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Fitoterapia 78 (2007) 446 – 447 www.elsevier.com/locate/fitote Phytochemical communication A new trimethoxychalcone

Fitoterapia 78 (2007) 446 447

Fitoterapia 78 (2007) 446 – 447 www.elsevier.com/locate/fitote Phytochemical communication A new trimethoxychalcone

www.elsevier.com/locate/fitote

Phytochemical communication

A new trimethoxychalcone from Crotalaria ramosissima

Meneni Srinivasa Rao a, , Raman Narukulla b

a Department of Biomedical sciences, University of Rhode island, Kingston, 02881, USA b Department of Chemistry, Argenta Discovery Ltd, Harlow CM19 5TR, U.K.

Received 25 January 2005; accepted 19 March 2007 Available online 11 April 2007 Dedicated to Prof. Helmut Duddeck on the occasion of his 60th birthday

Abstract

A new trimethoxychalcone ( 1) was isolated from the aerial parts of Crotalaria ramosissima . The structure was elucidated on the basis of 1 H NMR, 13 C NMR and MS methods. © 2007 Elsevier B.V. All rights reserved.

Keywords: Crotalaria ramosissima; Trimethoxychalcone; Spectroscopic methods

1. Plant

Crotalaria ramosissima (Fabaceae), collected from Regional Engineering College campus, (Warangal, Andhar- apradesh, India) in October 2002, was identified by Dr. V.S. Raju and Dr.A.Ragan, Department of Botany, Kakatiya University, Warangal, India. A voucher specimen (No. CR-27) has been deposited in the Herbarium of Department of Botany, Kakatiya University, Warangal, India.

2. Uses in traditional medicine

Crotalaria spp. contains a wide range of medicinal plants used in indigenous Indian medicine [1] .

3. Previously isolated classes of constituents

Prenylated chalcone [2] and flavanone [3] , chalcone [4], dihydrochalcones [5] .

4. New-isolated constituent

The trimethoxychalcone 1 ( Fig. 1 ) (yield: 0.12% from dried aerial parts).

Corresponding author. Tel.: +1 401 418 1990. E-mail address: srmeneni@mail.uri.com (M.S. Rao).

0367-326X/$ - see front matter © 2007 Elsevier B.V. All rights reserved.

M.S. Rao, R. Narukulla / Fitoterapia 78 (2007) 446447

447

Rao, R. Narukulla / Fitoterapia 78 (2007) 446 – 447 447 Fig. 1. Yellow needles; mp

Fig. 1.

Yellow needles; mp 164-166 °C; UV max (MeOH): 383, 324, 270, 230 nm; IR bands (KBr): 3376, 1635,1575, 1501, 1485, 1295, 1264 cm 1 ; 1 H-NMR (200 MHz, CDCl 3 ): δ 3.91 (3H, s , 4-OCH 3 ), 3.94 (6H, s , 3 and 5-OCH 3 ), 6.92(2H, s , H-2 and H-6), 7.56(1H, d , J 15.4 Hz, H- α ), 7.87(1H, d , J 15.4 Hz, H- β), 1.49(6H, s , 2 ×CH 3 ), 5.62(1H, d , J 10.1 Hz, H-3 ), 6.35(1H, d , J 9.0 Hz, H-8 ), 6.76(1H, d , J 10.1 Hz, H-4 ), 7.56(1H, d , J 9.0 Hz, H-7 ), 13.09(1H, s , 5-OH); 13 C-NMR (100 MHz, CDCl 3 ): δ 28.6(2×CH 3 ), 56.8(3 and 5-OCH 3 ), 61.6(4-OCH 3 ), 106.7(C-2, C-6), 130.7(C-1), 119.8(C- α ), 144.3(C- β ), 192.16(C = O), 153.9(C-3 and C-5), 141.6(C-4), 77.9(C-2 ), 108.6(C-8 ), 109.6(C-4 a), 113.7(C-6), 116.0(C-4), 128.5(C-3), 131.2(C-7), 159.9(C-8a), 159.6(C-5); EI-MS (direct inlet): m/z: 397 [M+H] + (11), 396(44), 381(70), 382(16), 190(10), 188(11), 187(100); elemental analysis C, 69.70; H, 6.25. Calc. for C 23 H 24 O 6 : C, 69.68; H, 6.10.

Acknowledgements

The authors wish to thank the University of Rhode Island, USA and The Open University, UK for providing financial assistance.

References

[1] The Wealth of India. Raw materials, vol. II. New Delhi: CSIR; 1950. [2] Khalilullah M, Sharma VM, Rao PS. Fitoterapia 1993;64:232. [3] Khalilullah M, Sharma VM, Rao PS, Raju KR. J Nat Prod 1992;55:229. [4] Rao MS, Rao PS, Toth G, Balazs B, Duddeck H. J Nat Prod 1998;61:1148. [5] Kumar JK, Narender T, Rao MS, Rao PS, Toth G, Balazs B, et al. J Braz Chem Soc 1999;10:278.