Chemistry of Natural Compounds, Vol. 45, No. 5, 2009
FLAVONOIDS FROM Chrysanthemum myconis
AND THEIR ANTIBACTERIAL ACTIVITY
1
1*
2
Nadjet Mezache, Salah Akkal, Hocine Laouar,
UDC 547.972
3
and Elisabeth Seguin
Chrysanthemum genus, Asteraceae family has been the subject of many phytochemical studies [1–5]. This paper
deals with the isolation and identification of two products from Chrysanthemum myconis, 6-methoxy-7-methylenedioxy
coumarine (1) and quercetagetin-7-O-glycoside (2), and the antibacterial activity of this flavonoid glycoside.
Chrysanthemum myconis (Asteraceae) was collected from Constantine (Algeria); 465 g of leaves and 650 g of dried
flowers were extracted with methanol (75%) for three times. The combined extracts were evaporated in vacuo, suspended in
water, and partitioned with EtOAc and n-butanol. Bidimensional thin-layer chromatography (TLC) permitted us to mix the
n-BuOH extracts but not the EtOAc extracts because of the chlorophylls. The EtOAc extract (3.20 g) of the leave were
subjected to silica gel column chromatography (CH Cl –EtOAc) and (EtOAc–MeOH) to afford compound 1 (2 mg). The
2
2
n-BuOH extract (16 g) was subjected to polyamide SC6 column chromatography (toluene–MeOH) to give compound 2, a
yellow sediment that is the constituent of the majority of the n-BuOH extract fractions.
1
The structures of the isolated compounds were determined by H NMR and mass and UV spectroscopic analysis.
+
1
Compound 1 showed MS: m/z 220 (M ), C H O . H NMR (CDCl , δ, ppm, J/Hz): 7.51 (1H, d, J = 9.6, H-3), 6.21
11
8
5
3
(1H, d, J = 9.6, H-4), 6.52 (1H, s, H-5), 6.12 (2H, s, -O-CH -O-), 3.85 (3H, s, OCH ) [6].
2
3
Compound 2, C H O . UV (λ , MeOH, nm): 258.5, 365.5; NaOH: 258.5, 454; AlCl : 230.5, 322.5, 442;
20 20 13
1
max
3
AlCl /HCl: 273.5, 389.5. H NMR (CD OD, δ, ppm, J/Hz): 4.95 (1H, d, J = 7.53, H-1′′glucose), 3.5–4.5 (6H of glucose), 6.85
3
3
(1H, s, H-8), 6.78 (1H, d, J = 8.52, H-5′), 7.57 (1H, dd, J = 2.19, 8.52, H-6′), 7.67 (1H, J = 2.19, H-2′) [7, 8].
Acid hydrolysis of 2 produced quercetagetin and D-glucose.
This is the first time that these compounds have been isolated from C. myconis.
Compound 2 was tested for antibacterial activity by the agar disc diffusion method against three strains of bacteria,
including Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, and Pseudomonas aeruginosa ATCC 27853.
Briefly, filter discs (6 mm in diameter) were impregnated with 60 mL of diluted quercetagetin-7-O-glycoside in DMSO and
8
then deposited on solid media plates on which was spread 0.1 mL of 10 cells per mL of a microorganism suspension. These
plates, after remaining at 4°C for 30 min, were incubated at 37°C for 24 h. The diameters of inhibition zones were measured
in millimeters. All tests were performed in duplicate. The compound was particularly found to possess strong antibactericidal
activity against the first bacteria (21 mm) and moderate activity against E. coli ATCC 25922 (11 mm). No activity was
observed against P. aeruginosa ATCC 27853.
REFERENCES
1.
2.
T. Osawa, A. Suzuki, S. Tamura, Y. Ohashi, and Y. Saburo, Tetrahedron Lett., 51, 5135 (1973).
A. Maatsuo, Y. Uchio, M. Nakayama, and S. Hayashi, Tetrahedron Lett., 22, 1885 (1974).
1) Department of Chemistry, University Mentouri, 25000 Constantine, Algeria, fax: 213 31 81 88 85, e-mail:
salah4dz@yahoo.fr; 2) Department of Biology, University Ferhat Abbas, Setif, Algeria; 3) Laboratoire de Pharmacognosie,
Universite de Rouen-Haute Normandie, UMR 6014-CNRS, Faculte de Pharmacie, 22 Boulevard Gambetta, F-76183 Rouen
Cedex 1, France. Published in Khimiya Prirodnykh Soedinenii, No. 5, p. 599, September–October, 2009. Original article
submitted January 1, 2008.
0009-3130/09/4505-0715 ©2009 Springer Science+Business Media, Inc.
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Mezache, Nadjet
