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Odinokov, V. N.; Galyautdinov, I. V.; Nedopekin, D. V.; Халилов, Л. М.

doi:10.1023/a:1022433423370

Cited by 11 publications

(6 citation statements)

References 2 publications

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“…Inokosterone was previously isolated from Achyranthes fauriei 18 and Zoanthus sp. 19 as a mixture of 25S-and 25R-epimers (2:1) (C-25 chemical shifts 36.7 and 36.4 ppm, respectively) but exclusively as the 25S-epimer from Serratula coronata (C-25 chemical shift 36.8 ppm) 5g . The structure of the latter substance was confirmed by HPLC data and its 13 C NMR spectrum, in which double-signals for C-22, C-24-C-27 were absent 13 .…”

Section: Resultsmentioning

confidence: 99%

Low-Polarity Phytoecdysteroids from the Juice of Serratula coronata L. (Asteraceae)

Odinokov

Kumpun

Galyautdinov

et al. 2005

Collect. Czech. Chem. Commun.

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Eleven phytoecdysteroids have been isolated and identified from the low polarity fractions of Serratula coronata juice by a combination of column chromatography and HLPC. Four of them are new, i.e. ecdysone 22-acetate 7, (25S)-inokosterone 26-acetate 9, 20,22-O-(R-ethylidene)-20-hydroxyecdysone 10 and 20,22-O-(R-ethylidene)-ajugasterone C 11. The biological activity of these new ecdysteroids in the Drosophila melanogaster B II cell bioassay is reported.

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Section: Resultsmentioning

confidence: 99%

Low-Polarity Phytoecdysteroids from the Juice of Serratula coronata L. (Asteraceae)

Odinokov

Kumpun

Galyautdinov

et al. 2005

Collect. Czech. Chem. Commun.

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“…To a solution of 0.2 g (0.36 mmol) of compound I (prepared according to [5], mp 233-234°C) in 2 ml of methanol we added under stirring 0.18 g (0.51 mmol) of CeCl 3 · 6 H 2 O, the mixture was cooled to -5°C, and 0.03 g (0.75 mmol) of NaBH 4 was added in one portion. The mixture was slowly warmed up to room temperature, stirred for 2 h, and evaporated under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

“…IR spectrum, ν, cm -1 : 850, 1245 (OSiMe 3 ). 1 C NMR spectrum, δ C , ppm: 0.2 q, 0.4 q, 1.9 q, 2.6 q (SiMe 3 ); 16.5 q (C 18 ); 19.8 t (C 11 ); 21.6 t (C 16 ); 21.8 q (C 21 ); 23.0 t (C 23 , 6β); 23.7 t (C 23 , 6α); 24.6 q (C 19 , 6α); 25.1 q (C 19 , 6β); 26.5 q and 26.8 q (C 26 , C 27 ); 27.9 t (C 4 ); 27.9 t (C 15 ); 28.6 q, 29.0 q, 29.4 q, and 30.1 q (Me 2 CO 2 ); 31.5 t (C 12 ); 32.2 d (C 9 ); 34.5 s (C 10 , 6β); 36.7 t (C 10 , 6α); 42.1 t (C 1 ); 42.4 d (C 5 (20R,22R)-6α,14α-and (20R,22R)-6β,14α-Dihydroxy-2,3 : 20,22-bis(isopropylidenedioxy)-5α-cholesta-7,24/(25)-dienes IXa and IXb. a.…”

Section: (20r22r)-6α(β)-hydroxy-2β3β : 2022-bis(isopropylidenedioxmentioning

confidence: 99%

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Stereochemistry of Hydride Reduction of 20-Hydroxyecdysone Derivatives

et al. 2005

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The 6-oxo group in 2,3 : 20,22-di-O-isopropylidene derivatives of 20-hydroxyecdysone and its 24,25/25,26-anhydro analog is reduced with NaBH 4 -CeCl 3 in a stereoselective fashion to afford the corresponding 6α-alcohols. In the first case, the reaction is accompanied by dehydration to give Δ 14 -bond. Reduction of the same substrates with NaBH 4 or LiAlH 4 in the absence of CeCl 3 leads to mixtures of 6α-and 6β-hydroxy derivatives, the latter prevailing. In all cases, epimerization at C 5 occurs.

