2400
J. Gao et al. / Bioorg. Med. Chem. Lett. 22 (2012) 2396–2400
Figure 3. The accumulation of intracellular ROS in MCF-7cells after 2 (1, 2, 3
MCF-7 cells treated with various concentrations of 2. (B) Column bar graphs show the fluorescence intensities of DCF in the MCF-7 cells treated with or without 2. Results
were expressed as the mean S.D. of three independent experiments. ⁄p <0.05 and ⁄⁄p <0.01 versus the 0
M saponin 2 group.
lM) treatment for 24 h. (A) Representative peak observed during flow cytometric analysis of the
l
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Figure 4. Saponin 2 induced the decrease of mitochondrial membrane potential
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(D
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for cancer treatment, and much more work about the biological
mechanism by which 2-induced apoptosis is currently ongoing.
23. General procedure for preparation of compounds 24–29: To a cooled solution
(ꢀ40 °C) of each aglycon (0.25 mmol, 21, 22, or 23), 4 Å molecular sieves
(400 mg) and dichloroacetimidate (300 mg, 0.25 mmol, 16 or 17) in anhydrous
Acknowledgments
CH2Cl2 (7 mL) was added TMSOTf (4.5 lL, 0.025 mmol) under N2 protection.
The mixture was stirred for 45 min, neutralized with Et3N, filtered and
concentrated under reduced pressure. The residue was dissolved in pyridine
This work was financially supported by National Natural
Science Foundation of China (No. 81172956) and the Shandong
Provincial Foundation (Nos. 06GG1102023 and ZR2010BQ004).
(10 mL) and added HF-Pyridine (400 lL) at 0 °C. The mixture was stirred at
room temperature for 24 h, poured into aq NaHCO3 (30 mL), and extracted
with EtOAc (3 ꢂ 30 mL). The combined EtOAc extracts are sequentially washed
with 5% aq HCl (3 ꢂ 80 mL), brine (3 ꢂ 80 mL), dried over Na2SO4 and
concentrated in vacuo. The crude product was purified by flash column
chromatography (SiO2) with a 5:1 solution of petroleum ether-EtOAc to afford
the partially protected glycosides 24–29 in the form of b isomer with the yields
ranging from 84% to 87% for two steps.
Supplementary data
Supplementary data associated with this article can be found, in
24. Carreira, E. M.; Bois, J. D. J. Am. Chem. Soc. 1995, 117, 8106.
25. Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron Lett. 2001, 42,
3857.
References and notes
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