Alkaloids from Delphinium aemulans
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ALKALOIDS FROM Delphinium aemulans
N. Ablajan,1,2 B. Zhao,1,3 J. Y. Zhao,1,3 D. R. Kodirova,4 Sh. Sh. Sagdullaev,4 and H. A. Aisa1,3*
Plants of the genus Delphinium (Ranunculaceae) number about 300 species and are broadly distributed over the northern hemisphere. China is inhabited by 113 endemic species [1], many of which are widely used in folk medicine as analgesic, anti-inflammatory, antiarrhythmic, cardioactive, antitumor, antifungal, and insecticidal agents [2–4]. D. aemulans Nevski is an endemic species of Central Asia. Phytochemical studies isolated from it 26 compounds including 22 diterpene alkaloids [5, 6]. Herein we communicate data on the isolation from D. aemulans of five C19-diterpenes known from the literature (1–5), one morphine (6), two tetrahydroisoquinolines (7 and 8), and five N-acyl derivatives of methyl anthranilate (9–13). All compounds were identified using PMR, 13C NMR, and 2D spectroscopic and ESI-MS mass spectrometric data that were identical to the literature data. All compounds were isolated from this plant for the first time. OCH3
16
H3CO
17
12
15
11
H3 CO
OCH3
N R2
OH OCH3
19
R1
N
OH
5
OCH3
H3 CO
R3
OCH3
1
HN
OCH3 OH
OH OCH3
R1
1
O O R3
R2
2, 3
4, 5
OH H3 CO
H3CO
4
4a
6
4
10
16
12 5
14 9 8
H3CO O
H3 CO
3'
N HO
6
7
8
1
3a
CH3
H3CO
6a
H3CO
7a
O
1
OR1
9
OH
7
O 5'
R2
3
1'
7
11
4'
3'
11a
9 1'
CH3
R3
H N
7'
N 1a
OCH3
O
5 1
N
8a
3
H3CO
1
8
9 - 13
2: R1 = R2 = OH, R3 = OCH3; 3: R1 = R2 = OCH3, R3 = OH; 4: R1 = H, R2 = OCH3, R3 = OH 5: R1 = OH, R2 = H, R3 = OAc; 9: R1 = R2 = H, R3 = CH3; 10: R1 = R3 = H, R2 = CH3 11: R1 = R2 = CH3, R3 = H; 12: R1 = R3 = CH3, R2 = H; 13: R1 = CH3, R2 = R3 = H
The aerial part of D. aemulans collected in July 2015 in Yutmin Province, Tarent District, Xinjiang, China was studied. Air-dried plant (10 kg) was ground in a blender, wetted with aqueous Na2CO3 (5%), stored for 3 h, and extracted with CHCl3 at room temperature. The extract was concentrated at reduced pressure. The residue was dissolved in H2SO4 (3%) and extracted with EtOAc. The acidic aqueous layer was made basic with Na2CO3 to pH 10. Alkaloids were extracted by EtOAc. Crude alkaloids were separated by column chromatography (CC) over silica gel with elution by CHCl3–MeOH (100:1, 60:1, 40:1, 20:1, 10:1, 5:1, and 1:1) to produce eight fractions (A-H). Fraction B was fractionated by CC over silica gel 1) Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, 830011, Urumqi, Xinjiang, P. R. China, e-mail: [email protected]; 2) University of Chinese Academy of Sciences, 100039, Beijing, P. R. China; 3) State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011, Urumqi, Xinjiang, P. R. China; 4) S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Repu
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