cytellin and spinasterol

Terpenoids from natural plant sources are valuable for their diverse biological activities that have important roles in the medical and agrochemical industries. In this study, we assessed the antioxidant, antifungal, and aphicidal activities of a mixture of spinasterol and 22,23-dihydrospinasterol from the leaves of Citrullus colocynthis. We used 1,1-diphenyl-2-picrylhydrazyl (DPPH) to assess antioxidant activity, and we measured antifungal activity using mycelium growth inhibition assays with three pathogenic fungi, Magnaporthe grisea, Rhizoctonia solani, and Phytophthora infestans. Aphicidal activity against adults of Myzus persicae was determined using in vitro and in vivo assays. Spinasterol and 22,23-dihydrospinasterol exhibited moderate antioxidant activity, even at lower concentrations: 19.98% at 0.78 µg mL

Topics: Antifungal Agents; Antioxidants; Citrullus colocynthis; Plant Leaves; Sitosterols; Stigmasterol; Triterpenes

Spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, were synthesized from commercially available stigmasterol by a four steps reactions. In addition, the effects of these phytosterols on cell growth and mitochondrial activity were evaluated on 158N murine oligodendrocytes, C6 rat glioma cells, and SK-N-BE human neuronal cells with the crystal violet test and the MTT test, respectively. The effects of spinasterol and schottenol were compared with 7-ketocholesterol (7KC) and ferulic acid, which is also present in argan and cactus pear seed oil. Whatever the cells considered, dose dependent cytotoxic effects of 7KC were observed whereas no or slight effects of ferulic acid were found. With spinasterol and schottenol, no or slight effects on cell growth were detected. With spinasterol, reduced mitochondrial activities (30-50%) were found on 158N and C6 cells; no effect was found on SK-N-BE. With schottenol, reduced mitochondrial activity were revealed on 158N (50%) and C6 (10-20%) cells; no effect was found on SK-N-BE. Altogether, these data suggest that spinasterol and schottenol can modulate mitochondrial activity and might therefore influence cell metabolism.

Topics: Animals; Cell Line; Cell Proliferation; Central Nervous System; Humans; Mice; Mitochondria; Phytosterols; Plant Oils; Pyrus; Rats; Seeds; Sitosterols; Stigmasterol

The objective of this study was to evaluate the biological activities of the major phytosterols present in argan oil (AO) and in cactus seed oil (CSO) in BV2 microglial cells. Accordingly, we first determined the sterol composition of AO and CSO, showing the presence of Schottenol and Spinasterol as major sterols in AO. While in CSO, in addition to these two sterols, we found mainly another sterol, the Sitosterol. The chemical synthesis of Schottenol and Spinasterol was performed. Our results showed that these two phytosterols, as well as sterol extracts from AO or CSO, are not toxic to microglial BV2 cells. However, treatments by these phytosterols impact the mitochondrial membrane potential. Furthermore, both Schottenol and Spinasterol can modulate the gene expression of two nuclear receptors, liver X receptor (LXR)-α and LXRβ, their target genes ABCA1 and ABCG1. Nonetheless, only Schottenol exhibited a differential activation vis-à-vis the nuclear receptor LXRβ. Thus Schottenol and Spinasterol can be considered as new LXR agonists, which may play protective roles by the modulation of cholesterol metabolism.

Topics: Animals; ATP Binding Cassette Transporter 1; ATP Binding Cassette Transporter, Subfamily G, Member 1; ATP-Binding Cassette Transporters; Cell Line; Gene Expression Regulation; Lipoproteins; Liver X Receptors; Membrane Potential, Mitochondrial; Mice; Microglia; Opuntia; Orphan Nuclear Receptors; Plant Oils; Seeds; Sitosterols; Sterols; Stigmasterol

To study the triterpenoids constituents from Wisteria sinensis Sweet Caulis.. The compounds were beta-solated and purified with silica gel and Sephadex LH-20 column chromatography from the petroleum ether extract. Their structures were determined on the basis of physicochemical properties and spectroscopic analysis.. They were identified as beta-sitosterol palmitate (1), alpha-spinasterol (2), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3beta-ol (3), (22E, 24R)-ergosta-5, 7, 22-trien-3beta-ol (4), (22E, 24R) -ergosta-7, 22-dien-3beta-ol (5), 11alpha, 12alpha-oxidotaraxerol (6), lupeol (7), betulinic acid (8), 22-oxo-3beta, 24-dihydroxyolean-12-ene (9), 2alpha, 3beta, 23-trihydroxyolean-12-ene (10), soyasapogenol E (11), 3alpha, 21beta-dihydroxy-olean-12-ene (12).. Compounds 1 - 12 are isolated from this plant for the first time.

