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EN
The crystal of racemic narlumicine, C21H21NO7, 6-[[6-[2-(dimethylamino) ethyl]-1,3-benzodioxol-5-yl]hydroxymethyl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one, have been investigated by X-ray diffraction methods. The crystal are monoclinic, space group P2-1c,a=10,792(2), b=18.064(4), c=10.053(3)A, beta=104.77(3)degree, Z=4. The structure was solved by direct methods and refined to R=0.036 for 2149 observed reflections. The three-cycle and two-cycle moieties are nearly planar and the dihedral angle between them is 63.5 degree. The sum of bond angles around the nitrogen atom is 330.2 degree. The fourth apex of the pyramid is pccupated by O-H...N hydrogen bond. The intermolecular hydrogen bond O-H...N (2.716(5)A) links the molecules into chains parallel to the y axis.
EN
A novel scheme for modeling 3D QSAR has been developed. A method involving multiple self-organizing neural network adjusted to be analyzed by the PLS (partial least squares) analysis was used to model 3D QSAR of the selected colchicinoids. The model obtained allows the identification of some structural determinants of the biological activity of compounds.
EN
Aegle marmelos Correa (Bael tree) is a medicinal fruit tree, widely used for healing purposes in various systems of medicines. Coumarins and alkaloids present in various parts of bael tree including roots and fruit pulp are the primary active constituents implicated for its biological activities. An efficient liquid chromatography–electrospray ionization—tandem mass spectrometry (LC—ESI—MS/MS) method was developed for identification and simultaneous determination of four coumarin derivatives, namely, umbelliferone, psoralene, marmin, and imperatorin, and an alkaloid, skimmianine, in root and stem bark of A. marmelos. The chromatographic separation of analytes was performed on Altima C18 (50 × 4.6 mm, 3 μm) column using methanol and 0.1% acetic acid in water (54:46, v/v) as the mobile phase under isocratic conditions. The LC–MS/MS parameters were optimized in the positive ionization mode using electrospray ionization source. The quantification of the analytes was performed using multiple reaction monitoring (MRM) transitions, umbelliferone (m/z 163.1 → 107.1), psoralene (m/z 187.2 → 131.1), marmin (m/z 333.5 → 163.2), imperatorin (m/z 271.1 → 203.1), and skimmianine (m/z 260.1 → 227.0). The extraction method was standardized for optimum yield of coumarin derivatives and the alkaloid in different extraction solvents. Higher yield of the analytes was found in methanolic extracts in comparisons to petroleum ether, chloroform, ethyl acetate, ethanol, and water. The method was validated for linear range, intra- and inter-batch precision and accuracy. The distribution of coumarin derivatives and an alkaloid was found to vary significantly in different plant samples, and their concentration was much higher in roots as compared to stem bark.
PL
Badano wpływ ostrego i 10-dniowego podawania ip alkaloidów protopinowych: allokryptopiny protopiny na aktywność aminotransferaz ALT i AST, a także oznaczano poziom a-fetoproteiny (AFP) oraz ß2-mikroglobuliny w surowicy krwi szczurów. Stwierdzono, że protopina zastosowana szczurom jednorazowo zwiększała, bądź zmniejszała aktywność AST. Protopina podawana przez 10 dni istotnie zwiększała, aktywność AST i pozostawała bez wpływu na aktywność ALT. Allokryptopina podana jednorazowo w dawce 0,1 LD50 istotnie zmniejszała, natomiast podawana przez 10 dni pozostawała bez wpływu na aktywność obu aminotransferaz. Oba badane alkaloidy nie wpływały na poziom AFP i ß2-mikroglobuliny.
EN
The effects of acute and 10-day treatment with protopine-type alkaloids: protopine and allocry- ptopine on the activity of aminotransferases (ALT, AST) were investigated in the serum of rats. Besides, the serum a-fetoprotein (AFP) and ß2-microglobulin levels were estimated. It was found that, the single treatment with protopine significantly increased or decreased the activity of AST. 10-day treatment with protopine did not affect the activity of ALT but a significant increase of the activity of AST was observed. Single administration of allocryptopine in a dose of 0,1 LD50 significantly decreased the activity of AST. No characteristic changes were found in the activity of aminotransferases in the serum rats receiving allocryptopine for 10-days. Single and 10-days treatment with investigated alkaloids did not affect in the serum of AFP and of ß2-microglobulin levels.
