Phytoecdysteroids from Silene praemixta


The waste products of the production of ecdysterone (3) from Silene praemixta M. Pop. (Caryophyllaceae) were investigated. The column chromatography of the technological waste has allowed to isolating 2-de- soxyecdysone (1), 2-deoxyecdysterone (2), ecdysterone (3) and 22-O-β-D-glucopyranoside of 2-deoxyecdy- sone (4). Glucoside 4 was found for the first time in the plant Silene praemixta. Ecdysteroids 1, 2 prevailed in the sum. Compounds 3 and 4 were minor components of the waste products. The identification of com- pounds 1-4 was carried out by using the modern me- thods of 1D and 2D NMR spectroscopy: 1H, 13C, DEPT, 1H-1H COSY, HSQC, NOESY, IR spectroscopy and ESI MS.

Share and Cite:

Agzamova, M. , Ogly Isaev, I. , Mamathanov, A. , Ogly Isaev, M. and Ibragimov, T. (2014) Phytoecdysteroids from Silene praemixta. Advances in Biological Chemistry, 4, 1-4. doi: 10.4236/abc.2014.41001.

The genus of Silene (Caryophyllaceae) is widely distributed in Uzbekistan and it is known as the rich source of phytoecdysteroids. The one main of them is the ecdysterone, which is possessed as an anabolic effect for human body [2]. The ecdysterone has the ability to adapt organism to experimental effects of environment and stimulate the operability [3].

The “Ecdisten” preparation is produced from the medicinal plants Raponticum and Silene at the Institute of the Chemistry of Plant Substances (Tashkent, Uzbekistan Academy of Sciences).


In the present paper the chemical composition of Silene praemixta plant was investigated. We described the isolation and structure elucidation of ecdysteroids from the waste product of this manufacture.

Four ecdysteroids were isolated and identified from Silene praemixta (1-3) and 22-O-β-D-glucopyranoside of 2-deoxyecdysone (4) (Figure 1).

Part of the waste extract (6.0 g) was subjected to column chromatography on silica gel with gradient elution by CH3Cl-MeOH (10:1), CH3Cl-MeOH-H2O (70:12:1) and (70:23:4) to afford 1-4. Steroids 1-2 were the main compounds of the plant extract while 3-4 compounds were found in scarce amount.

The identification of isolated compounds was carried out by using 1D and 2D NMR spectroscopy techniques: 1H, 13C, DEPT, 1H-1H COSY, HSQC, NOESY, IR spectroscopy and ESI MS. This spectral data identified steroid 1 as 2-deoxyecdysone, steroid 2 as 2-deoxyecdysterone, steroid 3-ecdysterone [4-7] and compound 4 as 22-O-β-D-glucopyranoside of 2-deoxyecdysone [8].


Using infrared spectrophotometer data we obtained information regarding presence of hydroxyl groups (3387 - 3409 sm−1) and 6-ketochromaphore (1639 - 1652 sm−1) of tested compounds according to ecdysteroids skeleton.  The mail role in the structure determination of isolated compounds plays NMR analysis which shows presence of signals of methyl groups at 0.64 and 1.57 ppm, corresponding to CH3-18, CH3-19 (CH3-21 represented as doublets in area 0.88 - 1.6 ppm). Signals of CH3-18 determined by presence of Δ7-6-keto-14α-oxygroup, and signals at C-7 in current system shown in area 5.75 - 6.25 ppm. All mentioned data distribute identification of isolated compounds 1-4 as 2-deoxy-α-ecdysone, 2-deoxyecdysterone, ecdysteron (3), 22-О-β-D-glucopyranosid- 2-deoxy-α-ecdysone. All chemical shifts of mentioned compounds correspond to literature data [4-8].

Figure 1. Isolated ecdysteroids from Silene praemixta.


General Methods

1H, 13C NMR (Table 1) spectra were run in CD3OD, C5D5N using TMS as internal reference on a Bruker Avance DRX 600 MHz spectrometer. ESI-MS spectra were recorded on a PE Q-STAR electrospray, ionization time of flight-tandem-mass spectrometry spectrometer. Silica gel 60 PF 254 was used for TLC. Infrared spectra were taken on Perkin Elmer Spectrum 100 FTIR sprectrophotometer, which are conformed with literature data.

2-Deoxy-α-ecdysone (1)-C27H44O5

1Н NMR 2-deoxy-α-ecdysone (400 МHz, C5D5N, δ, ppm, J/Hz, 0-TMS): 0.73 (CH3-18, s), 1.05 (CH3-19, s), 1.30 (CH3-21, d, 3J = 6.6), 1.39 (CH3-26 and CH3-27, s), 2.97 (H-17, m), 3.50 (H-9, m), 4.07 (H-22, m), 4.15 (H-3, w.s), 5.95 (H-7, d, 4).

1Н NMR 2-deoxy-α-ecdysone (400 МHz, CD3OD, δ, ppm, J/Hz, 0-HМDS): 0.66 (CH3-18, s), 0.88 (CH3-21, d, 3J = 6.8), 0.90 (CH3-19, s), 1.13 (CH3-26, s), 1.14 (CH3-27, s), 2.36 (H-5, dd, 12, 4), 3.14 (H-9, m), 3.54 (H-22, w.d), 3.92 (H-3, m), 5.75 (H-7, d, 2.3).

IR spectrum 2-deoxy-α-ecdysone (KBr, νmax, sm−1): 3387, 1640.

ES-MS Positive ion mode of 2-desoxy-α-ecdysone: 471.2 [M + Na]+.

ES-MS negative ion mode of 2-desoxy-α-ecdysone 447.1 [M − H].

