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At least 343 records · Page 19Linked to original sources
PubMed1999

Effect of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor on sterol absorption in hypercholesterolemic subjects.

To investigate the potential effects of high-dose 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitor on plasma phytosterol, total cholesterol (TC), low-density lipoprotein cholesterol (LDL-C), high-density lipoprotein cholesterol (HDL-C), and triglyceride (TG), hypercholesterolemic subjects received 40 or 80 mg/d simvastatin in a 24-week prospective clinical trial. Plasma lipid levels were analyzed enzymatically, and plasma phytosterol concentrations were determined using gas-liquid chromatography. The change in the plasma phytosterol-campesterol level was used as an indicator of cholesterol absorption in humans. Simvastatin treatment reduced plasma campesterol (-24%, P = .017) but did not affect circulating stigmasterol and sitosterol levels. A dose of 80 mg/d simvastatin produced a larger decrease (P = .050) in plasma campesterol (0.1680 mmol/L) than 40 mg/d (0.0237 mmol/L) versus baseline. There was a positive correlation between plasma campesterol and TC both before (r = .54, P = .027) and after (r = .63, P = .009) treatment. Plasma TC and TG levels did not differ between groups receiving 40 or 80 mg/d simvastatin. Simvastatin treatment reduced circulating TC, LDL-C, and TG by 40%, 50%, and 33% (P<.007), respectively. There was no significant effect of simvastatin on plasma HDL-C, but the HDL-C/LDL-C ratio increased 1.3-fold (P<.0001). In conclusion, this HMG-CoA reductase inhibitor reduces the plasma campesterol level, a marker of cholesterol absorption, which may contribute to the mechanism by which simvastatin decreases circulating cholesterol levels.

Adult↗
PubMed2000

Chemical constituents of two Mollinedia species.

A butanolide, marliolide, was isolated from the hexane extract of leaves of Mollinedia marliae (Monimiacae) along with the long chain fatty alcohol hexacosanol. Phytol and a mixture of sitosterol and stigmasterol were also isolated from leaves of both M. marliae and M. gilgiana. trans-N-Feruloyltyramine, a ferulic acid derivative, is the major constituent of the stems of M. gilgiana.

Magnetic Resonance Spectroscopy↗
PubMed2000

Dichromenoxanthones from Tovomita brasiliensis.

Two dichromenoxanthones [1,6-dihydroxy-6',6'-dimethylpyrano(2',3':3,4)-6'',6''-dimethylpyrano(2'',3'':7,8)xanthone (brasilixanthone A) and 1,6-dihydroxy-6',6'-dimethylpyrano(2',3':2,3)-6'',6''-dimethylpyrano(2'',3'':7,8)xanthone (brasilixanthone B)], along with betulinic acid, friedelin, sitosterol and stigmasterol were isolated from the roots and stems of Tovomita brasiliensis. Their structures were characterized on the basis of 1H and 13C NMR spectral data, including 2D NMR experiments.

Magnoliopsida↗
PubMed2001

Terpenoids from Guarea rhophalocarpa.

Four new terpenes including, two sandaracopimaradiene diterpenoids, ent-8(14),15-sandaracopimaradiene-2alpha,18-diol, and ent8(14),15-sandaracopimaradiene-2beta,18-diol, and two lanostane triterpenoids, 23-hydroxy-5alpha-lanosta 7,9(11),24-triene-3-one, and 5alpha-lanosta-7,9(11),24-triene-3alpha,23-diol, were isolated from the methanolic extract prepared from the leaves of G. rhopalocarpa together with the known steroid stigmasterol and the coumarin, scopoletin. The isolates showed weak antiprotozoal activity against Leishmania donovani promastigotes, and Trypanosoma brucei brucei blood stream trypomastigotes, and were devoid of interesting activity towards Plasmodium falciparum. The isolates did not show significant cytotoxic activity against KB cells.

Animals↗
PubMed2001

Membrane disruption and enzyme inhibition by naturally-occurring and modified chacotriose-containing Solanum steroidal glycoalkaloids.

