 4.6 mm, 3.5 µm) as stationary phase and methanol: water (98:02, v/v) as mobile phase. Retention times of STG and BSG were found to be 10.707 min and 11.870 min, respectively. The validated method was applied to evaluate content of these components in different extracts and some commercial herbal formulations containing fruits of Momordica charantia.

Topics: Chromatography, High Pressure Liquid; Fruit; Glucosides; Momordica charantia; Sitosterols; Stigmasterol

Bitter gourd fruits contain high amounts of charantin, stigmasterol glucoside and β-sitosterol glucoside, which have been shown to provide health benefits for humans. However, the bitterness of the fruit means they are rarely consumed. This study aimed to assess the effects of Lactobacillus plantarum fermentation, which has previously been reported to effectively reduce bitterness, on the contents of these compounds. The current results suggest that Lactobacillus plantarum fermentation should be considered as a potential approach to enhance the levels of these compounds in bitter gourd juice.

Topics: Fermentation; Glucosides; Humans; Lactobacillus plantarum; Momordica charantia; Sitosterols; Stigmasterol

Hedyotis caudatifolia Merr. et Metcalf. (HC), a folk medicine in Yao nationalities areas in China, was used to investigate the chemical constituents. Through silica gel and Sephadex LH-20 column chromatography, nine compounds were isolated and purified. By physical and chemical properties, IR, MS (EI-MS, high resolution EI-MS), 1D NMR ((1)H NMR, (13)C NMR) and 2D NMR (HSQC, (1)H-(1)H COSY, HMBC), their structures were identified as β-sitosterol (1), stigmasterol (2), scopolin (3), 2-hydroxy-1,7,8-trimethoxyanthracene-9,10-dione (4), oleanolic acid (5), ursolic acid (6), methyl barbinervate (7), β-daucosterol (8) and p-Hydroxybenzoic acid (9). These compounds were isolated from HC for the first time, and 4 a new anthraquinone whose biological activities are worth to be investigated in future. These compounds may contribute to the HC's pharmacological effects on treating diseases, and may be used as candidates for control index in establishing the quality control standard of HC.

Topics: Anthraquinones; China; Hedyotis; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plants, Medicinal; Sitosterols; Stigmasterol; Triterpenes; Ursolic Acid

To study the chemical constituents from the leaves of Acanthus ilicifolius.. The compounds were isolated by silica and gel column chromatographic methods and identified by spectoscopic analysis. The anti-influenza virus activities of these compounds were obtained by measuring the neuraminidase activity of influenza virus.. Five compounds were isolated and their structures were identified as blepharin(1), acteoside(2), isoverbascoside(3), daucosterol(4), and 3-O-β-D-glucopyranosyl-stigmasterol(5).. All the compounds are isolated from the leaves of Acanthus ilicifolius for the first time, and compounds 1 ~ 3 exhibit the anti-influenza virus activities.

Topics: Acanthaceae; Antiviral Agents; Glucosides; Orthomyxoviridae; Phenols; Phytochemicals; Plant Leaves; Sitosterols; Stigmasterol

To study the chemical constituents of Suaeda glauca.. The chemical constituents were isolated and purified with several separation and purification techniques. Their structures were identified by physicochemical properties and various spectroscopic methods.. Ten compounds were isolated from the ethyl acetate fraction as lignoceric acid (1), β-amyrin-n-nonyl ether(2), β-sitosterol(3), β-daucosterol(4), quercetin(5), luteolin(6), luteolin-7-O-β-D-glucoside(7), isorhamnetin(8), scopoletin (9) and stigmasterol(10).. Compounds 1, 2, 6, 7, 8, 9 and 10 are isolated from Suaeda genus for the first time and compounds 3 - 5 are isolated from this plant for the first time.

Topics: Acetates; Chenopodiaceae; Glucosides; Luteolin; Oleanolic Acid; Phytochemicals; Plant Extracts; Quercetin; Sitosterols; Stigmasterol

To study the chemical constituents of the aerial part of Stauntonia obovatifoliola.. The chemical constituents of ethyl acetate fraction were isolated and purified by several chromatography. Their structures were elucidated by their physiochemical properties and spectral methods.. Six known compounds were isolated and identified as lupeone(1), lupeol(2), stigmasterol(3),3beta-O-acetyloleanolic acid(4), resinone(5) and daucosterol(6).. Compounds 1-6 are isolated from this plant for the first time.

