Fitoterapia 73 Ž2002.

353᎐355

Phytochemical communication

Isolation and structural elucidation of

3,4⬘,5,7-tetraacetyl quercetin from Adina
cordifolia ž Karam ki Gaach/
Meneni S. Rao a,b, Helmut Duddeck b,
Roman Dembinski a,U
a
Department of Chemistry and Center for Biomedical Research, Oakland Uni¨ ersity, Rochester,
Michigan 48309, USA
b
Uni¨ ersitat
¨ Hanno¨ er, Institut fur
¨ Organische Chemie, Schneiderberg 1B, D-30167 Hanno¨ er,
Germany

Received 30 December 2001; accepted 12 April 2002

Abstract

3,4⬘,5,7-tetraacetyl quercetin Ž1. was isolated from the heartwood of Adina cordifolia. The
structure was elucidated on the basis of spectral evidence. 䊚 2002 Elsevier Science B.V. All
rights reserved.

Keywords: Adina cordifolia; Flavonol; Quercetin

Plant. The plant material was collected from the Pakhal Forest ŽWarangal, Andhra
Pradesh, India. in September 1999 and was identified by Dr V.S. Raju, Department
of Botany, Kakatiya University, Warangal, India. A voucher specimen ŽNo. 131. has
been deposited in the herbarium of the Department of Botany, Kakatiya Univer-
sity, Warangal, India.

Uses in traditional medicine. The plant Adina cordifolia has been used in oriental
medicine since ancient times as an essential component of various antiseptic and

U
Corresponding author. Fax: q1-248-370-2321.
E-mail address: dembinsk@oakland.edu ŽR. Dembinski..

0367-326Xr02r$ - see front matter 䊚 2002 Elsevier Science B.V. All rights reserved.
PII: S 0 3 6 7 - 3 2 6 X Ž 0 2 . 0 0 0 8 8 - 6
354 M.S. Rao et al. r Fitoterapia 73 (2002) 353᎐355

febrifuge prescriptions w1x. The A. cordifolia stem has been evaluated for its
antiulcer potential and active constituent showed interesting HqrKq ATPase
inhibitory activity w2x. Antifertility properties of the leaf extract of A. cordifolia
have been examined w3x.

Previously isolated classes of constituents. Ursolic acid, flavonoids from leaves w4x,
coumarin glycoside w5x, flavonoids w6᎐10x, saponins w11x, alkaloids w11᎐16x from
heartwood.

New-isolated constituent. 3,4⬘,5,7-tetraacetyl quercetin Ž1. Ž0.08% on air-dried

heartwood. ŽFig. 1..

Fig. 1. Structure of Ž1. and 13 C᎐ 1 H long-range correlation ŽHMBC..

3,4⬘,5,7-tetraacetyl quercetin Ž1.. mp 78 ⬚C; UV ␭max ŽMeOH. nm: 254, 270, 332; IR
bands ŽKBr.: 3093, 1774, 1652, 1623, 1506, 1479, 1371, 1195, 1178 cmy1 ; 1 H-NMR
Ž400 MHz, CDCl 3 .: ␦ 8.12 Ž1H, d, J 2.0 Hz, H-2⬘., 7.71 Ž1H, dd, J 8.5, 2.0 Hz,
H-6⬘., 7.68 Ž1H, d, J 8.5, H-5⬘., 7.24 Ž1H, d, J 2.5 Hz, H-8., 6.86 Ž1H, d, J 2.0 Hz,
H-6., 2.41, 2.33, 2.32, 2.31 Žeach 3H, s, CH 3 COO.. 13 C-NMR Ž100 MHz, CDCl 3 .: ␦
170.0 ŽC-5.U , 169.3 ŽC-4.U , 167.9, 167.9, 167.8, 167.8 Ž4 CH 3 C ⫽O., 156.9 ŽC-9.,
154.3 ŽC-7., 153.8 ŽC-2., 144.4 ŽC-4⬘., 142.3 ŽC-3⬘., 134.1 ŽC-3., 127.8 ŽC-1⬘., 126.7
ŽC-6⬘.UU , 126.5 ŽC-2⬘.UU , 123.9 ŽC-5⬘.UU , 114.8 ŽC-10., 114.2 ŽC-6.UU , 109.0 ŽC-8.UU ,
21.2, 21.1, 20.7, 20.5 Ž4 CH 3 .UU ; EI MS mrz Žrel. int..: 470 wMq, C 23 H 18 O 11 x Ž80.,
428 Ž81., 386 Ž86., 344 Ž88., 302 Ž90..
U13
C᎐ 1 H long-range correlation ŽHMBC. neither to H-6 nor H-8 was observed;
assignment may be reversed.
UU
Signals observed in 135 DEPT.

Acknowledgements

M.S. Rao and R. Dembinski thanks the Oakland University and Research
 M.S. Rao et al. r Fitoterapia 73 (2002) 353᎐355 355

Excellence Program in Biotechnology for supporting this research. This work is

also a part of the project ‘Biologically Active Natural Products: Synthetic Diversity’,
Department of Chemistry, Hannover University. The authors are thankful to Prof.
P.S. Rao for helpful discussions.

References
w1x Chopra RN, Nayar SL, Chopra IC. Glossary of Indian medicinal plants. New Delhi: C.S.I.R.
Publication, 1956, p. 7.
w2x Kasinadhuni VRR, Rajashekhar G, Rajagopalan R et al. Fitoterapia 1999;70:93.
w3x Sabir M, Razdan MK. Indian J Physiol Pharmacol 1970;14:209.
w4x Dayal R, Dobhal PC. J Indian Chem Soc 1993;70:181.
w5x Asheervadam Y, Rao PS, Murray RDH. Fitoterapia 1986;57:231.
w6x Srivastava SK. Can J Chem 1983;61:1827.
w7x Srivastava SK, Gupta HO. Planta Med 1983;48:58.
w8x Srivastava SK, Gupta RK, Gupta HO, Mishra M. Ind J Pharm Sci 1981;43:153.
w9x Srivastava SK, Gupta RK, Srivastava SD. Indian J Chem Sect B 1981;20B:833.
w10x Srivastava SD, Srivastava SK. Curr Sci 1986;55:21.
w11x Joshi S, Singb AK, Dhar DN. Himalayan Chem Pharm Bull 1986;3:26.
w12x Cannon JR, Ghisalberti EL, Lojanapiwatna V. J Sci Soc Thailand 1980;6:54.
w13x Merlini L, Nasini G. Gazz Chim Ital 1968;98:974.
w14x Brown RT, Rao KVJ, Rao PVS, Row LR. Chem Commun 1968;350.
w15x Brown RT, Row LR. Chem Commun 1967;453.
w16x Balazs
´ B, Toth´ G, Rao PS, Narender T, Rao NS, Horvath ´ G, Duddeck H. Magn Reson Chem
1999;37:751.