Chemical constituents of Crataeva nurvala (Buch-ham) leaves

*Corresponding Author:

S. B. Kalidhar
Department of Chemistry, CCS Haryana Agricultural University, Hisar-125 004, India.
E-mail: kalidhar@hau.ernet.in

Abstract

Chemical investigation of Crataeva nurvala leaves resulted in the isolation of four compounds, which are dodecanoic anhydride, methyl pentacosanoate, kaemferol-3-O-α-D-glucoside and quercitin-3-O-α-D-glucoside. Dodecanoic anhydride and methyl pentacosanoate are being reported for the first time from this plant. Kaemferol-3-O-α-D-glucoside and quercitin-3-O-α-D-glucoside have already been reported from this plant.

The genus Crataeva (family: Capparidaceae) is named in honour of the Greek botanist Crataevas. Crataeva nurvala is commonly known as barna and varuna [1] and distributed, throughout India and tropical regions of the world: wild or cultivated [2]. It is often found along streams and also in dry, deep boulder formations in sub Himalayan tract [3]. It is useful as a laxative, antipyretic, antilithic, antihelminthic, diuretic, demulcent, stomachic, alterative tonic in chest and blood diseases and is reported to cure disorders of urinary organs [4]. It is very useful as antiinflammatory drug and acts as a good contraceptive for women. This plant is known to possess immense pharmacological activity and antilithic properties [5]. The major component isolated from this plant is lupeol, which is used to treat hypercrystalluria, hyperoxaluria and hypercalciuria [6]. The compound is also widely used to treat urinary disorders like urolithiasis, and it decreases elevated concentration of oxalate, phosphorous and magnesium in renal tissue [7]. Lupeol also possesses antipyretic, analgesic, antiinflammatory activity [8]. Since there is scanty data on the chemical components of its leaves, we have undertaken the present study.

The melting points were determined on Ganson electrical melting point apparatus. ¹H NMR spectra were recorded on Bruker AC-300F 300 MHz NMR spectrometer in CDCl₃ using TMS as internal standard. Chemical shifts are given in δ (ppm), and CDCl₃ was used as solvent. IR spectra were recorded on Hitachi 570 infrared spectrophotometer. Mass spectra were recorded on VG70S 11-250J GC-MS-DS mass spectrometer.

Leaves of Crataeva nurvala (5 kg) were collected from Landscape, CCS H.A.U., Hisar. These were crushed, dried and extracted with hot methanol, each time refluxing for 6 h. The methanolic extract was concentrated over water bath under reduced pressure. The extractives were then subjected to silica gel (60-120 mesh) column chromatography. The column chromatography of Crataeva nurvala leaves afforded four compounds (A-D) using petroleum ether, benzene, ethyl acetate, methanol and their mixtures as eluents, as shown in the Table 1.

Table 1: Compounds isolated from the leaves of crataeva nurvala

Compound A (dodecanoic anhydride, 1, fig. 1) was obtained on elution with benzene-petroleum ether (1:9) and it crystallized from benzene, 10 mg, mp: 45° [9]. IR (K Br, ν_max in cm-1): 721, 798, 1023, 1163, 1257, 1463, 1731, 2848, 2914; 1H NMR (CDCl₃) δ, ppm: 2.25 (4H, t, J 7.0 Hz, 2 x -CH₂COO-), 1.60 (4H, m, 2 x -CH₂CH₂COO-), 1.25 (32H, br, 16 x -CH2-), 0.88 (6H, t, J 7.5 Hz, 2 x CH₃); GC-MS (m/z), 382 (M+ ), 354, 204, 176, 161, 133, 91.

Compound B (methyl pentacosanoate, 2) was obtained on elution with benzene-petroleum ether (1:3), 10 mg, mp: 62° [10]. IR (K Br, ν_max in cm^-1): 668, 758, 1215, 1710, 2401, 2917, 3020. ¹H NMR (CDCl₃) δ, ppm: 3.64 (3H, s, -OMe), 2.17 (2H, t, J 7.0 Hz, -CH₂COOMe), 1.54 (2H, m, CH₂CH₂COOMe), 1.25 (42H, br, 21x -CH₂- ), 0.88 (3H, t,.medknow.com). J 7.05 Hz, -CH₃); GC-MS (m/z): 396 (M⁺ ), 380, 281, 261, 254, 207, 157,148, 135, 122, 118, 105, 98, 95.

Compound C (kaempferol-3-O-α-D-glucoside, 3) was obtained on elution with methanol-ethyl acetate (1:49), 35 mg, mp: 178°[11]. It gave positive Mg/HCl test. IR (K Br, ν_max in cm^-1): 671, 801, 907, 1220, 1371, 1439, 1634, 2364,2931, 3484. The compound was acetylated with Ac₂O/Py:mp: 178°11 and its 1H NMR (CDCl₃) δ, ppm: 7.92 (2H, d, J 7.0 Hz, H-2’, H-6’), 7.26 (2H, d, J 7.0 Hz, H-3’, H-5’), 7.08 (1H, d, J 2.0 Hz, H-8), 6.78 (1H, d, J 2.0 Hz, H-6), 3.94 5.64 (7H, m, 7H of sugar), 2.33 (3H, s, -OAc), 2.17(6H, s, 2 x -OAc), 2.12 (3H, s, -OAc), 2.06 (3H, s, -OAc), 2.04 (3H, s, -OAc), 2.00 (3H, s, -OAc), 1.98 (3H, s, -OAc); GC-MS (m/z), 448 (M+), 279, 207, 167, 149, 132, 104, 83.

Compound D (quercitin-3-O-α-D-glucoside, 4) was obtained on elution with methanol-ethyl acetate (1:3), 40 mg, mp: 238°[12]. It responded to colour reaction with Mg/ HCl. IR (K Br, ν_max in cm^-1): 671, 801, 907, 1220, 1371, 1439, 1634, 2364, 2931, 3484. The compound was acetylated with Ac₂O/Py: mp: 238°¹² and its ¹H NMR (CDCl₃) δ, ppm: 7.89 (2H, m, J 7.0 Hz, H-2’), 7.98 (2H,dd, J 2.0 Hz, J 7.0 Hz, H-6’), 7.26 (1H, m, H-5’), 7.09 (1H, d, J 2.0 Hz, H-8), 6.78 (1 H, d, J 2.0 Hz, H-6), 3.92-5.60 (7H, m, 7H of sugar), 2.40 (3H, s, -OAc), 2.33(3H, s, -OAc), 2.17(3H, s, -OAc), 2.12 (3H, s, -OAc), 2.06 (3H, s, -OAc), 2.04 (3H, s, -OAc), 2.00 (3H, s, -OAc), 1.98 (3H, s, -OAc); GC-MS (m/z) 464 (M⁺), 279, 207, 170, 128, 97.

Kaemferol-3-O-α-D-glucoside and quercitin-3-O-α-D- glucoside have already been reported from this plant, while dodecanoic anhydride and methyl pentacosanoate are being reported for the first time from this plant. 3-O-methyl quercitin and quercitin are also being reported from the leaves of this plant [13].

Acknowledgements

Authors are thankful to Landscape Officer, CCS H.A.U., Hisar, for the supply of plant material.

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