Showing papers on "Stigmasterol published in 2003"
TL;DR: The present study shows that phytosterol chemically acts as an antioxidant, a modest radical scavenger, and physically as a stabilizer in the membranes.
Abstract: Phytosterol contained in vegetable oils is known to exert a hypocholesterolemic function. In the present study, the antioxidant effects of phytosterol and its components, beta-sitosterol, stigmasterol, and campesterol, against lipid peroxidation were examined by making a comparison with 2,2,5,7,8-pentamethyl-6-chromanol (PMC). It was found that these compounds exerted antioxidant effects on the oxidation of methyl linoleate in solution and its effect decreased in the order of: PMC >> phytosterol approximately campesterol approximately beta-sitosterol > stigmasterol. Phytosterol also suppressed the oxidation and consumption of alpha-tocopherol in beta-linoleoyl-gamma-palmitoyl phosphatidylcholine (PLPC) liposomal membranes, the effects being more significant than dimyristoyl PC of the same concentration. Stigmasterol accelerated the oxidation of both methyl linoleate in solution and PLPC liposomal membranes in aqueous dispersions, which was ascribed to the oxidation of allylic hydrogens at the 21- and 24-positions. Taken together, the present study shows that phytosterol chemically acts as an antioxidant, a modest radical scavenger, and physically as a stabilizer in the membranes.
224 citations
TL;DR: A green callus culture of Croton sublyratus Kurz established from the leaf explants appeared to actively synthesize two well-known phytosterols, beta-sitosterol and stigmasterol, which were found to have their 13C-labeling patterns consistent with the acquisition of isoprene units via both the mevalonate pathway and the deoxyxylulose pathway.
147 citations
TL;DR: The content of phytosterol oxidation products was determined in samples of crude vegetable oils: peanut, sunflower, maize, palm nut, and lampante olive oils that were intended for refining and not for direct consumption and found the 7 alpha- and 7 beta-hydroxy derivatives of beta-sitosterol, stigmasterol, and campesterol and the 7-keto-beta- sitosterol were the principal phytesterol oxides found.
Abstract: The content of phytosterol oxidation products was determined in samples of crude vegetable oils: peanut, sunflower, maize, palm nut, and lampante olive oils that were intended for refining and not for direct consumption. The 7 alpha- and 7 beta-hydroxy derivatives of beta-sitosterol, stigmasterol, and campesterol and the 7-keto-beta-sitosterol were the principal phytosterol oxides found in almost all of the oils analyzed. In some oils, the epoxy and dihydroxy derivatives of beta-sitosterol were also found at very low levels. The highest total concentrations of phytosterol oxides, ranging from 4.5 to 67.5 and from 4.1 to 60.1 ppm, were found in sunflower and maize oils, respectively. Lower concentrations were present in the peanut oils, 2.7-9.6 ppm, and in the palm nut oil, 5.5 ppm, whereas in the lampante olive oils, only three samples of the six analyzed contained a low concentration (1.5-2.5 ppm) of oxyphytosterols. No detectable levels of phytosterol oxides were found in the samples of palm and coconut oils. Bleaching experiments were carried out on a sample of sunflower oil at 80 degrees C for 1 h with 1 and 2% of both acidic and neutral earths. The bleaching caused a reduction of the hydroxyphytosterol with partial formation of steroidal hydrocarbons with three double bonds in the ring system at the 2-, 4-, and 6-positions (steratrienes). The same sunflower oil was deodorized at 180 degrees C under vacuum for 1 h, and no dehydration products were formed with a complete recovery of the hydroxyphytosterols. A bleaching test with acidic earths was carried out also with an extra virgin olive oil fortified with 7-keto-cholesterol, dihydroxycholesterol, and alpha-epoxy-cholesterol. There was no formation of steratrienes from these compounds, but dihydroxycholesterol underwent considerable decomposition and alpha-epoxycholesterol underwent ring opening with formation of the dihydroxy derivative, whereas 7-ketocholesterol was rather stable
87 citations
TL;DR: In this article, the authors characterize the phytosterols, phospholipids, unsaponifiable matter, and FA in oil from Virginia-grown canola among 11 canola genotypes grown at two locations during 1995-1996 significant variations existed for oil content and FA profiles.
