stigmasterol and lupeol

Asian corn borer (ACB) is a destructive insect pest of corn and causes up to 80% yield reduction in the Philippines. Synthetic insecticides have been used to control ACB but they pose a risk to human health and the environment. The use of synergists increases insecticide effectiveness and decreases the frequency of insecticide application. In line with this principle, we performed

Topics: Animals; Cocculus; Glutathione Transferase; Humans; Insecticides; Molecular Docking Simulation; Moths; Stigmasterol; Zea mays

This study investigated the direct citric acid hydrolysis extraction method to optimize phytosterols extraction from hickory husk. Single factor experiments followed by a three-level three-factor Box-Behnken experiments were performed. The optimal extraction parameters were determined as: pH of 2.0, liquid-to-solid ratio of 17.12: 1 mL/g, and temperature of 55.81 °C. Practical experiments were carried out in triplicate, and subsequently yielded phytosterols of 912.452 ± 17.452 μg/g DW, in good consistence with the predicted extraction yield of 902.874 μg/g DW. The conductivity of the extract was also found to play effective role under direct citric acid hydrolysis and recorded 36.30 ± 1.08 μs/cm at optimum extraction condition. β-Sitosterol stigmasterol, campsterol, ergosterol and lupeol were detected as main PSs and triterpenoids in hickory husk using UPLC-Triple-TOF/MS. Finally, the comparison between direct hydrolysis extraction and traditional solvent extraction showed that this new method was more effective and eco-friendlier to extract both free and conjugated phytosterols.

Topics: Carya; Citric Acid; Ergosterol; Hydrogen-Ion Concentration; Hydrolysis; Models, Theoretical; Pentacyclic Triterpenes; Phytosterols; Sitosterols; Stigmasterol; Triterpenes

The leaves of Garcinia epunctata Stapf have furnished two new phenolic glucosides, epunctosides A and B, along with 13 known secondary metabolites identified as lanceoloside A, betulinic acid, lupeol, stigmasterol, β-sitosterol, β-sitosterol-3-O-β-d-glucopyranoside, stigmasterol-3-O-β-d-glucopyranoside, luteolin-7-O-glucoside, quercitin-7-O-glucoside, amentoflavone, robustaflavone, 4'-O-methyl-amentoflavone and 4'-O-methyl-robustaflavone. All structures were established from chemical and spectroscopic evidence including 1D and 2D NMR data as well as by comparing the obtained spectroscopic data with literature. This is the first report of the presence of phenolic glucosides in the genus Garcinia.

Topics: Betulinic Acid; Biflavonoids; Garcinia; Glycosides; Pentacyclic Triterpenes; Phenols; Plant Leaves; Secondary Metabolism; Sitosterols; Stigmasterol; Triterpenes

Arthritis is a chronic inflammatory disease which reduces the life quality of affected individuals. Therapeutic tools used for treating inflammatory pain are associated with several undesirable effects.

Topics: Acute Pain; Administration, Cutaneous; Administration, Oral; Analgesics, Non-Narcotic; Animals; Anti-Inflammatory Agents, Non-Steroidal; Arthritis, Experimental; Brazil; Buddleja; Drug Stability; Drug Storage; Ethnopharmacology; Gels; Hot Temperature; Male; Mice; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Sitosterols; Stigmasterol; Viscosity

Lupeol and stigmasterol, major phytosterols in various herbal plants, possess anti-inflammatory activities and have been proposed as candidates for anti-cancer agents, but their molecular mechanisms are still unclear. Here, we investigated the effects of lupeol and stigmasterol on tumor and endothelial cells in vitro and their anti-cancer activities in vivo. Our results demonstrated that lupeol and stigmasterol suppressed cell viability, migration, and morphogenesis of human umbilical vein endothelial cells (HUVECs) but not cholangiocarcinoma (CCA) cells. Expression analyses showed that the treatment of both compounds significantly reduced the transcript level of tumor necrosis factor-α (TNF-α), and Western blot analyses further revealed a decrease in downstream effector levels of VEGFR-2 signaling, including phosphorylated forms of Src, Akt, PCL, and FAK, which were rescued by TNF-α treatment. In vivo, lupeol and stigmasterol disrupted tumor angiogenesis and reduced the growth of CCA tumor xenografts. Immunohistochemical analyses confirmed a decrease in CD31-positive vessel content and macrophage recruitment upon treatment. These findings indicate that lupeol and stigmasterol effectively target tumor endothelial cells and suppress CCA tumor growth by their anti-inflammatory activities and are attractive candidates for anti-cancer treatment of CCA tumors.

