Beta-sitosterol Glucoside Research Articles

A combination of beta-sitosterol and beta-sitosterol glucoside and normal function of the immune system: evaluation of a health claim pursuant to Article 13(5) of Regulation (EC) No1924/2006.

Following an application from Essential Sterolin Products (Pty) Ltd., submitted for authorisation of a health claim pursuant to Article 13(5) of Regulation (EC) No 1924/2006 via the Competent Authority of the Netherlands, the European Food Safety Authority (EFSA) Panel on Nutrition, Novel Foods and Food Allergens (NDA) was asked to deliver an opinion on the scientific substantiation of a health claim related to a combination of beta‐sitosterol and beta‐sitosterol glucoside and normal function of the immune system. The scope of the application was proposed to fall under a health claim based on newly developed scientific evidence. The food proposed by the applicant as the subject of the health claim is a combination of beta‐sitosterol and beta‐sitosterol glucoside in a ratio 100:1. The Panel considers that a combination of beta‐sitosterol and beta‐sitosterol glucoside in a ratio 100:1 is sufficiently characterised. The claimed effect proposed by the applicant is ‘normal function of the immune system by restoring balance between TH1‐TH2 mediated immunity’. The Panel notes that the claimed effect ‘normal function of the immune system by restoring balance between TH1‐ and TH2‐mediated immunity’ does not refer to a specific function of the body which can be assessed in vivo in humans by generally accepted methods, but rather to a mechanism of action by which the food/constituent could exert the claimed effect. The Panel considers that the claimed effect does not refer to any specific health claim as required by Regulation (EC) No 1924/2006. The Panel concludes that a cause and effect relationship cannot be established between the consumption of a combination of beta‐sitosterol and beta‐sitosterol glucoside in a ratio 100:1 and a beneficial physiological effect.

Bioassay Guided Isolation of Free Radical Scavenging Agent from the Bark of Bridelia retusa

Bioassay guided fractionation of ethyl acetate soluble fraction of methanolic extract of Bridelia retusa yielded tambulin (1), beta-sitosterol (2), and beta-sitosterol glucoside (3), and their structures were elucidated using modern spectroscopic techniques. Compounds 1-3 were evaluated for their antioxidant activity and compound 1 was found to be potent antioxidant. The DPPH assay showed that the compound 1 has potent antioxidant activity with IC50 166.15±1.92 SEM [muM] and the radical scavenging activity was found to be 86.03% where as the standard butylated hydroxy toluene (BHT) has IC50 value 128.83±2.1 SEM [muM]. The radical scavenging activity of standard butylated hydroxy toluene was about 86% .The total phenolic content in ethyl acetate soluble fraction was found to be 147.20±1.5 mg GAE/gm and the total flavonoid content was found to be 16.64±0.00 mg QE/gm.Journal of Institute of Science and Technology, 2015, 20(1): 97-101

Chemical constituents from leaves of Boehmeria nivea

To study the chemical constituents from the leaves of Boehmeria nivea. The leaves were extracted by 95% EtOH at room temprature, the chemical leaves were isolated and purified by repeated silica gel column chromatography, Sephadex LH-20 column chromatography and semipreparative HPLC, and their structures were identified by physical and chemical properties and spectroscpoic methods. One compound isolated from n-butanol fraction, four compounds were obtained from ethyl acetate fraction and three compounds from petroleum ether fraction. Their structures were elucidated as kiwiionoside (1), eugenyl beta-rutinoside (2), uracil (3), beta-sitosterol glucoside (4), 3-hydroxy-4-methoxy-benzoic acid (5), cholesterol (6), alpha-amyrin (7). nonacosanol (8). Compounds 1-3, 5-8 were isolated from the genus Boehmeria for the first time.

Bioactive Compounds from Sour Orange Inhibit Colon Cancer Cell Proliferation and Induce Cell Cycle Arrest

