Relevant bibliographies by topics / Solasodine Synthesis

Academic literature on the topic 'Solasodine Synthesis'

Author: Grafiati
Published: 10 December 2022
Last updated: 29 January 2023

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Journal articles on the topic "Solasodine Synthesis"

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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