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Nitro derivatives of naturally occurring [beta]-asarone and their anticancer activity.

1. Introduction

Acorus calamus (Acoraceae) also known as sweet flag in Indian traditional medicine is generally used for treatment of cough, fever, bronchitis, inflammation, depression, tumors, haemorrhoids, skin diseases, insomnia, hysteria, epilepsy, and loss of memory [1, 2]. While [beta]-asarone (2, 4, 5-trimethoxy-(Z)-1-propenylbenzene) was the main constituent (70 to 90%) of rhizomes of Acorus calamus [3], a-asarone (2, 4, 5-trimethoxy-(E)-1-propenylbenzene) was isolated as a minor component (8 to 14%) from the rhizomes of related species Acorus gramineus [4]. Comparative study of genotoxicity and cytotoxicity of [beta]-asarone and [alpha]-asarone was investigated and found that a-asarone was more toxic in the HepG2 cell system [5-7].

In continuation of our research on [beta]-asarone, we carried out different chemical conversions to get pharmacologically active compounds [8, 9]. Herein we report the preparation of nitro derivatives of [beta]-asarone and their biological activity. Nitro group is an important functional group because it can be easily converted into many functional groups [1012]. Psychoactive drugs, namely, amphetamines, are generally prepared by reduction of [beta]-methyl-[beta]-nitrostyrenes [13-16].

Generally nitration of alkenes and substituted styrenes was carried out by metal nitrites using NaN[O.sub.2]/AgN[O.sub.2] with iodine, NaN[O.sub.2]/[H.sub.2]S[O.sub.4] in ether (Bruckner's method), Cu (II)tetrafluoroborate with NaN[O.sub.2], alkyl halide and metal nitrite (Victor-Meyer reaction), and Hg[Cl.sub.2]-NaN[O.sub.2] [17-23]. Formation of nitryl iodide was first reported by Birchenbachin 1932 from AgN[O.sub.2]/[I.sub.2] [24]. Later on AgN[O.sub.2] was replaced with less expensive NaN[O.sub.2]/[H.sub.2]O/[I.sub.2]/EtOAc/ethylene glycol or KN[O.sub.2]/18-crown-6/[I.sub.2]/THF [25-27].

2. Results and Discussion

2.1. Chemistry. Naturally occurring [beta]-asarone when subjected to nitration with nitryl iodide (NaN[O.sub.2]/[I.sub.2]/ethylene glycol) obtained 1-(2,4,5-trimethoxy phenyl)-1-nitropropene (2) (Scheme 1) as yellow crystals. It showed a molecular ion peak at 253 ([M.sup.+.]) corresponding to the molecular formula [C.sub.12][H.sub.15]N[O.sub.5].[In.sup.1] H-NMR spectrum methyl group appeared as a doublet at [delta] 1.80 (/ = 7.6 Hz) with vinylic proton appearing as a quartet at [[delta].sub.H] 7.40 (] = 14.6 and 7.6 Hz) indicating that vinylic proton is adjacent to methyl group. When the methyl peak in PMR at S 1.80 was irradiated, enhancement of peaks at [delta] 6.67 and [delta] 7.40 corresponding to H-6 and vinylic proton was observed indicating that compound 2 is indeed 1-(2, 4, 5-trimethoxy phenyl)-(E)-1-nitropropene. The formation of compound 2 is quite unique and there was no report of formation of this earlier. Further proof that compound 2 is 1-nitropropenyl derivative has come from the fact that when it was subjected to modified Nef reaction using sodium borohydride (wherein [alpha],[beta]-unsaturated nitroalkenes yield corresponding ketones by hydrolysis of the corresponding nitronates [28, 29], it gave 1-(2, 4, 5-trimethoxy)phenyl-1propanone (3, isoacoromone)) [3]. Sy and By reported that nitration of substituted styrenes with nitryl iodide regioselectively yielded [beta]-nitrostyrenes (2-nitropropenyl derivatives) and not [alpha]-nitrostyrenes (1-nitropropenyl derivative) [24]. We have also prepared 1-(2, 4, 5-trimethoxy phenyl)-2nitropropene (1) by the nitration of [beta]-asarone with AgN[O.sub.2]/[I.sub.2] in ether and characterized it by recording its PMR spectrum. When the methyl peak in PMR at [delta]52.42 of compound 1 was irradiated, no enhancement of any other peaks was observed. The formation of compound 1 was confirmed by synthesizing the molecule through the condensation of 2, 4, 5-trimethoxy benzaldehyde with nitroethane [30, 31]. It is clear from these experiments that formation of nitro derivatives of [beta]-asarone depends on the solvent used during nitration.

