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Флавоноиды псоралеа и резеда

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25 views2 pages

Флавоноиды псоралеа и резеда

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Bahodir
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Chemistryof Natural Compounds, VoL 32, No.

6, 1996

FLAVONOIDS O F Psoralea drupaceae A N D Reseda luteola

M. P. Yuldashev, a ~ . Kh. Batirov, b V. M. Malikov, a UDC 547.972


and N. P. Yuldasheva a

Plants of the genus Psoralea L. (faro. Fabaceae) are rich in furocoumarins, and some of them exhibit an antiasthmatic,
antihysterical, and antiepileptic action. The drugs psoralen and psoberan areused in officinal medicine as photoseusitizing
agents for treating vitiligo and alopecia areata [1].
The furocoumarins psoralen and angelicin have been detected previously in the roots of Psoralea drupaceae Bunge
(drupe scurf pea) [2, 3].
The comminnted air-dry roots of the plant (400 g) gathered in September, 1989, in the environs of Alimtau, Republic
of Kazakhstan, were exhaustively extracted with ethanol. The alcoholic extract was concentrated in vacuum, diluted with water,
and extracted successively with chloroform and ethyl acetate. Chromatography of the chloroform fraction on silica gel in the
hexane-chloroform (9:1) system led to the isolation of psoralen and angelicin.
Chromatography of the ethyl acetate fraction on silica gel in the chloroform-methanol (9:1) system led to the isolation
of flavonoid (1).
Daidzin (1) (daidzein 7-O-fl-D-glucopyranoside) -- C2tH2009, mp 235-236"C, )hmx 263, 315 rim. The UV spectrum
was characteristic for isoflavone derivatives.
The PMR spectrum showed signals of the protons H-5 (8.18 ppm, d, 8.0 Hz), H-2 (7.93 ppm, s), H-6 (7.18 ppm, dd,
8.0 and 2.0 Hz), and H-8 (7.04 ppm, d, 2.0 Hz), of an anomeric proton (5.63 ppm, d, 6.5 Hz), and of the other protons of
the carbohydrate moiety (3.90-4.55 ppm).
The acid hydrolysis of substance (1) gave daidzein (4',7-dihydroxyisoflavone, C15Ht004, nap 276-277°C, M + 254)
and D-glucose. The acetylation of glycoside (1) gave a pentaacetate with nap 185-187°C the PMR spectrum of which contained
the signals of four acetoxy groups, a glucose residue, and one ArOCOCH 3 group [4].
This is the first time that daidzin has been isolated from P. drupaceae.
Plants of the Reseda L. genus (faro. Resedaceae) form a rich source of flavonoids. The epigeal parts of the plants are
used as diuretic and sudorific agents. The flowers have long been used for dyeing silk yellow. Some flavonoids of the plants
increase the resistance of capillaries and exert a cholagogic action [5]. Luteolin, cynaroside, luteolin 3'-O-fl-D-glucofuranoside,
apigenin, and luteolin 3',7-diglucoside have previously been isolated from this plant [5, 7].
The epigeal part of R. luteola L. (weld mignonette) was gathered in the flowering period in 1984 in the environs of
Tashkumir, Republic of Kyrgyzstan. An alcoholic extract from the comminuted air-dry raw material was concentrated in
vacuum, diluted with water, and extracted successively with chloroform and ethyl acetate. Chromatography of the ethyl acetate
fraction on a column of silica gel in a gradient system of chloroform and propan-2-ol led to the isolation of luteolin, cynaroside,
and flavonoids (2) and (3).
Kaempferol 3-O-fl-D-glucnside 7-ot-L-rhamnoside (2) -- C27H30015, nap 190-1920C, hmax 258, 266, 352 urn, which
are characteristic for 3-O-substituted flavonols.
The PMR spectrum (in Py-ds) showed signals of the protons of the CH3 group of rhamnose at 1.52 ppm (d, 6.5 Hz),
of the anomeric protons of L-rhamnose at 5.21 ppm (br.s) and of D-glucose at 5.52 ppm (d, 6.5 Hz), of the protons of the
sugar moiety at 3.74-4.68 ppm, and of the protons of aromatic rings at 6.64 ppm (d, 2.0 Hz, H-6), 6.80 ppm (d, 2.0 Hz, H-8),
7.14 ppm (d, 8.5 Hz, H-3',5'), and 8.30 ppm (in, H-2',6').
Acid hydrolysis gave kaempferol (3,4',5,7-tetrahydroxyflavone -- Ct5HI006, M + 286, mp 275-2770C), D-glucose,
and L-rhamn°se"

a) Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax
(3712) 40 64 75. b) Namangan Institute of Industrial Technology, Namangan, prosp. Dustlik, 12, tel. 4 26 22. Translated from
Khimiya PriroctnyldaSoedinenii, No. 6, pp. 949-951, November-December, 1996. Original article submitted June 3, 1996.

0009-3130/96/3206-0923515.00 ©1997 Plenum Publishing Corporation 923


The acetylation of substance (2) with acetic anhydride in pyridine gave a nonaacetate derivative with the composition
C45H48024 the mass spectrum of which showed, in addition to the peak of the molecular ion with m/z 972, intense peaks of
fragment ions: of an acylated tetraacetylhexose with m/z 331,271, and 169, and of a triacetylrhamnose with m/z 273, 213,
and 153 [7].
Brassidin (3) (isorhamnetin 3-O-B-D-glucoside 7-¢x-L-rhanmoside) - C28H32016, mp 219-221°C, kmax 255,266, 356
nm, which are characteristic for 3-substituted flavonols.
In the PMR spectrum (in PY-ds) of compound (3), in addition to the signals of the protons of the aglycon, we observed
signals of the anomeric protons of L-rhamnose (5.18 ppm, br.s), and of D-glucose (5.47 ppm, d, 6.5 Hz), of the CH3 group
of rhamnose (1.47 ppm, br.s), and of the other protons of the carbohydrate moiety in the 3.76-4.65 ppm interval. On acid
hydrolysis, glycoside (3) gave isorhamnetin (C16H1207, mp 305-307°C, M + 316, kmax 255, 266, 370 nm), D-glucose, and
L-rhanmose.
The acetylation of glycoside (3) with acetic anhydride in pyridine gave a nonaacetyl derivative with the composition
C45H50025, mp 116-118 °C, the mass spectrum of which contained, in addition to the peak of the molecular ion with m/z 1002,
intense peaks of fragment ions: of an acylated tetracetylglucose with m/z 331, 271,169, and of triacetylrbamnose with m/z 273,
213, 153 [8].
This is the first time that compounds (2) and (3) have been isolated from R. luteola.

REFERENCES

. Plant Resources of the USSR. Flowering Plants and their Chemical Composition and Use. The Families
Hydrangeaceae--Haloragaceae [in Russian], Nauka, Leningrad (1987) p. 175.
. Flora of the USSR [in Russian], Izd. Akad. Nauk SSSR, Moscow--Leningrad (1945), Vol. 11, p. 300.
3. N. K. Abubakirov and U. F. Khalmuradov, Khim. Prir. Soedin., 137 (1967).
4. G. G. Zapesochnaya and I. A. Samylina, Khim. Prir. Soedin., 671 (1974).
5. Plant Resources of the USSR. Flowering Plants and Their Chemical Composition and Use. The Families
Paeoniaceae--Thymelaeaceae [in Russian], Nauka, Leningrad (1986), p. 97.
. t~. Kh. Batirov, M. M. TadT.hibaev, and V. M. Malikov, Khim. Prir. Soedin., 728 (1979).
7. Z. P. Pakudina and A. S. Sadykov, Distribution of Flavones and Flavonols in Plants, and Their Physicochemical
Properties [in Russian], Fan, Tashkent (1970), p. 94.
. L. H/Srhammer, H. Wagner, and L. Farkas, Chem. Ber., 100, 2301 (1967).

924

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