Naturally-occurring 3beta-O-chacotriosides of solasodine (solamargine), of its 22S, 25S isomer tomatidenol (beta-solamarine), and of solanidine (chaconine), as well as ring E- and F-modified derivatives of solamargine were prepared and assayed in order to assess the relevance of aglycone structural features to membrane-disruption and enzyme-inhibitory activities of the related glycoalkaloids. A ring E-opened dihydro-derivative of solasodine (the chacotrioside of dihydrosolasodine A) did not bind to cholesterol, stigmasterol or ergosterol in vitro, disrupt PC/cholesterol liposomes or mammalian erythrocytes. or inhibit acetylcholinesterase in vitro. It did not synergise with the solatrioside of dihydrosolasodine A or solasonine (nor did solamargine with dihydrosolasodine A solatrioside) in haemolysis tests. The ring F modified derivative, N-nitrososolamargine, did not inhibit acetylcholinesterase in vitro, but lysed liposomes at > or = 150 microM and pH 7. Increasing the pH to 8 (but not 9) further enhanced disruption. The combination of N-nitrososolamargine and solasonine did not cause any disruption of liposomes. Beta-solamarine showed no anti-acetylcholinesterase activity in vitro at up to 100 microM, but disrupted liposomes at 75 and 150 microM, although not to the extent caused by solamargine or chaconine. In combination with both the (inactive) solatriosides, solasonine and solanine, 75 microM beta-solamarine produced synergistic effects, with liposome disruption greater than 150 microM beta-solamarine alone. Beta-solamarine, solamargine and chaconine showed similar haemolytic activity. Beta-solamarine synergised with the solatriosides solasonine and solanine in disrupting erythrocytes. Preliminary structure-activity relationships were evaluated for the active chacotriosides in an attempt to define the scope and limitations of this model study.

Acetylcholinesterase↗
PubMed1994

Triterpene saponins from Myrsine pellucida.

Quercitol, five saponins and 3-O-(6'-O-palmitoyl) beta-D-glucopyranosyl stigmasterol were isolated from the stem bark of Myrisine pellucida. These compounds are described for the first time in this plant and their structures were determined using a combination of 1H and 13C NMR, and mass spectroscopy. The two saponins are new compounds, 3-O-(alpha-L-rhamnopyranosyl (1-->2) beta-D-glucopyranosyl (1-->4) alpha-L-arabinopyranosyl) cyclamiretin A and 3-O-(beta-D-xylopyranosyl) (1-->2) beta-D-glucopyranosyl (1-->4) [beta-D-glucopyranosyl (1-->2)] alpha-L-arabinopyranosyl) cyclamiretin D.

Bolivia↗
PubMed2001

Sterol composition of Aureoumbra lagunensis, the Texas brown tide alga.

Aureoumbra lagunensis, the alga responsible for the "Texas brown tide", contains (E)-24-propylidenecholesterol (35.7% of total sterols) as its dominant sterol, in common with other members of the Pelagophyceae. Other major sterols are stigmasterol (22.2%), sitosterol (19.2%), cholesterol (14.1%), and (24R)-24-propylcholesterol (5.2%). Trace amounts of 24-methylenecholesterol, crinosterol, clerosterol, campesterol, dihydrobrassicasterol, and 24-isopropylcholesterol were also detected.

Chromatography, High Pressure Liquid↗
PubMed2001

Apianane terpenoids from Salvia officinalis.

Three apianane terpenoids, rel-(5S, 6S, 7S, 10R, 12S, 13R)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide, rel-(5S, 6S, 7R, 10R, 12S, 13R)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide and rel-(5S, 6S, 7S, 10R, 12R, 13S)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide were isolated from the leaves of Salvia officinalis, together with 15 known compounds, salvigenin, lupeol, beta-sitosterol, stigmasterol, physcion, carnosol, rosmadial, rosmanol, epirosmanol, isorosmanol, columbaridione, atuntzensin A, miltirone, carnosic acid and 12-O-methyl carnosic acid. Their structures were established on the basis of spectral evidence.

Magnetic Resonance Spectroscopy↗
PubMed2001

Cytotoxic isoflavones from Erythrina indica.