2.2. Biological Activity. Compounds 1 and 2 were screened for their anticancer activity against five human cancer cell lines by MTT assay (Table 1) with the naturally occurring [beta]-asarone and camptothecin taken as standards. Except in breast cancer cell line (MCF-7), compound 2 exhibited five to tenfold increase in activity compared to [beta]-asarone and twofold increase over compound 1.

2.2.1. Anticancer Assay. Cell lines were maintained in Dulbecco's Modified Eagle's Medium (Sigma-Aldrich Inc., USA) supplemented with 10% fetal bovine serum (Gibco BRL., USA) in a [CO.sub.2] incubator at 37[degrees]C. The cytotoxicity of the compounds was measured by MTT assay [32]. Five different kinds of human cancer cell lines, namely, HeLa (cervical), MCF-7 (breast), SW-982 (synovial), PC-3 (prostate cancer), and IMR-32 (neuroblastoma), were plated in a 96-well plate at the density of 10,000 cells per well. After 24 h, cells were treated with various concentrations of compounds from 200 [micro]M serially diluted up to 1.56 [micro]M using camptothecin as standard. The cells were further incubated for 48 h, and 20 [micro]L of MTT (5 mg/mL stock, Sigma-Aldrich Inc., USA) was added to each well and incubated for another three hours. The purple formazan crystals formed were dissolved by adding 100 [micro]L of DMSO to each well and absorbance was read at 570 nm in a spectrophotometer [SpectraMax 340]. The cell death was calculated as follows: test absorbance

Cell death = 100 - [(test absorbance/control absorbance) x 100]. (1)

The cytotoxic activity of compounds was expressed as the concentration in [micro]M at which they inhibit the cell growth by 50% ([IC.sub.50]).

3. Experimental

3.1. Chemistry. All chemicals were purchased from Laboratory Reagent (LR) grade. Fresh rhizome of Acorus calamus was collected from marshy areas of Kunigal in Karnataka, India in 2012. Melting points were recorded on an Acro melting point apparatus using a calibrated thermometer. Thin layer chromatography (TLC) and column chromatography (CC) were performed with [TLC silica gel 60 [F.sub.254]. Merck] and silica gel (Kieselgel 60, 230-400 mesh, Merck), respectively. Chromatograms were developed using hexane-EtOAc (8: 2, v/v). IR spectra were recorded on Thermo-Nicolet instrument in KBr discs. Mass spectra were recorded using GCMSQP2010S (direct probe). PMR spectra and [sup.13C] NMR spectra were recorded in CD[Cl.sub.3] with TMS (tetramethylsilane) as an internal standard on a Bruker AG spectrometer and chemical shifts were recorded in [delta] units.

3.2. 3-(2, 4, 5-Trimethoxy-(Z)-1-propenyl benzene). IR (KBr): 3421, 2939,1589,1512,1469,1211,1145,1029, 833 [cm.sup.-1].

[sup.1]H NMR (CD[Cl.sub.3], 200 MHz): [delta] 1.88 (3H, dd, J = 2.0, 7.0 Hz, C[H.sub.3]), 3.81 (3H, s, OC[H.sub.3]), 3.84 (3H, s, OC[H.sub.3]), 3.90 (3H, s, OC[H.sub.3]), 5.78 (1H, m, H-8), 6.49 (1H, m, H-7), 6.53 (1H, s, H-3), 6.84 (1H, s, H-6).

[sup.13]C NMR (CD[Cl.sub.3], 50 MHz): [delta] 153.58, 150.58, 143.26, 126.74, 126.42, 119.32, 116.71, 97.28, 56.98 (OC[H.sub.3]), 56.53 (OC[H.sub.3]), 56.38 (OC[H.sub.3]), 14.78 (C-9).

GC-MS (m/z) = 208 [[M].sup.+] (25), 193 (10), 165 (15), 150 (5), 135 (12), 119 (5), 105 (5), 91 (14).

3.3. 1-(2, 4, 5-Trimethoxy phenyl)-2-nitropropene (1). Iodine (1016 mg, 4 mmol) and AgN[O.sub.2] (616 mg, 4 mmol) were stirred in anhydrous ether (20 mL) at room temperature under nitrogen for 45 min. [beta]-Asarone (236 mg, 2 mmol) and pyridine (632 mg, 8 mmol) in ether were added and the mixture was stirred at room temperature for 30 h as per the reported procedure [24]. The dark brown liquid material obtained was chromatographed on silica and eluted with hexane/ethyl acetate to give pure product 1 which was crystallized from methanol (1-(2, 4, 5-trimethoxy phenyl)2-nitropropene exists in two modifications, yellow and red prisms, and depending on concentration and precipitation speed, one often gets a mixture of both species. Yellow crystal melts at 98-100[degrees]C and dark orange (red) crystal melts at 99-101[degrees]C. The red form transforms itself to the yellow form at 90[degrees]C) (238 mg, 73.2%).