2-Deoxyecdysterone (2)-C27H44O6

1Н NMR 2-deoxyecdysterone (600 МHz, C5D5N, δ, ppm, J/Hz, 0-TMS): 1.06 (CH3-19, s), 1.24 (CH3-18, s), 1.37 (CH3-26 and CH3-27, s), 1.60 (CH3-21, s), 3.04 (H-17, t, 9), 3.54 (H-9, m), 3.89 (H-22, w.d, 10.2), 4.12 (H-3, w.s), 6.25 (H-7, s).

1Н NMR 2-deoxyecdysterone (400 МHz, CD3OD, δ, ppm, J/Hz, 0-HМDS): 0.82 (CH3-18, s), 0.90 (CH3-19, s), 1.13 (CH3-21 and CH3-26, s), 1.14 (CH3-27, s), 2.05 (H-12, td, 12.9, 5), 2.35 (H-5 and H-17, m), 3.15 (H-9, m), 3.27 (H-22, m), 3.93 (H-3, m), 5.73 (H-7, d, 2.4).

IR-spectroscopy of 2-deoxyecdysterone (KBr, νmax, sm−1): 3388, 1639.

ES-MS Positive ion mode of 2-deoxyecdysterone 487.3 [M + Na]+.

ES-MS negative ion mode of 2-deoxyecdysterone 463.0 [M − H].

Ecdysteron (3)-C27H44O7

1Н NMR ecdysteron (600 МHz, C5D5N, δ, ppm J/Hz, 0-TMS): 1.06 (CH3-19, с), 1.22 (CH3-18, s), 1.36 (CH3-26 and CH3-27, s, 1.59 (CH3-21, s), 3.00 (H-5 and H-17, m), 3.59 (H-9, m), 3.87 (H-22,w.d, 10.2), 4.18 (H-2, m), 4.22 (H-3, w.s), 6.25 (H-7, d, 1.8).

1Н NMR ecdysteron (400 МHz, CD3OD, δ, ppm, J/Гц, 0-HМDS): 0.83 (CH3-18, s), 0.90 (CH3-19, s), 1.126 (CH3-21, s), 1.134 (CH3-26, s), 1.38 (CH3-27, s), 2.32

Table 1. 13C NMR spectra compounds of 1-4 (C5D5N, CD3OD, δ, ppm, 0-TMS).

(H-5 and H-17, m), 3.09 (H-9, m), 3.30 (H-22, m), 3.76 (H-2, m), 3.88 (H-3, m), 5.75 (H-7, d, 2.5).

IR-spectrum ecdysteron (KBr, νmax, sm−1): 3409, 1652.

ES-MS Positive ion mode of ecdysteron: 503.3 [M + Na]+.

ES-MS negative ion mode of ecdysteron: 479.1 [M − H].

22-О-β-D-Glucopyranosid-2-deoxy-α-ecdysone (4)- C33H54O10

Spectroscopy 1Н NMR 22-О-β-D-Glucopyranosid-2- deoxy-α-ecdysone (400 МHz, C5D5N, δ, ppm, J/Hz, 0-HМDS): 0.64 (CH3-18, s), 0.91 (CH3-19, s), 1.08 (CH3-21, d, 3J = 6.7), 1.19 (CH3-26, s), 1.23 (CH3-27, s), 3.36 (H-9, m), 3.86 (H-5 Glu, m), 3.98 (H-3, H-22 and H-2-Glu, m), 4.15 (H-3 Glu and H-4 Glu, m), 4.30 (H-6 Glu, dd, 2J = 11.4, 3J = 5.4), 4.47 (H-6’ Glu, dd, 2J = 11.4, 3J = 2.7), 4.92 (H-1 Glu, d, 3J = 7.7), 6.07 (H-7, d, 3J = 2).


Compound 22-О-β-D-Glucopyranosid-2-deoxy-α-ecdysone (4) was isolated from Silene praemixta M. Pop. for the first time.


This study was supported by the National Key Projects for Science and Technology Development of AS Uzbekistan during the five year plan period (FA-F3-T044)

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Saatov, Z., Gorovits, M.B. and Abubakirov, N.K. (1993) Phytoecdysteroids of plants of the genus Silene. Chemistry of Natural Compounds, 29, 551-557.
[2] Báthori, M., Tóth, N., Hunyadi, A., Márki, á. and Zádor, E. (2008) Phytoecdysteroids and anabolic-androgenic steroids—Structure and effects on humans. Current Medicinal Chemistry, 15, 75-91.
[3] Bobkov, Y.G., Vinogradov, V.M., Katkov, V.F., Losev, S.S. and Smirnov, A.V. (1984) Pharmacological improvement of fatigue. Medicine, Moscow, 208.
[4] Galbraith, M.N., Horn, D.H.S., Middleton, E.J. and Hackney R.J. (1968) Structure of deoxycrustecdysone, a second crustacean moulting hormone. Chemical Communications, 2, 83-85.
[5] Chong, Y.K., Galbraith, M.N. and Horn, D.H.S. (1970) Isolation of deoxyecrustecdysone, deoxyecdysone, and α-ecdysone from the fern Blechnum minus. Journal of the Chemical Society D: Chemical Communications, 18, 1217-1218.
[6] Saatov, Z., Usmanov, B.Z. and Abubakirov, N.K. (1979) Phytoecdyzones of Silene praemixta. II. Premistesteron. Chemistry of Natural Compounds, 15, 703-705.
[7] Baltaev, U.A. and Abubakirov, N.K. (1987) Phytoecdysteroids of Rhaponticum carthamoides. Chemistry of Natural Compounds, 23, 565-568.
[8] Lafont, R., Harmatha, J., Marion-Poll, F., Dinan, L. and Wilson, I.D. (2002) Ecdybase—The ecdysone handbook, 3rd Edition.

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.