Epidemiological studies suggest that dietary limonoids and phytosterols offer protection from certain types of cancers. Potential cancer preventive constituents of sour orange (Citrus aurantium L.) were isolated and identified from ethyl acetate extract. The structures of the compounds were identified by one-dimensional (1H or 13C) and two-dimensional (1H-H and 1H-13C) nuclear magnetic resonance experiments as limonexic acid and beta-sitosterol glucoside (SG). The identified compounds were tested for the potential inhibition of human colon cancer cell (HT-29) proliferation, apoptosis, and also noncancerous cells (COS-1). Cell proliferation, arrest of the cell cycle, and induction of apoptosis were assessed by MTT assay, flow cytometry, and nuclear staining methods, respectively. The MTT assay indicated that both compounds exhibited significant inhibition at various concentrations. These compounds did not show any toxic effects on noncancerous cells. These compounds caused 4-5-fold increases in the counts of G2/M stage cells at 50 microM, indicating a potential role in cell cycle arrest. These findings support the hypothesis that limonoids and phytosterols are effective apoptosis-promoting agents and incorporation of enriched fractions of these compounds in the diet may serve to prevent colon cancer. To the best of our knowledge, this is the first report of the isolation, identification, and cell proliferation assay for limonexic acid and SG from sour orange.

Antifungal constituents isolated from the seeds of Aegle marmelos

Antifungal constituents, 2-isopropenyl-4-methyl-1-oxa-cyclopenta[b]anthracene-5,10-dione and (+)-4-(2'-hydroxy-3'-methylbut-3'-enyloxy)-8H-[1,3]dioxolo[4,5-h]chromen-8-one in addition to known compounds imperatorin, beta-sitosterol, plumbagin, 1-methyl-2-(3'-methyl-but-2'-enyloxy)-anthraquinone, beta-sitosterol glucoside, stigmasterol, vanillin and salicin were isolated during phytochemical investigation on seeds of Aegle marmelos Correa.

Suppression of hepatitis B virus-derived human hepatocellular carcinoma by NF-κB-inducing kinase-specific siRNA using liver-targeting liposomes

Hepatitis B virus triggers an increase of NF-kappaB inducing kinase (NIK)-dependent NF-kappaB activation, followed by the promotion of hepatocellular carcinoma (HCC). Here, we examined the inhibitory effect of NIK-specific siRNA on NF-kappaB signaling and HCC. The results of this study indicated that these siRNAs suppressed HBV-derived HCC by regulating NIK activation. To exert a protective effect from degradation enzyme, cationic liposomes were contrived and modified to contain beta-sitosterol glucoside to target the asialoglycoprotein receptors in liver cancer cells. The cationic dimyristoyl diacyltrimethylammonium propane liposomes were prepared by a reverse-phase evaporation method with slight modification. beta-Sitosterol glucoside was added to the lipid mixture at the beginning of the liposome preparation for the purpose of liver targeting. These liposomes assisted the delivery of the siRNA to specific cells and protected it from various lyases, followed by the ultimate suppression of HCC.

Hepatoprotective Constituents from Cleome droserifolia

The effect of ethanol extract from aerial parts of Cleome droserifolia was investigated against carbon tetrachloride induced liver injury. The hepatoprotective activity was evaluated through the quantification of biochemical parameters and confirmed using histopathology analysis. Efficient hepatoprotective effect was achieved by crude extract, fractions and some pure compounds. The phytochemical studies showed that the petroleum ether fraction afforded two known guaiane sesquiterpenes buchariol (1) and teucladiol (2) in addition to daucosterol (beta-sitosterol glucoside) (3). The CHCl(3) fraction afforded three known flavonoid derivatives; 5,3'-dihydroxy-3,6,7,4',5'-pentamethoxyflavone (4), 5'-hydroxy-3,6,7,3',4',5'-hexamethoxyflavone (5) and luteolin (6) and a known dolabellane diterpene (1R,2R,3E,7E,11R,12S)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol (7). The active parts of the MeOH fraction afforded the previously unreported 3'-methoxy-3,5,4'-trihydroxy flavone-7-neohesperidoside (8) and a known megastigmane norterpene; (6S,9R)-roseoside (9).

Triterpenoid Saponins from the Seeds of Pharbitis nil

From the seeds of Pharbitis nil (Convolvulaceae), two new oleanene-type triterpene glycosides, pharbitosides A (1) and B (2), together with beta-sitosterol, beta-sitosterol glucoside (daucosterol), caffeic acid, and methyl caffeate were isolated. The structure of pharbitoside A (1) was elucidated to be queretaroic acid 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (1). Pharbitoside B (2) is a 21alpha-hydroxyoleanolic acid saponin carrying the same sugar moiety as that of pharbitoside A (1).