Abstract: There is little information available about phytosterols in canola (Brassica napa L) oil and the effects of genotype and growing locations from Virginia and the mid-Atlantic region of the United States, a potential area for the establishment of domestic production to provide edible oil Our objectives were to characterize the phytosterols, phospholipids, unsaponifiable matter, and FA in oil from Virginia-grown canola Among 11 canola genotypes grown at two locations during 1995–1996 significant variations existed for oil content and FA profiles, but not for contents of phospholipids, unsaponifiable matter, total phytosterols, campesterol, stigmasterol, and β-sitosterol, Total phytosterol content in the oil of Virginia-grown canola varied from 07 to 09% with a mean of 08% This concentration compared favorably with oil from Canadian canola, which typically contains 05 to 11% total phytosterols The mean contents of brassicasterol, campesterol, stigmasterol, β-sitosterol, Δ5-avenasterol, and Δ7-stigmatenol as percentages of total phytosterols in Virginia-grown canola were: 97, 320, 06, 493, 499, and 35%, respectively Growing location did not affect phytosterols in Virginia-grown canola oil but had significant effects on contents of phospholipids, and saturated (myristic, stearic, and arachidic) and unsaturated (palmitoleic, linoleic, linolenic, eicosenoic, and erucic) FA
68 citations
TL;DR: Investigation of the aerial parts of the medicinal plant Hypericum laricifolium led to the isolation of two new natural products, hentriacontanyl caffeate and nonacosanyl caffeates, which have anti-inflammatory effects.
Abstract: Investigation of the aerial parts of the medicinal plant Hypericum laricifolium led to the isolation of two new natural products, hentriacontanyl caffeate (1a), nonacosanyl caffeate (1b). In addition, stigmasterol, beta-sitosterol, 3-epi-betulinic acid (2), caffeic acid (3), ferulic acid, docosanol, p-hydroxybenzoic acid, 3,4-dimethoxy benzoic acid, quercetin (4), quercetin-3-O-galactoside (5), quercetin-3-O-rutinoside (6), quercetin-3-O-rhamnoside (7), quercetin-3-O-glucuronide (8) and shikimic acid were also isolated. The structures were determined by 1D- and 2D-NMR, mass spectrometry, and chemical transformations. The anti-inflammatory effects of the isolated compounds were discussed briefly.
45 citations
TL;DR: The analysis of 4 commonly available amaranth varieties revealed the presence of all three major phytosterols with a total sterol content being several fold higher than those found in other studied plants.
Abstract: The analysis of 4 commonly available amaranth varieties (Amaranthus K343, RRC1011, K433, K432) revealed the presence of all three major phytosterols (β-sitosterol, campesterol, stigmasterol) with a total sterol content being several fold higher than those found in other studied plants. Substantial differences in total phytosterol content and β-sitosterol content were found between the amaranth varieties. The most commonly cultivated amaranth variety in the United States, i.e., Amaranthus K343 was found to possess the highest levels of phytosterols of the varieties tested. The possibility of screening for superior amaranth varieties with various health properties is outlined.
38 citations
TL;DR: In this paper, the results of the analysis of a large number of oxidation products from sitosterol, campesterol, and stigmasterol by capillary column GC indicated that further efforts and optimization are required in this area.
Abstract: Although the structure of phytosterols is closely related to cholesterol, there is a gap in knowledge concerning the formation and occurrence of oxidation products from phytosterols. The main objective of this study was to isolate and characterize some side-chain oxidation products formed after autoxidation of stigmasterol. Another objective was to highlight the difficulties in the analysis of phytosterol and a mixture of their oxidation products by GC. Pure stigmasterol was oxidized at 120°C for 72 h in an air-ventilated oven. Preparative TLC separated the oxidation products, and the products were characterized with GC-MS and NMR. In addition to the common ring-structure oxidation compounds, three semipolar oxidation products—24-ethylcholest-5,22-dien-3β,25-diol, 24-ethylcholest-5,22-dien-3β,24-diol, and 24-ethyl-5,22-choladien-3β-ol-24-one—were characterized for the first time by TLC, GC-MS, and NMR. Moreover, the results of the analysis of a large number of oxidation products from sitosterol, campesterol, and stigmasterol by capillary column GC indicated that further efforts and optimization are required in this area.
35 citations
TL;DR: In this study, 3-hydroxysteroid oxidase from Streptomyces hygroscopicus was utilized to engineer oilseeds from rapeseed and soybean to modify the relative amounts of specific sterols to stanols, and several novel phytostanols were obtained.
34 citations
TL;DR: Coussaric acid, a triterpenoid based on an ursane skeleton, and an oleanane-type triterpene acid, 3-epi-spathodic acid, as well as four known compounds have been isolated from an EtOAc-soluble extract of the stems of Coussarea brevicaulis.
28 citations
Patent•
30 Jan 2003
TL;DR: A composition comprising at least one diacyl glycerol and at least three phytosterol and/or phytostanol esters dissolved or dispersed in an edible oil and or edible fat, and further optionally comprising monoglycerides is defined in this article.