Topics: Animals; Cell Proliferation; Cholangiocarcinoma; Down-Regulation; Human Umbilical Vein Endothelial Cells; Humans; Mice; Mice, Inbred C57BL; Neovascularization, Pathologic; Pentacyclic Triterpenes; Signal Transduction; Stigmasterol; Tumor Necrosis Factor-alpha; Vascular Endothelial Growth Factor A

Methicillin-resistant Staphylococcus aureus (MRSA) is an important pathogen with multiple antibiotic resistance that causes morbidity and mortality worldwide. Multidrug-resistant (MDR) MRSA with increased resistance to currently available antibiotics has challenged the world to develop new therapeutic agents. Stigmasterol and lupeol, from the plant Phyllanthus columnaris, exhibit antibacterial activities against MRSA. The aim of this study was to utilise next-generation sequencing (NGS) to provide further insight into the novel transcriptional response of MRSA exposed to stigmasterol and lupeol.. Time-kill analysis of one MRSA reference strain (ATCC 43300) and three clinical isolates (WM3, BM1 and KJ7) for both compounds was first performed to provide the bacteriostatic/bactericidal profile. Then, MRSA ATCC 43300 strain treated with both compounds was interrogated by NGS.. Both stigmasterol and lupeol possessed bacteriostatic properties against all MRSA tested; however, lupeol exhibited both bacteriostatic and bactericidal properties within the same minimum inhibitory concentration and minimum bactericidal concentration values against BM1 (12.5mg/mL). Transcriptome profiling of MRSA ATCC 43300 revealed significant modulation of gene expression with multiple desirable targets by both compounds, which caused a reduction in the translation processes leading to inhibition of protein synthesis and prevention of bacterial growth.. This study highlights the potential of both stigmasterol and lupeol as new promising anti-MRSA agents.

Topics: Anti-Bacterial Agents; Drug Combinations; Gene Expression Profiling; Gene Expression Regulation, Bacterial; Genes, Bacterial; Humans; Methicillin; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Pentacyclic Triterpenes; Ribosome Subunits; RNA, Ribosomal, 16S; Sequence Analysis; Staphylococcal Infections; Stigmasterol

The present study was structured to investigate the anti-inflammatory potential of the extracts, fractions and compounds isolated from Carissa carandas (L.) roots. Bioassay guided fractionation of methanol extract based on inhibitory potential towards proinflammatory mediators (TNF-α, IL-1β and nitric oxide (NO)) led to the identification of stigmasterol (1), lupeol (2), oleanolic acid (3), carissone (4) and scopoletin (5) as potential anti-inflammatory agents. Carissone (4) (IC50 = 20.1 ± 2.69 μg/mL) and scopoletin (5) (IC50 = 24.6 ± 1.36 μg/mL) exhibited significant inhibition of NO production comparable to specific NO inhibitor (L-NAME; IC50 = 19.82 ± 1.64 μg/mL) without affecting the cell viability. Also, 4 and 5 at a concentration of 30 μM were found to inhibit 41.88-53.44% of TNF-α and IL-1β. To the best of our knowledge, this is the first report displaying the anti-inflammatory effects of C. carandas (L.) roots, partially mediated by inhibition of TNF-α, IL-1β and NO.

Topics: Anti-Inflammatory Agents; Apocynaceae; Cell Line; Humans; Interleukin-1beta; Nitric Oxide; Oleanolic Acid; Pentacyclic Triterpenes; Plant Extracts; Plant Roots; Scopoletin; Sesquiterpenes, Eudesmane; Stigmasterol; Tumor Necrosis Factor-alpha

Structures of some bioactive phytochemicals in bran extract of the black rice cv. Riceberry that had demonstrated anti-cancer activity in leukemic cell line were investigated. After saponification with potassium hydroxide, separation of the unsaponified fraction by reversed-phase high performance liquid chromatography (HPLC) resulted in four sub-fractions that had a certain degree of anti-proliferation against a mouse leukemic cell line (WEHI-3 cell), this being IC50 at 24 h ranging between 2.80-467.11 μg/mL. Further purification of the bioactive substances contained in these four sub-fractions was performed by normal-phase HPLC. Structural characterization by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) resulted in, overall, the structures of seven phytosterols and four triterpenoids. Four phytosterols, 24-methylene-ergosta-5-en-3β-ol, 24-methylene-ergosta-7-en-3β-ol, fucosterol, and gramisterol, along with three triterpenoids, cycloeucalenol, lupenone, and lupeol, were found in the two sub-fractions that showed strong anti-leukemic cell proliferation (IC50 = 2.80 and 32.89 μg/mL). The other sterols and triterpenoids were campesterol, stigmasterol, β-sitosterol and 24-methylenecycloartanol. Together with the data from in vitro biological analysis, we suggest that gramisterol is a significant anti-cancer lead compound in Riceberry bran extract.

