gamma-sitosterol and betulin

To investigate the chemical constituents of the roots of Rhodomyrtus tomentosa and their antitumor activities.. Various column chromatographic techniques were used to isolate the compounds. The structures were elucidated by their physicochemical properties and spectra data. Moreover, MTT assay was used to evaluate the antitumor activity against melanoma SK-MEI-110 cells.. Thirteen compounds were obtained from the roots of Rhodomyrtus tomentosa, and their structures were determined as 2α, 3β, 23-trihydroxyoleana-11,13( 18)-dien-28-oic acid( 1),3β,23-dihydroxyolean-18-en-28-oic acid( 2), lupeol( 3), betulin( 4), betulinic acid( 5), friedelin( 6), β-sitosterol( 7), thero-2, 3-bis-( 4-hydroxy-3-methoxypheyl)-3-methoxy-propanol( 8), evafolin B( 9), β-hydroxypropiovanillone ( 10), 8, 8’-bis-( dihydroconiferyl)-diferuloylate( 11), gallate acid( 12) and methyl gallate( 13).. Compounds 1,2,8 ~ 10 and 13 are isolated from this plant for the first time. Compounds 1 ~ 6 exhibite inhibitory effects on melanoma SK-MEL-110 cells.

Topics: Betulinic Acid; Magnoliaceae; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Triterpenes

To investigate the chemical constituents from the branches and leaves of Syzygium samarangense.. The dried branches and leaves of Syzygium samarangense were powdered and extracted with 95% ethanol, then partitioned with petroleum ether, chloroform and ethyl acetate. The chloroform fraction was subjected to silica gel, Sephdex L-20 and preparative HPLC. The structures were identified by physicochemical properties and spectral data.. 14 compounds were respectively isolated and identified as ursolic aldehyde(1), betulin(2), betulinic aldehyde(3), betulinic acid(4), lupeol(5), β-sitosterol(6), 5, 7-dihydroxy-6-methylflavanone(7), 2', 4'-dihydroxy-6'-methoxy-3'-methyldihydrochalcone (8), 2', 4'-dihydroxy-6'-methoxy-3'-methylchalcone (9), 5, 7-dihydroxy-6, 8-dimethylflavanone (10), 5, 7-dihydroxyflavanone (11), 2', 4'-dihydroxy-6'-methoxy-3', 5'-dimethyldihydrochalcone (12), 2'-hydroxy-4', 6'-dimethoxy-3'-methylchalcone(13) and p-hydroxyb6nzaldehyde(14).. Compounds 1 - 4 and 14 are isolated from this plant for the first time.

Topics: Betulinic Acid; Pentacyclic Triterpenes; Phytochemicals; Plant Extracts; Plant Leaves; Sitosterols; Syzygium; Triterpenes

The goal was to determine dissolution potency of betulinol and wood sterols (WSs) from pulp and paper mill-contaminated sediments and the current stratification for assessment the load due to potential erosion in the river-like watercourse. Both compounds are wood extractives, which may be toxic to benthos and fish. This research continues a study in which other wood extractives, resin acids and their derivative, retene, were analysed. Sediments were collected from 1, 3.5, 12, 15, and 33 km downstream from the pulp and paper mills, and from 2 upstream reference sites. The dissolution potency into sediment-water elutriates (1 + 4 v/v) was studied by two agitation times and temperatures. The vertical amounts of extractives were determined from the uppermost 20 cm of sediment. The amounts of extractives potentially released were estimated from the sediment layers 0-2 and 2-5 cm by using spatial interpolation. According to the interpolation, the total amount of betulinol and β-sitosterol was calculated as kg/ha in the whole sediment area. Significant concentrations of betulinol (1,666 μg/g, dw) and WSs (2,886 μg/g, dw) were measured from the sediments. According spatial interpolation, the highest calculated amount of betulinol (4,726 kg/ha) and that of the most abundant WS, β-sitosterol (3,571 kg/ha), were in the lake where the effluents were discharged. In the dissolution experiment, the highest concentration of betulinol in sediment (0-10 cm) and elutriate was 412 μg/g (dw) and 165 μg/l, respectively. For WSs, concentrations were 768 μg/g (dw) in sediment and 273 μg/l in elutriate. In a worst-case scenario, betulinol may be desorbed to water in concentrations which are hazardous to aquatic animals. Instead WSs are not a risk in this study area. The amount of desorption varied depending on the concentration of contaminants in sediment, the nature of disturbance, and the sediment organic carbon content.

