gamma-sitosterol and fucosterol

This paper provides a method for the quantification of sterols in different types of calf feedstuffs based on soy, sunflower, hay, calf feed and a mixture of all of them. The free fraction and the total sterolic fraction, after saponification and acidic hydrolysis of the samples, are extracted by solvent and the sterols are identified/quantified by reversed phase HPLC coupled to tandem mass spectrometry by atmospheric pressure chemical ionization. After the recovery evaluation, the method is validated in terms of linearity (coefficient of determination R

Topics: Animal Feed; Animals; Atmospheric Pressure; Cattle; Cholesterol; Chromatography, High Pressure Liquid; Ergosterol; Glycine max; Helianthus; Phytosterols; Sitosterols; Stigmasterol; Tandem Mass Spectrometry

Chicories produce a wide range of vegetables with important nutritional value. We determined the variation of sterol, total polyphenol, nitrate contents and antioxidant capacity (SC, TPC, NC, AC) in endive leaves and stem-chicory novel vegetables, cultivated in two Italian regions. Within a given area, the SC was similar in smooth- and curly leafed endives (106.3-176.0 mg/kg FW); sitosterol and stigmasterol were major fractions (45-56 versus 38-43%). The stem SC was independent of landrace (101.5-118.6 mg/kg FW); sitosterol prevailed on stigmasterol and fucosterol (73-76 versus 12-14% versus 8-9%); the latter reached 15.7 mg/kg FW, conferring value as potential antidiabetes food. The planting site affected the AC and TPC of endives (893.1-1571.4 μmTE/100 g FW, 30.8-76.1 GAE100/g FW) and chicory stems (729.8-1152.5 μmTE/100 g FW; 56.2-124.4 GAE100/g FW), while the NC was recurrently below dangerous thresholds. PCA showed that environment was the major cause of variation, though it modestly affected these parameters.

Topics: Antioxidants; Asteraceae; Cichorium intybus; Crop Production; Crops, Agricultural; Food Contamination; Functional Food; Humans; Italy; Nitrates; Nutritive Value; Oxygen Radical Absorbance Capacity; Phenols; Phytosterols; Plant Leaves; Plant Stems; Principal Component Analysis; Sitosterols; Spatio-Temporal Analysis; Species Specificity; Stigmasterol

Structures of some bioactive phytochemicals in bran extract of the black rice cv. Riceberry that had demonstrated anti-cancer activity in leukemic cell line were investigated. After saponification with potassium hydroxide, separation of the unsaponified fraction by reversed-phase high performance liquid chromatography (HPLC) resulted in four sub-fractions that had a certain degree of anti-proliferation against a mouse leukemic cell line (WEHI-3 cell), this being IC50 at 24 h ranging between 2.80-467.11 μg/mL. Further purification of the bioactive substances contained in these four sub-fractions was performed by normal-phase HPLC. Structural characterization by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) resulted in, overall, the structures of seven phytosterols and four triterpenoids. Four phytosterols, 24-methylene-ergosta-5-en-3β-ol, 24-methylene-ergosta-7-en-3β-ol, fucosterol, and gramisterol, along with three triterpenoids, cycloeucalenol, lupenone, and lupeol, were found in the two sub-fractions that showed strong anti-leukemic cell proliferation (IC50 = 2.80 and 32.89 μg/mL). The other sterols and triterpenoids were campesterol, stigmasterol, β-sitosterol and 24-methylenecycloartanol. Together with the data from in vitro biological analysis, we suggest that gramisterol is a significant anti-cancer lead compound in Riceberry bran extract.

Topics: Animals; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cholesterol; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Leukemia; Mass Spectrometry; Mice; Molecular Structure; Oryza; Pentacyclic Triterpenes; Phytosterols; Phytotherapy; Plant Extracts; Seeds; Sitosterols; Stigmasterol; Triterpenes

