DOI 10.1007/s10600-025-04595-5
Chemistry of Natural Compounds, Vol. 61, No. 1, January, 2025
ISOLATION AND IDENTIFICATION OF FLAVONOIDS
FROM Artemisia persica
J. Umaraliev,1,2 A. Turak,1 A. A. Ganiev,3
N. B. Begmatov,3 Bo Zhao,1 Kh. M. Bobakulov,3,4*
N. D. Abdullaev,3 and J. Zhao1,2*
The genus Artemisia L. is rich in phenolic compounds and flavonoids that exhibit various biological properties,
including anticancer, antioxidant, anti-inflammatory, and antiviral activity [1]. Flavonoids are some of the main constituents
among the numerous biologically active compounds that are responsible for the many pharmacological properties of plants of
the genus Artemisia. This makes them valuable for phytotherapy [2, 3]. Many plants of the genus Artemisia are commonly
used in traditional Chinese medicine to treat diseases such as malaria, hepatitis, cancer, inflammation, and infections caused by
fungi, bacteria, and viruses [4, 5].
Herein, flavonoids from the aerial part of A. persica Boiss. collected in Pop District, Namangan Region, Republic of
Uzbekistan, during flowering in August 2020 were studied. The extract obtained by extracting air-dried plant raw material (13 kg)
with EtOH (95%) was fractionated by hexane, CHCl3, EtOAc, and n-BuOH using liquid−liquid extraction.
The CHCl3 fraction (348 g) was worked up over a column of silica gel (100–200 mesh) using a polarity gradient of
hexane, CHCl3 , and MeOH to afford 31 subfractions. Subfraction 6 (hexane–CHCl3, 80:1) was further fractionated into
11 fractions (A-L) by flash chromatography (BUCHI Sepacore C600, LiChroprep RP18 column, H2O–MeCN, 10→100%,
150 min). Fractions F and G were purified over a column of Sephadex LH-20 sorbent (CHCl3−MeOH, 10:1) to isolate compound 1
from fraction F and 2 from fraction G.
Compounds 3, 4, 8, 9, and 10 were obtained by initial workup of subfraction 4 (hexane–CHCl3, 100:1) over a column
of Sephadex LH-20 (MeOH mobile phase) followed by purification of them by semipreparative HPLC (Hanbon Sci&Tech,
XSelect HSS T3 OBD column, isocratic 30% MeCN–H3O+). Workup of subfraction 12 (hexane–CHCl3, 40:1) over a column
of Sephadex LH-20 (MeOH mobile phase) isolated 5 and 6. Compounds 11 and 12 were obtained by rechromatography of
subfraction 24 (CHCl3–MeOH, 9:1) over a column of Sephadex LH-20 (MeOH–H2O, 9:1).
A total of 12 flavonoids were isolated from the CHCl3 fraction. The structures of the isolated compounds were elucidated
using 1D and 2D NMR spectroscopy and comparison of obtained spectral data with the literature. The isolated flavonoids were
identified as hispidulin (1), chrysoeriol (2), 5-hydroxy-4′,7-dimethoxyflavone (3), santin (4), quercetin (5), patuletin (6),
homoeriodictyol (7), acacetin (8), genkwanin (9), pectolinarigenin (10), rutin (11), and patuletin-3-O-rutinoside (12).
Hispidulin (1), yellow powder, mp 254–256°C. The 1H and 13C NMR spectra agreed with those published [6].
Chrysoeriol (2), yellow powder, mp 305–306°C. The 1H and 13C NMR spectra agreed with those published [7].
5-Hydroxy-4′,7-dimethoxyflavone (3), yellow powder, mp 524–526°C. 1Í NMR (600 MHz, DMSO-d6, δ, ppm, J/Hz):
12.92 (1H, s, 5-OH), 8.06 (2H, d, J = 8.9, H-2′, 6′), 7.12 (2H, d, J = 8.9, H-3′, 5′), 6.93 (1H, s, H-3), 6.79 (1H, d, J = 2.3,
H-8), 6.38 (1H, d, J = 2.3, H-6), 3.87 (3H, s, 7-OCH3), 3.87 (3H, s, 4′-OCH3). 13Ñ NMR (150 MHz, DMSO-d6, δ, ppm):
1) State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and the Key Laboratory
of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of
Sciences, 830011, Urumqi, P. R. China, e-mail: zhaojy@ms.xjb.ac.cn; 2) University of Chinese Academy of Sciences, 100049,
Beijing, P. R. China; 3) S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic
of Uzbekistan, 77 Mirzo Ulugbek St., Tashkent, 100170, Uzbekistan, e-mail: khayrulla@rambler.ru; 4) National Research
University Tashkent Institute of Irrigation and Agricultural Mechanization Engineers, 39 Kori Niyazov St., Tashkent, 100000,
Uzbekistan. Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2025, pp. 132–134. Original article
submitted June 27, 2024.