Topics: Acetates; Gas Chromatography-Mass Spectrometry; Molecular Structure; Pentacyclic Triterpenes; Plant Components, Aerial; Rosaceae; Sitosterols; Stigmasterol; Triterpenes

To study the chemical constituents in ethyl acetate extraction of Semen Litchi.. The compounds were isolated and purified by column chromatography on silica gel and Sephadex LH-20 coupled with preparative silica gel TLC, their structures were identified by physicochemical properties and spectrum analysis.. Five compounds were isolated and identified as stigmasterol (1), P-hydroxy-benzaldehyde (2), protocatechuic acid (3), daucosterol (4) and kaempferol-3-O-beta-D-glucopyranoside (5).. Compounds 2 and 5 are obtained from this plant for the first time.

Topics: Benzaldehydes; Fruit; Hydroxybenzoates; Kaempferols; Litchi; Molecular Structure; Seeds; Sitosterols; Stigmasterol

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

The cluster of neurodegenerative disorders in the western Pacific termed amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC) has been repeatedly linked to the use of seeds of various species of cycad. Identification and chemical synthesis of the most toxic compounds in the washed cycad seeds, a variant phytosteryl glucosides, and even more toxic cholesterol β-D-glucoside (CG), which is produced by the human parasite Helicobacter pylori, provide a possibility to study in vitro the mechanisms of toxicity of these compounds. We studied in detail the effects of CG on the respiratory activities and generation of reactive oxygen species (ROS) by nonsynaptic brain and heart mitochondria oxidizing various substrates. The stimulatory effects of CG on respiration and ROS generation showed strong substrate dependence, suggesting involvement of succinate dehydrogenase (complex II). Maximal effects on ROS production were observed with 1 μmol CG/1 mg mitochondria. At this concentration the cycad toxins β-sitosterol-β-D-glucoside and stigmasterol-β-D-glucoside had effects on respiration and ROS production similar to CG. However, poor solubility precluded full concentration analysis of these toxins. Cholesterol, stigmasterol and β-sitosterol had no effect on mitochondrial functions studied at concentrations up to 100 μmol/mg protein. Our results suggest that CG may influence mitochondrial functions through changes in the packing of the bulk membrane lipids, as was shown earlier by Deliconstantinos et al. (Biochem Cell Biol 67:16-24, 1989). The neurotoxic effects of phytosteryl glucosides and CG may be associated with increased oxidative damage of neurons. Unlike heart mitochondria, in activated neurons mitochondria specifically increase ROS production associated with succinate oxidation (Panov et al., J Biol Chem 284:14448-14456, 2009).

Topics: Animals; Brain; Cell Respiration; Cholesterol; Dimethyl Sulfoxide; Glucosides; Hydrogen Peroxide; In Vitro Techniques; Mitochondria; Rats; Rats, Sprague-Dawley; Reactive Oxygen Species; Sitosterols; Stigmasterol

Phytochemical investigations of four Garcinia spp. from Indonesia, i.e. Garcinia griffithii T. Anderson, Garcinia celebica L., Garcinia cornea L. and Garcinia cymosa K. Schum (Clusiaceae), have resulted in the isolation of a xanthone, 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone, 1,7-dihydroxyxanthone, isoxanthochymol, beta-sitosterol-3-O-beta-D-glucoside and stigmasterol-3-O-beta-D-glucoside from the stem bark of G. griffithii; friedelin and 3beta-hydroxy-23-oxo-9,16-lanostadien-26-oic acid or garcihombronane D from leaves of G. celebica; 23-hydroxy-3-oxo-cycloart-24-en-26-oic acid and epicatechin from stem bark of G. cornea; (+/-)-morelloflavone, morelloflavone-7-O-beta-D-glucoside or fukugiside, the triterpene 3beta-hydroxy-5-glutinen-28-oic acid and canophyllol from stem bark of G. cymosa. The xanthone and garcihombronane D displayed a selective activity against Plasmodium falciparum; isoxanthochymol and the triterpene beta-hydroxy-5-glutinen-28-oic acid a broad but non-selective antiprotozoal activity.