New and sustainable sources of long-chain (LC, ≥C₂₀) omega-3 oils containing DHA (docosahexaenoic acid, 22:6ω3) are required to meet increasing demands. The lipid content of the oilseed of a novel transgenic, DHA-producing land plant, Camelina sativa, containing microalgal genes able to produce LC omega-3 oils, contained 36% lipid by weight with triacylglycerols (TAG) as the major lipid class in hexane extracts (96% of total lipid). Subsequent chloroform-methanol (CM) extraction recovered further lipid (~50% polar lipid, comprising glycolipids and phospholipids) and residual TAG. The main phospholipid species were phosphatidyl choline and phosphatidyl ethanolamine. The % DHA was: 6.8% (of total fatty acids) in the TAG-rich hexane extract and 4.2% in the polar lipid-rich CM extract. The relative level of ALA (α-linolenic acid, 18:3ω3) in DHA-camelina seed was higher than the control. Major sterols in both DHA- and control camelina seeds were: sitosterol, campesterol, cholesterol, brassicasterol and isofucosterol. C₁₆-C₂₂ fatty alcohols, including iso-branched and odd-chain alcohols were present, including high levels of iso-17:0, 17:0 and 19:0. Other alcohols present were: 16:0, iso-18:0, 18:0 and 18:1 and the proportions varied between the hexane and CM extracts. These iso-branched odd-chain fatty alcohols, to our knowledge, have not been previously reported. These components may be derived from wax esters, or free fatty alcohols.

Topics: Brassicaceae; Cholestadienols; Cholesterol; Fatty Acids, Omega-3; Gas Chromatography-Mass Spectrometry; Phospholipids; Phytosterols; Plant Oils; Plants, Genetically Modified; Seeds; Sitosterols; Stigmasterol; Triglycerides

To study the chemical constituents of Fructus Broussonetiae.. Column chromatography with silic gel was employed to isolate and purify the 80% alcohol extract of Fructus Broussonetia, and the constituents were identified by spectral methods.. Six compounds were isolated from 80% ethanol extract. Their structures were identified as Isoterihanine (1), Chelerythrine (2), Trillin (3), Sucrose (4), beta-sitosterol (5) and Fucosterol (6).. These compounds are isolated from Fructus Broussonetiae for the first time.

Topics: Benzophenanthridines; Broussonetia; Fruit; Molecular Structure; Plants, Medicinal; Sitosterols; Spectrophotometry, Ultraviolet; Stigmasterol; Sucrose

The incorporation of [1-13C]-labeled glucose into the irregular monoterpene artemisia ketone, the regular monoterpenes camphor and beta-thujone, the sesquiterpene germacrene D, the diterpene trans-phytol and beta-sitosterol and isofucosterol has been studied in axenic cultures of Tanacetum vulgare L. (Asteraceae). Quantitative 13C NMR spectroscopic analysis of the resulting labeling patterns showed that the isoprene units of the monoterpenes and the diterpene are formed via the methylerythritol phosphate (MEP) pathway, whereas the isoprene building blocks of the sesquiterpene and the sterols originate from the mevalonic acid (MVA) pathway.

Topics: Bicyclic Monoterpenes; Camphor; Diterpenes; Magnetic Resonance Spectroscopy; Monoterpenes; Sesquiterpenes, Germacrane; Sitosterols; Stigmasterol; Tanacetum; Terpenes

The first committed step in the conversion of cycloartenol into Delta(5) C24-alkyl sterols in plants is catalyzed by an S-adenosyl-methionine-dependent sterol-C24-methyltransferase type 1 (SMT1). We report the consequences of overexpressing SMT1 in tobacco (Nicotiana tabacum), under control of either the constitutive carnation etched ring virus promoter or the seed-specific Brassica napus acyl-carrier protein promoter, on sterol biosynthesis in seed tissue. Overexpression of SMT1 with either promoter increased the amount of total sterols in seed tissue by up to 44%. The sterol composition was also perturbed with levels of sitosterol increased by up to 50% and levels of isofucosterol and campesterol increased by up to 80%, whereas levels of cycloartenol and cholesterol were decreased by up to 53% and 34%, respectively. Concomitant with the enhanced SMT1 activity was an increase in endogenous 3-hydroxy-3-methylglutaryl coenzyme A reductase activity, from which one can speculate that reduced levels of cycloartenol feed back to up-regulate 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and thereby control the carbon flux into sterol biosynthesis. This potential regulatory role of SMT1 in seed sterol biosynthesis is discussed.