Topics: Ethanol; Molecular Structure; Plant Stems; Sitosterols; Stigmasterol; Triterpenes; Wisteria

Bioassay-guided fractionation of the N-hexane and CHCl₃ phases of the methanol extract of the roots of Conyza canadensis (L.) Cronquist led to the isolation of two new dihydropyranones named conyzapyranone A (1) and B (2), and the known 4 Z,8 Z-matricaria- γ-lactone (3), 4 E,8 Z-matricaria- γ-lactone (4), 9,12,13-trihydroxy-10(E)-octadecenoic acid (5), epifriedelanol (6), friedeline (7), taraxerol (8), simiarenol (9), spinasterol (10), stigmasterol, β-sitosterol, and apigenin. The structures were determined by means of ESIMS and 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, NOESY, HSQC, and HMBC experiments. The isolated compounds were evaluated for their antiproliferative activities and were demonstrated to exert considerable cell growth-inhibitory activity against human cervix adenocarcinoma (HeLa), skin carcinoma (A431), and breast adenocarcinoma (MCF-7) cells. Some of the active components, including 2, 4, and 10, proved to be substantially more potent against these cell lines than against noncancerous human foetal fibroblasts (MRC-5) and can therefore be considered selective antiproliferative natural products.

Topics: Antineoplastic Agents, Phytogenic; Apigenin; Cell Line, Tumor; Chemical Fractionation; Chromatography, High Pressure Liquid; Conyza; Female; Humans; Hydroxy Acids; Magnetic Resonance Spectroscopy; Molecular Structure; Oils, Volatile; Oleanolic Acid; Oleic Acids; Plant Extracts; Plant Roots; Pyrones; Sitosterols; Stigmasterol

The roots of Cyathula officinalis Kuan are widely used in Chinese medicine for the treatment of inflammatory disorders. Here, the ability of C. officinalis Kuan to downregulate matrix metalloproteinase (MMP)-13 was examined since MMP-13 is an important enzyme for the degradation of the cartilage collagen matrix, especially under arthritic conditions. The ethanol extract of C. officinalis Kuan as well as the N-hexane and chloroform soluble fractions were found to potently inhibit MMP-13 induction in IL-1 β-treated SW1353 cells, a human chondrosarcoma cell line, at 50-200 µg/mL. Activity-guided separation led to the isolation of six compounds, palmitic acid (1), β-sitosterol (2), α-spinasterol (3), atractylenolide I (4), 1,3-diacetoxy-tetradeca-6E,12E-dien-8,10-dyn (5), and N-trans-feruloyl-3-methyldopamine (6). Among these, 4 and 5 exhibited MMP-13 downregulating activity in IL-1 β-treated SW1353 cells. And 4 also showed anti-oedematous activity against λ-carageenan-induced paw edema in mice at 20-200 mg/kg, p. o. The results of this study provide information that can help elucidate the action mechanism of C. officinalis Kuan. In addition, the results presented here suggest that C. officinalis Kuan and its constituents may have the potential for chondroprotection against cartilage degrading disorders.

Topics: Acetates; Alkynes; Amaranthaceae; Animals; Carrageenan; Cartilage; Cell Line, Tumor; Chondrocytes; Chondrosarcoma; Disease Models, Animal; Dopamine; Down-Regulation; Edema; Humans; Hypolipidemic Agents; Interleukin-1beta; Lactones; Male; Matrix Metalloproteinase 13; Medicine, Chinese Traditional; Mice; Mice, Inbred ICR; Phytotherapy; Plant Extracts; Plant Roots; Sesquiterpenes; Sitosterols; Stigmasterol

Preparative high-speed counter-current chromatography (HSCCC), as a continuous liquid-liquid partition chromatography with no solid support matrix, combined with evaporative light scattering detection (ELSD) was employed for systematic separation and purification of non-chromophoric chemical components from Chinese medicinal herb Adenophora tetraphlla (Thunb.), Fisch. Nine compounds, including alpha-spinasterol, beta-sitosterol, nonacosan-10-ol, 24-methylene cycloartanol, lupenone, 3-O-palmitoyl-beta-sitosterol, 3-O-beta-d-glucose-beta-sitosterol, eicosanoic acid and an unknown compound, were obtained. The compounds were all above 95% determined by high-performance liquid chromatography (HPLC)-ELSD, and their structures were identified by (1)H NMR and chemical ionization mass spectroscopy (CI-MS). The results demonstrate that HSCCC coupled with ELSD is a feasible and efficient technique for systematic isolation of non-chromophoric components from traditional medicinal herbs.