Topics: Animals; Antimalarials; Antiprotozoal Agents; Benzophenones; Catechin; Flavones; Garcinia; Glucosides; Indonesia; Lanosterol; Molecular Structure; Plant Bark; Plant Leaves; Plants, Medicinal; Plasmodium falciparum; Sitosterols; Stigmasterol; Triterpenes; Xanthones

To study the chemical constituents from the petroleum ether fraction of Buxus microphylla.. The petroleum ether fraction of Buxus microphylla was isolated and identified by silica gel column chromatography. And the anticancer activity of different chemical constituents was measured by MTT reduction test.. Eight compounds were isolated and identified as lupeol (1), butulin (3), beta-sitosterol (4), stigmasterol (5), dibutyl phthalate (6), 3beta, 30-dihydroxy-lup-20 (29) ene (7), daucosterol (8). Compound 7 inhibited KB cells' proliferation in a dose-dependent manner.. Compounds 2 - 5, 7, 8 are isolated from this genus for the first time. Compound 7 has certainly anticancer effects.

Topics: Buxus; Chromatography, Thin Layer; Dibutyl Phthalate; Ethers; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Stigmasterol

An activity-guided fractionation method was used to isolate anticancer components from Nuruk (Rhizopus oryzae KSD-815:KSD-815). Dried powder of KSD-815 was extracted with 80% methanol and partitioned successively using nhexane, ethyl acetate, n-butanol, and water. The n-hexane and n-butanol fractions showed a strong antimigratory effect on human cancer cells. Both of these fractions were subjected to separation and purification procedures using silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies to afford four purified compounds. These were identified as ergosterol peroxide (1), stigmast- 5-en-3beta,7beta-diol (2), ergosta-7,22-dien-3beta,5alpha,6beta,9alpha-tetraol (3), and daucosterol (4), respectively, by spectroscopic methods such as nuclear magnetic resonance spectrometry, mass spectrometry, and infrared spectroscopy, and comparison with those in the literature. Compounds 1-4 were isolated from KSD-815 for the first time. Compounds 1 and 4 inhibited the migration of MDA-MB-231 cells at concentrations lower than 20 micronM.

Topics: Breast Neoplasms; Cell Line, Tumor; Cell Movement; Edible Grain; Ergosterol; Female; Food Microbiology; Humans; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Rhizopus; Sitosterols; Spectrophotometry, Infrared; Sterols; Stigmasterol

To study chemical constituents of Changium smyrnioides Wolff.. The chemical components were isolated and purified by silica gel column and recrystallization. The chemical structures were elucidated on the basis of physico-chemical properties and spectral data.. Ten compounds were isolated and identified as lignoceric acid (1), beta-sitosterol (2), stigmasterol (3), 5-hydroxy-8-methoxypsoralen (4), glycerylmonopalmitate (5), L-pyroglutamic acid (6), succinic acid (7), vanillic acid-4-O-beta-D-glucopyranoside (8 ), vanillic acid (9), daucosterol (10).. Compounds 1, 4, 5, 6, 8 and 9 are obtained from the plant for the first time.

Topics: Apiaceae; Fatty Acids; Hydrolyzable Tannins; Plant Roots; Plants, Medicinal; Pyrrolidonecarboxylic Acid; Sitosterols; Stigmasterol; Succinic Acid; Vanillic Acid

To study the chemical constituents of Rhizoma Cyperi.. The constituents were separated and purified by silica gel column chromatography, their structures were identified on the basis of physico-chemical properties and spectral data.. Six compounds were isolated and identified as physicion (1), hexadecanoic acid (2), beta-sitosterol (3), stigmasterol (4), catenarin (5), daucosterol (6).. Compounds 1, 4, 5 were isolated from this plant for the first fime.

Topics: Cyperus; Emodin; Magnetic Resonance Spectroscopy; Palmitic Acid; Plants, Medicinal; Rhizome; Sitosterols; Spectrophotometry, Ultraviolet; Stigmasterol

To study the chemical constituents of Dendobium crystallinum.. Compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography. Their structures were identified by physicochemical properties and spectral analyses.. Nine compounds were obtained and identified as: 4, 4'-dihydroxy-3, 5-dimethoxybi-benzyl (1), gigantol (2), naringenin (3) , p-hydroxybenzoic acid (4), n-tetracosyl trans-p-cou-marate (5), n-octacosy trans-p-coumarate (6), n-hexacosyl trans-ferulate (7), stigmasterol (8), daucosterol (9).. All these compounds were obtained from this plant for the first time, compounds 1 and 4 were isolated firstly from the genus.

