Chapter 4. Synthesis of quercetin derivatives
4.5. Statistical analysis
실험 결과는 3번 반복실험 후 (SPSS version 22)를 이용하여 통계처리 하였으며, 실 험에 의해 얻어진 값들의 평균을±표준편차로 나타내었다. 대조군과 실험군 사이의 통계학적 유의성 검증은 t-Test 사용하였으며, p<0.05 수준에서 검정하였다.
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Table 8. Information of reactants (quercetin, 4-Nitrobenzyl bromide, Na2CO3, and DMSO)
Quercetin syn EXP ①
Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
4-Nitrobenzyl bromide 216.03 1.2 0.42885 g
Na2CO3 105.99 1.2 0.2104 g
DMSO 15 ml
Table 9. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc (7:3) 1~13
Hexane:EtOAc (5:5) 14~23
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Fig. 44. TLC bands of open column fractionations of nucleophile 4-Nitrobenzyl bromide reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 10. Information of loading solvents and test tube numbers
Label Test tube no.
Quercetin syn EXP ①-1 3
Quercetin syn EXP ①-2 4
Quercetin syn EXP ①-3 5~7
Quercetin syn EXP ①-4 8~10
Quercetin syn EXP ①-5 11~14
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Table 11. Information of reactants (quercetin, Benzyl bromide, Na2CO3, and DMSO)
Quercetin syn EXP ② Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
Benzyl bromide 171.03 1.2 236 μl
Na2CO3 105.99 1.2 0.2104 g
DMSO 15 ml
117
Fig. 45. TLC bands of synthesized quercetin derivatives after reaction for 4.5, 5.5, 11, and 6.6 hr.
Table 12. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc (8:2) 1~9
Hexane:EtOAc (7:3) 10~13
Hexane:EtOAc (5:5) 14~15
Hexane:EtOAc (3:7) 16~17
Hexane:EtOAc (0:10) 18~21
After 4.5 hr After 5.5 hr After 6.6 hr
118
Fig. 46. TLC bands of open column fractionations of nucleophile benzyl bromide reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 13. Information of samples and test tube numbers
Label Test tube no.
Quercetin syn EXP ②-1 1
Quercetin syn EXP ②-2 2~4
Quercetin syn EXP ②-3 5~10
Quercetin syn EXP ②-4 11
Quercetin syn EXP ②-5 12
Quercetin syn EXP ②-6 13~21
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Table 14. Information of reactants (quercetin, 4-Bromophenethyl bromide, Na2CO3, and DMSO)
Quercetin syn EXP ③
Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
4-Bromophenethyl bromide 263.96 1.2 303 μl
Na2CO3 105.99 1.2 0.2104 g
DMSO 15 ml
.
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Fig. 47. TLC bands of synthesized quercetin derivatives after reaction for 3.5, 4.5, 11, and 20.5 hr.
Table 15. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc (7:3) 1~2
Hexane:EtOAc (5:5) 3~7
Hexane:EtOAc (3:7) 8~9
Hexane:EtOAc (0:10) 10~15
After 3 hr 30 min
After 4 hr 30 min
After 11 hr
After 20 hr 30 min
Q
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Fig. 48. TLC bands of open column fractionations of nucleophile 4-Bromophenethyl bromide reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 16. Information of samples and test tube numbers
Labeling Test tube no.
Quercetin syn EXP ③-1 1
Quercetin syn EXP ③-2 2,3
Quercetin syn EXP③-3 4,5
Quercetin syn EXP ③-4 6,7
Quercetin syn EXP ③-5 8~12
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Table 17. Information of reactants (quercetin, 4-Methylphenethyl bromide, Na2CO3, and DMSO)
Quercetin syn EXP ④
Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
4-Methylphenethyl bromide 199.09 1.5 3,783 μl
Na2CO3 105.99 1.5 0.2630 g
DMSO 11 ml
123
Fig. 49. TLC bands of synthesized quercetin derivatives after reaction for 5, 6, 22, and 28 hr.
Table 18. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc 8:2 1
Hexane:EtOAc 7:3 2~7
Hexane:EtOAc 5:5 8,9
Hexane:EtOAc 3:7 10,11
EtOAc 10 12~15
After 5 hr
After 6 hr
After 22 hr
After 28 hr
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Fig. 50. TLC bands of open column fractionations of nucleophile 4-Methylphenethyl bromide reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 19. Information of samples and test tube numbers
Label Test tube no.
