Chemistry of Natural Compounds, Vol. 38, No. 5, 2002
ALKALOIDS OF Veratrum lobelianum GROWING IN GEORGIA
T. Sh. Suladze and V. Yu. Vachnadze
UDC 547.944/945
Studies of the accumulation dynamics of alkaloids in the epigeal part of Veratrum lobelianum Bernch. during the start
of growth showed that the qualitative and quantitative compositions vary substantially as a function of plant height.
Herein we present results from an investigation of alkaloids of the epigeal part of V. lobelianum (2.5 kg, 20-25 cm
height) collected in Kazbegi district. Alkaloids were extracted by ethanol. The extracts were dried and treated with acetic acid
(
10%, pH 3.5-4.0). The acid-soluble bases were extracted by CHCl and basicified with ammonia. The solvent was removed.
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The solid (4.45 g) was chromatographed over a silica-gel column (375 g) with elution by CHCl :CH OH (97:3). Alkaloid
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3
fractions (1.52 g) isolated from the first eluates were separated preparatively on silica-gel plates using CHCl :CH OH (6:1).
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3
The solution of total bases was placed at the plate origin as narrow bands so that each 0.15 mL of solution of concentration
5 mg/1.5 mL was 1.5 cm long. After development, the band above R 0.39 was removed from the plate and eluted by
1
f
CHCl :C H :CH OH (4.5:4.5:1).
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6
6
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We obtained an amorphousbase(0.067g, mp235-240°C), the IRspectrum ofwhich (KBr pellets) exhibited absorption
-1
bands at 3400 (NH), 1740, 1250 (OCOCH ), 1715 (CO), and 1635 (C=C) cm . PMR (CDCl ): 0.95 (3H, d, CH -27), 0.98 (3H,
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d, CH -21), 1.05 (3H, s, CH -19), 2.10 (3H, d, CH -18), 2.29 (1H, m, H-20), 2.81 (1H, m, H-22), 3.40 (1H, m, H-23), 4.50 (1H,
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3
3
1
3
m, H-3), 5.38 (1H, m, H-6). C NMR (CDCl , 75 MHz): 73.75 (C-3, d), 21.60 (COCH , q), 170.50 (COCH , s).
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3
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The base was subjected to alkaline hydrolysis. The hydrolysate was diluted with water and extracted by CHCl . The
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CHCl was removed to afford an amorphous base, the IR spectrum of which exhibited absorption bands at 3300, 3200 (–OH,
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-1
=
NH), 1715 (=CO), and 1635 cm (conjugated double bond). These correspond to absorption bands in the IR spectrum of
jervine [1]. A mixed sample of the obtained alkaloid and jervine on paper chromatography (PC) and TLC in various solvent
systems appeared as one inseparable spot [1, 2]. Acetic acid was identified by PC in the alkaline solution after removal of
jervine [4].
A comparison of the results and the literature data [3] leads to the conclusion that the base isolated by us is O-
acetyljervine.
REFERENCES
1.
2.
3.
N. L. Machaidze and I. S. Sikharulidze, Khim. Prir. Soedin., 659 (1982).
N. V. Bondarenko, Khim. Prir. Soedin., 801 (1984).
Attaurrahman, R. A. Ali, T. Parveen, M. I. Choudhary, B. Sener, and S. Turkoz, Phytochemistry, 30, 1, 368
(1991).
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.
I. M. Hais and K. Macek, Eds., Handbuch der Papierchromatographie, Vol. I. Grundlagen und Technik, G.
Fischer, Jena (1958).
I. G. Kutateladze Institute of Pharmacochemistry, Academy of Sciences of Georgia, Tbilisi, fax (95532) 53 67 51.
Translated from Khimiya Prirodnykh Soedinenii, No. 5, p. 383, September-October, 2002. Original article submitted July 2,
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002.
©
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009-3130/02/3805-0470$27.00 2002 Plenum Publishing Corporation
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Suladze