Topics: Bibenzyls; Chromatography; Dendrobium; Drugs, Chinese Herbal; Flavanones; Guaiacol; Magnetic Resonance Spectroscopy; Parabens; Sitosterols; Stigmasterol

Two new and seven known withanolides along with beta-sitosterol, stigmasterol, beta-sitosterol glucoside, stigmasterol glucoside, alpha+beta glucose were isolated from the roots of Withania somnifera. Among the known compounds, Viscosa lactone B, stigmasterol, stigmasterol glucoside and alpha+beta glucose are being reported from the roots of W. somnifera for the first time. One of the new compounds contained the rare 16beta-acetoxy-17(20)-ene the other contained unusual 6alpha-hydroxy-5,7alpha-epoxy functional groups in the withasteroid skeleton. The structures were elucidated by spectroscopic methods and chemical transformations.

Topics: Glucosides; Molecular Structure; Plant Extracts; Plant Roots; Sitosterols; Stigmasterol; Withania; Withanolides

The ethanol extract from Akebia quinata was seperated by dichloromethane, n-butanol in sequence. Six compounds were isolated and identified as beta-sitosterol (I), delta(5,22) stigmasterol (II), oleanolic acid (III), hederagenin (IV), daucosterol (V), delta(5,22) stigmasterol-3-O-beta-D-glycopyranoside (VI). Compound VI was isolated from Akebia plants for the first time.

Topics: Glucosides; Magnoliopsida; Molecular Structure; Oleanolic Acid; Plant Stems; Plants, Medicinal; Sitosterols; Sterols; Stigmasterol; Triterpenes

To study the chemical constituents from Lamium maculatum L. var Kansuense.. The chemical constituents were isolated and repeatedly purified by silica gel column chromatography and the structures were elucidated by the NMR spectra and physico-chemical properties.. Ten compounds were obtained and they were identified as D-mannitol, beta-sitosterol, stigmasterol, rutin, 3'-methylquercetin-3-O-rutinoside, n-butyl-beta-D-fructopyranoside, daucosterol, acteoside, 20-hydroxyecdysone, allantoin.. All the compounds were obtained from L. maculatum L. var Kansuense for the first time.

Topics: Allantoin; Ecdysterone; Glucosides; Lamiaceae; Mannitol; Phenols; Plants, Medicinal; Rutin; Sitosterols; Stigmasterol

Bio-active constituents were expected to abstain from Homalomena occuta.. Extracts from the plant with 95% alcohol were distributed by several solvents and isolated via column chromatography on silica and Saphadex 20-LH gel.. Thirteen compounds were isolated from this plant. Among them seven natural products were identified via spectral methods as beta-stigmastol(H1) beta-D-Glucopyranoside(3)- stigmast-5-en-3-yl(H2); oplodiol(1); oplopanone(2); homalomenol(3); bullatantriol(4); 1 beta, 4 beta, 7 alpha-trihydroxyeudesmane(5).. All these compounds were isolated from this plant for the first time.

Topics: Araceae; Naphthols; Plants, Medicinal; Rhizome; Sitosterols; Stigmasterol

The factors responsible for ALS-parkinsonism dementia complex (ALS-PDC), the unique neurological disorder of Guam, remain unresolved, but identification of causal factors could lead to clues for related neurodegenerative disorders elsewhere. Earlier studies focused on the consumption and toxicity of the seed of Cycas circinalis, a traditional staple of the indigenous diet, but found no convincing evidence for toxin-linked neurodegeneration. We have reassessed the issue in a series of in vitro bioassays designed to isolate non-water soluble compounds from washed cycad flour and have identified three sterol beta-d-glucosides as potential neurotoxins. These compounds give depolarizing field potentials in cortical slices, induce alterations in the activity of specific protein kinases, and cause release of glutamate. They are also highly toxic, leading to release of lactate dehydrogenase (LDH). Theaglycone form, however, is non-toxic. NMDA receptor antagonists block the actions of the sterol glucosides, but do not compete for binding to the NMDA receptor. The most probable mechanism leading to cell death may involve glutamate neuro/excitotoxicity. Mice fed cycad seed flour containing the isolated sterol glucosides show behavioral and neuropathological outcomes, including increased TdT-mediated biotin-dUTP nick-end labelling (TUNEL) positivity in various CNS regions. Astrocytes in culture showed increased caspase-3 labeling after exposure to sterol glucosides. The present results support the hypothesis that cycad consumption may be an important factor in the etiology of ALS-PDC and further suggest that some sterol glucosides may be involved in other neurodegenerative disorders.