Topics: Animals; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cholesterol; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Leukemia; Mass Spectrometry; Mice; Molecular Structure; Oryza; Pentacyclic Triterpenes; Phytosterols; Phytotherapy; Plant Extracts; Seeds; Sitosterols; Stigmasterol; Triterpenes

The first phytochemical investigation of the bark of Akschindlium godefroyanum (Kuntze) H. Ohashi (Fabaceae), a Thai herbal medicine, resulted in the isolation of two new flavanonols, 7,3',5'-trihydroxy-5-methoxyflavanonol (1) and 7,4'-dihydroxy-5,3'-dimethoxyflavanonol (2), and eight known compounds comprising one flavonol, geraldol (3); three flavanonols, (+)-taxifolin (4), (+)-fustin (5) and aromadendrin 5-methyl ether (6); one catechin, (-)-epigallocatechin (7); one triterpenoid, lupeol (8); one steroid, stigmasterol (9) and one steroid glycoside, stigmasterol-3-O-β-d-glucoside (10). Their structures were identified by spectroscopic methods.

Topics: Fabaceae; Flavonoids; Flavonols; Glucosides; Glycosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pentacyclic Triterpenes; Plant Bark; Plants, Medicinal; Stigmasterol; Thailand

A new sesquiterpenoid, malayscaphiol (1), and three known compounds, lupeol (2), lupenone (3) and stigmasterol (4), were isolated from the methanolic extract of the stem bark of Scaphium macropodum. The structures of the isolated compounds were determined using several spectroscopic methods, including UV-vis, FT-IR, 1D and 2D NMR, and mass spectrometer. Major isolated compounds were assayed for cytotoxicity and anti-acetylcholinesterase activities. The chemotaxonomy significance of this plant was also discussed.

Topics: Antineoplastic Agents, Phytogenic; Drug Screening Assays, Antitumor; Malaysia; Malvaceae; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pentacyclic Triterpenes; Plant Bark; Polycyclic Compounds; Sesquiterpenes; Spectroscopy, Fourier Transform Infrared; 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

Previous methods for the quantitative analysis of phytosterols have usually used GC-MS and require elaborate sample preparation including chemical derivatization. Other common methods such as HPLC with absorbance detection do not provide information regarding the identity of the analytes. To address the need for an assay that utilizes mass selectivity while avoiding derivatization, a quantitative method based on LC-tandem mass spectrometry (LC-MS-MS) was developed and validated for the measurement of six abundant dietary phytosterols and structurally related triterpene alcohols including brassicasterol, campesterol, cycloartenol, β-sitosterol, stigmasterol, and lupeol in edible oils. Samples were saponified, extracted with hexane and then analyzed using reversed phase HPLC with positive ion atmospheric pressure chemical ionization tandem mass spectrometry and selected reaction monitoring. The utility of the LC-MS-MS method was demonstrated by analyzing 14 edible oils. All six compounds were present in at least some of the edible oils. The most abundant phytosterol in all samples was β-sitosterol, which was highest in corn oil at 4.35 ± 0.03 mg/g, followed by campesterol in canola oil at 1.84 ± 0.01 mg/g. The new LC-MS-MS method for the quantitative analysis of phytosterols provides a combination of speed, selectivity and sensitivity that exceed those of previous assays.

Topics: Cholestadienols; Cholesterol; Chromatography, Liquid; Molecular Structure; Pentacyclic Triterpenes; Phytosterols; Plant Oils; Reproducibility of Results; Sitosterols; Stigmasterol; Tandem Mass Spectrometry; Triterpenes

To study the chemical constituents of the aerial part of Stauntonia obovatifoliola.. The chemical constituents of ethyl acetate fraction were isolated and purified by several chromatography. Their structures were elucidated by their physiochemical properties and spectral methods.. Six known compounds were isolated and identified as lupeone(1), lupeol(2), stigmasterol(3),3beta-O-acetyloleanolic acid(4), resinone(5) and daucosterol(6).. Compounds 1-6 are isolated from this plant for the first time.