Bioassay-directed fractionation of the CH(2)Cl(2)-MeOH (1:1) extract of the stem bark of Erythrina indica, has resulted in the isolation of two new isoflavone derivatives named indicanines D and E together with 11 known compounds including: six isoflavones (genistein, wighteone, alpinumisoflavone, dimethylalpinumisoflavone, 8-prenyl erythrinin C, and erysenegalensein E), one cinnamate (erythrinassinate B), two pentacyclic triterpenes (oleanolic acid and erythrodiol), and two phytosterols (stigmasterol and its 3-O-beta-D-glucopyranoside). The structures of the new compounds were elucidated by means of spectroscopic analysis. The in vitro cytocidal activity against KB cells of some of the isolated compounds is also reported.

Antineoplastic Agents, Phytogenic↗
PubMed2002

Eremophilanolides and other constituents from the Argentine liverwort Frullania brasiliensis.

Two eremophilanolides, 5-epidilatanolides A and B, as well as a new natural bibenzyl were isolated from an Argentine collection of the liverwort Frullania brasiliensis, along with the known eudesmane-type sesquiterpene lactones nepalensolide A, nepalensolide B, (+)-frullanolide, and (+)-dihydrofrullanolide, the hopanoid zeorin, the four sterols stigmasta-4,22-dien-3,6-dione, stigmasta-4,22-dien-3-one, stigmasterol, and sitosterol, and a trace amount of atraric acid. The structure and stereochemistry of the eremophilanolides and the bibenzyl were established by a combination of extensive NMR spectroscopy experiments and X-ray crystallographic analysis. Absolute configurations of the new compounds were derived on the basis of CD spectra.

Bibenzyls↗
PubMed2002

A prenylated xanthone from Allanblackia floribunda.

A new prenylated xanthone, named allanxanthone A, was isolated from the stem bark of Allanblackia floribunda in addition to known compounds, 1,5-dihydoxyxanthone, 1,5,6-trihydroxy-3,7-dimethoxyxanthone, stigmasterol and stigmasteryl-3-O-beta-D-glucopyranoside. The structure of the new compound was assigned as 1,3,5-trihydroxy-2-(3-methylbut-2-enyl)-4-(1,1-dimethylprop-2-enyl) xanthone, by means of spectroscopic analysis. The 13C NMR spectral data of 1,5-dihydroxyxanthone is reported here for the first time as well as the in vitro cytotoxic activity of xanthone metabolites against the KB cell line.

Cameroon↗
PubMed2002

6-Methylcryptoacetalide, 6-methyl-epicryptoacetalide and 6-methylcryptotanshinone from Salvia aegyptiaca.

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 3beta-hydroxy-olean-12-en-28-oic acid, 3beta-hydroxy-oleana-11,13(18)-dien-28-oic acid, sitosterol-3beta-glucoside, sitosterol, stigmasterol, 5-hydroxy-7,3',4'-trimethoxyflavone and 5, 6-dihydroxy-7,3',4'-trimethoxyflavone were isolated.

Abietanes↗
PubMed2002

Sphingolipids from Conyza canadensis.

Sphingolipid 1 and its corresponding beta-D-glucopyranoside derivative 2 have been isolated from the ethylacetate fraction of Conyza canadensis along with beta-sitosterol 3, stigmasterol 4, beta-sitosterol 3-O-beta-D-glucoside 5 and harmine 6, reported for the first time from this species. The structures of 1 and 2 were elucidated through spectroscopy including two-dimensional NMR.

Conyza↗
PubMed2003

Ent-pimarane type diterpenes from Gnaphalium gaudichaudianum.

Fractionation of the methanol extract of Gnaphalium gaudichaudianum DC afforded one new and six known ent-pimarane diterpenes together with velutin, squalene and stigmasterol. The structure of the new compound was established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. Two of the isolated compounds exhibited moderate toxicity in the Artemia salina toxicity test.

Abietanes↗
PubMed2003

Phytochemistry of the mopane, Colophospermum mopane.

