290
D. Toczek et al.
9.6 Concluding Remarks
The above results suggest that polyphenol glycosides possess ability to form
complexes with calcium ions contained in calcium oxalate, the main component of kidney stones. Described above experiments and computations indicate
Table 9.6 The number of contacts O–Ca
2 + .
(N), relative interaction energy (ΔΔE int ), relative
enthalpy (ΔH), and relative free enthalpy (ΔG) for glucoside complexes, the atomic charge on Ca
and the C = O∙∙∙Ca
2 +
distance. Energy in kcal/mol, atomic Mulliken charge in electron, distance
in angstrom. The reference lowest interaction energy amounts to − 233.0 kcal/mol. (Springer and
the original publisher/Journal of molecular modeling, Theoretical studies of structure, energetics
and properties of Ca
2 +
complexes with alizarin glucoside, Toczek et al. [57], Table 9.3, original
copyright (2013) with kind permission from Springer Science and Business Media)
N
ΔΔE int ΔH ΔΔE int − ΔH ΔG
Atomic
charge on
Ca
2 +
Distances
C = O∙∙∙Ca
2 +
a_Gli_1S5_gt_
BEFO1O2_Ca(85)
5
7.8
13.0 − 5,2
12.8 1.367
2.28
a_Gli_1S5_gt_
BEFO1O2_Ca(-161)
5
8.4
16.9 − 8.5
16.6 1.373
2.30
a_Gli_1C4_gg_
BDFO1O2_Ca
5
9.5
9.1 0.4
10.1 1.374
2.28
a_Gli_1C4_gt_
BDFO1O9_Ca(-85)
5
14.5
23.2 − 8.7
23.6 1.356
2.34 (O9)
a_Gli_OS4_tg_BDO1O2_
Ca(75)
4
17.2
14.8 2.4
14.3 1.422
2.27
a_Gli_OS4_tg/
gg_BDO1O2_Ca(77)
4
18.4
12.6 5.8
12.4 1.426
2.27
a_Gli_OS4_gt_BDO1O2_
Ca(72)
4
18.7
18.8 − 0.1
17.9 1.423
2.27
a_Gli_25B_gt_DFO1O2_
Ca
4
23.3
25.3 − 2.0
24.6 1.409
2.26
a_Gli_1S5_gt_EFO1O9_
Ca
4
24.4
25.9 − 1.5
25.2 1.378
2.31 (O9)
b_Gli_OS2_gg_
CEFO1O2_Ca(-95)
5
0.0
0.0 0.0
0.0 1.365
2.28
b_Gli_O3B_gg_
CEFO1O2_Ca(168)
5
2.5
5.9 − 3.4
6.5 1.373
2.32
b_Gli_O3B_gg_
CEFO1O9_Ca(-42)
5
9.2
16.1 6.9
16.7 1.335
2.35 (O9)
b_Gli_2S4_gg/
gt_EFO1O2_Ca(-121)
4
14.5
15.5 − 1.0
15.7 1.410
2.27
b_Gli_OS4_gt_EFO1O9_
Ca(-75)
4
22.6
26.8 − 4.2
25.2 1.374
2.33 (O9)
b_Gli_OS2_gt_CFO1O2_
Ca
4
23.7
24.5 − 0.8
23.1 1.395
2.26
b_Gli_2SO_gg_
BEO1O2_Ca
4
29.5
32.3 − 2.8
31.7 1.411
2.27
b_Gli_4C1_gt_EFO1O9_
Ca(-59)
4
33.8
31.2 2.6
30.2 1.372
2.33 (O9)
b_Gli_4C1_gt_EFO1O9_
Ca(-83)
4
34.5
25.6 8.9
24.8 1.383
2.32 (O9)
D. Toczek et al.
9.6 Concluding Remarks
The above results suggest that polyphenol glycosides possess ability to form
complexes with calcium ions contained in calcium oxalate, the main component of kidney stones. Described above experiments and computations indicate
Table 9.6 The number of contacts O–Ca
2 + .
(N), relative interaction energy (ΔΔE int ), relative
enthalpy (ΔH), and relative free enthalpy (ΔG) for glucoside complexes, the atomic charge on Ca
and the C = O∙∙∙Ca
2 +
distance. Energy in kcal/mol, atomic Mulliken charge in electron, distance
in angstrom. The reference lowest interaction energy amounts to − 233.0 kcal/mol. (Springer and
the original publisher/Journal of molecular modeling, Theoretical studies of structure, energetics
and properties of Ca
2 +
complexes with alizarin glucoside, Toczek et al. [57], Table 9.3, original
copyright (2013) with kind permission from Springer Science and Business Media)
N
ΔΔE int ΔH ΔΔE int − ΔH ΔG
Atomic
charge on
Ca
2 +
Distances
C = O∙∙∙Ca
2 +
a_Gli_1S5_gt_
BEFO1O2_Ca(85)
5
7.8
13.0 − 5,2
12.8 1.367
2.28
a_Gli_1S5_gt_
BEFO1O2_Ca(-161)
5
8.4
16.9 − 8.5
16.6 1.373
2.30
a_Gli_1C4_gg_
BDFO1O2_Ca
5
9.5
9.1 0.4
10.1 1.374
2.28
a_Gli_1C4_gt_
BDFO1O9_Ca(-85)
5
14.5
23.2 − 8.7
23.6 1.356
2.34 (O9)
a_Gli_OS4_tg_BDO1O2_
Ca(75)
4
17.2
14.8 2.4
14.3 1.422
2.27
a_Gli_OS4_tg/
gg_BDO1O2_Ca(77)
4
18.4
12.6 5.8
12.4 1.426
2.27
a_Gli_OS4_gt_BDO1O2_
Ca(72)
4
18.7
18.8 − 0.1
17.9 1.423
2.27
a_Gli_25B_gt_DFO1O2_
Ca
4
23.3
25.3 − 2.0
24.6 1.409
2.26
a_Gli_1S5_gt_EFO1O9_
Ca
4
24.4
25.9 − 1.5
25.2 1.378
2.31 (O9)
b_Gli_OS2_gg_
CEFO1O2_Ca(-95)
5
0.0
0.0 0.0
0.0 1.365
2.28
b_Gli_O3B_gg_
CEFO1O2_Ca(168)
5
2.5
5.9 − 3.4
6.5 1.373
2.32
b_Gli_O3B_gg_
CEFO1O9_Ca(-42)
5
9.2
16.1 6.9
16.7 1.335
2.35 (O9)
b_Gli_2S4_gg/
gt_EFO1O2_Ca(-121)
4
14.5
15.5 − 1.0
15.7 1.410
2.27
b_Gli_OS4_gt_EFO1O9_
Ca(-75)
4
22.6
26.8 − 4.2
25.2 1.374
2.33 (O9)
b_Gli_OS2_gt_CFO1O2_
Ca
4
23.7
24.5 − 0.8
23.1 1.395
2.26
b_Gli_2SO_gg_
BEO1O2_Ca
4
29.5
32.3 − 2.8
31.7 1.411
2.27
b_Gli_4C1_gt_EFO1O9_
Ca(-59)
4
33.8
31.2 2.6
30.2 1.372
2.33 (O9)
b_Gli_4C1_gt_EFO1O9_
Ca(-83)
4
34.5
25.6 8.9
24.8 1.383
2.32 (O9)