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At least 199 records · Page 11Linked to original sources
PubMed2003

Brominated sesquiterpenes from the red alga Laurencia obtusa.

Four new sesquiterpenes, (8R)-8-bromo-10-epi-beta-snyderol (1), (8S)-8-bromo-beta-snyderol (2), 5-bromo-3-(3'-hydroxy-3'-methylpent-4'-enylidene)-2,4,4-trimethylcyclohexanone (3), and the epoxide 4, have been isolated from the chloroform-methanol extract of Laurencia obtusa, together with the three known compounds alpha-snyderol (5), alpha-snyderol acetate (6), and stigmasterol. The structures of the isolated compounds were elucidated through spectroscopic analyses. Compound 1 showed antimalarial activity, with IC(50) values of 2700 and 4000 ng/mL against the D6 and W2 clones of Plasmodium falciparum, respectively.

Animals↗
PubMed2004

A new 3,4-seco-lupane derivative from Lasianthus gardneri.

A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, beta-sitosterol, ursolic acid, and stigmasterol 3-O-beta-d-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of (13)C and (1)H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.

Glucosides↗
PubMed1999

First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols.

[formula: see text] A novel pentacyclic polyhydroxylated sterol, xestobergsterol A (1a), has been synthesized in 24 steps and in good overall yield from stigmasterol 17. The key steps of the synthesis are the Breslow remote functionalization of the polyoxygenated steroid derived from 25 and the base-catalyzed epimerization-aldol condensation of the dione derived from 27.

Carbohydrate Sequence↗
PubMed2004

Lipid rafts in higher plant cells: purification and characterization of Triton X-100-insoluble microdomains from tobacco plasma membrane.

A large body of evidence from the past decade supports the existence of functional microdomains in membranes of animal and yeast cells, which play important roles in protein sorting, signal transduction, or infection by pathogens. They are based on the dynamic clustering of sphingolipids and cholesterol or ergosterol and are characterized by their insolubility, at low temperature, in nonionic detergents. Here we show that similar microdomains also exist in plant plasma membrane isolated from both tobacco leaves and BY2 cells. Tobacco lipid rafts were found to be greatly enriched in a sphingolipid, identified as glycosylceramide, as well as in a mixture of stigmasterol, sitosterol, 24-methylcholesterol, and cholesterol. Phospho- and glycoglycerolipids of the plasma membrane were largely excluded from lipid rafts. Membrane proteins were separated by one- and two-dimensional gel electrophoresis and identified by tandem mass spectrometry or use of specific antibody. The data clearly indicate that tobacco microdomains are able to recruit a specific set of the plasma membrane proteins and exclude others. We demonstrate the recruitment of the NADPH oxidase after elicitation by cryptogein and the presence of the small G protein NtRac5, a negative regulator of NADPH oxidase, in lipid rafts.

Blotting, Western↗
PubMed2004

Plants express a lipid transfer protein with high similarity to mammalian sterol carrier protein-2.

This is the first report describing the cloning and characterization of sterol carrier protein-2 (SCP-2) from plants. Arabidopsis thaliana SCP-2 (AtSCP-2) consists of 123 amino acids with a molecular mass of 13.6 kDa. AtSCP-2 shows 35% identity and 56% similarity to the human SCP-2-like domain present in the human D-bifunctional protein (DBP) and 30% identity and 54% similarity to the human SCP-2 encoded by SCP-X. The presented structural models of apo-AtSCP-2 and the ligand-bound conformation of AtSCP-2 reveal remarkable similarity with two of the structurally known SCP-2s, the SCP-2-like domain of human DBP and the rabbit SCP-2, correspondingly. The AtSCP-2 models in both forms have a similar hydrophobic ligand-binding tunnel, which is extremely suitable for lipid binding. AtSCP-2 showed in vitro transfer activity of BODIPY-phosphatidylcholine (BODIPY-PC) from donor membranes to acceptor membranes. The transfer of BODIPY-PC was almost completely inhibited after addition of 1-palmitoyl 2-oleoyl phosphatidylcholine or ergosterol. Dimyristoyl phosphatidic acid, stigmasterol, steryl glucoside, and cholesterol showed a moderate to marginal ability to lower the BODIPY-PC transfer rate, and the single chain palmitic acid and stearoyl-coenzyme A did not affect transfer at all. Expression analysis showed that AtSCP-2 mRNA is accumulating in most plant tissues. Plasmids carrying fusion genes between green fluorescent protein and AtSCP-2 were transformed with particle bombardment to onion epidermal cells. The results from analyzing the transformants indicate that AtSCP-2 is localized to peroxisomes.

