cytellin and friedelin

Topics: Cannabis; Cholesterol; Hydroponics; Oleanolic Acid; Phytosterols; Plant Extracts; Plant Roots; Sitosterols; Stigmasterol; Triterpenes

Luehea species are found in almost all Central and South American countries. The present work describes the phytochemical study, isolation, and structural characterisation of friedelin, β-friedelinol, lupeol, pseudotaraxasterol, β-sitosterol, betulinic acid, taraxasterol, (-)-epicatechin, β-sitosterol-3-O-β-d-glucopyranoside, and (+)-epicatechin-(4β→8)-epicatechin from stem barks of Luehea ochrophylla Mart. The structural identification of the isolated compounds was mainly performed by NMR analyses and comparison with the data from literature. These compounds were isolated for the first time in the genus Luehea, except β-sitosterol glucopyranoside, (-)-epicatechin, and lupeol. Hexane extract (HE) and dichloromethane (DF) and ethyl acetate (AF) fractions exhibited antiparasitic activity against amastigote (intracellular) and trypomastigote culture forms of Trypanosoma cruzi. The ethanol extract (EE), DF, and ethanol fraction (EF) exhibited considerable antifungal activity against Candida albicans. Moreover, extracts and fractions exhibited significant percentage of capture free radicals of 2,2-diphenyl-picrylhydrazyl (DPPH) when compared to the standard of ascorbic acid.

Topics: Animals; Anti-Infective Agents; Antioxidants; Antiparasitic Agents; Betulinic Acid; Chlorocebus aethiops; Drug Evaluation, Preclinical; Glucosides; Inhibitory Concentration 50; Magnetic Resonance Spectroscopy; Malvaceae; Pentacyclic Triterpenes; Plant Bark; Plant Extracts; Sitosterols; Sterols; Triterpenes; Vero Cells

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 study the chemical constituents from Hibiscus syriacus leaves and their α-glucosidase inhibitory activities.. Column chromatography including macroporous resins, silica gel and Sephadex LH-20 were used for the isolation and purification of all compounds. Spectroscopic methods including physical and chemical properties, 1H-NMR and 13C-NMR were used for the identification of structures. Their α-glucosidase inhibitory activities were detected by a 96-well microplate.. 15 compounds were isolated and identified as β-sitosterol(1), β-daucostero (2), β-amyrin (3), oleanolic acid (4), stigmast-4-en-3-one (5), friedelin (6), syriacusin A (7), kaempferol (8), isovitexin (9), vitexin (10), apigenin (11), apigenin-7-O-β-D-glucopyranoside (12), luteolin-7-O-β-D-glucopyranoside (13), vitexin-7-O-β-D-glucopyranoside (14) and rutin (15).. All the compounds are isolated from the leaves of Hibiscus syriacus for the first time. Taking acarbose as positive control, the α-glucosidase inhibitory activities of 15 compounds were evaluated. Compounds 7 and 9 have shown strong α-glucosidase inhibitory activities with IC50 of 39.03 ± 0.38 and 32.12 ± 0.62 mg/L, inhibition ratio of 94.95% and 97.15%, respectively.

Topics: alpha-Glucosidases; Apigenin; Glucosides; Glycoside Hydrolase Inhibitors; Hibiscus; Kaempferols; Luteolin; Oleanolic Acid; Phytochemicals; Plant Leaves; Sitosterols; Stigmasterol; Triterpenes

To investigate the chemical constituents of the leaves of Clerodendrum trichotomum.. The chemical constituents of petroleum ether extract of the leaves of Clerodendrum trichotomum were isolated and purified by various chromatographic techniques, such as silica gel, ODS, Sephadex LH-20, semi-preparative HPLC and recrystallization. The structures of these isolated compounds were identified by spectroscopic analysis (1 H-NMR,13 C-NMR,2D-NMR and MS).. Ten compounds were isolated and identified from petroleum ether extract, containing four triterpenes, lupeol(1), friedelin(2), betulinic acid(3) and taraxerol(4); four sterols, 22-dehydroclerosterol(5), clerosterol(6), stigmasterol(7) and sitosterol(8); one diterpenoid, transphytol(9), and one alkaloid, 1H-indole-3-carboxylic acid(10).. Compound 10 is obtained from the genus Clerodendrum for the first time, and seven compounds (1,3-4, and 7-10) are firstly isolated from this plant.