Topics: Acetates; Gas Chromatography-Mass Spectrometry; Molecular Structure; Pentacyclic Triterpenes; Plant Components, Aerial; Rosaceae; Sitosterols; Stigmasterol; Triterpenes

Studies on the chemical constituents from the stem bark of Grewia optiva have led to the isolation of two new compounds, grewialin (1) and optivanin (2), along with three known constituents which were hitherto unreported from this species. The structures of the new constituents have been elucidated by spectral studies including 1D and 2D NMR experiments (HSQC, HMBC, COSY, NOESY and J-resolved) as well as HR EI-MS spectroscopic data analysis, as 2S*-(3-hydroxy-4-methoxyphenyl)-3R*-methyl-2H-[1,4]-dioxin [2,3]-chromen-7(3H)-one (1); a coumarinolignan and 3-hydroxy-1-(3-hydroxy-4-methoxyphenyl) propan-1-one (2). The known compounds were identified as β-sitosterol, stigmasterol and lupeol by comparing their spectral data with those reported in the literature.

Topics: Grewia; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Sitosterols; Stigmasterol

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

The Lecythidaceae family is composed of 25 genera and 400 species that occur in the form of trees with a pantropical distribution. The genera Cariniana belongs to the family Lecythidaceae, and there are few reports considering these species. In this work, fractionation of the dichloromethane fraction obtained from the aqueous extract of the stem bark of Cariniana domestica (Mart) Miers, popularly known as Jequitibá-roxo, led to the isolation of two mixtures of triterpenoids: lupeol and β-amyrin and β-sitosterol and stigmasterol. The structures of the isolated compounds were elucidated by spectroscopic (NMR) and chromatographic (GC-MS) techniques as well as literature data comparisons. β-Sitosterol, stigmasterol, lupeol and β-amyrin were quantified in dichloromethane fraction by high-performance liquid chromatography (HPLC/DAD). The dichloromethane fraction was also investigated for antioxidant and antifungal activities. The isolated compounds and their biological activities are reported for the first time for the species C. domestica.

Topics: Antifungal Agents; Antioxidants; Chromatography, High Pressure Liquid; Gas Chromatography-Mass Spectrometry; Lecythidaceae; Magnetic Resonance Spectroscopy; Methylene Chloride; Molecular Structure; Oleanolic Acid; Pentacyclic Triterpenes; Plant Bark; Plant Extracts; Saccharomyces cerevisiae; Sitosterols; Stigmasterol; Triterpenes

The effects of aqueous and ethanolic extracts of Costus igneus (stem) and isolated compounds lupeol and stigmasterol on calcium oxalate urolithiasis have been studied in male albino Wistar rats. Ethylene glycol feeding resulted in hyperoxaluria as well as increased renal excretion of calcium and oxalate. The increased deposition of stone-forming constituents in the urine, serum, and kidney homogenate of urolithic rats was significantly (p < 0.05) lowered by treatment using aqueous and ethanolic extracts of C. igneus (stem), and isolated compounds lupeol and stigmasterol. The calcium oxalate crystal deposition in the kidney was significantly greater in ethylene glycol-induced urolithic rats. After administration of aqueous and ethanolic extract of C. igneus, the deposition of calcium and oxalate was significantly lowered. Treatment with lupeol and stigmasterol significantly reduced the deposition of calcium and oxalate in the kidney, and also in the blood serum; the lipid profile serum total cholesterol (TC), triglycerides (TG), low-density lipoprotein (LDL) and high-density lipoprotein (HDL) levels at 50 and 100 mg/kg were significantly (p < 0.05) lowered in urolithiatic rats. From this study, we conclude that both the treatments with aqueous and ethanolic extract of C. igneus (stem) and isolated compounds lupeol and stigmasterol had an inhibitory effect on calcium oxalate urinary stone. Lupeol and stigmasterol were identified from the stem of C. igneus by high-performance thin layer chromatography technique. The isolated compounds were confirmed by Fourier transform infrared (FTIR) and (13)C NMR spectra.