Abstract: A composition comprising at least one diacylglycerol and at least one phytosterol and/or phytostanol ester dissolved or dispersed in an edible oil and/or edible fat, and further optionally comprising monoglycerides.Phytosterol esters may be beta-sitosterol, campesterol, stigmasterol and brassicasterol esters. Phytostanol esters may be stigmasterol, campestanol and sitostanol. The phytosterol and/or phytostanol esters are preferably esters of C14-C22, preferably C16-C18 saturated or unsaturated fatty acids, particularly oleic, linoleic, linolenic, palmitic and stearic acids. The diacylglycerol(s) are preferably 1,3-di-fatty acyl glycerol(s).The invention also provides a process for preparing compositions enriched with triacylglycerol(s) and phytosterol and/or phytostanol esters of mainly unsaturated fatty acid(s) or of mainly saturated fatty acid(s).The invention also relates to dietary food supplements and alimentary products comprising the composition of the invention.
28 citations
TL;DR: Sterols, triterpenes, volatiles, polar and other constituents in aerial parts of Carthamus lanatus were analyzed by gas chromatography-mass spectrometry and over 90 compounds were identified most of them new for the species.
Abstract: Sterols, triterpenes, volatiles, polar and other constituents in aerial parts of Carthamus lanatus were analyzed by gas chromatography-mass spectrometry. Over 90 compounds were identified most of them new for the species. Sitosterol and stigmasterol were the most abundant of 10 sterols identified in the sterol fraction. Taraxasterol, alpha- and beta-amyrine prevailed in the triterpene fraction. Volatiles, sterols and a fraction of the dichloromethane extract showed strong cytotoxicity (Artemia salina assay).
TL;DR: Cell suspension cultures from hypocotyl-derived callus of Hyssopus officinalis were found to produce two sterols i.
Abstract: Cell suspension cultures from hypocotyl-derived callus of Hyssopus officinalis were found to produce two sterols i. e. beta-sitosterol (1) and stigmasterol (2), as well as several known pentacyclic triterpenes with an oleanene and ursene skeleton. The triterpenes were identified as oleanolic acid (3), ursolic acid (4), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (5), 2alpha,3beta-dihydroxyurs-12-en-28-oic acid (6), 2alpha,3beta,24-trihydroxyolean-12-en-28-oic acid (7), and 2alpha,3beta,24-trihydroxyurs-12-en-28-oic acid (8). Compounds 5-8 were isolated as their acetates (6, 8) or bromolactone acetates (5, 7).
TL;DR: The species Hyptis fasciculata Benthia is a shrub that is still unknown by the chemical point of view as mentioned in this paper, and it has been studied in our group using their aerial parts.
Abstract: The species Hyptis fasciculata Benth. is a shrub that is still unknown by the chemical point of view. This species has been studied in our group using their aerial parts. After many cromatographic processes over silica gel column, it was possible to isolate free triterpene (betulinic acid) and triterpenes in mixture (ursolic acid with betulinic acid and ursolic acid with oleanolic acid), one steroid mixture (sitosterol and stigmasterol) and a mixture of steroid with cafeic acid (stigmasterol and cafeic acid) and with lignan (sitosterol and sesamin). These compounds were identified by nuclear magnetic ressonance 1H and 13C.
TL;DR: In this paper, the methylene chloride extract of Alpinia nutans was investigated for its antioxidant constituents, and the antioxidant activity was measured on isolates 1-4 using ferric thiocyanate (FTC) and diphenylpicrylhydrazyl (DPPH) free radical scavenging techniques.
Abstract: The methylene chloride extract of Alpinia nutans was investigated for its antioxidant constituents. 5,6-Dehydrokawain (1), flavokawin-B (2), 1,7-diphenyl-5-hydroxy-6-hepten-3-one (3), (-)-pinocembrin (4) and a mixture of stigmasterol and β-sitosterol were isolated. The antioxidant activity was measured on isolates 1-4 using ferric thiocyanate (FTC) and diphenylpicrylhydrazyl (DPPH) free radical scavenging techniques.
Journal Article•
TL;DR: In this article, column chromatography of the ethyl acetate extract of the leaves of Vitex parviflora yielded, among others, samples 1 and 2. These were bioassayed with the micronucleus test and were found to be antimutagenic.
