This document describes the extraction and determination of chemical structures of flavonoids found in Tanacetumparthenium, a plant species native to Iran. Through a process of extraction with methanol, filtration, evaporation, and fractionation using silica gel chromatography, the researchers isolated and identified four flavonoid compounds from the plant's aerial parts. Nuclear magnetic resonance spectroscopy and mass spectrometry were used to determine the chemical structures of the isolated compounds, which were identified as a flavonol, kaempferol, fisetin, and naringenin.

1. J. Sci. I. A. U (JSIAU), Vol 18, No. 68, Summer 2008
Extraction and Determination of Chemical Structure of
Flavonoids in Tanacetumparthenium(L.)Schultz. Bip. fromIran
A. Shafaghat*
Chemistry Department, Khalkhal Branch, Islamic
Azad University, Khalkhal, Iran
F. Salimi
Chemistry Department, Ardabil Branch, Islamic
Azad University, Ardabil, Iran

2. Genus Tanacetum
Family Compositae or
Asteraceae
Common name
Feverfew
Common uses
Flavonoids and a number
of related sesquiterpene
lactones are considered
to be responsible for its
activities.

3. Experimental
method: Dried and
powdered aerial
parts
With methanol, filtration
& evaporation then
washing with petroleum
ether
70g crude
residue 12g fraction
4g fraction
(Ethyl acetate
extract)
19 main fractions
Silica gel
Merck
Petroleum
ether
AcOEt
Methanol

4. 19 main fractions
Fraction (1)
Chromatographed
with CHCl3
7 Subfractions
Subfraction
no.4 80mg
Rechromatographed
35 Fractions
Combined 17-29
fractions (23mg)
Fraction (5)
6 Subfractions
Most polar purified
on silica gel
(CHCl3 : MeOH)
Fraction (9)
Divided into 6
subfractions
(H2O : MeOH)
Subfraction
with medium
polarity (15mg)
Further
resolved
on silica
gel
(CHCl3 :
MeOH)
3 Subfractions
3rd one
Subfraction
no.5 (25mg)
Further
purified
On silica
gel

5. Compound No.1 (
Flavonol )HNMR
(8.25, m, 2H)
(8.25, m, 2H)
(7.59, m, 2H)
(7.59, m, 2H)
(7.53, m, 1H)
(8.15, d, J=8.2, 1H)
(7.5, m, 1H)
(7.82, m, 1H)
(7.78,d, J=8.2, 1H)
Mass
[MH+ ] ion at m/z 239
CNMR
15 signals
9 CH 6 quaternary Cs

6. Compound No.2 (
Kaempferol )HNMR
(6.95, d, J=8.4Hz)
(6.95, d, J=8.4Hz)
(8.06, d, J=8.4Hz)
(8.06, d, J=8.4Hz))
(6.46, d, J=1.9Hz)
(6.2, d, J=1.9Hz)
Mass
[M+ ] ion at m/z 286
CNMR
15 signals
9 CH 6 quaternary Cs

7. Compound No.3 ( Fisetin )
HNMR
(6.94, d, J=8.2)
(6.93, dd, J=8.2 1.9Hz)
(6.95, d, J=1.9Hz)
(7.73, d, J=3Hz)
(7.58, dd, J=8.2, 3Hz)
(7.96, d, J=8.2Hz)
Mass
[M+] ion at m/z 286.2
CNMR
15 signals
9 CH 6 quaternary Cs

8. Compound No.4 (Naringenin)
(6.81, d, 2H)
(7.32, d, 2H)
(5.9, d, J=1.9Hz)
(6.81, d, 2H)
(7.32, d, 2H)
(3.25, dd, 1H)
(5.9, d, J=1.9Hz)
Mass
[M+] ion at m/z 272
CNMR
15 signals
9 CH 6 quaternary Cs

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10. Thank You