Topics: Biological Transport; Carbon; Cholesterol; Cloning, Molecular; Gene Expression Regulation, Enzymologic; Gene Expression Regulation, Plant; Hydroxymethylglutaryl CoA Reductases; Methyltransferases; Nicotiana; Phytosterols; Plant Leaves; Plants, Genetically Modified; Seeds; Sitosterols; Stigmasterol; Triterpenes

The sterol fraction of Gynostemma pentafillum contains beta-sito sterol and isofucosterol. The identification of these compounds has been carried out through NMR and MS data.

Topics: Phytosterols; Plants; Sitosterols; Stigmasterol

The extent and site(s) of inhibition of cholesterol absorption by plant sterols, sitosterol and fucosterol, were studied in rats. The intragastric administration of a single emulsified lipid meal containing 25 mg [3H]cholesterol and 25 mg of either sitosterol or fucosterol inhibited the lymphatic absorption of cholesterol by 57% and 41%, respectively, in 24 hr. Less than 2% of each plant sterol was absorbed in the 24-hr period. In contrast, neither plant sterol (50 microM) inhibited cholesterol absorption when co-administered with equimolar amounts of cholesterol in phospholipid-bile salt micelles nor was either absorbed from the micellar solution. A series of in vitro studies was conducted to identify the site(s) of plant sterol inhibition of cholesterol absorption and to account for the difference in inhibitory effectiveness of sitosterol and fucosterol. A comparison of the micellar solubility of each sterol alone and in equimolar binary mixtures (to 2.0 mM) revealed that the solubility of individual sterols decreased in the following order: cholesterol, fucosterol, sitosterol, and that in binary mixtures cholesterol solubility was decreased by sitosterol and, to a lesser extent, by fucosterol relative to its solubility alone. A comparison between micellar-solubilized cholesterol and either sitosterol or fucosterol for binding to isolated brush border membranes, intestinal mucin, or for esterification by either cholesterol esterase or acyl coenzyme A:cholesterol acyltransferase revealed moderate to no competition. The data suggest that plant sterols displace cholesterol from bile salt (taurocholate) micelles and that sitosterol is more effective than fucosterol in this capacity.

Topics: Absorption; Animals; Anticholesteremic Agents; Binding, Competitive; Cholesterol; Esterification; Gastric Mucins; In Vitro Techniques; Intestinal Absorption; Lymphatic System; Male; Micelles; Microvilli; Mucous Membrane; Phytosterols; Rats; Rats, Inbred Strains; Sitosterols; Solubility; Sterol Esterase; Stigmasterol

The modulation of angiotensin converting enzyme (ACE) levels was studied using fucosterol, one of phytosterols, in cultured bovine carotid endothelial cells. Addition of fucosterol to the culture medium resulted in the decrease of ACE activity of endothelial cells; however, fucosterol did not directly inhibit ACE activity. Dexamethasone elevated the levels of ACE in normal cells, but this effect was not seen in the fucosterol-treated cells. Receptor assays showed that the amount of glucocorticoid receptors in fucosterol-treated cells decreased to an undetectable level. These results indicate that fucosterol lowers the ACE levels on the endothelial cells by inhibiting the synthesis of glucocorticoid receptors involved in the regulation of ACE levels.

Topics: Cells, Cultured; Dexamethasone; Endothelium; Peptidyl-Dipeptidase A; Phytosterols; Receptors, Glucocorticoid; Sitosterols; Stigmasterol

We have succeeded in corroborating the enhancing effect of vitamin A, vitamin C, sitosterol and fucosterol on the fibrinolytic activity of endothelial cells. The assay system consisted of an in situ dissolution of a fibrin layer coated onto a culture dish, over which endothelial cells were grown in a culture medium containing 10% serum. The dissolution was enhanced by the addition of these vitamins and phytosterols to the culture medium.

Topics: Animals; Ascorbic Acid; Cattle; Cells, Cultured; Endothelium; Fibrin; Fibrinolysis; Phytosterols; Sitosterols; Stigmasterol; Vitamin A

The sterol fraction of Equisetum arvense L. contains, essentially, the following sterols: beta-sitosterol (60.0%), campesterol (32.9%), isofucosterol (5.9%) and cholesterol (trace amounts). The identification of the compounds has been carried out through NMR and MS, while the corresponding percentage have been desumed from the GLC and HPLC data.

Topics: Cholesterol; Chromatography, Gas; Chromatography, High Pressure Liquid; Magnetic Resonance Spectroscopy; Phytosterols; Plants, Medicinal; Sitosterols; Stigmasterol