EN
Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report the synthesis of five new vindoline derivatives, 15-(2-methoxyphenyl)vindoline 11, 15-(3-methoxyphenyl)vindoline 12, 15-(2-nitrophenyl)vindoline 13, 15-(3-cyanophenyl)vindoline 15, and 15-(4-cyanophenyl)vindoline 16 using the Suzuki-Miyaura reaction as the key step. X-Ray analysis of compound 16 is also reported
EN
 Biotransformation of deuterated-4'-O-methylnorbelladine into alkaloids galanthamine and lycorine in tissue cultures of Leucojum aestivum was demonstrated using HPLC coupled to mass spectrometry. GC-MS screening was also carried to investigate other native and deuterated alkaloids. A total of six labeled alkaloids were identified indicating that 4'-O-methyl-d3-norbelladine is incorporated into three different groups of Amaryllidaceae alkaloids that are biosynthesized by three modes of intramolecular oxidative phenol coupling.
EN
The alkaloids dehydrocorydalmine and oxyberberine isolated from Argemone mexicana were assessed against spore germination of some fungi, e.g., Alternaria cajani, Bipolaris sp., Helminthosporium sp., Fusarium udum and Curvularia sp. While dehydrocorydalmine inhibited 100% spore germination of the fungi Helminthosporium sp. and Curvularia sp. at 5 000 ppm, oxyberberine showed similar activity against spore germination of Bipolaris sp. and Curvularia sp. All the five fungi were significantly inhibited at 1 000 to 5 000 ppm concentrations.
PL
Określano wpływ alkaloidów dehydrokorydalminy i oksyberberyny wyosobnionych z Argemone mexicana na kiełkowanie zarodników niektórych grzybów, w tym Alternaria cajani, Bipolaris sp., Helminthosporium sp., Fusarium udum i Curvularia sp. Podczas gdy dehydrokory-dalmina inhibowała w 100% kiełkowanie zarodników grzybów Helminthosporium sp. i Curvularia sp. w stężeniu 5 000 ppm, oksyberberyna wykazywała podobną aktywność przeciwko kiełkowaniu zarodników Biopolaris sp. i Curvularia sp. Wszystkie pięć grzybów było istotnie inhibitowane w stężeniach od 1 000 do 5 000 ppm.
EN
The objective of our studies were seeds of two lupin species Lupinus luteus L. and Lupinus angustifolius L. cvs. Lord and Graf respectively. Lupin seeds were germinated at 15 and 24°C and during two, three and four days. In the lupin sprouts antinutritional factors: alkaloids and raffinose family oligosaccharides (RFOs) and five nitrogen fractions: non protein (Nnp), albumin (A), globulin (G), glutelin and prolamin (Gt+P) and nitrogen residue fraction (Nr) were determined. The level of these compounds was compared with the proper ones of initial material (not germinated seeds). These studies showed that the germination process clearly affects the decrease of antinutritional factors: RFOs and alkaloids. The decrease level of these compounds depended on such factors like, lupin species and used germination conditions. It was found on the base of nitrogen analysis of particular protein fractions that the germination process of lupin seeds causes deep quantitative and qualitative changes in fractional composition of lupin proteins. It especially concerns the decrease of globulin and residual fraction content and distinct increase of Nnp fraction. The changes in other fractions were not so unequivocal in comparison with the mentioned above and depended on lupin species, temperature and time of germination. Qualitative changes of A, G and Gt+P fractions caused by germination were confirmed by gel electrophoresis (SDS-PAGE). The amino acid analysis of seeds and sprouts of Nnp fractions showed an increased content of Asp, Ser, Ala, Pronon essential amino acids (NEAA), and Val, Met, iLeu, Leu, Thressential amino acids (EAA). Simultaneously a decrease of Glu, Arg (NEAA), Phe, Lis, Cys (EAA) contents was observed. Generally the germination process causes the decrease of total NEAA and an increase of total EAA in Nnp fractions of both lupin species.
EN
Biological activity of secondary plant substances: glucosinolates, alkaloids and saponins in relation to Colorado potato beetle, Leptinotarsa decemlineata was studied in detail. Larvae and adult insects were reared on potato leaves sprayed with tested compounds applied in three different concentrations. The insect behaviour, mortality and weight changes were observed. Among examined chemicals saponins proved to be the most active against Colorado potato beetle. They showed antifeedant properties and caused high larval mortality.
PL
Badano aktywność biologiczną wtórnych związków roślinnych: glukozynolanów, alkaloidów i saponin wyrażoną ich wpływem na rozwój stonki ziemniaczanej (Leptinotarsa decemlineata Say). Prowadzono hodowle larw oraz chrząszczy stonki na liściach ziemniaka traktowanych badanymi związkami, w 3 różnych stężeniach. Określono zachowanie, przeżywalność oraz zmiany wagi zarówno larw jak i chrząszczy w trakcie trwania hodowli. Spośród testowanych związków najwyższą aktywność biologiczną w stosunku do stonki wykazały saponiny - powodując znaczne ograniczenie żerowania oraz wysoką śmiertelność owadów, przy czym larwy były znacznie bardziej wrażliwe niż chrząszcze. Działanie saponin nie polegało na ich toksycznym działaniu lecz wykazały one silne właściwości antyfidantne w stosunku do stonki ziemniaczanej.
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