Ž .Fitoterapia 73 2002 353�355

Phytochemical communication

Isolation and structural elucidation of3,4�,5,7-tetraacetyl quercetin from Adina

ž /cordifolia Karam ki Gaach

Meneni S. Raoa,b, Helmut Duddeckb,Roman Dembinskia,�

aDepartment of Chemistry and Center for Biomedical Research, Oakland Uni�ersity, Rochester,Michigan 48309, USA

bUni�ersitat Hanno�er, Institut fur Organische Chemie, Schneiderberg 1B, D-30167 Hanno�er,¨ ¨Germany

Received 30 December 2001; accepted 12 April 2002

Abstract

Ž .3,4�,5,7-tetraacetyl quercetin 1 was isolated from the heartwood of Adina cordifolia. Thestructure was elucidated on the basis of spectral evidence. � 2002 Elsevier Science B.V. Allrights reserved.

Keywords: Adina cordifolia; Flavonol; Quercetin

ŽPlant. The plant material was collected from the Pakhal Forest Warangal, Andhra.Pradesh, India in September 1999 and was identified by Dr V.S. Raju, Department

Ž .of Botany, Kakatiya University, Warangal, India. A voucher specimen No. 131 hasbeen 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 orientalmedicine since ancient times as an essential component of various antiseptic and

� Corresponding author. Fax: �1-248-370-2321.Ž .E-mail address: dembinsk@oakland.edu R. Dembinski .

0367-326X�02�$ - see front matter � 2002 Elsevier Science B.V. All rights reserved.Ž .PII: S 0 3 6 7 - 3 2 6 X 0 2 0 0 0 8 8 - 6

( )M.S. Rao et al. � Fitoterapia 73 2002 353�355354

� �febrifuge prescriptions 1 . The A. cordifolia stem has been evaluated for itsantiulcer potential and active constituent showed interesting H��K� ATPase

� �inhibitory activity 2 . Antifertility properties of the leaf extract of A. cordifolia� �have been examined 3 .

� �Previously isolated classes of constituents. Ursolic acid, flavonoids from leaves 4 ,� � � � � � � �coumarin glycoside 5 , flavonoids 6�10 , saponins 11 , alkaloids 11�16 from

heartwood.

Ž . ŽNew-isolated constituent. 3,4�,5,7-tetraacetyl quercetin 1 0.08% on air-dried. Ž .heartwood Fig. 1 .

Ž . 13 1 Ž .Fig. 1. Structure of 1 and C� H long-range correlation HMBC .

Ž . Ž .3,4�,5,7-tetraacetyl quercetin 1 . mp 78 �C; UV �max MeOH nm: 254, 270, 332; IRŽ . �1 1bands KBr : 3093, 1774, 1652, 1623, 1506, 1479, 1371, 1195, 1178 cm ; H-NMR

Ž . Ž . Ž400 MHz, CDCl : � 8.12 1H, d, J 2.0 Hz, H-2� , 7.71 1H, dd, J 8.5, 2.0 Hz,3. Ž . Ž . ŽH-6� , 7.68 1H, d, J 8.5, H-5� , 7.24 1H, d, J 2.5 Hz, H-8 , 6.86 1H, d, J 2.0 Hz,. Ž . 13 Ž .H-6 , 2.41, 2.33, 2.32, 2.31 each 3H, s, CH COO . C-NMR 100 MHz, CDCl : �3 3

Ž .� Ž .� Ž . Ž .170.0 C-5 , 169.3 C-4 , 167.9, 167.9, 167.8, 167.8 4 CH C�O , 156.9 C-9 ,3Ž . Ž . Ž . Ž . Ž . Ž .154.3 C-7 , 153.8 C-2 , 144.4 C-4� , 142.3 C-3� , 134.1 C-3 , 127.8 C-1� , 126.7

Ž .�� Ž .�� Ž .�� Ž . Ž .�� Ž .��C-6� , 126.5 C-2� , 123.9 C-5� , 114.8 C-10 , 114.2 C-6 , 109.0 C-8 ,Ž .�� Ž . � � � Ž .21.2, 21.1, 20.7, 20.5 4 CH ; EI MS m�z rel. int. : 470 M , C H O 80 ,3 23 18 11

Ž . Ž . Ž . Ž .428 81 , 386 86 , 344 88 , 302 90 .�13 1 Ž .C� H long-range correlation HMBC neither to H-6 nor H-8 was observed;

assignment may be reversed.�� Signals observed in 135 DEPT.

Acknowledgements

M.S. Rao and R. Dembinski thanks the Oakland University and Research

( )M.S. Rao et al. � Fitoterapia 73 2002 353�355 355

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

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