0009-3130/25/6101-0153 ©2025 Springer Science+Business Media, LLC
153
163.61 (C-2), 103.70 (C-3), 181.97 (C-4), 161.18 (C-5), 98.02 (C-6), 165.19 (C-7), 92.73 (C-8), 157.26 (C-9), 104.72 (C-10),
122.69 (C-1′), 128.38 (C-2′, 6′), 114.59 (C-3′, 5′), 162.42 (C-4′), 56.07 (7-OCH3), 55.59 (4′-OCH3) [8].
Santin (4), yellow powder, mp 305–306°C. 1Í NMR (400 MHz, DMSO-d6, δ, ppm, J/Hz): 12.73 (1H, s, 5-OH),
10.81 (1H, br.s, 7-OH), 8.02 (2H, d, J = 9.0, H-2′, 6′), 7.13 (2H, d, J = 9.0, H-3′, 5′), 6.58 (1H, s, H-8), 3.86 (3H, s, OCH3), 3.79
(3H, s, OCH3), 3.76 (3H, s, OCH3). 13Ñ NMR (100 MHz, DMSO-d6, δ, ppm): 155.25 (C-2), 137.60 (C-3), 178.22 (C-4),
152.39 (C-5), 131.17 (C-6), 157.44 (C-7), 94.08 (C-8), 151.60 (C-9), 104.67 (C-10), 122.22 (C-1′), 129.99 (C-2′, 6′), 114.24
(C-3′, 5′), 161.34 (C-4′), 59.97 (OCH3), 59.76 (OCH3), 55.44 (OCH3) [9].
Quercetin (5), yellow powder, mp 316–317°C. The 1H and 13C NMR spectra agreed with those published [10].
Patuletin (6), yellow powder, mp 268–270°C. 1Í NMR (600 MHz, DMSO-d6, δ, ppm, J/Hz): 12.56 (1H, s, 5-OH),
7.67 (1H, d, J = 2.2, H-2), 7.54 (1H, dd, J = 8.5, 2.2, H-6), 6.88 (1H, d, J = 8.5, H-5), 6.52 (1H, s, H-8), 3.76 (3H, s, 6-OCH3).
13Ñ NMR (150 MHz, DMSO-d , δ, ppm): 146.91 (C-2), 135.38 (C-3), 176.02 (C-4), 151.72 (C-5), 130.80 (C-6), 151.35 (C-7),
6
93.60 (C-8), 157.17 (C-9), 103.35 (C-10), 121.97 (C-1′), 115.57 (C-2′), 144.99 (C-3′), 147.65 (C-4′), 115.02 (C-5′), 120.00
(C-6′), 60.00 (6-OCH3) [11].
Homoeriodictyol (7), yellow powder, mp 224–226°C. 1Í NMR (400 MHz, DMSO-d6, δ, ppm, J/Hz): 12.19 (1H,
br.s, 5-OH), 8.40 (1H, br.s, 4′-OH), 7.08 (1H, d, J = 1.8, H-2′), 6.89 (1H, dd, J = 8.1, 1.8, H-6′), 6.79 (1H, d, J = 8.1, H-5′), 5.82
(1H, d, J = 1.9, H-8), 5.80 (1H, d, J = 1.9, H-6), 5.38 (1H, dd, J = 12.8, 2.9, H-2), 3.78 (3H, s, 3′-OCH3), 3.26 (1H, dd, J = 17.1,
12.8, H-3α), 2.63 (1H, dd, J = 17.1, 2.9, H-3β). 13Ñ NMR (100 MHz, DMSO-d6, δ, ppm): 78.52 (C-2), 42.11 (C-3), 195.47
(C-4), 162.77 (C-5), 96.24 (C-6), 166.0 (C-7), 95.49 (C-8), 163.53 (C-9), 102.0 (C-10), 129.57 (C-1′), 111.13 (C-2′), 146.94
(C-3′), 147.53 (C-4′), 115.15 (C-5′), 119.61 (C-6′), 55.66 (3′-OCH3) [12].
Acacetin (8), yellow powder, mp 228–230°C. 1Í NMR (500 MHz, DMSO-d6, δ, ppm, J/Hz): 12.93 (1H, s, 5-OH),
10.87 (1H, s, 7-OH), 8.03 (2H, d, J = 9.0, H-2′, 6′), 7.11 (2H, d, J = 9.0, H-3′, 5′), 6.86 (1H, s, H-3), 6.51 (1H, d, J = 2.1, H-8),
6.21 (1H, d, J = 2.1, H-6), 3.86 (3H, s, 4′-OCH3). 13Ñ NMR (125 MHz, DMSO-d6, δ, ppm): 163.30 (C-2), 103.54 (C-3),
181.79 (C-4), 161.47 (C-5), 98.90 (C-6), 164.23 (C-7), 94.05 (C-8), 157.35 (C-9), 103.78 (C-10), 122.83 (C-1′), 128.32 (C-2′,
6′), 114.58 (C-3′, 5′), 162.31 (C-4′), 55.56 (4′-OCH3) [13].
