Chemistry of Natural Compounds, Vol. 43, No. 3, 2007
FLAVONOIDS FROM Scutellaria phyllostachya ROOTS
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G. U. Siddikov, M. P. Yuldashev, and Sh. V. Abdullaev
UDC 547.972
In continuation ofthe studyofflavonoids from plants ofthe genusScutellaria L. (Lamiaceae) [1], westudiedflavonoids
from S. phyllostachya Juz. roots.
Ground air-dried roots of S. phyllostachya that were collected in Namangan District ofthe Republic ofUzbekistan were
extracted nine times at room temperature with ethanol (80%). The condensed alcoholic extract was diluted with water and
worked up successively with CHCl , EtOAc, and n-BuOH. The solvents were distilled off to afford CHCl (20.0 g), EtOAc
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3
(15.0 g), and n-BuOH (23.0 g) extracts.
The EtOAc extract (18.0 g) was chromatographed over a column of silica gel with gradient elution by CHCl :i-PrOH
3
(
95:5 85:15).
Elution ofthecolumnbyCHCl :i-PrOH(95:5)isolatedchrysin-7-O-β-D-methylglucuronide(0.15g)andapigenin-7-O-
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β-D-glucuronide (0.13 g). Elution of the column by CHCl :i-PrOH (90:10) afforded baicalein-7-O-β-D-glucopyranoside
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(
0.12 g). Finally, elution of the column by CHCl :i-PrOH (85:15) isolated oroxyloside (0.18 g).
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The n-BuOH extract (23.0 g) was chromatographed over a column of silica gel with gradient elution byCHCl :i-PrOH
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(
95:5 85:15). Elution of the column by CHCl :i-PrOH (90:10) isolated scutellarein-7-O-β-D-glucuronide (0.15 g). Elution
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of the column by CHCl :i-PrOH (90:10) produced apigenin-7-O-β-D-glucoside (0.10 g) and norwogonine-7-O-β-D-glucoside
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(
0.18 g). Elution by CHCl :i-PrOH (85:15) afforded wogoniside (0.24 g) and luteolin-7-O-β-D-glucuronide (0.15 g).
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Chrysin-7-O-β-D-methylglucuronide (1), C H O , mp 184-186°C (MeOH). UV spectrum (EtOH, λmax, nm):
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2 20 10
−
1
2
70, 305. IR spectrum (KBr, ν, cm ): 3510-3320 (OH), 1660 (γ-pyrone C=O), 1728 (ester C=O). PMR spectrum (100 MHz,
C D N, δ, ppm, J/Hz): 3.48 (3H, s, COOCH ), 4.00-4.67 (3H, m, H-2″, H-3″, H-4″), 4.84 (1H, d, J = 8.5, H-5″), 5.88 (1H, d,
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5
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J = 6.5, H-1″), 6.70 (1H, d, J = 2, H-6), 6.78 (1H, s, H-3), 6.97 (1H, d, J = 2, H-8), 7.51-7.73 (3H, m, H-3′,4′,5′), 7.15-7.73 (2H,
+
m, H-2′,6′), 12.49 (1H, br.s, 5-OH). Acid hydrolysis of 1 produced chrysin (C H O , mp 290-292°C, [M] 254) and
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5 10 4
D-glucuronic acid (PC, n-BuOH:C H N:H O, 6:4:3) [2].
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5
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Apigenin-7-O-β-D-glucuronide (2), C H O , mp 173-176°C, [α] -115.0°. UV spectrum (EtOH, λmax, nm):
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1
18 11
D
−
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70sh, 335; +ZrOCl 295, 390. IR spectrum (KBr, ν, cm ): 3400 (OH), 1730 (COOH), 1650 (γ-pyrone C=O), 1600, 1580
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(
aromatic C=C). Acid hydrolysis of 2 produced apigenin and D-glucuronic acid (PC, n-BuOH:C H N:H O, 6:4:3) [3].
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Baicalein-7-O-β-D-glucopyranoside (3), C H O , mp 206-207°C (dec.). UV spectrum (EtOH, λmax, nm): 279,
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1 20 10
−
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14; +AlCl 290, 341. IR spectrum (KBr, ν, cm ): 3385 (OH), 1660 (γ-pyrone C=O), 1622, 1584 (aromatic C=C). Acid
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hydrolysis of 3 produced baicalein and D-glucose (PC, n-BuOH:C H N:H O, 6:4:3) [4].
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Oroxyloside (oroxylin-7-O-β-D-glucuronide) (4), C H O , mp 193-195°C. UV spectrum (EtOH, λ , nm): 280,
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20 11
max
+
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15; +CH COONa 281, 316. Acid hydrolysis of 4 produced oroxylin A (mp 217-218°C, C H O , [M] 284) and
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D-glucuronic acid (PC, n-BuOH:C H N:H O, 6:4:3) [5].
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5
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Scutellarein-7-O-β-D-glucoside (5), C H O , mp 193-195°C. UV spectrum (MeOH, λ , nm): 288, 337;
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1
20 11
max
+
+
CH COONa 290, 340; +AlCl 292sh, 306, 371. Acid hydrolysis of5 produced scutellarein (mp>340°C, C H O , [M] 286)
3 3 15 10 6
and D-glucose (PC, n-BuOH:C H N:H O, 6:4:3) [5].
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Apigenin-7-O-β-D-glucoside (6)(cosmosiin), C H O , mp203-205°C. UV spectrum (EtOH, λmax, nm): 268, 339;
21 20 10
+
CH COONa 267, 339; +AlCl 279, 301, 343; +CH COONa 267, 397. PMRspectrum (100 MHz, C D N, δ, ppm, J/Hz): 3.59-
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.64 (sugar protons), 5.72 (1H, d, J = 7.0, H-1″), 6.64 (1H, d, J = 2.5, H-6), 6.78 (1H, s, H-3), 6.96 (1H, d, J = 2.5, H-8), 7.12
(
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2H, d, J = 8.0, H-3′,5′), 7.81 (2H, d, J = 8.0, H-2′,6′), 13.62 (1H, br.s, 5-OH). Acid hydrolysis of 6 produced apigenin (mp 345-
+
46°C, C H O , [M] 270) and D-glucose (PC, n-BuOH:C H N:H O, 6:4:3) [6].
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) Namangan State University; 2) S. Yu. Yunusov Institute of the ChemistryofPlant Substances, AcademyofSciences
of the Republic of Uzbekistan, Tashkent, e-mail: ximiya@list.ru. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp.
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70-271, May-June, 2007. Original article submitted March 13, 2007.
©
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009-3130/07/4303-0324 2007 Springer Science+Business Media, Inc.
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