Topics: Betulinic Acid; Clerodendrum; Indoles; Oleanolic Acid; Pentacyclic Triterpenes; Plant Leaves; Sitosterols; Sterols; Stigmasterol; Triterpenes

Leaves and branches of Machaerium hirtum Vell. (Fabaceae), native to South America, were subjected to phytopharmacological investigation in order to identify its major chemical constituents and evaluate its extracts, fractions and isolated compounds in assays for anti-inflammatory activities. These were performed using mouse ear edema model, pleurisy and myeloperoxidase activity assays. Six compounds were isolated and identified as the flavanones swertisin and isovitexin, the alkaloid 4-hydroxy-N-methylproline, the triterpenes friedelin and lupeol, and the steroids sitosterol and stigmasterol. These compounds were identified by nuclear magnetic resonance of (1)H and (13)C data, in comparison with literature.

Topics: Animals; Anti-Inflammatory Agents; Apigenin; Edema; Fabaceae; Magnetic Resonance Spectroscopy; Mice; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Proline; Sitosterols; Stigmasterol; Triterpenes

Triterpenoid compounds found in free and ester forms in extracts of entire fruits and leaves and in fruit and leaf cuticular waxes of bilberry (Vaccinium myrtillus L.) collected in Finland and Poland were identified and quantitated by gas chromatography-mass spectrometry coupled to a flame ionization detector (GC-MS/FID). The main bilberry triterpenoid profile consisted of α- and β-amyrin, α- and β-amyrenone, campesterol, cholesterol, citrostadienol (in berries), cycloartanol, erythrodiol, lupeol, 24-methylenecycloartanol, sitosterol, sitostanol, stigmasterol, stigmasta-3,5-dien-7-one, uvaol, oleanolic and ursolic aldehydes, and oleanolic, ursolic, 2α-hydroxyoleanolic, and 2α-hydroxyursolic acids. Friedelin and D:A-friedooleanan-3β-ol were found only in Finnish plants, whereas D:C-friedours-7-en-3β-ol and taraxasterol were found only in Polish plants. To our knowledge, this is the first thorough description of triterpenoid compounds in this species. The presented results revealed that the triterpenoid profile of bilberry varied considerably between different organs of the plant, regardless of the plant origin, as well as between plant samples obtained from the two geographical locations.

Topics: Anthocyanins; Cholesterol; Finland; Fruit; Gas Chromatography-Mass Spectrometry; Molecular Structure; Oleanolic Acid; Phytosterols; Plant Extracts; Plant Leaves; Poland; Sitosterols; Triterpenes; Vaccinium myrtillus

To study the chemical constituents of Pileostegia viburnoides var. glabrescens.. The compounds were isolated and purified by various techniques. Their structures were determined by physicochemical properties and spectral analysis.. Five compounds were isolated and identified as friedelin (1), beta-sitosterol (2), umbelliferone (3), daucosterol (4) and skimmin (5).. All the compounds were isolated from this genus for the first time.

Topics: Magnetic Resonance Spectroscopy; Molecular Structure; Saxifragaceae; Sitosterols; Triterpenes; Umbelliferones

To investigate chemical constituents of the root bark of Tripterygium hypoglaucum.. Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and their structures were identified on the basis of spectral data (MS, 1H-NMR and 13C-NMR).. Twelve compounds were isolated and identified as friedelin (1), 3-oxo-olean-9(11),12-diene (2), canophyllal (3), 3-acetoxy oleanolic acid (4), triptophenolide (5), triptonoterpene methyl ether (6), tricosanoic acid (7), beta-sitosterol (8), stearic acid (9), glut-5-en-3beta,28-diol (10), palmitic acid (11) and daucostorol (12).. Compounds 1, 2, 3, 7 and 10 were isolated from T. hypoglaucum and 7 from the genus Tripterygium for the first time.