Abstract: Column chromatography of the ethyl acetate extract of the leaves of Vitex parviflora yielded, among others, samples 1 and 2. These were bioassayed with the micronucleus test and were found to be antimutagenic. Determination of the constituents of these samples by NMR analyses indicated the presence of phytol 1a in sample 1, with lupeol 1b and β-amyrin 1c as impurities (< 10%) and sitosterol (2a) and stigmasterol (2b) in sample 2.
01 Jan 2003
TL;DR: To study the chemical constitutes in the lipophilic part from the leafy body of Marchantia convoluta, the compounds were isolated by column chromatography on silica gel and their structures were identified by physical, chemical properties and spectral analysis.
Abstract: To study the chemical constitutes in the lipophilic part from the leafy body of Marchantia convoluta. The compounds were isolated by column chromatography on silica gel and their structures were identified by physical, chemical properties and spectral analysis. Two compounds were isolated and identified as β-sitosterol and stigmasterol. The two compounds were obtained from this plant for the first time.
Journal Article•
TL;DR: In this article, the chemical constituents of Impatiens balsamina flowers were extracted by chromatography and solvant extration and the structures were identified on the basis of spectral analysis.
Abstract: Objective: To study the chemical constituents of the flowers of Impatiens balsamina L.. Methods: The compounds were isolated by chromatography and solvant extration and the structures were identified on the basis of spectral analysis. Results: Four compounds were isolated and identified as stigmasterol(1), kaempferol(2), Kaempferol 3 glucoside(3) and Kaempferol 3 glucosyl rhamnoside(4). Conclusions: All the compounds were isolated from the flowers which were cultured for the first time in China.
TL;DR: In this article, the sterols of Griffonia simplicifolia seeds oil were studied and the main sterols were β-sitosterol, stigmasterol, and campesterol.
Abstract: Lipids, fatty acids and sterols of Griffonia simplicifolia seeds oil were studied. Fatty acid composition is 18:2 - 60 %, 16:0, 18:0, 18:1 - 9-18 %, and 20:0 - 3-4 %. The main sterol is β-sitosterol - 60 %, stigmasterol is 29 %, and campesterol is 11 %. Linoleic acid can be relatively simply enriched to 95 % separating the other fatty acids as urea adducts.
Patent•
15 Nov 2003
TL;DR: The process of separating and purifying stigmasterol from plant sterol includes: the first step of adding solvent absolute ethyl alcohol, n-propanol or n-butanol, heating to dissolve, slowly lowering temperature to crystallize, filtering, centrifugally separating and vacuum drying; and the second step, adding separating solvent into the product of the first stage, heating-to-dissolve, slowly decreasing temperature to crystalize and filtering; with the separation capable of being repeated for 2 or 3 times as discussed by the authors.
Abstract: The process of separating and purifying stigmasterol from plant sterol includes: the first step of adding solvent absolute ethyl alcohol, n-propanol or n-butanol, heating to dissolve, slowly lowering temperature to crystallize, filtering, centrifugally separating and vacuum drying; and the second step of adding separating solvent into the product of the first step, heating to dissolve, slowly lowering temperature to crystallize and filtering; with the separation capable of being repeated for 2 or 3 times. The present invention has separate material concentration and separation refining steps, and has greatly raised stigmasterol purity and yield and no environmental pollution.
Journal Article•
TL;DR: In this paper, the characteristics of the solubility of stigmasterol and b-sitosterol in a solvent of cyclohexanone or n-pentanol at different temperatures and the phase diagram of Stigmasters under room temperature were determined.
Abstract: The characteristics of the solubility of stigmasterol and b-sitosterol in a solvent of cyclohexanone or n-pentanol at different temperatures and the phase diagram of stigmasterol /b-sitosterol / cyclohexanone (or n-pentanol) under room temperature were determined. The experimental results show that the solubility of b-sitosterol in n-pentanol or cyclohexanone is larger than that of stigmasterol in the same solvent at the same condition, and that the solubility of b-sitosterol increases much faster with temperature in cyclohexanone than that of stigmasterol. The recrystallization for separating and purifying stigmasterol and b-sitosterol from phytosterol using n-pentanol or cyclohexanone as a solvent was studied. The content of stigmasterol and b-sitosterol in the crystal product was analyzed by IR and UV spectra motheds.
Journal Article•
TL;DR: In this paper, the contents of β -sitosterol and stigmasterol in phytosterol were determined by IR spectra method, and the results showed the linear relationship between the ratio of the feature peak areas of IR spectras and the ratios of the contents.
Abstract: The contents of β -sitosterol and stigmasterol in phytosterol were determined by IR spectra method. The results showed the linear relationship between the ratio of the feature peak areas of IR spectra and the ratio of the contents of stigmasterol and β -sitosterol. The contents of the composition in the phytosterol obtained by IR spectra are close to those obtained by gas chromatogram method, which indicates that it is an useful and convenient method to determine the content of stigmasterol by IR spectra.
