Fitoterapia 70 Ž1999.

200]202

Phytochemical communication

Constituents of Crotalaria trifoliastrum roots

M.S. Rao a , J.K. Kumar a , P.S. Rao a , G. Toth
´ b, A. Simonb,
b c,U
´ , H. Duddeck
B. Balazs
a
Department of Chemistry, Kakatiya Uni¨ ersity, Warangal, 506009, Andra Pradesh, India
b
Technical 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, Hungary
c
Uni¨ 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. ŽFabaceae., roots Ž1 kg, shade-died. collected

during 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.

Use in traditional medicine. Purgative w1x.

Previously isolated classes of constituents. Pyrrolizidine alkaloids w1x.

New-isolated constituents. Betulinic acid Ž1. w2]4x Ž10 mg., medicagenin Ž2. w5x Ž50
mg., 1-O-methyl-myo-inositol Ž3. w6x Ž40 mg..

U
Corresponding author. Tel.: q49 511 762 4615; fax: q49 511 762 4616; e-mail:
duddeck@mbox.oci.uno-hannover.de

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 8 . 0 0 0 3 0 - 6
 M.S. Rao et al. r Fitoterapia 70 (1999) 200]202 201

Betulinic acid (1). 1 H-NMR Ž500 MHz, CDCl 3 .: d 0.95 ŽH-1 a ., 1.70 ŽH-1 b ., 1.57
ŽH-2 a ., 1.62 ŽH-2 b ., 3.13 ŽH-3, dd, J 11.5, 4.9 Hz., 0.71 ŽH-5, ddd, J 9.1, 2.0, 2.0
Hz., 1.55 ŽH-6 a ., 1.45 ŽH-6 b ., 1.42 ŽH-7a ., 1.42 ŽH-7b ., 1.33 ŽH-9, ddd, J 12.7, 2.6
Hz., 1.45 ŽH-11 a ., 1.25 ŽH-11 b ., 1.07 ŽH-12 a ., 1.73 ŽH-12 b ., 2.30 ŽH-13, ddd, J
12.9, 11.6, 3.7 Hz., 1.18 ŽH-15 a ., 1.53 ŽH-15 b ., 1.43 ŽH-16 a ., 2.23 ŽH-16 b ., 1.63
ŽH-18, ddd, J 11.4, 11.4 Hz., 3.02 ŽH-19, ddd, J 11.4, 10.7, 4.8 Hz., 1.40 ŽH-21 a .,
1.93 ŽH-21 b ., 1.43 ŽH-22 a ., 1.91 ŽH-22 b ., 0.95 ŽH-23., 0.75 ŽH-24., 0.86 ŽH-25.,
0.97 ŽH-26., 1.01 ŽH-27., 4.59 ŽH-29E, dd, J 2.2, 1.0 Hz., 4.71 ŽH-29Z, d, J 2.2 Hz.,
1.69 ŽH-30, d, J 1.0 Hz.. 13 C-NMR data are consistent with literature data. w4]6x
However, according to our data the pairwise assignments of C-18rC-19 and
C-15rC-21 should be reversed.

Medicagenin (2). 1 H-NMR Ž500 MHz, CDCl 3 .: d 7.53 ŽH-a ., 7.75 ŽH-b ., 7.58
ŽH-2., 6.85 ŽH-3., 7.62 ŽH-69., 3.37 ŽH-10 ., 5.19 ŽH-20 ., 1.67 ŽH-40 ., 1.79 ŽH-50 .,
3.31 ŽH-10 ., 5.34 ŽH-2q. , 1.79 ŽH-4q. , 1.75 ŽH-5q. ; 13 C-NMR Ž500 MHz, CDCl 3 .:
193.8 ŽC s O., 118.6 ŽC-a ., 145.2 ŽC-b ., 127.9 ŽC-1., 131.6 ŽC-2., 117.0 ŽC-3., 161.5
202 M.S. Rao et al. r Fitoterapia 70 (1999) 200]202

ŽC-4., 114.5 ŽC-19., 163.4 ŽC-29., 116.8 ŽC-39., 161.3 ŽC-49., 121.1 ŽC-59., 129. 4
ŽC-69., 22.7 ŽC-10 ., 123.4 ŽC-20 ., 132.5 ŽC-30 ., 26.0 ŽC-40 ., 18.0 ŽC-50 ., 29.3 ŽC-1q.
123.5 ŽC-2q. 134.1 ŽC-3q. 26.0 ŽC-4q. , 18.0 ŽC-5q. .

1-O-methyl-myo-inositol (3). 1 H-NMR Ž500 MHz, CD3 OD.: d 3.36 ŽH-1., 3.64
ŽH-2., 3.75 ŽH-3., 3.99 ŽH-4., 4.00 ŽH-5., 3.80 ŽH-6., 3.59 ŽOCH 3 ..
NMR data based on extensive 1D and 2D experiments Žgs-COSY, TOCSY,
NOESY, HMQC, HMBC on a Bruker DRX-500.; all assignments unequivocal.

Acknowledgements

M.S.R. thanks the University Grant Commission ŽUGC., New Delhi, for the
award of Council of Scientific and Industrial Research India ŽCSIR.. J.K.K. thanks
CSIR for a reward of Senior Research Fellowship ŽSRF.. This work was supported
by the Deutsche Forschungsgemeinschaft ŽDu 98r12. and the Hungarian Academy
of Sciences ŽProject No. 89., Hungarian National Research Foundation ŽOTKA
No. T 026264., and by the Fonds der Chemischen Industrie.

References
w1x Culvenor CC, J., Smith LW. Aust J Chem 1962;15:121.
w2x Sholichin M, Yamasaki K. Chem Pharm Bull 1980;28:106.
w3x Indrayanto G, Voelter W. Chem Ztg 1983;107:238.
w4x Kitajima J, Shindo M. Chem Pharm Bull 1990;38:714.
w5x Ranga Rao GV, Rao PS, Raghava Raju K. Phytochemistry 1987;26:2866.
w6x Dorman DE, Angyal SL, Roberts JD. J Am Chem Soc 1970;92:1351.