Fitoterapia 71 2000.
587589
Phytochemical communication
Major dicaffeoylquinic acids from Artemisia
ulgaris
Andree
Carnat a , Annie Heitz b, Didier Fraisse a ,
Andre-Paul
Carnat a , Jean-Louis Lamaisona,U
Laboratoire de Pharmacognosie et Phytotherapie,
Faculte de Pharmacie, Uni ersite dAu ergne,
28 place Henri Dunant, F-63000 Clermont-Ferrand, France
b
CBS, CNRS INSERM, Faculte de Pharmacie, Uni ersite de Montpellier I, 15 a enue Charles
Flahault, F-34060 Montpellier Cedex
1, France
Received 13 December 1999; accepted 18 February 2000
Abstract
The two major caffeoylquinic acids, 3,5-di-O-caffeoylquinic acid and 1,5-di-O-caffeoylquinic acid, were new-isolated from the flowering tops of Artemisia ulgaris yield 2.0%
and 0.3% on dry weight, respectively. and characterized by spectroscopic analysis. 2000
Elsevier Science B.V. All rights reserved.
Keywords: Artemisia ulgaris; Caffeoylquinic acids
Plant. Artemisia ulgaris L. Asteraceae. flowering tops were collected in July 1998
in Puy-de-Dome
France. and authenticated by Prof. J.-L. Lamaison. A voucher
specimen is deposited in the herbarium of the Faculty of Pharmacy of ClermontFerrand.
Uses in traditional medicine. Commonly used in European traditional medicine as
a choleretic and for amenorrhoea and dysmenorrhoea w1x.
U
Corresponding author. Tel.: q33-4-73-60-80-26; fax: q33-4-73-28-28-49.
E-mail address: jllamaison@[Link] J. Lamaison..
0367-326Xr00r$ - see front matter 2000 Elsevier Science B.V. All rights reserved.
PII: S 0 3 6 7 - 3 2 6 X 0 0 . 0 0 1 6 3 - 5
588
A. Carnat et al. r Fitoterapia 71 (2000) 587589
Previously isolated constituents. Other phenolic acids as caffeic and chlorogenic
acids w2x.
New-isolated constituents. 3,5-Di-O-caffeoylquinic acid 1. w3x yield: 2.0% on dry
weight. and 1,5-di-O-caffeoylquinic acid 2. w4,5x 0.3.. Caffeoylquinic acids from
artichoke have been reported as choleretic w6x.
3,5-Di-O-caffeoylquinic acid (1). White powder; UV max MeOH.: 218, 237,
300sh, 326 nm; 1 H-NMR 300 MHz, DMSO-d6 .: 7.48 1H, d, J 16.0 Hz, H-7.,
7.46 1H, d, J 16.0 Hz, H-7 ., 7.05 1H, d, J 2.0 Hz, H-2., 7.03 1H, d, J 2.0 Hz,
H-2 ., 7.00 1H, dd, J 8.1, 2.0 Hz, H-6., 6.97 1H, dd, J 8.1, 2.0 Hz, H-6 ., 6.76
1H, d, J 8.1 Hz, H-5., 6.22 1H, d, J 16.0 Hz, H-8., 5.27 1H, m, H-5., 5.16 1H,
m, H-3., 3.72 1H, dd, H-4., 2.11 1H, dd, H-2 a ., 1.94 1H, dd, H-6 a ., 1.81 1H, dd,
H-6 b ., 1.76 1H, dd, H-2 b .; 13 C-NMR DMSO-d6 .: 80.0 C-1., 35.9 C-2., 72.5
C-3., 69.9 C-4., 71.1 C-5., 38.8 C-6., 175.0 C-7., 125.5 C-1., 114.3 C-2., 145.4
C-3., 148.1 C-4., 115.4 C-5., 120.9 C-6., 144.2 C-7., 114.4 C-8., 165.9
C-9., 125.4 C-1 ., 114.3 C-2 ., 145.8 C-3 ., 148.4 C-4 ., 115.4 C-5 ., 120.9
C-6 ., 144.2 C-7 ., 114.4 C-8 ., 165.6 C-9 ..
A. Carnat et al. r Fitoterapia 71 (2000) 587589
589
1,5-Di-O-caffeoylquinic acid (2). White powder; UV max MeOH.: 217, 241, 300sh,
325 nm; 1 H-NMR 300 MHz, DMSO-d6 .: 7.46 1H, d, J 16.0 Hz, H-7., 7.34 1H,
d, J 16.0 Hz, H-7 ., 7.06 1H, d, J 1.9 Hz, H-2., 7.00 1H, d, J 1.9 Hz, H-2 ., 6.94
1H, dd, J 8.2, 1.9 Hz, H-6., 6.90 1H, dd, J 8.2, 1.9 Hz, H-6 ., 6.73 1H, d, J 8.2
Hz, H-5 ., 6.70 1H, d, J 8.2 Hz, H-5., 6.21 1H, d, J 16.0 Hz, H-8., 6.12 1H, d, J
16.0 Hz, H-8 ., 5.24 1H, m, H-5., 4.00 1H, m, H-3., 3.50 1H, dd, H-4., 2.49 1H,
dd, H-2 a ., 2.33 1H, dd, H-6 a ., 2.16 1H, dd, H-2 b ., 1.78 1H, dd, H-6 b .; 13 C-NMR
DMSO-d6 .: 80.0 C-1., 34.2 C-2., 69.0 C-3., 72.5 C-4., 70.6 C-5., 37.9 C-6.,
176.9 C-7., 124.8 C-1., 114.3 C-2., 145.8 C-3., 149.3 C-4., 115.6 C-5., 121.1
C-6., 144.8 C-7., 113.6 C-8., 166.2 C-9., 125.4 C-1 ., 114.3 C-2 ., 145.8
C-3 ., 148.4 C-4 ., 115.6 C-5 ., 120.4 C-6 ., 143.2 C-7 ., 116.1 C-8 ., 165.6
C-9 . w5x.
Acid hydrolysis of 1 and 2 gave caffeic acid, identified by chromatographic
comparison with authentic samples TLC, HPLC, UV..
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