Agar↗
PubMed2002

Central nervous system activity of Leucas inflata Benth. in mice.

The analgesic activity of the methanol and acetone extracts of Leucas inflata L. (family Labiatae) was evaluated in mice using different experimental models. The effect of the two extracts on pentobarbitone-sleeping time, motor activity, sensorimotor coordination, carrageen induced inflammation, and brewer's yeast-induced pyrexia has also been investigated. The two crude extracts have been phytochemically analyzed and some constituents isolated and characterized. These included stigmasterols, a chromone and coumarins. Extracts of L. inflata L., given at single oral doses of 0.25, 0.5, 1.0 or 2.0 g/kg, significantly and dose-dependently, reduced formalin-induced pain, acetic acid induced abdominal constrictions and increased the reaction time in the hot-plate test. Both extracts caused significant and dose-related impairment in the sensorimotor control and ambulatory and total motor activity of treated mice. Both extracts exhibited anti-inflammatory action by reducing paw edema of treated mice. The extracts did not significantly affect the rectal temperature of normothermic mice. However, they were effective in preventing Brewers yeast induced pyrexia. It is concluded that the crude methanol and acetone extract of L. inflata has CNS depressant properties, manifested as antinociception and sedation. Both extracts have anti-inflammatory and antipyretic actions.

Analgesics↗
PubMed2005

Sterols from the pericarp of Sphaerophysa salsula DC.

A new stigmasterol, (24S)-stigmast-5-en-7beta-ethoxy-3beta-ol (2) together with three known sterols have been isolated from the ethanolic extract of the pericarp of Sphaerophysa salsula (Pall.) DC, and their structures elucidated mainly on the basis of the spectral data and comparison with the literature.

China↗
PubMed2002

Clerodane diterpenoids from Ajuga bracteosa Wall.

The whole plant of Ajuga bracteosa afforded five compounds including one new clerodane diterpenoid designated as Bracteonin-A (1) 6alpha-acetoxy, 15 (R&S)-methoxy, 18-(4'-hydroxy, 3'-beta-methyl, 3'-alpha-acetoxy, butyryloxy) neoclerodane. The other compounds identified were 14,15-dihydroajugapitin, 14-hydro-15-hydroxy ajugapitin, beta-sitosterol, and stigmasterol. The structural elucidation was carried out by spectroscopic techniques.

Ajuga↗
PubMed2006

Sterols isolated from Tubifex tubifex.

Four 3beta-hydroxysterols isolated from chloroform extract from Tubifex tubifex were shown to have the structures stigmast-23-en-3-ol, stigmast-7,14-dien-3-ol, 22-dehydrocholesterol, and 24 methylenecholesterol based on spectroscopic methods. Stigmasterol and beta-sitosterol were also investigated on the basis of mass spectral analyses and compared with known compounds.

Animals↗
PubMed2002

A single daily dose of soybean phytosterols in ground beef decreases serum total cholesterol and LDL cholesterol in young, mildly hypercholesterolemic men.

