*Corresponding author. Tel./fax:#33-3-20-96-40-39. E-mail address:fbailleu@phare.univ-lille2.fr (F. Bailleul)
Biochemical Systematics and Ecology 28 (2000) 1031}1033
Two major
#
avonoids from
Ballota nigra
Marie-Caroline Bertrand
!
, Franc
7
ois Tillequin
"
,
Franc
7
ois Bailleul
!
,
*
!Laboratoire de Pharmacognosie, Faculte&des Sciences Pharmaceutiques et Biologiques, Universite de Lille 2, BP 83, 59006 Lille Cedex, France
"Laboratoire de Pharmacognosie, Faculte& des Sciences Pharmaceutiques et Biologiques,
URA au CNRS no. 1310, 4, Avenue de l'Observatoire, 75006 Paris, France
Received 7 October 1999; accepted 20 December 1999
Abstract
Two lactoylated#avonoids, luteolin-7-lactate and luteolin-7-glucosyl-lactate were isolated
from Ballota nigra. They should be used for the chemical standardization of this drug of
medicinal interest.( 2000 Elsevier Science Ltd. All rights reserved.
Keywords: Ballota nigra; Flavonoid lactates; Luteolin-7-lactate; Luteolin-7-glucosyl-lactate
1. Subject and source
Ballota nigraL. (Lamiaceae) is a perennial herb which is commonly distributed in
Western Europe where#owering aerial parts are used in medicine for treating cough
and more especially for neurosedative activities (Wichtl and Anton, 1999). Ballota
nigra was collected in 1996 in the vicinity of Angers (France) and identi"ed in comparison with an authentic sample cultivated in the University of Lille Botanical Garden (France). A voucher specimen is kept in the Department of Pharmacognosy of that University (No. B.n. 5).
2. Previous work
Previous investigations of the aerial parts resulted in the isolation of the#avonoids apigenin-7-glucoside, vicenin-2 (Darbour et al., 1986) and tangeretin (Kisiel and
Piozzi, 1995) and the labdane diterpenoids ballotinone (Savona et al., 1976a),
ballonig-rine (Savona et al., 1976b), 7a-acetoxymarrubiin (Savona et al., 1977a), ballotenol
(Savona et al., 1977b), preleosibirin (Bruno et al., 1986) and 13-hydroxyballonigrinolide (Seidel et al., 1996a). Recent studies of an alcoholic extract led to the isolation of seven phenylpropanoid glycosides: verbascoside, forsythoside B, arenarioside, ballotetroside, alyssonoside, lavandulifolioside and angoroside A and a non-glycosidic derivative: (#)-(E)-ca!eoyl-L-malic acid (Seidel et al., 1996b, 1997 and Didry et al., 1999).
Pharmacological studies were carried out on the major phenylpropanoid
deriva-tives isolated from Ballota nigra. These compounds could account for the
neur-osedative activity of the drug. In addition, they exhibit potent antioxidant activities which are of therapeutic interest (Daels-Rakotoarison et al., 2000; Seidel et al., 2000).
3. Present study
A MeOH : H
2O 3 : 7 extract of the dried aerial parts of Ballota nigra(120 g) was
submitted to repeated gel"ltration chromatographies (Sephadex LH-20 eluting with
H
2O). Fractions containing1 and 2 were further puri"ed separatively by CC on
cellulose eluting with H
2O a!ording the known #avonoids luteolin-7-O-lactate
1(90 mg) and luteolin-7-O-[2-O-b-D-glycopyranosyl-lactate]2(94 mg). Spectral data
(UV, 1H and 13C NMR) of 1 and 2 are identical to those previously described
(Nawwar et al., 1989). The spectra are available from the Lille laboratory. Chemical correlations (treatment with CH
2N2, controlled acid and alkaline hydrolysis) were
used to con"rm the linkages of the di!erent moieties which were not previously
unambiguously determined as1and2.
4. Chemotaxonomic signi5cance
The isolation of 1 and 2 from Ballota nigra is of chemotaxonomic interest as
lactoylated#avonoids are very rare plant constituents here reported for the"rst time
in the genusBallota. Up till now these two compounds were only described in one
species of the related genusMarrubium,M.vulgare(Nawwar et al., 1989).
It should be emphasized that1and2are the major#avonoids isolated fromBallota nigra, other#avonoids previously described being present only in very small amounts.
Consequently,1and2should be used for the chemical standardization of the drug
and its extracts of medicinal interest.
Acknowledgements
Authors are grateful to Agence Franc7aise de SeHcuriteH Sanitaire des Produits de
SanteH *UniteH de PharmacopeHe for"nancial support (Grant No. 179).
References
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