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Journal articles on the topic 'Solasodine Synthesis'

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Published: 10 December 2022
Last updated: 29 January 2023

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1

Wojtkielewicz, Agnieszka, Urszula Kiełczewska, and Jacek W. Morzycki. "Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate." Molecules 24, no. 6 (March 21, 2019): 1132. http://dx.doi.org/10.3390/molecules24061132.

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A two-step synthesis of solasodine pivalate from diosgenin pivalate is described. The key transformation involves the reaction of diosgenin pivalate with benzyl carbamate (CbzNH2) promoted by TMSOTf. During the reaction the F-ring of the spiroketal moiety opens up with a simultaneous introduction of a Cbz-protected amino group in position 26. A one-pot deprotection of 26-amine with AcBr/BuOH followed by the N-cyclization affords solasodine pivalate in 45% overall yield.
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2

Paczkowski, C., M. Kalinowska, and Z. A. Wojciechowski. "UDP-glucose:solasodine glucosyltransferase from eggplant (Solanum melongena L.) leaves: partial purification and characterization." Acta Biochimica Polonica 44, no. 1 (March 31, 1997): 43–53. http://dx.doi.org/10.18388/abp.1997_4438.

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Uridine 5'-diphosphoglucose-dependent glucosyltransferase which catalyzes the glycosylation of solasodine i.e. UDP-glucose:solasodine glucosyltransferase, is present in leaves, roots, unripe fruits and unripe seeds of eggplant (Solanum melongena L.). The glucosylation product is chromatographically identical with authentic solasodine 3 beta-D-monoglucoside, a putative intermediate in the biosynthesis of solasodine-based glycoalkaloids characteristic of the eggplant. The enzyme was purified about 50-fold from crude cytosol fraction of eggplant leaves by ammonium sulphate precipitation and column chromatography on Q-Sepharose and Sephadex G-100. The native enzyme has a molecular mass of approx. 55 kDa and pH optimum of 8.5. Divalent metal ions are not required for its activity but the presence of free-SH groups is essential. Besides solasodine (Km = 0.04 microM), the enzyme effectively glucosylates tomatidine, another steroidal alkaloid of the spirosolane type, but it is virtually inactive towards the solanidane-type steroidal alkaloids such as solanidine or demissidine. The enzyme is specific for UDP-glucose (Km = 2.1 microM) since unlabelled ADP-, GDP-, CDP- or TDP-glucose could not effectively compete with UDP-[14C]glucose used as the sugar donor for solasodine glucosylation. Moreover, no synthesis of labelled solasodine galactoside was observed when UDP-[14C]glucose was replaced with UDP-[14C]galactose.
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3

Kiełczewska, Urszula, Jacek W. Morzycki, Lucie Rárová, and Agnieszka Wojtkielewicz. "The synthesis of solasodine F-homo-analogues." Organic & Biomolecular Chemistry 17, no. 40 (2019): 9050–58. http://dx.doi.org/10.1039/c9ob01888c.

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An efficient synthesis of F-homosolasodine analogues containing the 5/7 spirohemiaminal moiety was elaborated. The method benefited from an easy opening of diosgenin F-ring and the introduction of a cyano group in position 26.
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4

Kou, Yi, Myong Chul Koag, Young Cheun, Aram Shin, and Seongmin Lee. "Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate." Steroids 77, no. 11 (September 2012): 1069–74. http://dx.doi.org/10.1016/j.steroids.2012.05.002.

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5

Zhang, Gui-Ping, Si-Da Shen, Min Lei, and Li-Hong Hu. "A facile and efficient method for the synthesis of solasodine from diosgenin." Tetrahedron 67, no. 33 (August 2011): 5894–96. http://dx.doi.org/10.1016/j.tet.2011.06.058.

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6

Zha, Xiao Ming, Fei Ran Zhang, Jia Qi Shan, Yi Hua Zhang, Jun O. Liu, and Hong Bin Sun. "Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives." Chinese Chemical Letters 21, no. 9 (September 2010): 1087–90. http://dx.doi.org/10.1016/j.cclet.2010.04.020.

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7

Zha, Xiaoming, Hongbin Sun, Jia Hao, and Yihua Zhang. "Efficient Synthesis of Solasodine,O-Acetylsolasodine, and Soladulcidine as Anticancer Steroidal Alkaloids." Chemistry & Biodiversity 4, no. 1 (January 2007): 25–31. http://dx.doi.org/10.1002/cbdv.200790003.

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8

Manosroi, J., A. Manosroi, and P. Sripalakit. "EXTRACTION OF SOLASODINE FROM DRY FRUITS AND LEAVES OF SOLANUM LACINIATUM AIT. AND THE SYNTHESIS OF 16-DEHYDROPREGNENOLONE ACETATE FROM SOLASODINE BY PHASE-TRANSFER CATALYSIS." Acta Horticulturae, no. 679 (February 2005): 105–11. http://dx.doi.org/10.17660/actahortic.2005.679.12.