Topics: Animals; Calcium Oxalate; Calibration; Chromatography, Thin Layer; Costus; Kidney; Male; Pentacyclic Triterpenes; Plant Extracts; Plant Stems; Rats; Rats, Wistar; Stigmasterol; Urolithiasis

The Herb Rhinacanthus nasutus (L.) Kurz, which is native to Thailand and Southeast Asia, has become known for its antioxidant properties. Neuronal loss in a number of diseases including Alzheimer's disease is thought to result, in part, from oxidative stress. Glutamate causes cell death in the mouse hippocampal cell line, HT-22, by unbalancing redox homeostasis, brought about by a reduction in glutathione levels, and amyloid-β has been shown to induce reactive oxygen species (ROS) production. Here in, we show that ethanol extracts of R. nasutus leaf and root are capable of dose dependently attenuating the neuron cell death caused by both glutamate and amyloid-β treatment. We used free radical scavenging assays to measure the extracts antioxidant activities and as well as quantifying phenolic, flavonoid and sterol content. Molecules found in R. nasutus, lupeol, stigmasterol and β-sitosterol are protective against glutamate toxicity.

Topics: Acanthaceae; Alzheimer Disease; Amyloid beta-Peptides; Animals; Antioxidants; Cell Line; Glutamic Acid; Glutathione; Hippocampus; Mice; Neuroprotective Agents; Neurotoxicity Syndromes; Oxidative Stress; Pentacyclic Triterpenes; Plant Extracts; Plant Leaves; Plant Roots; Reactive Oxygen Species; Sitosterols; Stigmasterol

To isolate and identify the chemical constituents of the root of Chloranthus multistachys Pei.. The compounds were isolated by column chromatography, semi-preparative thin layer chromatography and related techniques, their structures were elucidated through spectroscopic analyses.. Nine compounds were isolated and identified as: lupeol (I), cycloeucalenol (II), isofragidin (III), daphnin (IV), umbelliferone (V), palmitic acid (VI), stigmasterol (VII), beta-sitosterol (VIII), beta-daucosterol (IX).. Except VI, all compounds are isolated from this plant for the first time.

Topics: China; Coumarins; Magnoliopsida; Molecular Structure; Pentacyclic Triterpenes; Phytosterols; Plant Roots; Plants, Medicinal; Stigmasterol; Umbelliferones

In this study, five compounds, lupeol (1), epilupeol (2), β-sitosterol (3), stigmasterol (4) and p-methoxybenzaldehyde (5) were isolated from the petroleum ether and dichloromethane fractions of a methanolic extract of the stem bark of Delonix regia. Antimicrobial screening of the different extracts (15 μg mm-2) was conducted by the disc diffusion method. The zones of inhibition demonstrated by the petroleum ether, carbon tetrachloride and dichloromethane fractions ranged from 9-14 mm, 11-13 mm and 9-20 mm, respectively, compared to kanamycin standard with the zone of inhibition of 20-25 mm. In brine shrimp lethality bioassay, the carbon tetrachloride soluble materials demonstrated the highest toxicity with LC50 of 0.83 μg mL-1, while petroleum ether and dichloromethane soluble partitionates of the methanolic extract revealed LC50 of 14.94 and 3.29 μg mL-1, respectively, in comparison with standard vincristine sulphate with LC50 of 0.812 μg mL-1. This is the first report on compounds separation from D. regia, their antimicrobial activity and cytotoxicity.

Topics: Animals; Anti-Bacterial Agents; Antifungal Agents; Benzaldehydes; Fabaceae; Kanamycin; Microbial Sensitivity Tests; Pentacyclic Triterpenes; Plant Extracts; Sitosterols; Stigmasterol

To study the chemical constituents from the petroleum ether fraction of Buxus microphylla.. The petroleum ether fraction of Buxus microphylla was isolated and identified by silica gel column chromatography. And the anticancer activity of different chemical constituents was measured by MTT reduction test.. Eight compounds were isolated and identified as lupeol (1), butulin (3), beta-sitosterol (4), stigmasterol (5), dibutyl phthalate (6), 3beta, 30-dihydroxy-lup-20 (29) ene (7), daucosterol (8). Compound 7 inhibited KB cells' proliferation in a dose-dependent manner.. Compounds 2 - 5, 7, 8 are isolated from this genus for the first time. Compound 7 has certainly anticancer effects.

