546-40-7

Usage

InChI:InChI=1/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23-,24-,25-,26-,27?/m0/s1

Upstream product

• 4847-09-0 (3S,8S,9S,10R,13S,14S,17R)-17-[(S)-1-((2S,5S)-1-Chloro-5-methyl-piperidin-2-yl)-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 

Downstream Products

• 129850-54-0 (22R,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 
• 129939-91-9 (22S,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 
• 129938-50-7 (22R,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16α-diol 
• 129850-53-9 (22S,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16β-diol 
• 65027-00-1 22-Isoteimine 
• 1176-36-9 (3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-((2S,5S)-5-methyl-piperidin-2-yl)-ethyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 
• 29271-49-6 Etioline 

Relevant academic research and scientific papers

Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities

Steroidal glycosides (1-18), including 10 new compounds (1-10), were isolated from the bulbs of Fritillaria meleagris (Liliaceae). The structures of the new compounds were determined by two-dimensional (2D) NMR analysis, and by hydrolytic cleavage followed by spectroscopic and chromatographic analysis. The isolated compounds and their aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells. Morphological observation and flow cytometry analysis showed that 5β-spirostanol glycoside (2) and a cholestane derivative (17a) induced apoptotic cell death in HL-60 cells through different mechanisms of action. Furthermore, the (22R)-spirosolanol glycoside (11) selectively induced apoptosis in A549 cells without affecting the caspase-3 activity level.

Partial Synthesis of the Steroid Alkaloids Teinemine, 22-Isoteinemine, Etioline, and 25-Isoetioline

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).