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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, USAb Department of Chemistry, Argenta Discovery Ltd, Harlow CM19 5TR, U.K.

Received 25 January 2005; accepted 19 March 2007

Dedicated to Prof. Helmut Duddeck on the occasion of his 60th birthday

Available online 11 April 2007

Abstract

A new trimethoxychalcone (1) was isolated from the aerial parts of Crotalaria ramosissima. The structure was elucidated on the

basis of1H NMR, 13C 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).

Fitoterapia 78 (2007) 446447

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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.doi:10.1016/j.fitote.2007.03.011

mailto:srmeneni@mail.uri.comhttp://dx.doi.org/10.1016/j.fitote.2007.03.011http://dx.doi.org/10.1016/j.fitote.2007.03.011mailto:srmeneni@mail.uri.com

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Yellow needles; mp 164-166 C; UV max (MeOH): 383, 324, 270, 230 nm; IR bands (KBr): 3376, 1635,1575,

1501, 1485, 1295, 1264 cm1; 1H-NMR (200 MHz, CDCl3): 3.91 (3H, s, 4-OCH3), 3.94 (6H, s, 3 and 5-OCH3),

6.92(2H, s, H-2 and H-6), 7.56(1H, d, J15.4 Hz, H-), 7.87(1H, d, J15.4 Hz, H-), 1.49(6H, s, 2 CH3), 5.62(1H, d,

J10.1 Hz, H-3), 6.35(1H, d, J9.0 Hz, H-8), 6.76(1H, d, J10.1 Hz, H-4), 7.56(1H, d, J9.0 Hz, H-7), 13.09(1H, s,

5-OH);13C-NMR (100 MHz, CDCl3): 28.6(2CH3), 56.8(3 and 5-OCH3), 61.6(4-OCH3), 106.7(C-2, C-6), 130.7(C-1),

119.8(C-), 144.3(C-), 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 C23H24O6: 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.

Fig. 1.

447M.S. Rao, R. Narukulla / Fitoterapia 78 (2007) 446447