BACKGROUND: Consumption of phytosterol-supplemented margarine lowers total plasma cholesterol (TC) and LDL-cholesterol concentrations in older middle-aged hypercholesterolemic individuals. The effects of incorporating phytosterols into lower-fat foods on the plasma lipids of young men at increased risk of developing cardiovascular disease have not been studied. OBJECTIVE: We tested the hypothesis that a single daily dose of soybean phytosterols added to ground beef will lower plasma TC and LDL-cholesterol concentrations in mildly hypercholesterolemic young men. DESIGN: In a triple-blind, 4-wk study, 34 male college students with elevated plasma TC (5.85 +/- 0.70 mmol/L), LDL cholesterol (4.02 +/- 0.60 mmol/L), and TC:HDL cholesterol (5.5 +/- 1.2) were randomly assigned to the control (ground beef alone) or treatment (ground beef with 2.7 g of phytosterols) group. The phytosterol mixture was two-thirds esterified and one-third nonesterified and consisted of beta-sitosterol (48%), campesterol (27%), and stigmasterol (21%). RESULTS: Consumption of phytosterol-supplemented ground beef lowered plasma TC and LDL-cholesterol concentrations and TC:HDL cholesterol from baseline by 9.3%, 14.6%, and 9.1%, respectively (P < 0.001). The LDL particle size did not change, suggesting that the decrease was primarily of particle number. The decreases were similar in subjects with (n = 8) and without (n = 9) a family history of premature cardiovascular disease. No significant changes were found in the control group. CONCLUSION: Phytosterol-supplemented ground beef effectively lowers plasma TC and LDL cholesterol and has the potential to become a functional food to help reduce the risk of cardiovascular disease.

Adult↗
PubMed1988

Sterol synergism in Paramecium tetraurelia.

Paramecium tetraurelia is a naturally occurring sterol auxotroph with an absolute nutritional requirement for one of a small group of structurally related phytosterols. We report here a quantitative study demonstrating that a low, otherwise sub-supportive, concentration (approximately 0.020-0.050 micrograms ml-1) of an essential phytosterol (stigmasterol) is adequate for growth of this ciliate, provided that a second, relatively non-specific sterol is available at a higher concentration (1.0 micrograms ml-1) to allow for membrane biosynthesis. This phenomenon, referred to as sterol synergism, has been observed in a broad taxonomic range of organisms, with the conclusion that small amounts of specific sterols are required to perform some previously unknown, vital metabolic or regulatory function. Paramecium promises to be an excellent model organism for the elucidation of essential sterol function.

Animals↗
PubMed1979

Axenic Paramecium caudatum. I. Mass culture and structure.

To establish and grow Paramecium caudatum in mass axenic culture the culture medium of Soldo, Godoy & van Wagtendonk was modified by substituting phosphatidylethanolamine (PE) for TEM-4T and by a 10-fold increase in folic acid. Population densities of 4000 to 6000 cells/ml and a generation time of 20-26 h are regularly obtained. Optimal growth is obtained with PE-stigmasterol ratios between 40:1 to 400:1. Cells from 1-day-old axenic cultures have many lipid bodies aggregated in clumps (which disappear in 2 to 3 days) as well as foci of rough endoplasmic reticulum bordered by dictyosomes. The latter suggests a very active metabolism. Crystalline sheets found in both food vacuoles and lysosomes presumably play a role in digestion. Axenically grown cells also have abundant Golgi bodies (dictyosomes) and by late log phase become filled with lysosomes.

Animals↗
PubMed1990

Interaction of iturin A, a lipopeptide antibiotic, with Saccharomyces cerevisiae cells: influence of the sterol membrane composition.

The binding of the membrane-active lipopeptide antibiotic iturin A to yeast cells was studied using radioactive iturin A. Saccharomyces cerevisiae had a maximum binding capacity of 5.6 x 10(9) molecules per single cell. The Scatchard plot of binding showed a biphasic profile, with a lower dissociation constant for small concentrations of iturin A. The break of slope at 30 microM iturin A corresponds to the micellization of antibiotic in solution. The binding is also dependent on the nature of the sterol present in the membrane. A mutant yeast strain with a membrane containing cholesterol instead of ergosterol showed the highest affinity for iturin A and the highest sensitivity to this antibiotic, as measured by K+ ion release. In contrast the presence of stigmasterol increased the resistance of the cells to iturin A.

Anti-Bacterial Agents↗
PubMed2004

Rapid quantification of free and esterified phytosterols in human serum using APPI-LC-MS/MS.

A novel analytical platform based on liquid chromatography and tandem mass spectrometry using atmospheric pressure photoionization was applied for the simultaneous quantification of free and esterified beta-sitosterol, campesterol, brassicasterol, and stigmasterol. The total time for sample pretreatment and analysis could be reduced from approximately 3 h [gas chromatography-mass spectrometry (GC-MS)] to 15 min. The detection limits of the different phytosterols ranged between 0.25 and 0.68 microg/l. Linear ranges were between 1 and 1,000 microg/l. The within-run and between-run variabilities ranged between 1.4% and 9.9%. The analytical sensitivity was at least 150-fold higher compared with GC-MS. Our new method allows a rapid and simultaneous determination of free and esterified phytosterols in serum.