31 Dec 2003
TL;DR: In this article, the authors investigated the lipid contents of Ocimum basilicum L. herb and revealed the presence of amyrins, -sitosterol, stigmasterol and ursolic acid besides nine fatty acids, the majors were oleic, linoleic, palmitic and Linolinic acids.
Abstract: Investigation of the lipid contents of Ocimum basilicum L. herb revealed the presence of & amyrins, -sitosterol, stigmasterol and ursolic acid besides nine fatty acids, the majorswere oleic, linoleic, palmitic and Linolinic acids. Forskolin diterpenoid was isolated andidentified from the semipurified extract. The hypotensive and cardiovascular effects of bothethanolic and the semipurified extract of the herb was similar to that of Forskolin.
01 Jan 2003
TL;DR: In this article, a search for secondary metabolites, of biological, clinical or pharmaceutical interest on the seeds and roots of Senna bicapsularis (Caesalpiniaceae), resulted in the isolation of 1,8-dihydroxy-3-methoxy-6-methyl anthraquinone (physcion), 1.8-Dihydrox-3methyl anthrasquioxioxymethylanthraquinones (chrysophanol), and stig masterol-dehydro stigmasterol mixture.
Abstract: Search for secondary metabolites, of biological, clinical or pharmaceutical interest on the seeds and roots of Senna bicapsularis (Caesalpiniaceae), resulted in the isolation of 1,8-dihydroxy-3-methoxy-6-methyl anthraquinone (physcion), 1,8-dihydroxy-3-methyl anthraquinone (chrysophanol) and stigmasterol-dehydro stigmasterol mixture.
Posted Content•
Journal Article•
TL;DR: In this article, the separation and purification of b-sitosterol and stigmasterol from phytosterol by the crystallization method using n-pentanol and cyclohexanone as solvents were studied based on the difference of the solubilities of stig masterol and b-stoberol and the variation of solubility with temperature.
Abstract: The separation and purification of b-sitosterol and stigmasterol from phytosterol by the crystallization method using n-pentanol and cyclohexanone as solvents were studied based on the difference of the solubilities of stigmasterol and b-sitosterol and the variation of solubility with temperature. The experimental results show that the content of b-sitosterol is more than 87% after the third fractional crystallization in cyclohexanone and the content of stigmasterol is more than 92% after the fifth crystallization in n-pentanol or cyclohexanone.
TL;DR: From the whole plant of Salvia aegyptiaca, 6-methylcryptoacetalide, 6methyl-epicryptoacet alide and 6methylcryptotanshinone have been isolated and characterized, mainly by spectroscopic means.
Abstract: From the whole plant of Salvia aegyptiaca , 6-methylcryptoacetalide, 6-methyl-epicryptoacetalide and 6-methylcryptotanshinone have been isolated and characterized, mainly by spectroscopic means. In addition to these novel diterpenoids, the known compounds 3β-hydroxy-olean-12-en-28-oic acid, 3β-hydroxy-oleana-11,13(18)-dien-28-oic acid, sitosterol-3β-glucoside, sitosterol, stigmasterol, 5-hydroxy-7,3′,4′-trimethoxyflavone and 5, 6-dihydroxy-7,3′,4′-trimethoxyflavone were isolated.
Patent•
23 Jul 2003
TL;DR: In this paper, a skin whitening composition containing stigmasterol having an excellent melamine production-inhibiting action, together with conventional cosmetic materials is provided, which exhibits excellent whitening effects as compared to albutin and hydroxyanisole.
Abstract: PURPOSE: A skin whitening composition containing stigmasterol having an excellent melamine production-inhibiting action, together with conventional cosmetic materials is provided. The stigmasterol exhibits excellent whitening effects as compared to albutin and hydroxyanisole and does not cause irritation to the skin even for a long-term use. CONSTITUTION: A skin whitening composition contains 0.00001 to 10% by weight of stigmasterol represented by the formula(1) as an effective ingredient. The stigmasterol is obtained by extracting Dioscorea opposita Thumb. in ethanol. For an example, 0.1% by weight of Dioscorea opposita Thumb. extract is mixed with 1,3-butylene glycol, 4,0% by weight of glycerine, 0.1% by weight of oleyl alcohol, 0.5% by weight of polysorbate 20, 15.0% by weight of ethanol, a trace amount of preservatives and fragrances, 0.05% by weight of benzophenone-9 and the balance of purified water to produce a skin lotion containing stigmasterol.