A 606 Plonta Med.
59, Supplement Issue 1993
Prodeiphinidins and Dihydroflavonol
Glucosides from Cistus incanus
A. Danne, F. Petereit, and A. Nahrstedt
Institut fur Pharmazeutische Biologie und Phytochemie,
Westfälische-Wilhelms-Universität, HittorfstraBe 56,
D-48149 Munster, F.R.G.
A decoction of the air-dried, above-ground parts of
Cistus incanus L. (Cistaceae) is mainly used in traditional med-
icine by the inhabitants of northern Greece (Chalkidiki) as an
anti-inflammatory agent for various skin diseases.
In continuation of our research (1) on the chemical
composition of the active extract, we now report on the iso-
lation and identification of five prodeiphinidins and three dihy-
droflavonol glucosides. An acetone/H20 extract was shaken
with EtOAc, the remaining H20-phase was separated by CC on
Sephadex LH 20, MCI CHP 20P, HPLC on Hypersil ODS, and
preparative TLC on silica gel.
The prodeiphinidins isolated were epigallocat-
echin-(4/3--÷8)-catechin (2) and epigallocatechin-(4J3—*8)-gal-
locatechin (3,4), the novel galloylated isomers epigallocat-
echin-3-O-gallate-(4/3--*8)-gallocatechin, epigallocatechin-3-
O-gallate-(4$—*6)-gallocatechin, and the trimer gallocatechin-
(4a—*8)-gallocatechin-(4a—*8)-gallocatechin (5). Dihydromy-
ricetin 3'-O-f3-u-glucoside (6), and dihydrokaempferol 7-O-J3-
D-glucoside (7), and dihydroquercetion 7-O-13-o-glucoside were
also identified. The structures were established by 1H-NMII,
1H-1H COSY, DCI-MS, CD, and [ajg°' of the peracetate
derivatives and chemical degradation in comparison with
published data.
References
Petereit, F., Kolodziej, H., Nahrstedt, A. (1992) in: Plant Polyphenols,
(Hemingway, B. W., Laks, P. E., eds.), pp. 729—737, Plenum Press,
New York.
2
Gupta, B. K., Haslam, B. (1981) J. Chem. Soc., PerkinTrans. 1,1148.
Lee, M., Morimoto, S., Nonaka, G., Nishioka, G.-I. (1992) Phyto-
chemistry 31, 2117.
Tanaka, T., Ishida, N., Ishimatsu, M., Nonaka, G., Nishioka, I. (1992)
Chem. Pharm. Bull. 40, 2092.
Tits, M., Angenot, L., Poukens, P., Wan B., Dierckxsens, Y. (1992)
Phytochemistry 31, 971.
6
Lundgren, L. N., Theander, 0. (1988) Phytochemistry 27, 829.
Foo, L. Y., Karchesy, J. J. (1989) Phytochemistry 28, 1237.
2' -Oxygenated Flavonoids from
Eupatorium bunifolium
L. Muschietti, V. Martino, C. Ferraro, andJ. Coussio
IQUIMEFA, Instituto de Quimica y Metabolismo del
Fármaco (UBA-CONICET), Cátedra de Farmacognosia,
Facultad de Farmacia y Bioqulmica, Universidad de Buenos
Aires, Junin 956, 1113 Buenos Aires, Argentina
Eupatoriuin buniifolium H. et A. (Compositae) grows
in Northeastern and Central Argentina. It is known under the
common names of romero, romerillo, or romero colorado and
is used as a tincture (1), and for its hepatoprotective (2) and
disinfectant (3) properties.
Posters
Previous works on this plant led to the isolation of
various 6-methoxyflavonoids, triterpenoid compounds (4),
hydroxycinnamic acids and their derivatives (4, 5), and
flavonoid glycosides (5). In the present work, we report the iso-
lation and structure elucidation of two highly oxygenated
flavonoids I and 2, both of which exhibit 2' -oxygenation.
R1
O 1 JH—.L0 R3
H3CO-'ff"OCH3
OH 0
1 P1 P5 OH5 P2 H
2 e' H, e2 OH5
Extraction and isolation: Air-dried, finely ground
aerial parts of F. bunitfolium (1680 g) were extracted succes-
sively with C6H6, CH2C12, Me2CO, and MeOH. Chromatographic
separation of the dichloromethane extract afforded brickellin
(I) and 5,7,5' -trihydroxy-3,6,2' ,4' -tetramethoxyflavone (2).
Downloaded by: Universite Laval. Copyrighted material.
The oxygenation patterns of these flavonoids were
determined on the basis of their unusual paper chromato-
graphic properties and from their UV, mass, and 1H-NMR
spectra. In the case of brickellin (1) (6), chromatographic com-
parison with an authentic sample was also performed.
Compound 2, C59H1509; UV: = 256, 267sh,
305, 345; MS: in/z (rel. mt.) 390 (Mt, 100), 375 (58), 373
(18), 359 (56), 347 (8), 208 (11), 193 (21), 181 (8), 167 (10),
139 (8); 1H-NMR (CDC13): S = 3.88 (5, 3H), 3.91 (5, 3H), 3.92 (s,
3H), 6.58 (s, 1H, H-8), 6.62 (s, 1H, H-3'), 7.10 (s, 1H, H-6').
From the above evidence, compound 2 was
identified as 5,7,5' -trihydroxy-3,6,2' ,4' -tetramethoxyflavone,
and as far as we know, this is the first report of this compound.
References
Zardini, B. (1984) Acta Farm. Bonaerense 3, 77.
2
Saggese, D. (1949) Yerbas Medicinales Argentinas, p. 111, Saggese,
Buenos Aires, Argentina.
Rojas Acosta, B. (1905) Plantas Medicinales de Corrientes, p. 8, Imp.
' Gadolo, Buenos Aires, Argentina.
Caula, S., Villar, S., Martino, V., Coussio, J., Ferraro, G. (1991) Rev.
Lalinoamer. Quim. 22/1, 1—3.
Muschietti, L., Martino, V., Ferraro, G., Coussio, J. (1990) An. Asoc.
Quim.Argenl. 78, 329—331.
6
liouma, M., Roberts, M., Matlin, S., Stacey, V., Timmermaon, T.,
Mabry, T., Brown, B. (1985) Phytochemistry 24, 1367—1368.