Phytoecdysteroids from five species of the genus Silene

Full text of DOI:10.1007/s10600-007-0049-6

Chemistry of Natural Compounds, Vol. 43, No. 1, 2007
PHYTOECDYSTEROIDS FROM FIVE SPECIES OF THE GENUS
N. Sh. Ramazonov, N. Z. Mamadalieva, and I. D. Bobaev
Silene
UDC 547.926
Herein we communicate results from a study of five species of the genus
gray—oasis soil of the experimental plot of the ICPS AS RU.
that have been introduced to the
Silene
Several principal ecdysteroidswerefoundin the plants using TLC with vanillin—H SO and column chromatography.
2
4
These included ecdysterone (1), polipodin B (2), 2-deoxyecdysteron-22- -benzoate (3), integristerone A (4), ecdysteron-22- -
O
O
benzoate (5), tomentesterone A (6), tomentesterone B(7), and 2-deoxyecdysterone (8), which were found in
(6-8),
S. tomentella
(1, 2, 4, 5),
(1-5),
(1, 2, 4), and
(1, 4, 5, 8) [1-5]. Plant seeds were obtained
S. wallichiana
S. viridiflora
S. nutans
S. tatarica
from the Botanical Garden of the Republic of Uzbekistan.
OR
OR
2
R
1
3
HO
OH
OR
3
R
4
R
1
HO
HO
OH
OH
HO
H
R
2
O
O
1, 2, 4, 5
3, 6 - 8
1: R1 = R2 = R3 = R4 = H; 2: R1 = R3 = R4 = H, R2 = OH; 3: R1 = OH, R2 = COC6H5, R3 = H
4: R1 = OH, R2 = R3 = R4 = H; 5: R1 = R2 = R4 = H, R3 = COC6H5; 6: R1 = H, R2 = Ac, R3 = COC6H5
7: R1 = R2 = H, R3 = COC6H5; 8: R1 = OH, R2 = R3 = H
-1
The study of the aerial part of
isolated both 1 and 3. Absorptions in the IR spectrum at 1705 and 1285 cm
S. nutans
in combination with bands typical of a benzene ring (1610, 1587, 730) suggested that 3 was an aromatic ester. This was also
consistent with five aromatic protons at 7.53 ppm (3H) and 8.28 (2H) in the PMR spectrum in addition to strong peaks in the
mass spectrum for ions with / 122 (C H O ), 105 (C H O), and 77 (C H ), which are characteristic of benzoic acid.
m z
7
6
2
7
5
6 5
The neutral fraction from base saponification of 3 contained 2-deoxyecdysterone (8); the acidic fraction, benzoic acid.
Compared with the PMR spectrum of 3, that of 8 showed a significant strong-field shift for CH -21 (Table 1). This
3
suggested that benzoic acid in 3 was esterified at the C-22 hydroxyl.
Comparison of the proton chemical shifts for 8 and 3 showed that the signal for C-22 was also shifted. This was
consistent with bonding of the benzoic acid to the C-22 hydroxyl. An analogous strong-field shift was noted for ecdysteron-22-
-benzoate (5) (Table 1).
O
Thus, 3 is 2-deoxyecdysteron-22- -benzoate. This compound was isolated earlier from
[6, 7] but was
S. tatarica
O
isolated from
for the first time.
S. nutans
The known compounds tomentesterone A and B were isolated from
from this plant for the first time.
. 2-Deoxyecdysterone was isolated
S. tomentella
The isolated pure ecdysteroids were identified using IR, PMR, and mass spectroscopyand bycomparison with standard
S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan,
samples.
Tashkent, fax (99871) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 97-98, January-February, 2007.
Original article submitted October 31, 2006.
0009-3130/07/4301-0117 ©2007 Springer Science+Business Media, Inc.
117

TABLE 1. Proton Chemical Shifts of Ecdysterone (1), 2-Deoxyecdysteron-22-O-benzoate (3), Ecdysteron-22-O-benzoate (5),
and 2-Deoxyecdysterone (8) (C5D5N, δ, ppm, 0 = HMDS)
Compound
C atom
1
3
5
8
H-2
H-3
H-7
H-9
1.00
4.30
6.21
3.57
3.81
1.19
1.06
1.55
1.34
-
-
1.11
6.25
3.38
3.77
1.23
1.07
1.81
1.32
1.00
1.30
6.22
3.60
3.76
1.21
1.10
1.78
1.32
-
1.11
6.22
3.52
3.85
1.22
1.05
1.58
1.38
-
H-22
CH3-18
CH3-19
CH3-21
CH3-26/27
Aromatic protons
7.53 (3H),
8.28 (2H)
7.10 (3H),
8.27 (2H)
______
Signals for methyl protons appear as singlets; H-7 in 1, as a doublet with J = 1 Hz, in the others, as a broad singlet; H-2, H-3,
and H-9, as multiplets.
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