Cholestadienols↗
PubMed2006

Afzeliixanthones A and B, two new prenylated xanthones from Garcinia afzelii ENGL. (Guttiferae).

Two new prenylated xanthones, afzeliixanthones A (1) and B (2), together with three known xanthones (3-5) and two phytosterols, beta-sitosterol and stigmasterol, were isolated from the CH2Cl2/MeOH (1:1) extract of the stem bark of Garcinia afzelii ENGL. collected in the South West Province of Cameroon. Structures were mainly established using one and two-dimensional NMR and mass spectroscopies. The antioxidant activities of the crude extracts as well as the new compounds (1) and (2) were evaluated.

Antioxidants↗
PubMed2003

Pfaffia paniculata-induced changes in plasma estradiol-17beta, progesterone and testosterone levels in mice.

The present study undertook chemical analysis of components of Pfaffia paniculata roots. In addition, an animal experiment was conducted in which mice had ad libitum access to water enriched with powdered P. paniculata root for 30 days. Changes in plasma concentrations of estradiol-17beta and progesterone in female mice and of testosterone in male mice were ascertained. The results revealed that P. paniculata roots contain two types of phytosteroids, beta-sitosterol and stigmasterol, in addition to other compounds such as pfaffic acid, allantoin, saponins, beta-sitosteryl-beta-D-glucoside, and stigmasteryl-beta-D-glucoside. Regarding changes in plasma concentrations of hormones, levels of the sex hormones estradiol-17beta, progesterone and testosterone were clearly higher for mice that drank P. paniculata root-enriched water than for mice that drank plain water. Powdered P. paniculata root is easily dissolved in feed or water, and as no adverse reactions were seen in mice within 30 days of oral intake, consumption of P. paniculata for long periods of time appears safe.

Amaranthaceae↗
PubMed1980

Determination of the sterol composition of diets used in dietary management of hyperlipoproteinemia.

A simplified rapid quantitative method for determination of sterols in food is described. The lipids were extracted in chloroform-methanol and saponified. The unpolar components, containing the sterols, were extracted with petroleum-ether (PE) and prepared for the gas liquid chromatography (GLC). Progesterone (4-pregnene-3, 20-dione) was used as an internal standard for the GLC analysis. The recovery of the procedure was studied by adding cholesterol-7-alpha-3H before extracting the lipids. Average recovery of the method was 87.4 +/- 8.5%. The analytical errors for determination of the sterol content of three different diets were 10, 20, 25 and 15% for cholesterol, campesterol, stigmasterol and beta-sitosterol respectively.

Cholesterol↗
PubMed2001

[Residual chemicals in natural rubber products for food contact use].

The residues of additives and other chemicals were investigated by GC/MS in natural rubber products for food contact, which included nipples, packing, gloves and a net for ham. The packings and gloves contained 980-6,570 micrograms/g of vulcanization accelerators, such as zinc dimethyldithiocarbamate, zinc diethyldithiocarbamate (EZ), zinc di-n-buthyldithiocarbamate (BZ) and 2-mercaptobenzothiazole. Some samples contained BHT, Irganox 1076 and Yoshinox 2246R as antioxidants; dibutyl phthalate and di(2-ethylhexyl) phthalate as plasticizers; and palmitic acid, stearic acid, palmitamide, stearamide and hydrocarbons as lubricants. Two unknown peaks were identified as stigmasterol and beta-sitosterol, and others were estimated to be fucosterol, oryzanol and alpha-sitosterol. These sterols are widely distributed in plants, so their origin was presumed to be the rubber plants. The sterols were detected at a level of 340-2,940 micrograms/g in all natural rubber samples. A migration test was carried out for some samples. No chemicals were released into water, 4% acetic acid or 20% ethanol at 60 degrees C for 30 min, though BHT, Yoshinox 2246R, EZ, BZ and sterols were released into n-heptane at 25 degrees C for 60 min.

Antioxidants↗