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“…These findings reflected formation of double C 14 =C 15 bond in stachysterone B conjugates VII and VIII (cf. [5]). …”

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confidence: 99%

(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde conjugates with 20-hydroxyecdysone, stachysterone B, and their 20,22-acetonides

et al. 2010

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Conjugates consisting of ecdysteroid and α-tocopherol analog fragments were synthesized for the first time from 20-hydroxyecdysone and (6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde.Ecdysteroids (insect ecdysis, metamorphosis, and diapause hormones) are present not only in insect organisms, but also (in considerably higher concentrations) in plants from which these unique polyhydroxylated sterols were isolated. The properties and some chemical transformations of ecdysteroids were studied [1,2]. It was found that ecdysteroids are nontoxic for warm-blooded animals. Versatile physiological effect of ecdysteroids on humans and animals was revealed: they were found to control mineral, carbohydrate, lipid, and protein exchange, normalize sugar and cholesterol concentration in blood, stimulate hemopoietic activity, and exert immunomodulatory effect [3]. The diversity of physiological action of ecdysteroids is determined to some extent by their antioxidant properties, for many diseases are related to oxidative stress [4].We believed that a promising way of enhancing pharmacological effect of ecdysteroids may be conjugation with natural phenolic antioxidants such as α-tocopherol and its analogs. For this purpose, we examined reactions of 20-hydroxyecdysone (I) and its 2,3-and 20,22-acetonides II and III with (6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde (IV). The reaction of ecdysteroid I with 2 equiv of aldehyde IV, catalyzed by phosphomolybdic acid (PMA), gave 62% of the corresponding bis-adduct V (Scheme 1). This reaction occurred at a higher rate in the presence of p-toluenesulfonic acid as catalyst, but the yield of bis-acetal V did not change. Bis-adduct V was also formed in the reaction of 20-hydroxyecdysone 2,3-acetonide (II) with an equimolar amount of aldehyde IV in the presence of TsOH or PMA, but the yield was lower (35%). Under analogous conditions, from 20,22-acetonide III we obtained 60% of 2,3-adduct VI. Presumably, the formation of bis-adduct V from 2,3-acetonide II is favored due to known lability of compound II in acid medium [1].Apart from 20-hydroxyecdysone conjugates V and VI, from the reaction mixtures we isolated the corresponding 14,15-anhydro derivatives VII and VIII in 26 and 20% yield, respectively. Compounds VII and VIII can be regarded as analogous stachysterone B conjugates. 20-Hydroxyecdysone conjugates V and VI were subjected to debenzylation by hydrogenation over Pd/C in ethanol solution. As a result, the corresponding hydroxy derivatives IX and X were smoothly formed. The MALDI-TOF mass spectrum of bis-adduct IX contained [M + H] + ion peak. In the 1 H and 13 C NMR spectra of compounds V-X we observed signals from all protons iand carbon nuclei in the ecdysteroid and chroman fragments, in keeping with the assumed structure of their molecules.Monoadduct VI displayed in the 13 C NMR spectrum (in the region typical of acetal carbon atoms) signals from quaternary (δ C 106.97 ppm) and tertiary (δ C 101.97 ppm) carbon atoms in the 20,22-O-isopropylidene (cf. [5]) and eth...

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Cited by 11 publications

References 2 publications

Low-Polarity Phytoecdysteroids from the Juice of Serratula coronata L. (Asteraceae)

Low-Polarity Phytoecdysteroids from the Juice of Serratula coronata L. (Asteraceae)

Stereochemistry of Hydride Reduction of 20-Hydroxyecdysone Derivatives

(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde conjugates with 20-hydroxyecdysone, stachysterone B, and their 20,22-acetonides

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