The polyphenolic pool of the heartwood of the mopane, Colophospermum mopane Kirk ex J. Leonard, exhibits extreme diversity and complexity. It comprises a variety of monomeric flavonoids, e.g. flavan-3-ols, flavan-3,4-diols including the mopanols and peltogynols, flavonols, dimeric proanthocyanidins, e.g. proguibourtinidins, profisetinidins, promopanidins, propeltogynidins, and a variety of profisetinidin-type triflavanoids. The di- and tri-meric proanthocyanidins are accompanied by several functionalized tetrahydropyrano- and hexahydrodipyrano-chromenes (phlobatannins) that originate from the bi- and tri-flavanoids, respectively, via rearrangement of the pyran heterocycle(s). Owing to the predominance of the 5-deoxy (A-ring) flavan-3-ols, the chain terminating moieties in the biosynthesis of oligo- and poly-meric proanthocyanidins, the di- and tri-meric analogs also exhibit diversity as far as interflavanyl bonding positions are concerned. Such heterogeneity results from the reduced nucleophilicity of the A-rings of 5-deoxy flavan-3-ols, compared to the A-rings of the 5-oxy analogs (catechins), hence permitting alternative centers to participate in proanthocyanidin formation. Biomimetic-type syntheses were extensively utilized to unequivocally establish constitution and absolute stereochemistry of both the conventional and pyran ring rearranged-type di- and tri-meric compounds. Comprehension of the intricate mechanistic and stereochemical course of the pyran ring rearrangement reactions also contributed significantly to unambiguous structure elucidations. The aerial parts of the mopane are rich in essential oils that comprise mainly alpha-pinene and limonene, which are presumably responsible for the strong turpentine odor of the pods. The leaves also contain significant concentrations of beta-sitosterol and stigmasterol which are apparently the source of sterols in various organs of the mopane moth, Gonimbrasia belina. Three diterpenes, dihydrogrindelic acid, labd-13E-en-15-oate and dihydrogrindelaldehyde are present in the bark and seeds, the latter compound exhibiting significant cytotoxicity against a human breast cancer cell line.

Antineoplastic Agents↗
PubMed1997

Properties of plasma membranes of Phsp 70-ipt transformed tobacco (Nicotiana tabacum).

Application of 10 successive daily heat shocks reduced the growth of control tobacco (Nicotiana tabacum L. cv. Petit Havana SR1) plants by about 15%; for Phsp 70-ipt transformed plants this is about 48%. The shoot diameter of these ipt-transformed plants increased by about 75%. In addition, in heat shock treated ipt-plants (IPT-HS) the upper lateral buds grew out due to a reduction of apical dominance. The older leaves of IPT-HS plants had a higher chlorophyll content. In spite of the observed effects due to a higher endogenous cytokinin content in the IPT-HS plants, no significant changes were observed on the plasma membrane fatty acid composition, nor on its fluidity as determined from the steady-state fluorescence anisotropy of DPH. Only a minor change in the plasma membrane free sterol composition was found as evidenced by a 20% decrease in the stigmasterol to sitosterol ratio in IPT-HS, indicative for a possible anti-senescence effect of enhanced endogenous cytokinins, but without significant effects on the plasma membrane function.

Cell Membrane↗
PubMed1998

Lignans and sesquiterpene lactones from Artemisia sieversiana and Inula racemosa.

The aerial parts of Artemisia sieversiana afforded, in addition to beta-sitosterol, stigmasterol and daucosterol, two novel lignans as well as one known and three new guaianolides. The roots of Inula racemosa gave beta-sitosterol, daucosterol and isoalantolactone. The structures were determined by a combination of spectral methods (IR, EIMS, 1H and 13C NMR, DEPT, COSY, NOESY and HETCOR). All isolates were subjected to antifungal tests. Isoalantolactone, a major sesquiterpene lactone of I. racemosa, was found to be active against the human pathogenic fungi. Aspergillus flavus, A. niger, Geotrichum candidum, Candida tropicalis and C. albicans at concentrations of 50, 50, 25, 25 and 25 micrograms/ml, respectively. The taxonomic significance of the characterized constituents is discussed briefly.

Antifungal Agents↗
PubMed1998

Anthraquinones from hairy root cultures of Cassia obtusifolia.

Hairy root cultures of Cassia obtusifolia clones transformed with Agrobacterium rhizogenes strain 9402 were established to investigate the anthraquinone production. Seven anthraquinones, together with betulinic acid, stigmasterol and sitosterol were isolated from the hairy roots. Their chemical structures were elucidated on the basis of chromatographic and spectral data. The effects of culture conditions and rare earth element Eu(3+) on the production of six free anthraquinones have also been investigated. It was found that changes of the elements in the culture medium and addition of rare earth element Eu(3+) can greatly influence the contents of free anthraquinones in the hairy roots.

Journal Article↗