Topics: Acids; Environmental Monitoring; Geologic Sediments; Industrial Waste; Paper; Phenanthrenes; Resins, Plant; Sitosterols; Triterpenes; Water Pollutants, Chemical; Wood

A sensitive, selective and robust densitometric high-performance thin-layer chromatographic method was developed and validated for five marker compounds, namely betulin, lupeol, oleanolic acid, 3-acetyloleanolic acid and β-sitosterol, known for their various therapeutic activities. The marker compounds have been isolated from the stem bark of Betula utilis, well characterized by the spectral analysis, and their simultaneous quantitative determination carried out by high-performance thin-layer chromatography (HPTLC) method. The resolution of marker compounds was carried out on silica-gel 60 plates, using n-hexane:ethyl acetate (8:2 v/v) as the mobile phase. The HPTLC densitometry was performed at 500-nm wavelength after the post chromatographic derivatization with ceric ammonium sulfate reagent. The optimized method provided good linear relation (r>0.9960) for all the investigated analytes. The method is simple, and reproducible, which may be applied for quantitative analysis of the above-mentioned marker compounds.

Topics: Betula; Chromatography, High Pressure Liquid; Oleanolic Acid; Pentacyclic Triterpenes; Plant Bark; Plant Extracts; Plant Stems; Sitosterols; Triterpenes

This study to identify anti-influenza components of the bark of Alnus japonica resulted in the isolation of four lupane-type triterpenes (1-4) and one steroid (5). Their structures were characterized on the basis of physicochemical properties, NMR evidence, and ESI-MS data compared with reported data in the literature. Betulinic aldehyde (3) exhibited a particularly strong anti-influenza effect against KBNP-0028 relative to a positive control.

Topics: Alnus; Animals; Antiviral Agents; Cell Survival; Cells, Cultured; Chick Embryo; Dose-Response Relationship, Drug; Fibroblasts; Influenza A Virus, H9N2 Subtype; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Bark; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Steroids; Structure-Activity Relationship; Triterpenes

Two new triterpenoids taraxer-14-ene-1alpha,3beta-diol (1) and 3beta-hydroxytaraxer-14-ene-1-one (2), together with the known triterpenes taraxerol (3), betulin (4), betulinic acid (5), sumaresinolic acid (6), and 5-hydroxy-2-methoxy-1,4-naphthoquinone (7), 5,7-dihydroxy-6,8-dimethylchromone (8), alpha-monpalmitin (9), palmitic acid (10), 6beta-hydroxystigmast-4-en-3-one (11), beta-sitostero1 (12), have been isolated from the petroleum ether fraction of the ethanolic extract of Pterospermum heterophyllum. Their structures were established by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-8 were evaluated against several human cancer cell lines. Compound 1 showed in vitro selective cytotoxicity against human lung cancer cell lines (A549) with an IC(50) value of 1.22 microM. Compound 7 showed significant cytotoxicity against the A549, HCT-8, Bel7402, BGC-823, and A2780 cancer cell lines with IC(50) values of 0.21, 0.55, 0.40, 0.59, and 0.34 microM, respectively. However, the other compounds were inactive (IC(50)>10 microM).

Topics: Antineoplastic Agents, Phytogenic; Betulinic Acid; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Female; Humans; Malvaceae; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Palmitic Acid; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Stereoisomerism; Terpenes; Triterpenes

To study the chemical constituents from the roots of Pterospermum heterophyllum.. The chemical constituents of P. heterophyllum were isolated and purified by silica gel and sephadex LH-20 column chromatography. Their structures were identified on the basis of spectroscopic data and physicochemical properties.. Nine compounds were isolated and identified as taraxerol (1), betulin (2), betulinic acid (3), sumaresinolic acid (4), 2-methoxy-5-hydroxy-1, 4-naphthoquinone (5), 5, 7-dihydroxy-6, 8-dimethylchromone (6), alpha-monpalmitin (7), palmitic acid (8), beta-sitosterol (9).. Compounds 2-7 were isolated from this genus for the first time.

Topics: Betulinic Acid; Chromatography; Malvaceae; Naphthoquinones; Oleanolic Acid; Palmitic Acid; Pentacyclic Triterpenes; Plant Roots; Sitosterols; Triterpenes