Topics: Buxus; Chromatography, Thin Layer; Dibutyl Phthalate; Ethers; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Stigmasterol

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

As part of a continuing interest in exploring the chemistry of Brazilian medicinal plants, three new labdane diterpenoids, 6alpha-acetoxymanoyl oxide (1), 6alpha-malonyloxymanoyl oxide (2), and 6alpha-malonyloxy-n-butyl ester manoyl oxide (3), together with the known betulinic acid, lupeol, sitosterol, and stigmasterol, were isolated from the aerial parts of Stemodia foliosa. The structures of 1-3 were established on the basis of interpretation of spectroscopic data, including HRESIMS, and 1D and 2D NMR techniques. All compounds were tested against a bacteria panel consisting of Staphylococcus aureus, Bacillus cereus, B. subtilis, B. anthracis, Micrococcus luteus, Mycobacterium smegmatis, and M. phlei. Compound 2 showed moderate activity against these strains, with MIC values in the range 7-20 microg/mL.

Topics: Anti-Bacterial Agents; Bacillus anthracis; Bacillus cereus; Bacillus subtilis; Betulinic Acid; Brazil; Diterpenes; Microbial Sensitivity Tests; Micrococcus luteus; Molecular Structure; Mycobacterium phlei; Mycobacterium smegmatis; Pentacyclic Triterpenes; Plants, Medicinal; Scrophulariaceae; Sitosterols; Staphylococcus aureus; Stigmasterol; Triterpenes

An accurate and sensitive method, combining soxhlet extraction, solid phase-extraction and capillary gas chromatography is described for the quantitative determination of one triterpene (lupeol) and three sterols (stigmasterol, campesterol and beta-sitosterol) and the detection of another triterpene (alpha-amyrin) from the aerial part of Justicia anselliana. This is the first method allowing the quantification of sterols and triterpenes in this plant. It has been fully validated in order to be able to compare the sterol and triterpene composition of different samples of J. anselliana and therefore help to explain the allelopathic activity due to these compounds. This method showed that the aerial part of J. anselliana contained (292+/-2)mg/kg of lupeol, (206+/-1)mg/kg of stigmasterol, (266+/-2)mg/kg of campesterol and (184+/-9)mg/kg of beta-sitosterol.

Topics: Acanthaceae; Calibration; Cholesterol; Chromatography, Gas; Molecular Structure; Pentacyclic Triterpenes; Phytosterols; Plant Components, Aerial; Reference Standards; Reproducibility of Results; Sensitivity and Specificity; Sitosterols; Solid Phase Extraction; Sterols; Stigmasterol; Triterpenes

To Study liposoluble constituents of Teurium labiosum.. The constituents were isolated and purified by silica gel column and Sephadex LH-20 chromatography. Their structures were elucidated by physicochemical properties and spectral analysis.. Six compounds were obtained and identified as stearic acid (I), alpha-spinasterol (II), Methyl phaeophorbide a (III), friedelino (IV), lupeol (V) and stigmasta-5,22-dien-3beta-ol (VI).. All these compounds are obtained from this plant for the first time.

Topics: Alcohols; Lamiaceae; Magnetic Resonance Spectroscopy; Oleanolic Acid; Pentacyclic Triterpenes; Plants, Medicinal; Solvents; Stearic Acids; Stigmasterol; Triterpenes

A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, beta-sitosterol, ursolic acid, and stigmasterol 3-O-beta-d-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of (13)C and (1)H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.

Topics: Glucosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pentacyclic Triterpenes; Plant Stems; Rubiaceae; Sitosterols; Sri Lanka; Stigmasterol; Triterpenes; Ursolic Acid

To study the chemical constituents from Caesalpinia decapetala (Roth) Alston.. Chromatography and spectroscopic analysis were employed to isolate and elucidate the chemical constituents in the plant.. Seven compounds were isolated and elucidated as lupeol acetate(I), lupeol(II), oleanoic acid(III), pentacosanoic acid 2,3-dihydroxypropyl ester(IV), 1-(26-hydroxyhexacosanoyl)-glycerol(V), stigmasterol(VI), beta-sitosterol(VI).. I approximattely VII were isolated from this plant for the first time.

Topics: Caesalpinia; Chromatography, Thin Layer; Glycerides; Molecular Structure; Oleanolic Acid; Pentacyclic Triterpenes; Plants, Medicinal; Sitosterols; Stigmasterol; Triterpenes

Three known compounds were isolated from the petroleum ether extract of the whole plant of Lindernia ciliata. They are beta-sitosterol, stigmasterol and lup-20(29)-en-3 beta-ol. Their structures were established by IR, MS, 1HNMR and 13CNMR spectroscopy.

Topics: Drugs, Chinese Herbal; Pentacyclic Triterpenes; Sitosterols; Stigmasterol; Triterpenes