IR (KBr): 2945, 1612, 1509, 1490, 1335, 1278, 1216, 1136 cm-1.

[sup.1]H NMR (CD[Cl.sub.3], 400 MHz): [delta] 2.42 (3H, s, H-9), 3.85 (3H, s, OC[H.sub.3]), 3.87 (3H, s, OC[H.sub.3]), 3.94 (3H, s, OC[H.sub.3]), 6.54 (1H, s, H-3), 6.87 (1H, s, H-6), 8.30 (1H, s H-7).

[sup.13]C NMR (CD[Cl.sub.3], 100 MHz): [delta] 153.58, 152.44, 145.58, 142.26, 128.74, 133.01, 111.64, 97.28, 56.78 (OC[H.sub.3]), 56.53 (OC[H.sub.3]), 56.05 (OC[H.sub.3]), 14.58 (C[H.sub.3]).

GC-MS (m/z) = 253 [[M.sup.+.]] (42), 207 (100), 192 (70), 177 (62), 161 (28), 149 (25), 131 (12), 121 (30), 107 (12).

3.4. Synthesis of 1. To a solution of2, 4, 5-trimethoxy benzaldehyde (7.6 g, 38.7 mmol) in nitroethane (27 g, 386 mmol) was added ammonium acetate (1.7 g, 22.0 mmol) and the reaction mixture heated to 75-80[degrees]C for 3hrs. After completion of the reaction, nitroethane was removed under vacuum, and oily orange mass was triturated with hot methanol (3 x 50 mL). Methanol extract was concentrated and allowed to stand at room temperature. Yellow crystals (75-78% yield) were obtained having the melting point 98-100[degrees]C. 1-(2, 4, 5-Trimethoxy phenyl)-2-nitropropene obtained by nitration of [beta]-asarone using AgN[O.sub.2]/[I.sub.2]/ether was identical with this synthetic compound on TLC, mp, and mmp.

3.5. 1-(2, 4, 5-Trimethoxy phenyl)-1-nitropropene (2). A mixture of [micro]-asarone (10 g, 48 mmol) in 150 mL of ethyl acetate containing iodine (18.28 g, 72 mmol) at 0[degrees]C was added to a solution of sodium nitrite (13.24 g, 192 mmol), ethylene glycol (8.93 g, 144 mmol), and water 20 mL. The reaction mixture was stirred at room temperature for 48 hrs under nitrogen and the ethyl acetate layer was separated, washed with water and then with 10% thiosulphate, and dried over MgS[O.sub.4] Ethyl acetate layer was evaporated and recrystallized from methanol to obtain a yellow crystalline compound (70-75% yield).

MP: 158-160[degrees]C. IR (KBr): 2948,1645,1346,1214,1032, 829, 769 [cm.sup.-1].

[sup.1]H NMR (CD[Cl.sub.3], 400 MHz): [delta] 1.80 (3H, d, J = 7.6 Hz, [CH.sub.3]), 3.76 (3H, s, OC[H.sub.3]), 3.83 (3H, s, OC[H.sub.3]), 3.93 (3H, s, OC[H.sub.3]), 6.57 (1H, s, H-3), 6.67 (1H, s, H-6), 7.40 (1H, q, J = 14.6 and 7.6 Hz, H-8).

[sup.13]C NMR (CD[Cl.sub.3], 100 MHz): [delta] 152.64, 151.44, 149.58, 142.86, 133.74, 115.01, 109.64, 97.28, 56.73 (OC[H.sub.3]), 56.33 (OC[H.sub.3]), 56.05 (OC[H.sub.3]), 14.28 (C[H.sub.3]).

GC-MS (m/z) = 253 [[M.sup.+.]] (74), 207 (100), 192 (40), 177 (55), 161 (26), 149 (24), 131 (12), 121 (32).

3.6. 1-(2, 4, 5-Trimethoxy)phenyl-1-propanone (3). To a solution of compound 2 (1 g, 4.46 mmol) in methanol (25 mL) was added sodium borohydride (0.5 g, 3.2 mmol) and stirred the reaction mixture at 25-30[degrees]C for 30 minutes. Completion of the reaction was confirmed by TLC. The reaction mixture was concentrated under vacuum and acidified with dilHCl to pH about 4.0 and extracted with C[H.sub.2][Cl.sub.2] (2 x 15 mL) washed with water and dried over [Na.sub.2]S[O.sub.4]. Evaporation of C[H.sub.2][Cl.sub.2] layer followed by crystallization from methanol gave colourless crystals.

MP: 108-109[degrees]C.

IR (KBr): 2959, 1712, 1649, 1618, 1510, 1215, 1028, 810, 750 [cm.sup.-1].

