stigmasterol and friedelin

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

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.

Topics: Alkynes; Antineoplastic Agents, Phytogenic; Asteraceae; Cell Line, Tumor; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Furaldehyde; Furans; Glucosides; Humans; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Sesquiterpenes; Stigmasterol; Triterpenes

A phytochemical study carried out on the plant, Calophyllum wallichianum has led to the isolation of a new coumarin, wallimarin T (1) and a known coumarin, calanolide E (2) along with two common triterpenes, friedelin (3) and stigmasterol (4). The structures of these compounds were elucidated with the aid of spectroscopic analyses such as FT-IR, GC-MS, and NMR. MIC assay against the Bacillus bacteria were conducted on the extracts and this gave MIC values ranging from 0.313 to 1.25 mg/mL. Compound 2 was weakly inhibitory towards the Bacilli strains with MIC values ranging from 0.25-0.50 mg/mL. Wallimarin T (1) was not active towards all four bacteria. Overall, the extracts exhibited weak bactericidal properties whereas compound 2 was not bactericidal on the tested bacteria. The hexane and chloroform extracts of the plant were found to be inhibitors to the growth of Bacillus megaterium, Bacillus cereus, Bacillus pumilus and Bacillus subtilis.

Topics: Anti-Bacterial Agents; Bacillus; Calophyllum; Coumarins; Magnetic Resonance Spectroscopy; Malaysia; Microbial Sensitivity Tests; Molecular Structure; Phytochemicals; Plant Bark; Plant Extracts; Spectroscopy, Fourier Transform Infrared; Stigmasterol; 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

Jatropha tanjorensis was investigated scientifically to generate evidence for the efficacies reported in traditional systems and the results are given here.. Different concentrations of the solvent extracts of leaves and four isolated compounds were tested against human pathogenic microorganisms such as gram-positive bacteria of Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermis, gram-negative bacteria of Aeromonas hydrophila, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Proteus mirabilis, Proteus vulgaris, Salmonella paratyphi, Salmonella paratyphi A, Vibrio alcaligenes, Vibrio cholerae and fungi of Aspergillus fumigatus, Candida albicans, Microsporum gypseum and Trichophyton rubrum by agar-well diffusion and disk diffusion methods.. In agar-well diffusion method, maximum activity was recorded in a concentration-dependent manner. The extracts recorded activity against bacteria such as 17-26, 15-25 and 13-24 mm to methanol extract and 15-24, 14-23 and 12-22 mm to chloroform extract at 50, 25 and 12.5 mg/ml respectively and fungi such as 9-15 mm to A. fumigatus and 5-16 mm to T. rubrum. Maximum activity was 30-46, 27-43 and 17-40 mm to friedelin and 23-46, 28-44 and 18-41 mm to R (+) 4-hydroxy-2-pyrrolidinone against bacteria and 12-37, 8-34 and 31-33 mm to friedelin and 12-40, 11-35 and 10-33 mm to R (+) 4-hydroxy-2-pyrrolidinone against fungi at 10, 5 and 2.5mg respectively.. The present study concludes that friedelin, β-amyrin, stigmasterol and R (+) 4-hydroxy-2-pyrrolidinone present in the methanol extract could be responsible for the broad spectrum of antimicrobial activity and provide scientific evidence.

Topics: Anti-Bacterial Agents; Antifungal Agents; Bacteria; Fungi; Humans; Jatropha; Microbial Sensitivity Tests; Oleanolic Acid; Plant Extracts; Plant Leaves; Pyrrolidinones; Stigmasterol; Triterpenes

To study the chemical constituents of Codonopsis lanceolata.. Chemical constituents were separated with the column chromatographic, and their structures were identified by chemical and spectroscopic methods.. Six compounds were isolated and identified as syringin (1), shikimic acid (2), friedelin (3), alpha-spinasterol (4), stigmasterol (5), stigmasta-7-dien-3beta-ol (6).. Compounds 3-6 are isolated from this plant for the first time.

Topics: Codonopsis; Glucosides; Magnetic Resonance Spectroscopy; Phenylpropionates; Plant Roots; Plants, Medicinal; Shikimic Acid; Stigmasterol; Triterpenes

The insecticidal activities of extracts from different parts of Cacalia tangutica (Franch.) H.-M. and two active ingredients, friedelin and stigmasterol, against Musca domestica L., Aedes albopictus (Skuse), and Spodoptera litura (F.) cells (SL cells) are reported. Extracts from leaves, flowers, and roots are highly active against adult M. domestica and the fourth-instar larvae of Ae. albopictus. The foliar extract was the most active with LC50 values of 1.74 mg/g and 196.94 microg/ml against adult M. domestica and fourth-instar larvae of Ae. albopictus, respectively. Extracts from stems were the least active. Friedelin and rotenone were highly active and equitoxic to these two insect species. The LC50 value of friedelin in adult M. domestica 48 h after treatment was 129.27 microg/g. The activity of stigmasterol on these two insect species was not obvious. However, the cytotoxicity of stigmasterol to S. litura cells was significantly greater than that of either friedelin or rotenone. At 25 microg/ml, the mortality of cells 24 h after treatment with stigmasterol was 23.0%. In contrast, friedelin and rotenone at the same concentration produced 16 and 18% mortality, respectively. Our results indicate differences between cytotoxicity in vitro and insect toxicity in vivo.

Topics: Aedes; Animals; Asteraceae; Female; Houseflies; Insecticides; Larva; Male; Plant Extracts; Stigmasterol; Triterpenes

Two new triterpenoids, 18alpha,19beta-20(30)-taraxasten-3beta,21alpha-diol (cichoridiol) (1) and 17-epi-methyl-6-hydroxyangolensate (intybusoloid) (2), were obtained from the methanolic extract of seeds of Cichorium intybus along with 11 known compounds, lupeol (3), friedelin (4), beta-sitosterol (5), stigmasterol (6), betulinic acid (7), betulin (8), betulinaldehyde (9), syringic acid (10), vanillic acid (11) 6,7-dihydroxycoumarin (12), and methyl-alpha-D-galactopyranoside (13). Compounds 1, 1a, and 11 showed a good alpha-glucosidase inhibitory activity.

Topics: alpha-Glucosidases; Cichorium intybus; Glycoside Hydrolase Inhibitors; Molecular Structure; Pentacyclic Triterpenes; Plants, Medicinal; Saccharomyces; Seeds; Triterpenes

Four compounds, stigmasterol, D-hurulon-14-en-3-ol, stigma-delta7.22-dien-3beta-palmitate and friedelin were isolated from the root of Aster albscens for the first time. Their structures were elucidated by spectral methods.

Topics: Asteraceae; Drugs, Chinese Herbal; Palmitates; Stigmasterol; Triterpenes