Fitoterapia. 2002, 73/4: 353-355

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 University, 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: [email protected] 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

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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

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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.

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