[sup.1]H NMR (CD[Cl.sub.3], 200 MHz): [delta] 1.18 (3H, t, J = 7.2 Hz, [CH.sub.3]), 2.99 (2H, q, J = 14.5 & 7.2 Hz, C[H.sub.2]), 3.85 (3H, s, OC[H.sub.3]), 3.87 (3H, s, OC[H.sub.3]), 3.91 (3H, s, OC[H.sub.3]), 6.50 (1H, s, H-3), 743 (1H, s, H-6).

[sup.13]C NMR (CD[Cl.sub.3], 50 MHz): d 200.73 (C=O), 155.16, 153.58, 143.09, 119.19, 112.80, 96.56, 56.28 (OC[H.sub.3]), 56.18 (O[CH.sub.3]), 56.10 (OC[H.sub.3]), 37.07 (C[H.sub.2]), 8.63 (C[H.sub.3]).

GC-MS (m/z) = 224 [[M.sup.+.]] (38), 195 (100), 180 (10), 165 (5), 151 (10), 137 (12), 122 (32), 109 (5).

4. Conclusions

[beta]-Asarone (2,4, 5-trimethoxy-(Z)-1-propenylbenzene) when subjected to nitration gave 1-(2, 4, 5-trimethoxy phenyl)2-nitropropene (1) and 1-(2, 4, 5-trimethoxy phenyl)-1nitropropene (2). Preparation of compound 2 is reported here for the first time. The cytotoxic activities of these nitro derivatives were compared with [beta]-asarone in five human cancer cell lines namely MCF-7, SW-982, HeLa, PC-3 and IMR-32 using MTT assay. Except in breast cancer line (MCF-7) compound 2 exhibited five- to tenfold increase in activity compared to [beta]-asarone and twofold increase over compound 1.

Conflict of Interests

The authors declare that there is no conflict of interests regarding the publication of this paper.


The authors express sincere thanks to Dr. Anil Kush, CEO of Vittal Mallya Scientific Research Foundation, for his keen interest and encouragement, to DBT, Government of India, for the financial support (Grant no. BT/PR11756/ AGR/05/456/2009t), and Mr. A. C. Karunakara and Mr. K. Rijesh for technical assistance. Their thanks are due to NMR Research facilities, I. I. Sc., Bangalore, for recording the spectra.


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Suvarna Shenvi, (1) Latha Diwakar, (2) and G. Chandrasekara Reddy (1)

(1) Chemical Sciences Division, Vittal Mallya Scientific Research Foundation, BTMII Stage, Bangalore 560076, India

(2) Department of Biological Sciences, Vittal Mallya Scientific Research Foundation, BTM II Stage, Bangalore 560076, India

Correspondence should be addressed to G. Chandrasekara Reddy;

Received 21 July 2014; Accepted 15 September 2014; Published 1 October 2014

Academic Editor: Jochen Lehmann

Table 1: Cytotoxic activity for nitro derivatives
of [beta]-asarone by MTT assay.

                                         I[C.sub.50] values
                                           ([micro]M) (a)

Compounds               HeLa (b)              MCF-7 (c)

1                 39.24 [+ or -] 4.40    73.65 [+ or -] 3.26
2                 25.03 [+ or -] 4.32    74.28 [+ or -] 6.28
[beta]-Asarone    126.11 [+ or -] 6.82          >150
Camptothecin       3.09 [+ or -] 0.34    27.34 [+ or -] 9.89

                   I[C.sub.50] values
                     ([micro]M) (a)

Compounds              SW-982 (d)             PC-3 (e)

1                 42.65 [+ or -] 11.42   30.05 [+ or -] 6.13
2                  11.84 [+ or -]3.23    25.44 [+ or -] 6.76
[beta]-Asarone    129.35 [+ or -]8.12           >150
Camptothecin       9.15 [+ or -]0.36     3.42 [+ or -] 0.35

Compounds              IMR-32 (f)

1                 47.14 [+ or -] 8.43
2                 18.10 [+ or -] 2.14
[beta]-Asarone            >150
Camptothecin       5.07 [+ or -] 1.32

(a) [IC.sub.50]: each set of data represents mean [+ or -] S.D
from three different test results in triplicate and is
expressed as the concentration of test compound which
inhibits the cell growth by 50%.

(b) HeLa: human cervical cancer; (c) MCF-7: human breast
cancer; (d) SW-982: human synovial sarcoma; (e) PC-3: human
prostate cancer; (f) IMR-132: human neuroblastoma.
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Title Annotation:Research Article
Author:Shenvi, Suvarna; Diwakar, Latha; Reddy, G. Chandrasekara
Publication:International Journal of Medicinal Chemistry
Article Type:Report
Geographic Code:9INDI
Date:Jan 1, 2014
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