Fitoterapia 70 Ž1999.

449]450

Phytochemical communication

Anacrotine } a crotanecene alkaloid from

Crotalaria trifoliastrum
M.S. Rao, P.S. RaoU
Department of Chemistry, Kakatiya Uni¨ ersity, Warangal - 506 009, A.P. India

Received 2 November 1998; accepted Žrevised. 18 January 1999

Abstract

The isolation and NMR spectra of anacrotine Ž1. from Crotalaria trifoliastrum seeds are
reported. Q 1999 Elsevier Science B.V. All rights reserved.

Keywords: Crotalaria trifoliastrum; Anacrotine; Alkaloids

Plant. Crotalaria trifoliastrum Willd ŽFabaceae., seeds collected in September]Oc-

tober 1997 at Bheemadevarapalli, Karimnagar District, A.P., India, and identified
by Dr V.S. Raju and Dr Ragan, Department of Botany, Kakatiya University,
Warangal. A voucher specimen is deposited in the Department of Botany, Kakatiya
University, Warangal.

Uses in traditional medicine: Roots are used as a purgative w1x.

U
Corresponding author.

0367-326Xr99r$ - see front matter Q 1999 Elsevier Science B.V. All rights reserved.
PII: S 0 3 6 7 - 3 2 6 X Ž 9 9 . 0 0 0 5 9 - 3
450 M.S. Rao, P.S. Rao r Fitoterapia 70 (1999) 449]450

Previously isolated classes of constituents: Alkaloids w2x from the fruits, medica-
genin w3x and munchiwarin w4x from the roots.

New isolated constituents: Anacrotine Ž1. w5x Žyield: 0.02% from dried seeds..

Anacrotine Ž1.. Mp 193]1958C; w a x D q308 Žc 1, MeOH.; UVmax ŽMeOH.: 220

nm; IR bands ŽKBr.: 3406, 1725, 1028, 1078, 1109 and 1281 cmy1 ; 1 H-NMR Ž400
MHz, CDCl 3 .: d 6.2 Ž1H, s, H-2., 5.70 Ž1H, d, H-20., 4.05, 5.45 Ž2H, dd, H-9., 5.23
Ž1H, t, H-7., 3.40, 3.90 Ž2H, m, H-3., 2.6, 3.4 Ž2H, t, H-5., 2.39 Ž2H, m, H-14., 4.60
Ž3H, m, H-6., 1.85 Ž1H, m, H-13., 1.82 Ž3H, s, H-21., 1.32 Ž3H, s, H-18., 0.96 Ž3H,
d, H-19.; 13 C-NMR Ž100 MHz, CDCl 3 .: 131.5 ŽC-1., 136.5 ŽC-2., 63.5 ŽC-3., 58.5
ŽC-5., 74.8 ŽC-6., 75.5 ŽC-7., 74.4 ŽC-8., 60.7 ŽC-9., 76.8 ŽC-12., 38.3 ŽC-13., 169.6
ŽC-16., 25.2 ŽC-18., 11.3 ŽC-19., 134.3 ŽC-20., 15.2 ŽC-21.; MS m r z Žrel. int..: 351
wMxq ŽC 18 H 25 O6 N., 335, 334, 307, 306, 292, 364, 262, 236, 234, 225, 194, 181, 152
Ž100%., 136, 135, 118, 93 Ž100%., 80, 67, 53.

Acknowledgements

The authors wish to thank Prof. D.J. Robins, Department of Chemistry, Univer-
sity of Glasgow, UK for providing the high field spectral data of the compound and
to Dr Raju and Dr Ragan, Department of Botany, KUC for identifying the plant.
M.S.R. thanks the University Grants Commision ŽUGC., New Delhi for the award
of Senior Research Fellowship ŽSRF..

References
w1x Chopra RN, Nayar SL, Chopra IC. Glossary of Indian Medicinal Plants, CSIR, New Delhi, 1956, p.
81.
w2x Culvenor CCJ, Smith LW. Aust J Chem 1962;15:121.
w3x Rao MS, Kumar JK, Rao PS, Toth G, Simon A, Balazs B, Duddeck H. Fitoterapia Žin press..
w4x Yang S-W, Cordell GA, Lotter H et al. J Nat Prod 1998;61:1274.
w5x Atal CK, Kapur KK, Culvenor CCJ, Smith LW. Tetrahedron Lett 1966; 537.