Farnesyl phenol compound, medicine composition thereof and application of farnesyl phenol compound
A technology of farnesylphenol and compounds, applied in the field of farnesylphenol compounds and their pharmaceutical compositions, capable of solving problems such as drug resistance, and achieving the effect of easy preparation and wide sources
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Embodiment 1
[0044] This embodiment mainly prepares a kind of farnesyl phenolic compound grifolin, and its structural formula is as follows:
[0045]
[0046] The preparation method is as follows: soak the fresh fruit body of Nigella nigella with ethanol at room temperature, and evaporate to dryness under reduced pressure to obtain 250 g of extract. The extract was crudely fractionated with normal phase silica gel and eluted with petroleum ether / ethyl acetate gradient. Ethyl acetate / acetone (20:1, V / V) obtained Fragment 1, which was eluted with chloroform / ethyl acetate (10:1, V / V) on a normal phase silica gel column to obtain compound grifolin. Among them, the compound grifolin is a yellow oil, and its molecular formula is C 22 h 32 o 2 .
[0047] The structure determination data are as follows: 1 H-NMR (CDCl 3):6.24(2H,s,H-1and H-3),5.28(1H,t,J=7.0Hz,H-2'),5.09(2H,m,H-6'and H-10'), 3.40(2H,t,J=7.0Hz, H-1'),2.21(3H,s,H-8),2.14~1.96(8H,m,H-4',H-5',H-8' and H-9'),1.69(3H,s,H-12'),...
Embodiment 2
[0049] This embodiment mainly prepares a kind of compound Ac-grifolin; Its structural formula is as follows:
[0050]
[0051] The preparation method of compound Ac-grifolin is as follows:
[0052]
[0053] Add 0.33g (1mmol) grifolin in the round bottom flask of 10mL, under N 2 Under protective conditions, 20 mL of anhydrous dichloromethane DCM was added, followed by 1.02 g (10 mol) of acetic anhydride and 0.79 g (10 mol) of pyridine. After reacting at room temperature for 8 hours, the solvent DCM was distilled off under reduced pressure. Add water, extract with ethyl acetate, wash the ethyl acetate phase with water three times, then wash with brine, anhydrous Na 2 SO 4 After drying, the solvent was distilled off under reduced pressure. Flash column chromatography with 4:1 eluent of chloroform and petroleum ether gave a pale yellow oil (compound Ac-grifolin); the yield was 92%.
[0054] The structure determination data are as follows: 1 HNMR (CDCl 3 ,500MHz)δ:6.24...
Embodiment 3
[0056] In this example, the inhibition experiments of Taxol (paclitaxel), grifolin and Ac-grifolin on the paclitaxel-resistant human lung adenocarcinoma cell line (A549 / Taxol) were mainly carried out. Specific steps are as follows:
[0057] Experimental reagents: RPMI1640 medium, fetal bovine serum were purchased from Biological Industries; PBS, Hank's balanced salt solution (HBSS), penicillin and streptomycin were purchased from Hyclone; 0.25% trypsin (containing EDTA) was purchased from Gibico Company; Taxol was purchased from Sigma-Aldrich; MTS reagent was purchased from Promega.
[0058] Experimental method: A549 / Taxol cells were mixed with prepared Taxol, grifolin and Ac-grifolin solutions on a 96-well cell culture plate, and three replicate wells were set, while a blank control without drugs was set. At 37°C, 5% CO 2 After culturing for 48 hours under the same conditions, the cytotoxicity was detected by the MTS colorimetric method, and the OD value was measured by a m...
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