Genkwanin (9), yellow powder, mp 279–281°C. 1Í NMR (500 MHz, DMSO-d6, δ, ppm, J/Hz): 12.97 (1H, s, 5-OH),
10.40 (1H, s, 4′-OH), 7.69 (2H, d, J = 8.9, H-2′, 6′), 6.94 (2H, d, J = 8.9, H-3′, 5′), 6.84 (1H, s, H-3), 6.76 (1H, d, J = 2.3,
H-8), 6.37 (1H, d, J = 2.3, H-6), 3.87 (3H, s, 7-OCH3). 13Ñ NMR (125 MHz, DMSO-d6, δ, ppm): 164.06 (C-2), 103.02 (C-3),
181.94 (C-4), 161.21 (C-5), 97.95 (C-6), 165.12 (C-7), 92.67 (C-8), 157.23 (C-9), 104.67 (C-10), 121.07 (C-1′), 128.57 (C-2′, 6′),
115.98 (C-3′, 5′), 162.31 (C-4′), 56.04 (7-OCH3) [14].
Pectolinarigenin (10), yellow powder, mp 231–232°C. 1Í NMR (500 MHz, DMSO-d6, δ, ppm, J/Hz): 13.04 (1H, s,
5-OH), 10.73 (1H, s, 7-OH), 8.03 (2H, d, J = 9.0, H-2′, 6′), 7.11 (2H, d, J = 9.0, H-3′, 5′), 6.87 (1H, s, H-3), 6.62 (1H, s, H-8),
3.86 (3H, s, 4′-OCH3), 3.76 (3H, s, 6-OCH3). 13Ñ NMR (125 MHz, DMSO-d6, δ, ppm): 163.36 (C-2), 103.06 (C-3), 182.18
(C-4), 152.78 (C-5), 131.38 (C-6), 157.34 (C-7), 94.31 (C-8), 152.43 (C-9), 104.15 (C-10), 122.86 (C-1′), 128.32 (C-2′, 6′),
114.58 (C-3′, 5′), 162.31 (C-4′), 59.96 (6-OCH3), 55.56 (4′-OCH3) [15].
Rutin (11), yellow powder, mp 242–244°C. The 1H and 13C NMR spectra agreed with those published [16].
Patuletin-3-O-rutinoside (12), yellow powder, mp 217–220°C. 1Í NMR (400 MHz, DMSO-d6, δ, ppm, J/Hz):
12.61 (1H, br.s, 5-OH), 7.55 (1H, dd, J = 8.4, 2.2, H-6′), 7.52 (1H, d, J = 2.2, H-2′), 6.84 (1H, d, J = 8.4, H-5′), 6.47 (1H, s, H-8),
5.33 (1H, d, J = 7.2, H-1′′), 4.39 (1H, d, J = 1.6, H-1′′′), 3.75 (3H, s, 6-OCH3), 3.72 (1H, m, H-6′′a), 3.41 (1H, dd, J = 3.4, 1.6,
H-2′′′), 3.30 (1H, m, H-6′′b), 3.29 (1H, m, H-3′′′), 3.28 (1H, m, H-5′′′), 3.27 (1H, m, H-3′′), 3.24 (1H, m, H-2′′), 3.23 (1H, m,
H-5′′), 3.09 (1H, t, J = 9.3, H-4′′′), 3.07 (1H, t, J = 9.0, H-4′′), 1.01 (3H, d, J = 6.2, H-6′′′). 13Ñ NMR (100 MHz, DMSO-d6,
δ, ppm): 156.39 (C-2), 132.92 (C-3), 177.32 (C-4), 152.24 (C-5), 131.71 (C-6), 151.93 (C-7), 94.12 (C-8), 159.36 (C-9),
103.63 (C-10), 121.17 (C-1′), 116.17 (C-2′), 144.92 (C-3′), 148.62 (C-4′), 115.32 (C-5′), 121.58 (C-6′), 101.36 (C-1′′), 74.12
(C-2′′), 75.89 (C-3′′), 70.00 (C-4′′), 76.52 (C-5′′), 67.05 (C-6′′), 100.80 (C-1′′′), 70.40 (C-2′′′), 70.59 (C-3′′′), 71.89 (C-4′′′),
68.29 (C-5′′′), 17.79 (C-6′′′), 59.88 (6-OCH3) [17].
Thus, compounds 1–12 were isolated for the first time from the aerial part of A. persica according to the
phytochemical studies.
The activity of the isolated flavonoids for absorption of DPPH free radicals was evaluated using vitamin C (ascorbic
acid) as a standard with an IC50 value of 4.5 ± 0.3 μg/mL. Patuletin and rutin also demonstrated potent antioxidant activity
with IC50 values of 12.7 ± 1.2 and 11.2 ± 0.9 μg/mL, respectively. On the other hand, 5-hydroxy-4′,7-dimethoxyflavone and
genkwanin showed relatively lower antioxidant activity with IC50 values of 42.3 ± 3.5 and 36.7 ± 3.2 μg/mL, respectively.
154
ACKNOWLEDGMENT
The work was supported by large special projects of Xinjiang-Uyghur Autonomous Region, PRC (No. 2022A03018-1),
the Program of International Stipend Financing Initiative (PIFI Program) of the Chinese Academy of Sciences
(Grant No. 2024VBA0020), the Central Asian Center for Drug Discovery and Development, Chinese Academy of Sciences,
and the Budgetary Program of Basic Scientific Research, AS, RUz.
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