Topics: Amyotrophic Lateral Sclerosis; Animals; Astrocytes; Biological Assay; Cells, Cultured; Cerebral Cortex; Cholesterol; Cycas; Dementia; Glucose; Glucosides; Guam; Humans; In Vitro Techniques; Male; Mice; Neurons; Neurotoxins; Parkinsonian Disorders; Patch-Clamp Techniques; Phytosterols; Plant Extracts; Rats; Rats, Sprague-Dawley; Receptors, N-Methyl-D-Aspartate; Seeds; Sitosterols; Stigmasterol

To study the chemical constituents of Gymnotheca involucrata.. Separating the constituents by means of chromatography and identifying their structures on the basis of NMR spectra and TLC with authentic samples.. From the methanolic extract of the whole plant of G. involucrata, three compounds were isolated and identified as kaempferol-4',7-dimethyl-3-O-glucoside, daucosterol and stigmasterol.. All the three compounds were isolated from this genus for the first time.

Topics: Flavonoids; Glucosides; Kaempferols; Magnoliopsida; Plants, Medicinal; Sitosterols; Stigmasterol

To separate compounds from the root of Gypsophila oldhamiana.. Chemical and chromatographic methods were used to separate the compounds. IR, MS, NMR were used to determine the structures of compounds.. Compound pentacosanoic acid, lacceroic acid, beta-sitosterol, alpha-spinasterol, daucosterol and sucrose were identified.. All the above compounds were obtained from this genus for the first time.

Topics: Caryophyllaceae; Plant Roots; Plants, Medicinal; Sitosterols; Stigmasterol

Two steroids and two lipids were isolated from the ethanolic extract of Spirodela polyrrhiza. Their structures were identified by spectral analysis and chemical evidence, which were identified as stigmasterol, monopalmitic glycerate, daucosterol and palmitic acid. Monopalmitic glycerate was discovered from this plant for the first time.

Topics: Chromatography, Thin Layer; Drugs, Chinese Herbal; Glycerides; Magnoliopsida; Palmitic Acid; Plants, Medicinal; Sitosterols; Stigmasterol

Ecliptasaponin C (1), a new triterpenoid glucoside, was isolated together with daucosterol (2) and stigmasterol-3-O-glucoside (3) from Eclipta alba. Based on spectral analysis, chemical evidence and hydrolytic results, it's structure was deduced as 3-beta-O-beta-D-glucopyranosyl-19beta-hydroxy olean-12-ene-28-oic acid 28-O-beta-D-glucopyranoside, Compounds 2 and 3 were obtained from Eclipta for the fist time.

Topics: Asteraceae; Drugs, Chinese Herbal; Glucosides; Sitosterols; Stigmasterol

Ethyl octacosate, docosyl hexylate, a new compound stigmast-4-ene-1,3-dione, beta-sitosterol and daucosterol were isolated and identified from the roots and rhizomes of Amomum villosum cultivated in Xishuangbanna, Yunnan. Two compounds daucosterol and emodin monoglycoside were isolated and identified from the stems of A. villosum.

Topics: Drugs, Chinese Herbal; Emodin; Glycosides; Molecular Structure; Plant Roots; Plant Stems; Plants, Medicinal; Sitosterols; Stigmasterol

A new bergenin derivative isolated from the root of Ardisia crenata was determined to be 11-o-syringylbergenin by spectral methods. Other compounds were identified as spinasterol, series fatty acids, beta-sitosterol-beta-D-glucoside, norbergenin and sucrose respectively. The last three were obtained for the first time from the genus of Ardisia.

Topics: Benzopyrans; Chemical Phenomena; Chemistry; Drugs, Chinese Herbal; Sitosterols; Stigmasterol; Sucrose