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Phytochemical communication

Constituents of Crotalaria trifoliastrum rootsM.S. Rao a, J.K. Kumar a, P.S. Rao a, G. Toth b, A. Simonb,

B. Balazs b, H. Duddeck c,Ua Department of Chemistry, Kakatiya Uni ersity, Warangal, 506009, Andra Pradesh, India

bTechnical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry of the Technical Uni ersity, Szent Gellert ter 4, H-1111

Budapest, HungarycUni ersitat Hanno er, Institut fur Organische Chemie, Schneiderberg 1B, D-30167 Hanno er,

Germany

Received 11 May 1998; accepted 24 June 1998

Keywords: Crotolaria trifoliastrum ; Betulinic acid; Medicagenin; O-methylinositol

. .Plant. Crotolaria trifoliastrum . Willd. Fabaceae , roots 1 kg, shade-died collectedduring September and October 1997 at Bheemadevarapalli, Karimnagar District, A. P., India and identified by Dr V.S. Raju and Dr Ragan, Department of Botany,Kakatiya University, Warangal. Voucher specimen deposited in the Department of

Botany, Kakatiya University, Warangal.

w xUse in traditional medicine. Purgative 1 .

w xPreviously isolated classes of constituents. Pyrrolizidine alkaloids 1 .

. w x . .w xNew-isolated constituents. Betulinic acid 1 2 4 10 mg , medicagenin 2 5 50. . w x .mg , 1-O-methyl- myo-inositol 3 6 40 mg .

U

Corresponding author. Tel.: q 49 511 762 4615; fax: q 49 511 762 4616; e-mail:duddeck@mbox.oci.uno-hannover.de

0367-326Xr 99r $ - see front matter 1999 Elsevier Science B.V. All rights reserved. .PII: S 0 3 6 7 - 3 2 6 X 9 8 0 0 0 3 0 - 6

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( ) 1 . . . Betulinic acid 1 . H-NMR 500 MHz, CDCl : 0.95 H-1 , 1.70 H-1 , 1.573 . . . H-2 , 1.62 H-2 , 3.13 H-3, dd , J 11.5, 4.9 Hz , 0.71 H-5, ddd , J 9.1, 2.0, 2.0

. . . . . Hz , 1.55 H-6 , 1.45 H-6 , 1.42 H-7 , 1.42 H-7 , 1.33 H-9, ddd , J 12.7, 2.6

. . . . . Hz , 1.45 H-11 , 1.25 H-11 , 1.07 H-12 , 1.73 H-12 , 2.30 H-13, ddd , J . . . . .12.9, 11.6, 3.7 Hz , 1.18 H-15 , 1.53 H-15 , 1.43 H-16 , 2.23 H-16 , 1.63

. . .H-18, ddd , J 11.4, 11.4 Hz , 3.02 H-19, ddd , J 11.4, 10.7, 4.8 Hz , 1.40 H-21 , . . . . . .1.93 H-21 , 1.43 H-22 , 1.91 H-22 , 0.95 H-23 , 0.75 H-24 , 0.86 H-25 , . . . .0.97 H-26 , 1.01 H-27 , 4.59 H-29 E, dd , J 2.2, 1.0 Hz , 4.71 H-29Z, d, J 2.2 Hz , . 13 w x1.69 H-30, d, J 1.0 Hz . C-NMR data are consistent with literature data. 4 6

However, according to our data the pairwise assignments of C-18 r C-19 andC-15r C-21 should be reversed.

( ) 1 . . . Medicagenin 2 . H-NMR 500 MHz, CDCl : 7.53 H- , 7.75 H- , 7.583 . . . . . . .H-2 , 6.85 H-3 , 7.62 H-6 , 3.37 H-1 , 5.19 H-2 , 1.67 H-4 , 1.79 H-5 ,

. q . q . q . 13 .3.31 H-1 , 5.34 H-2 , 1.79 H-4 , 1.75 H-5 ; C-NMR 500 MHz, CDCl :3 . . . . . .193.8 C s O , 118.6 C- , 145.2 C- , 127.9 C-1 , 131.6 C-2 , 117.0 C-3 , 161.5

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. . . . . .C-4 , 114.5 C-1 , 163.4 C-2 , 116.8 C-3 , 161.3 C-4 , 121.1 C-5 , 129. 4 . . . . . . q .C-6 , 22.7 C-1 , 123.4 C-2 , 132.5 C-3 , 26.0 C-4 , 18.0 C-5 , 29.3 C-1

q . q . q . q .123.5 C-2 134.1 C-3 26.0 C-4 , 18.0 C-5 .

( ) 1 . .1-O-methyl-myo-inositol 3 . H-NMR 500 MHz, CD OD : 3.36 H-1 , 3.643 . . . . . .H-2 , 3.75 H-3 , 3.99 H-4 , 4.00 H-5 , 3.80 H-6 , 3.59 OCH .3

NMR data based on extensive 1D and 2D experiments gs-COSY, TOCSY,.NOESY, HMQC, HMBC on a Bruker DRX-500 ; all assignments unequivocal.

Acknowledgements

.M.S.R. thanks the University Grant Commission UGC , New Delhi, for the .award of Council of Scientific and Industrial Research India CSIR . J.K.K. thanks

.CSIR for a reward of Senior Research Fellowship SRF . This work was supported .by the Deutsche Forschungsgemeinschaft Du 98 r 12 and the Hungarian Academy

. of Sciences Project No. 89 , Hungarian National Research Foundation OTKA.No. T 026264 , and by the Fonds der Chemischen Industrie.

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