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9

Kiełczewska, Urszula, Radek Jorda, Gabriel Gonzalez, Jacek W. Morzycki, Haresh Ajani, Katarína Svrčková, Šárka Štěpánková, and Agnieszka Wojtkielewicz. "The synthesis and cholinesterase inhibitory activities of solasodine analogues with seven-membered F ring." Journal of Steroid Biochemistry and Molecular Biology 205 (January 2021): 105776. http://dx.doi.org/10.1016/j.jsbmb.2020.105776.

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10

Gazaliev, A. M., S. D. Fazylov, S. N. Balitskii, and R. Z. Kasenov. "Synthesis of organophosphorus derivatives of lupinine and solasodine and investigation of their cholinergic activities." Chemistry of Natural Compounds 28, no. 5 (September 1992): 472–73. http://dx.doi.org/10.1007/bf00630654.

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11

Shukla, Aniruddha, Shridhar Patil, and Sudhakar Bharti. "Microbial conversion of solasodine to 1-androstene-3,17-dione (AD), a key intermediate for androgen synthesis." Letters in Applied Microbiology 15, no. 3 (September 1992): 86–88. http://dx.doi.org/10.1111/j.1472-765x.1992.tb00732.x.

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12

Wu, Jing-Jing, Yong Shi, and Wei-Sheng Tian. "Facile synthesis of solasodine based on a mild halogenation-ring opening reaction of spiroketals in steroidal sapogenins." Tetrahedron Letters 56, no. 10 (March 2015): 1215–17. http://dx.doi.org/10.1016/j.tetlet.2015.01.149.

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13

Bora, Biswa Jyoti, and Dipak Kumar Goswami. "PHARMACOGNOSTIC AND PHYTO-PHYSICOCHEMICAL EVALUATION OF Solanum xanthocarpum Serb. & Wendl." International Ayurvedic Medical Journal p5, no. 5 (July 25, 2021): 2968–75. http://dx.doi.org/10.46607/iamj02p5052021.

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Medicinal plants are the backbone of Traditional systems of medicine like Ayurveda and Siddha. Solanum xanthcarpum (Solanaceae) (SX) is one of the most widely used medicinal herbs in Ayurvedic Pharmacopia. Me- dicinal plants have been of age-long remedy for human diseases because they contain components of therapeutic value. Plants are rich sources of ecologically developed secondary metabolites, which are potential remedies for different ailments. Kantakari (SX) of the family Solanaceae is one of the ‘dasamoola' and widely used drugs in Ayurveda. Dasamoola means a combination of ten plant roots together. It comprises roots of five big or major trees (Brihat panchmoola) and roots of five small trees or major herbs (Laghu panchmoola). Various studies indicated that SX contains steroidal glycoalkaloid solasodine, β-solamagrine and solasonine. The indigenous uses of plants also indicate anti-inflammatory, Antispermatogenic, Antidiabetic, Antiasthmatic, Molluscidal activity, useful in in- fantile atopical dermatitis, Cytoprotective, anticancer, insecticidal, insect repellent properties and diuretic activities. Therefore, the present investigation was intended to evaluate the preliminary phytochemical characters of this plant. The data and results of Phytochemical studies in the present study would facilitate discovery for the synthesis of more potent drugs. Keywords: Solanum xanthocarpum, Dasamoola, ethnobotanical uses, pharmacognosy, pharmacological activities,
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14

Rodriguez, J., R. Segovia, E. Guerreiro, F. Ferretti, G. Zamarbide De Sosa, and R. Ertola. "Production of solasodine by microbial hydrolysis of glycoalkaloids of Solanum eleagnifolium Cav. and its application to the synthesis of 16-dehydropregnenolone acetate." Journal of Chemical Technology and Biotechnology 29, no. 8 (April 24, 2007): 525–30. http://dx.doi.org/10.1002/jctb.503290810.

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15

thi Quyen, Le, Helmut Ripperger, Günter Adam, and Klaus Schreiber. "Solanum Alkaloids, 126. Degradation of Solasodine to 16β,22-Epoxy-23,24-dinorchol-5-ene-3β,22β-diol and Partial Synthesis of (23s)-23-Hydroxysolasodine." Liebigs Annalen der Chemie 1993, no. 2 (February 12, 1993): 167–72. http://dx.doi.org/10.1002/jlac.199319930130.

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16

LE THI QUYEN, LE THI QUYEN, H. RIPPERGER, G. ADAM, and K. SCHREIBER. "ChemInform Abstract: Solanum Alkaloids. Part 126. Degradation of Solasodine to 16β,22- Epoxy-23,24-dinorchol-5-ene-3β,22β-diol and Partial Synthesis of (23S)-23-Hydroxysolasodine." ChemInform 24, no. 25 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199325227.

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17

Cui, Changzhi. "Synthesis of solasodine glycoside derivatives and evaluation of their cytotoxic effects on human cancer cells." Drug Discoveries & Therapeutics, 2012. http://dx.doi.org/10.5582/ddt.2012.v6.1.9.

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18

Zha, Xiaoming, Hongbin Sun, Jia Hao, and Yihua Zhang. "Efficient Synthesis of Solasodine (Ia), O-Acetylsolasodine (Ib), and Soladulcidine (II) as Anticancer Steroidal Alkaloids." ChemInform 38, no. 20 (May 15, 2007). http://dx.doi.org/10.1002/chin.200720179.

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