Two New Benzofurans from Gastrodia elata and their DNA Topoisomerases I and II Inhibitory Activities

Two new benzofurans, 1-furan-2-yl-2-(4-hydroxyphenyl)-ethanone (1) and 5-(4-hydroxybenzyloxymethyl)-furan-2-carbaldehyde (2), together with five known compounds, 4-hydroxybenzyl methyl ether (3), 5-(hydroxymethyl)-furfural (4), gastrodin (5), beta-sitosterol (6) and beta-sitosterol glucoside (7) were isolated from the rhizome of Gastrodia elata Blume. In DNA topoisomerase I and II inhibition assays in vitro at a concentration of 20 microM, 1 showed potent inhibitory activity, 66% and 71% inhibition, respectively, compared to the positive control compounds, camptothecin and etoposide, 71% and 22% inhibition, respectively. All of these compounds exhibited weak or no cytotoxicities against human colon carcinoma cell line (HT-29), human breast carcinoma cell line (MCF-7) and human hepatocellular carcinoma cell line (HepG-2).

Phytochemical Study ofActaea rubraand Biological Screenings of Isolates

A phytochemical study on the chemical constituents of the roots of Actaea rubra led to the isolation and characterization of eleven xylosides of 9,19-cyclolanostane type triterpenes including the new rubraside A (1) and a beta-sitosterol glucoside. The structures of the isolates were determined with the help of spectroscopic data including 2-dimensional NMR as well as comparison with reported data. The compounds were tested for cytotoxic, estrogenic, antioxidant, and anticomplement activities. They were found inactive in the tested assays, except for 4, which showed moderate anticomplement activity.

Spinoside, new coumaroyl flavone glycoside fromAmaranthus spinosus

Spinoside, new coumaroyl flavone glycoside was isolated from the n-butanol fraction of the mathanolic extract of the whole plant of Amaranthus spinosus and assigned the structure 7-p-coumaroyl apigenin 4-O-beta-D-glucopyranoside (1) on the basis of spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition alpha- xylofuranosyl uracil (2), beta-D-ribofuranosyl adenine (3) and beta-sitosterol glucoside (4) have also been isolated for the first time from this species.

β-Sitosterol, β-Sitosterol Glucoside, and a Mixture of β-Sitosterol and β-Sitosterol Glucoside Modulate the Growth of Estrogen-Responsive Breast Cancer Cells In Vitro and in Ovariectomized Athymic Mice

We hypothesized that the phytosterols beta-sitosterol (BSS), beta-sitosterol glucoside (BSSG), and Moducare (MC; BSS:BSSG = 99:1) could modulate the growth of estrogen-dependent human breast cancer cells in vitro and in vivo. The present study evaluated the estrogenic and antiestrogenic effects of BSS, BSSG, and MC (0.001 to 150 micromol/L) on the proliferation of Michigan Cancer Foundation 7 (MCF-7) cells in vitro. Both BSS (>1 micromol/L) and MC (>50 micromol/L) increased MCF-7 cell proliferation. Treatment with 150 micro mol/L of BSS and MC increased cell growth by 2.4 and 1.5 times, respectively, compared to the negative control (NC) group. However, BSSG had no effect at the concentrations tested. The effects of dietary BSS, BSSG, and MC on the growth of MCF-7 cells implanted in ovariectomized athymic mice were also evaluated. Estrogenic effects of the phytosterols were evaluated in the NC, BSS, BSSG, and MC treatment groups, and antiestrogenic effects were evaluated in the 17 beta-estradiol (E(2)), E(2) + BSS, E(2) + BSSG, and E(2) + MC treatment groups. Mice were treated with dietary BSS (9.8 g/kg AIN93G diet), BSSG (0.2 g/kg diet), or MC (10.0 g/kg diet) for 11 wk. Dietary BSS, BSSG, and MC did not stimulate MCF-7 tumor growth. However, dietary BSS, BSSG, and MC reduced E(2)-induced MCF-7 tumor growth by 38.9% (P < 0.05), 31.6% (P = 0.08), and 42.13% (P < 0.05), respectively. The dietary phytosterols lowered serum E(2) levels by 35.1, 30.2, and 36.5% in the E(2) + BSS, E(2) + BSSG, and E(2) + MC groups, respectively (P < 0.05), compared to that of the E(2) treatment group. Estrogen-responsive pS2 mRNA expression in tumors did not differ among groups, but expression of the antiapoptotic marker B-cell lymphoma/leukemia-2 (bcl-2) in tumors from the E(2) + MC group was downregulated, compared to that of the E(2) treatment group. In summary, BSS and MC stimulated MCF-7 cell growth in vitro. Although BSSG comprises only 1% of MC, BSSG made MC less estrogenic than BSS alone in vitro. However, dietary BSS and MC protected against E(2)-stimulated MCF-7 tumor growth and lowered circulating E(2) levels.

