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Fitoterapia 78 (2007) 446 – 447

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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, 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 1H 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).

⁎ 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
M.S. Rao, R. Narukulla / Fitoterapia 78 (2007) 446–447 447

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; 1H-NMR (200 MHz, CDCl3): δ 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, J 15.4 Hz, H-α), 7.87(1H, d, J 15.4 Hz, H-β), 1.49(6H, s, 2 × CH3), 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);13C-NMR (100 MHz, CDCl3): δ 28.6(2 × CH3), 56.8(3 and 5-OCH3), 61.6(4-OCH3), 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-8′a), 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.