Topics: Campanulaceae; Chromatography, High Pressure Liquid; Countercurrent Distribution; Light; Phytosterols; Plant Roots; Sitosterols; Stigmasterol; Triterpenes

The wood and bark of four Acacia species growing in Portugal, namely, A. longifolia, A. dealbata, A. melanoxylon, and A. retinodes, were investigated for their sterol content. The lipids fractions of the different wood and bark samples were isolated, and the sterols were identified and quantified by GC-MS. Two delta7 sterols, specifically, spinasterol and dihydrospinasterol, were the main sterols found in considerable amounts, particularly in wood tissues (more than 0.5 g/kg of dry wood in the case of A. melanoxylon and A. retinodes). The corresponding unusual steryl glucosides were also identified in significant amounts in the wood and bark extracts.

Topics: Acacia; Gas Chromatography-Mass Spectrometry; Glucosides; Phytosterols; Plant Stems; Portugal; Sitosterols; Stigmasterol; Wood

To separate compounds from the root of Gypsophila oldhamiana.. Chemical and chromatographic methods were used to separate the compounds. IR, MS, NMR were used to determine the structures of compounds.. Compound pentacosanoic acid, lacceroic acid, beta-sitosterol, alpha-spinasterol, daucosterol and sucrose were identified.. All the above compounds were obtained from this genus for the first time.

Topics: Caryophyllaceae; Plant Roots; Plants, Medicinal; Sitosterols; Stigmasterol

Eight compounds were separated from the roots of Achyrathes bidentata by repeated chromatography. On the basis of physicochemical properties and spectral analysis their structures were elucidated as alpha-spinasterol (1), beta-sitosterol (2), chrysophanol (3), dibutyl phthalate (4), palmitic acid (5), alpha-spinasterol-3-O-beta-D-glucoside (6), daucosterol (7) and ecdysterone (8). Compounds 1-7 were isolated from the plant for the first time.

Topics: Anthraquinones; Drugs, Chinese Herbal; Magnoliopsida; Molecular Structure; Plants, Medicinal; Sitosterols; Stigmasterol

A new bergenin derivative isolated from the root of Ardisia crenata was determined to be 11-o-syringylbergenin by spectral methods. Other compounds were identified as spinasterol, series fatty acids, beta-sitosterol-beta-D-glucoside, norbergenin and sucrose respectively. The last three were obtained for the first time from the genus of Ardisia.

Topics: Benzopyrans; Chemical Phenomena; Chemistry; Drugs, Chinese Herbal; Sitosterols; Stigmasterol; Sucrose

Effects of spinasterol and sitosterol on plasma and liver cholesterol levels and biliary and fecal sterol and bile acid excretions were examined with male mice. Both phytosterols were added to the diet at a 1% concentration and fed to mice for 15 days. Spinasterol increased the fecal cholesterol excretion and decreased the plasma and liver cholesterol levels, the bile acid pool size and the fecal bile acid excretion, especially those derived from chenodeoxycholic acid. Fecal coprostanol excretion remained unchanged. These changes were similar to those produced by sitosterol. These data led to the conclusions 1) that spinasterol, as well as sitosterol, inhibits cholesterol absorption, resulting in decreases of the plasma and liver cholesterol levels and 2) that when cholesterol absorption is inhibited, the synthesis of bile acids, especially that of chenodeoxycholic acid, decreases, suggesting that the dietary cholesterol is preferentially metabolized to chenodeoxycholic acid in mice.

Topics: Animals; Bile; Bile Acids and Salts; Body Weight; Cholesterol; Feces; Liver; Male; Mice; Phospholipids; Phytosterols; Sitosterols; Sterols; Stigmasterol

Topics: Plant Extracts; Plants, Medicinal; Sitosterols; Stigmasterol