Antioxidant caffeic acid derivatives from leaves of Parthenocissus tricuspidata.

Five caffeic acid derivatives; methyl ester of caffeoylglycolic acid (1), dimethyl ester of caffeoyltartaric acid (2), dimethyl ester of caffeoyltartronic acid (3), monomethyl ester of caffeoyltartronic acid (4), methyl ester of caffeic acid (5), and some other secondary metabolites including; quercetin, quercetin 3-O-beta-D-glucuronide methyl ester, kaempferol, 3,5,7,4'-O-tetramethylkaempferol, beta-sitosterol glucoside, 2alpha-hydroxyursolic acid and 2,24-dihydroxyursolic acid, have been isolated and characterized. All the isolated compounds were characterized with the help of NMR spectroscopy and mass spectrometry. Structure of compound 3 was also confirmed by a single X-ray crystallographic technique. Isolates were evaluated for antioxidant activities and most of the tested compounds were found to be potent in DPPH free radical scavenging (IC50 = 4.56-14.17 microg/mL) and superoxide anion scavenging (IC50 = 0.58-7.39 microg/mL) assays.

Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.

Cytotoxicity-based, bioassay-guided fractionation of the chloroform-soluble extracts of both the roots and leaves of Picramnia latifolia led to the isolation of two new anthrone C-glycosides, picramniosides G (1) and H (2), two new oxanthrone C-glycosides, mayosides D (3) and E (4), and a new benzanthrone natural product, 6,8-dihydroxy-10-methyl-7H-benz[de]anthracen-7-one (5), together with 10 known compounds, 6,8-dihydroxy-4-methyl-7H-benz[de]anthracen-7-one (6), nataloe-emodin (7), chrysophanein, chrysophanol, 1,5-dihydroxy-7-methoxy-3-methylanthraquinone, pulmatin, 7-hydroxycoumarin, 7-hydroxy-6-methoxycoumarin, beta-sitosterol, and beta-sitosterol glucoside. The structures of 1-5 were established by spectroscopic methods, including 1D and 2D NMR, HRMS, and CD data interpretation. The cytotoxic activity of all isolates was evaluated in a small panel of human cancer cell lines. Compound 7 exhibited significant in vitro cytotoxic activity in the tested cell lines, but no significant activity was observed with an in vivo hollow fiber model at doses of 6.25, 12.5, 25, and 50 mg/kg/injection.

Phytochemical constituents of Cirsium setidens Nakai and their cytotoxicity against human cancer cell lines.

Five terpenes (1-5), three fatty acids (6-8), two sterols (9 and 11), and a monogalactosyldiacyl glycerol (10) were isolated from the methylene chloride extract of the aerial part of Cirsium setidens. Their chemical structures were determined to be alpha-tocopherol (1), 25-hydroperoxycycloart-23-en-3beta-ol (2), 24-hydroperoxycycloart-25-en-3beta-ol (3), mokko lactone (4), transphytol (5), 9,12,15-octadecatrienoic acid (6), 9,12-octadecadienoic acid (7), hexadecanoic acid (8), acylglycosyl beta-sitosterol (9), (2R)-1,2-O-(9z,12z,15z-dioctadecatrienoyl)-3-O-beta-D-galactopyranosyl glycerol (10) and beta-sitosterol glucoside (11) by spectral evidences. Compound 3 exhibited significant cytotoxic activity against five human cancer cell lines with its ED50 values ranging from 2.66 to 11.25 microM.

Antibacterial constituents against Helicobacter pylori of Brazilian medicinal plant, Pariparoba

Four known compounds have been isolated from the aerial parts of the Brazilian medicinal plant Pariparoba (Pothomorphe umbellata). They were an alkaloid, a flavone, a dihydrocalcone, and a steroid. The chemical structures were established to be N-benzoylmescaline, wogonin, uvangoletin, and beta-sitosterol glucoside using spectral methods. Among these compounds, the main component N-benzoylmescaline showed significant antibacterial activity against Helicobacter pylori.

Liver Targeting Liposomes Containing .BETA.-Sitosterol Glucoside with Regard to Penetration-Enhancing Effect on HepG2 Cells.

