322 0009-3130/16/5202-0322
©
2016 Springer Science+Business Media New York
Chemistry of Natural Compounds, Vol. 52, No. 2, March, 2016
METHOD FOR OBTAINING TOTAL FLAVONOIDS FROM
Climacoptera subcrassa AND THEIR BIOLOGICAL ACTIVITY
A. K. Kipchakbaeva,
1
R. A.-A. Khamid,
1,2
B. K. Eskalieva,
1*
G. Sh. Burasheva,
1
Zh. A. Abilov,
1
S. R. Numonov,
3
and H. A. Aisa
3
Isolation of biologically active compounds (BAC) from plants is an important step in drug manufacturing. Therefore,
the analysis of and search for modern and effective methods for isolating valuable BAC raw materials for the drug industry
have definite theoretical and practical interest [1, 2].
Column chromatography over macroporous AV-8 resin was used to separate total flavonoids. This method was used
for the first time to separate total flavonoids from the aerial part of Climacoptera subcrassa (Chenopodiaceae).
Total flavonoids from C. subcrassa were purified over the macroporous adsorption resin. Their contents were
determined using UV spectrophotometry. The conditions for purifying them using AV-8 macroporous resin were optimized.
EtOH (70%) gave the highest yield (3.4 g) of flavonoids from the plant (100 g); 50% EtOH, 2.2 g; 80% EtOH, 2.75 g; and 95%
EtOH, 1.60 g. The maximum static adsorption capacity was 23.06 mg/g of resin; adsorption rate, 89.22 mL/min; absorption
time, 2 h at 80°C. Under these conditions, up to 90.8% of total flavonoids were isolated. Total flavonoids from the 70%
EtOH extract showed pronounced antioxidant activity with IC
50
= 49.66 ± 4.57 g/mL. The standard was vitamin C with
IC
50
= 5.34 ± 0.42 g/mL [3, 4].
Compounds 1–5 were isolated using AV-8 macroporous resin and HPLC and were identified using physicochemical
data and comparisons with the literature.
Quercetin (1). C
15
H
10
O
7
, light-yellow crystals, mp 315–316C. ESI-MS, m/z 301.03 [M – H]
–
.
1
Í NMR spectrum
(400 MHz, MeOH-d
4
, , ppm, J/Hz): 7.73 (1H, d, J = 2.0, H-2), 7.63 (1H, dd, J = 2.0, 8.5, H-6), 6.89 (1H, d, J = 8.5, H-5),
6.39 (1H, d, J = 1.9, H-8), 6.19 (1H, d, J = 1.9, H-6) 5.
Quercetin 3-O--D-Glucopyranoside (2). C
21
H
20
O
12
, light-yellow crystals, mp 269–271C. ESI-MS m/z: 477
[M – H]
–
, 315 [M – H – 162]
–
.
1
Í NMR spectrum (400 MHz, Py-d
5
, , ppm, J/Hz): 7.89 (1H, d, J = 2.4, H-2), 7.55 (1H, dd,
J = 8.8, 2.4, H-6), 7.06 (1H, d, J = 1.6, H-8), 7.04 (1H, d, J = 8.8, H-5), 7.03 (1H, s, H-3), 6.86 (1H, d, J = 1.6, H-6), 5.56 (1H,
d, J = 7.2, H-1), 4.57 (1H, d, J = 12.4, H-6), 4.43 (1H, d, J = 8.8, H-3), 4.40 (1H, dd, J = 12.4, 5.2, H-6), 4.37 (1H, d,
J = 8.8, H-2), 4.37 (1H, d, J = 8.8, H-4), 4.25 (1H, d, J = 8.8, H-5), 3.80 (3H, s, OCH
3
).
13
C NMR spectrum (100 MHz,
Py-d
5
, , ppm): 165.2 (C-2), 105.2 (C-3), 183.3 (C-4), 163.6 (C-5), 101.1 (C-6), 164.5 (C-7), 95.8 (C-8), 158.3 (C-9), 107.0
(C-10), 124.7 (C-1), 114.9 (C-2), 149.5 (C-3), 152.5 (C-4), 112.5 (C-5), 119.3 (C-6), 56.3 (OCH
3
), 102.2 (C-1), 75.2
(C-2), 78.9 (C-3), 71.5 (C-4), 79.7 (C-5), 62.7 (C-6) [6].
Rutin (3). C
27
H
30
O
16
, light-yellow crystals, mp 242C. ESI-MS m/z: 609 [M – H]
–
, 301 [M – H – 162 – 146]
–
.
1
Í NMR
spectrum (400 MHz, Py-d
5
, , ppm, J/Hz): 7.66 (d, J = 1.7, Í-2), 7.63 (dd, J = 8.4, 1.7, Í-6), 6.8 (d, J = 8.4, Í-5), 6.4 (d,
J = 1.7, Í-8), 6.2 (d, J = 1.6, Í-6), 5.19 (d, J = 7.5, Í-1), 4.5 (s, Í-1), 0.8 (3Í, s, ÑÍ
3
) 6.
3-O-Methylquercetin (4). C
16
H
12
O
7
, light-yellow crystals, mp 269–271C. ESI-MS m/z 315 [M – H]
–
.
1
Í NMR
spectrum (400 MHz, Py-d
5
, , ppm, J/Hz): 8.64 (1H, d, J = 2.2, H-2), 8.14 (1H, dd, J = 8.4, 2.2, H-6), 7.59 (1H, s), 7.41 (1H,
d, J = 8.5, H-5), 7.22 (1H, d, J = 1.5), 6.78 (1H, d, J = 2.0, H-8), 6.74 (1H, d, J = 2.0, H-6), 3.91 (3H, s, OCH
3
).
13
C NMR
spectrum (100 MHz, Py-d
5
, , ppm): 145.3 (Ñ-2), 137.9 (Ñ-3), 177.3 (Ñ-4), 162.4 (Ñ-5), 99.2 (Ñ-6), 165.5 (Ñ-7), 94.3 (Ñ-8),
157.5 (Ñ-9), 104.5 (Ñ-10), 123.8 (Ñ-1), 116.7 (Ñ-2, 5), 147.1 (Ñ-3), 147.7 (Ñ-4), 121.0 (Ñ-6), 55.4 (OCH
3
) [7].
1) Al-Farabi Kazakh National University, Department of Chemistry and Chemical Technology, 71 Al-Farabi Prosp.,
Almaty, 050040 Kazakhstan, fax: (+7 727) 292 37 31, e-mail: balakyz@mail.ru; 2) Al Azhar University, Faculty of Pharmacy,
Assiut, Egypt; 3) Xinjiang Technical Institute of Physics and Chemistry, CAS, 830011, Urumqi, P. R. China. Translated from
Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2016, pp. 281–282. Original article submitted May 8, 2015.
DOI 10.1007/s10600-016-1630-7