Quercetin syn EXP ④-1 1
Quercetin syn EXP ④-2 2
Quercetin syn EXP ④-3 3
Quercetin syn EXP ④-4 4
Quercetin syn EXP ④-5 5~6
Quercetin syn EXP ④-6 7
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Table 20. Information of reactants (quercetin, (s)-(+)-Citronellyl bromide, Na2CO3, and DMSO)
Quercetin syn EXP ⑤
Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
(s)-(+)-Citronellyl bromide 219.16 1.5 4,899 μl
Na2CO3 105.99 1.5 0.2630 g
DMSO 11 ml
126
Fig. 51. TLC bands of synthesized quercetin derivatives after reaction for 4, 15, 21, and 24 hr.
Table 21. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc 8:2 1~4
Hexane:EtOAc 7:3 5~6
Hexane:EtOAc 5:5 7
Hexane:EtOAc 3:7 8~10
EtOAc 10 11~12
After 4 hr
After 15 hr
After 21 hr
After 24 hr
127
Fig. 52. TLC bands of open column fractionations of nucleophile (s)-(+)-Citronellyl bromide reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 22. Information of samples and test tube numbers
Label Test tube no.
Quercetin syn EXP ⑤-1 1,2
Quercetin syn EXP ⑤-2 4
Quercetin syn EXP ⑤-3 4
Quercetin syn EXP ⑤-4 5~7
Quercetin syn EXP ⑤-5 8
Quercetin syn EXP ⑤-6 9
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Table 23. Information of reactants (quercetin, 1-Bromo-2-methylpropane, Na2CO3, and DMSO)
Quercetin syn EXP ⑥
Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
1-Bromo-2-methylpropane 137.02 1.5 2,699 μl
Na2CO3 105.99 1.5 0.2630 g
DMSO 12 ml
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Fig. 53. TLC bands of synthesized quercetin derivatives after reaction for 4, 15, and 21 hr.
Table 24. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc (7:3) 1~2
Hexane:EtOAc (5:5) 3~6
Hexane:EtOAc (3:7) 7~8
EtOAc (0:10) 9~10
After 4 hr
After 15 hr
After 21 hr
130
Fig. 54. TLC bands of open column fractionations of nucleophile 1-Bromo-2-methylpropane reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 25. Information of samples and test tube numbers
Label Test tube no.
Quercetin syn EXP ⑥-1 1
Quercetin syn EXP ⑥-2 2
Quercetin syn EXP ⑥-3 3,4
Quercetin syn EXP ⑥-4 5
Quercetin syn EXP ⑥-5 6
Quercetin syn EXP ⑥-6 7,8,9
131
Table 26. Information of reactants (quercetin, oleyl bromide, Na2CO3, and DMSO)
Quercetin syn EXP ⑦
Molecular Weight (g/mol)
Equivalent (eq)
Using weight
Quercetin 302.24 1 0.5 g
Oleyl bromide 331.37 1.5 8,256 μl
Na2CO3 105.99 1.5 0.2630 g
DMSO 12 ml
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Fig. 55. TLC bands of synthesized quercetin derivatives after reaction for 23 and 30 hr.
Table 27. Information of loading solvents and test tube numbers
Loading solvent Test tube no.
Hexane:EtOAc (8:2) 1~5
Hexane:EtOAc (7:3) 6~9
Hexane:EtOAc (5:5) 10~11
Hexane:EtOAc (3:7) 12~15
After 23 hr
After 30 hr
133
Fig. 56. TLC bands of open column fractionations of nucleophile oleyl bromide reacted with quercetin. Note that ‘Q’ is marked quercetin.
Table 28. Information of samples and test tube numbers
Label Test tube no.
Quercetin syn EXP ⑦-1 1
Quercetin syn EXP ⑦-2 2
Quercetin syn EXP ⑦-3 3
Quercetin syn EXP ⑦-4 4,5
Quercetin syn EXP ⑦-5 6~10
Quercetin syn EXP ⑦-6 11,12
Quercetin syn EXP ⑦-7 13,14
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