The aim of this study was to examine the interaction of soybean-derived sterylglucoside (SG) with the human hepatoblastoma cell line HepG2 with regard to the penetration-enhancing effect of beta-sitosterol glucoside (Sit-G) to clarify the accumulation of SG-containing liposomes (SG-liposomes) to the liver in vivo. The approach was based on measurement of the association of SG-liposomes labeled with 1,1'-dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate (Dil) in terms of asialoglycoprotein receptor (ASGP-R)-mediated endocytosis, affinity of Sit-G using lAsys and the association of FITC-dextran 4400 (FD-4) increased by Sit-G with the cells. The association of SG-liposomes was decreased by addition of asialofetuin, suggesting that SG-liposomes might be taken up via ASGP-R. Sit-G showed higher affinity with HepG2 cells than HeLa cells, and enhanced the association of FD-4 depending on the incubation time and Sit-G concentrations. Significant positive correlations were found between Sit-G and FD-4 association with the cells, indicating that Sit-G enhanced the drug penetration by distribution in cell membranes. The high degree of liver association of SG-liposomes in vivo might be related to recognition of glucose residues of SG by ASGP-R and to the high affinity and penetration-enhancing effect of Sit-G with hepatocytes.

Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx.

The 95% EtOH extract of the seeds of Alpinia blepharocalyx (Zingiberaceae) showed significant antiproliferative activity towards human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Chemical investigation of the extract led to the isolation of forty-four new (1-44) and one known (45) diarylheptanoids, eleven phenolic compounds (46-56) together with beta-sitosterol glucoside (57). Almost all the isolated compounds showed significant antiproliferative activity in a concentration-dependent manner. Among the compounds, epicalyxin F (17) exhibited the most potent activity against the proliferation of colon 26-L5 carcinoma cells with an ED50 value of 0.89 microM, while calyxin B (2) exhibited the most potent activity against human HT-1080 fibrosarcoma cells with an ED50 value of 0.69 microM. Moreover, calyxins B (2) and K (11), epicalyxins F (17), I (20) and K (22), 6-hydroxycalyxin F (25), blepharocalyxin B (27) and mixtures of 7 and epicalyxin G (18) and of calyxin J (10) and epicalyxin J (21) possessed more potent activity than a clinically used anticancer drug, 5-fluorouracil, towards HT-1080 fibrosarcoma cells. Analysis of the structure activity relationship suggested that the position of the attachment of a chalcone or a flavanone moiety does not affect the activity, although their presence in association causes a substantial enhancement of the antiproliferative activity. Moreover, the conjugated double bond of the chalcone moiety and the phenolic hydroxyl group potentiate the antiproliferative activity of the compounds.

Phytochemical investigation of Aglaia andamanica.

Four new compounds, the limonoid 24-epi-melianodiol (8), the tirucallane aglaiodiol (9), and the two cyclopentatetrahydrobenzopyran derivatives pyramidaglain A (11) and B (12) were isolated from the leaves of Aglaia andamanica Hiern (Meliaceae), together with the eleven known constituents beta-sitosterol, beta-sitosterol glucoside, cycloart-23E-ene-3 beta,25-diol (1), three flavonoids 5-hydroxy-3,4',7-trimethoxyflavone (2), retusin (3) and pachypodol (4), the tirucallane 24-epi-piscidinol A (5), the lignan yangambin (6), the limonoid melianodiol (7), the bisamide pyramidatine (10) and the amino acid N-methyl-trans-4-hydroxy-L-proline (13). All structures were established by means of detailed spectroscopic analysis.

Saponins isolated from Allium chinense G. Don and antitumor-promoting activities of isoliquiritigenin and laxogenin from the same drug.

Investigation of the Chinese crude drug "Xiebai," the bulbs of Allium chinense G. Don (Liliaceae), led to the isolation of 2 saponins, xiebai-saponin I (laxogenin 3-O-beta-xylopyranosyl (1-->4)-[alpha-arabinopyranosyl (1-->6)-beta-glucopyranoside) (1) and laxogenin 3-O-alpha-arabinopyranosyl (1-->6)-beta-glucopyranoside (2), and the aglycone, laxogenin (3), together with 2 chalcones, isoliquiritigenin (4) and isoliquiritigenin-4-O-glucoside (5), and beta-sitosterol glucoside (6). Compounds 1-5 were tested in vitro for their inhibitory effect on the 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32Pi-incorporation into phospholipids of HeLa cells. In addition to this, laxogenin (3) was proven to have an antitumor-promoting activity in a two-stage lung carcinogenesis experiment.