- Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives
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Solasodine 11 is a steroidal alkaloid with various biological activities. Herein, 8 novel solasodine derivatives were synthesized and their effect on prostate cancer cell proliferation was assessed in vitro. Significant improvement in antiproliferative activity was achieved among some of the synthetic analogs. In particular, 19 exhibited the most potent inhibitory effect against the proliferation of PC-3 cell line (IC50=3.91μmol/L).
- Zha, Xiao Ming,Zhang, Fei Ran,Shan, Jia Qi,Zhang, Yi Hua,Liu, Jun O.,Sun, Hong Bin
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scheme or table
p. 1087 - 1090
(2011/10/05)
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- Solanum Alkaloids, 124, Preparation of N-Hydroxyspirosolane Alkaloids
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The N-Hydroxyspirosolane alkaloids N-hydroxysolasodine (1) and N-hydroxytomatidine (10) as well as the N-hydroxy-22,26-epiminocholestene 7 have been prepared by oxidation of the respective amines 2, 11, and 5 with hydrogen peroxide in the presence of selenium dioxide.Key Words: Solasodines / Tomatidines / Alkaloids / Solanum steroid alkaloids / Spirosolanes / Steroids
- Ripperger, Helmut
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p. 1091 - 1094
(2007/10/02)
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- Partial Synthesis of the Steroid Alkaloids Teinemine, 22-Isoteinemine, Etioline, and 25-Isoetioline
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The rare 16α-hydroxylated steroid alkaloids teinemine , 22-isoteinemine , etioline , and 25-isoetioline are synthesized from the abundant spirosolane alkaloids tomatid-5-en-3β-ol and solasodine , respectively.The crucial stages of these syntheses are the conversion of 1 or 15 into the N-protected (22S,25S)-, (22R,25S)-, and (22S,25R) -22,26-epimino-3β-hydroxycholest-5-en-16-ones 6, 7, and 18 as well as their reductions with sodium/2-propanol to the 16α-hydroxy compounds teinemine (8), 22-isoteinemine (10), and (22S,25R)-22,26-epiminocholest-5-ene-3β,16α-diol (19), respectively.By treatment with sodium methanolate the N-chloro derivatives 9 and 11 of 8 and 10 afford etioline (12).In an analogous manner, the N-chloro derivative 20 of 19 is converted into 25-isoetioline (21).
- Quyen, Le thi,Ripperger, Helmut,Schreiber, Klaus
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p. 143 - 149
(2007/10/02)
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- TWO STEROIDAL ALKALOIDS, HAPEPUNINE AND ANRAKORININE, FROM THE MATURE FRITILLARIA CAMTSCHATCENSIS
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Key word Index - Fritillaria camtschatcensis; Liliaceae; N-methyl-22,26-epiminocholestene; spirosolane. After acid hydrolysis of a glycosidic fraction from aerial parts of Fritillaria camtschatcensis, in addition to solanidine, tomatidenol, and solasodine, two N-methyl-22,26-epiminocholestenes, hapepunine and anrakorinine, were isolated and their structures elucidated by physical and chemical methods.
- Kaneko,Ko,Nakaoka, Utako,Tanaka, Mikako,Yoshida, Naotoshi,Mitsuhashi, Hiroshi
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p. 157 - 160
(2007/10/02)
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