Topics: Chromatography; Diterpenes; Fatty Acids, Unsaturated; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oleanolic Acid; Organic Chemicals; Palmitic Acid; Plant Roots; Sitosterols; Stearic Acids; Tripterygium; Triterpenes

Twigs of Calophyllum cordato-oblongum Thw. have been shown to contain cordatolide A-OMe, cordatolide B-OMe, cordatolide C-OMe, cordatolide A, cordatolide B, oblongulide, cordatooblongic acid, friedelin, canophyllol, and sitosterol. Methylation of cordatolide B and the attempted methylation of cordatolide A under acidic conditions gave cordatolide B-OMe and 11,12-anhydrocordatolide. Cordatolide A-OMe, cordatolide C-OMe and 11,12-anhydrocordatolide are new compounds.

Topics: Anti-HIV Agents; Calophyllum; Coumarins; Magnetic Resonance Spectroscopy; Methyl Ethers; Methylation; Molecular Structure; Plant Extracts; Sitosterols; Triterpenes

To investigate the chemical constituents of Grewia biloba and find its bioactive compounds.. Compounds were isolated by silica gel, MCI, Sephadex LH-20 and Rp-18 column chromatography, and purified by recrystallization. Their structures were elucidated by spectral analysis and other methods.. Six compounds were isolated and identified as friedelin (1) epi-friedelan-3-ol (2), heneicosanoic acid (3), beta-sitosterol (4), Propyl palmitate (5), eatechin (6), respectively.. Compounds 1-3, 5, 6 are isolated from Grewia genus for the first time and compounds 4 is isolated from Grewia biloba for the first time.

Topics: Fatty Acids; Grewia; Magnetic Resonance Spectroscopy; Palmitates; Plant Bark; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

A new pentacyclic triterpenoid, 2alpha,3beta-dihydroxylup-12-en-28-oic acid (1) and a rarely encountered pentacyclic triterpenoid, 3beta-hydroxylup-12-en-28-oic acid (2), together with five known compounds, friedelin (3), 3beta-friedelinol (4), betulinic acid (5), oleanolic acid (6) and beta-sitosterol (7) were isolated from the chloroform extract of stem bark of Eugenia grandis (Syn: Syzygium grande). The structure and stereochemistry of the new compound (1) and the rarely encountered compound (2) were established by 1D and 2D NMR spectroscopic techniques. All the above isolated compounds from this plant are reported for the first time.

Topics: Betulinic Acid; Deuterium; Magnetic Resonance Spectroscopy; Molecular Conformation; Oleanolic Acid; Pentacyclic Triterpenes; Protons; Reference Standards; Sensitivity and Specificity; Sitosterols; Stereoisomerism; Syzygium; Triterpenes

To study the chemical constituents from the roots and rhizomes of Clematis hexapetala.. The compounds were separated by means of solvent extraction, repeated chromatography with silica gel and HPLC. The structures were determined by spectral analysis.. Nine compounds were isolated as friedelin (1) , anemonin (2) , beta-sitosterol (3) , palmitic acid (4) , vanillic acid (5) , isolariciresinol (6) , 5-hydroxumethyl-5H-furan-2-one (7) , n-nonane (8) , daucosterol (9).. All the compounds were isolated from the plant for the first time.

Topics: Clematis; Furans; Lignin; Naphthols; Palmitic Acid; Plant Roots; Plants, Medicinal; Rhizome; Sitosterols; Triterpenes

The chemical constituents of Salacia hainanensis were studied for the first time. Five compounds were isolated from the roots of the plant by silica-gel column chromatography and reverse phase preparative chromatography. Four of them have been identified as friedelin, beta-sitosterol, ursolic acid and mangiferin.

Topics: China; Chromatography, Thin Layer; Molecular Structure; Plant Roots; Plants, Medicinal; Salacia; Sitosterols; Triterpenes; Ursolic Acid; Xanthones

To study chemical constituents of the above ground part of Salix oritrepha.. Using chromatography to isolate compounds and their structure were identified by physical, chemical and spectral techniques.. Four compounds were isolated and elucidated as beta-sitosterol, beta-sitosteryl-3-O-glucoside, friedelin, luteolin-7-O-glucoside.. All of them were isolated from S. oritrepha for the first time. Friedelin from the plants of genus Salix for the first time.

Topics: Flavonoids; Glucosides; Luteolin; Plant Components, Aerial; Plants, Medicinal; Salix; Sitosterols; Tibet; Triterpenes

Friedelin, epifriedelinol, beta-amyrin, beta-sitosterol, beta-sitosterol 3-beta-D-glucopyranoside, and naringin were isolated from the dried rhizome of Drynaria quercifolia. The methanol extract showed broad and concentration-dependent antibacterial activity.

Topics: Anti-Bacterial Agents; Anti-Infective Agents; Bacteria; Candida albicans; Dose-Response Relationship, Drug; Flavanones; Flavonoids; Humans; Microbial Sensitivity Tests; Oleanolic Acid; Phytotherapy; Plant Extracts; Plant Roots; Plants, Medicinal; Sitosterols; Triterpenes

Six crystalline substances were isolated from the stem and root of Syzygium buxifolium and identified as friedelin, beta-sitosterol, ursolic acid, pomolic acid, oleanolic acid and beta-daucosterol.

Topics: Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plant Roots; Plant Stems; Plants, Medicinal; Sitosterols; Syzygium; Triterpenes; Ursolic Acid

To study the chemical constituents of the leaves of Quercus mongolica.. Using techniques of silical gel column chromatography and HNMR, 13CNMR.. Four compounds were isolated and identified as friedelin, glutinol, lupeo and beta-sitosterol respectively.. All the compounds were isolated from this plant for the first time.

Topics: Drugs, Chinese Herbal; Molecular Structure; Pentacyclic Triterpenes; Plant Leaves; Plants, Medicinal; Quercus; Sitosterols; Triterpenes

Four compounds were isolated from the fat soluble fraction of the leaves of Vaccinium bracteatum and identified as friedelin (I), epifriedelinol (II), beta-sitosterol(III) and ursolic acid(IV) by IR, NMR and MS. Compound III and IV are isolated from the leaves of this plant for the first time.

Topics: Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plant Leaves; Plants, Medicinal; Sitosterols; Triterpenes; Ursolic Acid

Topics: Drugs, Chinese Herbal; Sitosterols; Triterpenes

Six compounds were isolated from Agapetes obouata. On the basis of physico-chemical constants and spectral analysis they were identified as friedelin (I), fernenal (II), beta-sitosterol (III), daucosterol (IV), beta-sitosterol glucutonide (V) and n-tridecane (VI) respectively.

Topics: Drugs, Chinese Herbal; Plants, Medicinal; Sitosterols; Triterpenes

In this paper four compounds isolated from the stem of Premna crassa are described. Their structures have been identified as friedelin, epifriedelanol, stearic acid and beta-sitosterol respectively by comparing their chemical and spectroscopic data with those of the authentic samples.

Topics: Drugs, Chinese Herbal; Oleanolic Acid; Sitosterols; Stearic Acids; Triterpenes

Topics: Anti-Ulcer Agents; Benzopyrans; Benzoquinones; Drugs, Chinese Herbal; Flavonoids; Isoflavones; Quinones; Sitosterols; Triterpenes