Phytoecdysteroids from the juice of Serratula coronata L. (Asteraceae)

Odinokov, V. N.; Galyautdinov, I. V.; Nedopekin, D. V.; Халилов, Л. М.; Шашков, А. С.; Качала, В. В.; Dinan, Laurence; Lafont, René

doi:10.1016/s0965-1748(01)00106-0

Cited by 64 publications

(29 citation statements)

References 7 publications

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“…1 H and 13 C spectra together with 1 H, 1 H-COSY and 1 H, 13 C-HMQC spectra were used for complete (or nearly complete) structure assignment of carbon and proton signals. Characteristic NMR data of compounds 2, 3, 5, 7-14 (Tables II-IV) correspond with the published data of carthamosterone 3 (2), makisterone C 3,22 (3), 3-epi-20-hydroxyecdysone 23,24 (5), integristerone A 25,26 (7), integristerone B 25 (8), isovitexirone 4 (9), 22-oxo-20-hydroxyecdysone 27 (10), taxisterone 26,28 (11), rubrosterone 26,29 (12), dihydrorubrosterone 26,30 (13) and poststerone 26,31 (14), summarised in the Ecdysone 24 . Integristerones A and B (7, 8) were found in the related Rhaponticum integrifolium 25 .…”

supporting

confidence: 80%

Minor Ecdysteroid Components of Leuzea carthamoides

Vokáč

Budêšínský

Harmatha

2002

Collect. Czech. Chem. Commun.

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Fourteen minor ecdysteroid components were isolated and identified from the roots of Leuzea carthamoides (Willd.) DC. Two of them are new phytoecdysteroids: leuzeasterone (1) a six-member side-chain lactone, and (24Z)-29-hydroxy-24(28)-dehydromakisterone C (4) a structurally related sitostane type analogue and assumed biogenetic precursor of 1. The next one, 5α-20-hydroxyecdysone (6), is a rare A/B-ring trans-annelated epimer of the most common phytoecdysteroid 20-hydroxyecdysone. Further compounds: makisterone C (3), 3-epi-20-hydroxyecdysone (5), integristerone A (7), integristerone B (8), 22-oxo-20-hydroxyecdysone (10), taxisterone (11), rubrosterone (12), dihydrorubrosterone (13) and poststerone (14), are new constituents of L. carthamoides, though already reported as compounds isolated from other natural sources. Two earlier reported minor Leuzea ecdysteroids: the five-membered side-chain lactone carthamosterone (2) and the 11-hydroxy-substituted analogue isovitexirone (9), are also included because they are now better characterised. Certain previously described Leuzea ecdysteroids were not found in our material, which may indicate geographic, seasonal or cultivar variations.The abundant occurrence of ecdysteroids in Leuzea carthamoides DC. (syn. Rhaponticum carthamoides (Willd.) Iljin) is interesting from several viewpoints. First is the large structure variability of all so far isolated ecdysone analogues 2-8 and second is their high content in the roots or seeds of this plant 9 . L. carthamoides is endemic in Siberia, but is also cultivated as a medicinal plant on a large scale in Europe. This is why L. carthamoides can serve as a rich source of ecdysteroids, insect moulting hormone analogues,

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supporting

confidence: 80%

Minor Ecdysteroid Components of Leuzea carthamoides

Vokáč

Budêšínský

Harmatha

2002

Collect. Czech. Chem. Commun.

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“…9-Dehydro-14-desoxy-9α,14α-epoxy-20-hydroxyecdysone or (20R,22R)-9α,14α-Epoxy-2β,3β,20,22,25-pentahydroxy-5β-cholest-7-en-6-one (9) and 14-Desoxy-14α-hydroperoxy-20-hydroxyecdysone or 2β,3β,20,22,25-Pentahydroxy-14α-hydroperoxy-5β-cholest-7-en-6-one (5). Compound 1 (2 g, 4.17 mmol) (prepared according to [6], mp 246ºC) in anhydrous THF (10 ml) was added to a solution of Li (0.35 g, 50 mmol) in ammonia (50 ml, distilled from Na). The mixture was stirred at -33ºC for 0.5 h, NH 4 Cl (4.0 g) was added, and the reaction mixture was left for the ammonia to evaporate in air.…”

Section: Methodsmentioning

confidence: 99%

“…A similar low field shift (∆δ ~ 22 ppm) is also observed for the C-14 signal (Tables 1 and 2). There are also marked changes in the 1 H NMR spectra of oxetanes 9-12 when compared with the corresponding spectra of the starting compounds [4][5][6]. Hence the H-9 signal is absent in the 1 H NMR spectra and the H-7 signal is shifted to low field (∆δ 0.1-0.2 ppm) and changed from a doublet to a singlet.…”

mentioning

confidence: 99%

Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton

Odinokov

Galyautdinov

Ibragimova

et al. 2008

Chem Heterocycl Comp

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The reaction of ecdysteroids (20-hydroxyecdysone and its acetonides) with lithium in liquid ammonia gave novel analogs with an oxetane 9α,14α-oxacycle in the steroid skeleton. In aqueous alcohol solution the 9,14-oxa analogs rearrange to the more stable 9α,13α−oxa analogs through a 1,2-migration of the 18-Me group from the C-13 to the C-14 atom.Although widely used in the chemistry of steroids [1, 2] for the selective reduction of a double bond in conjugated enones, a reaction with alkali metals in liquid ammonia has been little studied amongst the series of ecdysteroids. It is only known that the reaction of 20-hydroxyecdysone diacetonide with lithium in liquid ammonia solution gives a 14α-hydroperoxy derivative rather than the corresponding 7,8-dihydro analog [3].We have found that the action of a solution of lithium in liquid ammonia on the ecdysteroids 20-hydroxyecdysone (1), its 2,3:20,22 diacetonide (2), and the 20,22-acetonide (3) and 2,3-acetonide (4) and subsequent treatment of the reaction mixture with NH 4 Cl gives the corresponding 14α-hydroperoxides 5-8 together with the previously unknown 9α,14α-oxa derivatives 9-12 which are analogs of ecdysteroids with an oxetane ring in the steroid skeleton (Scheme 1). In the case of compound 1 the corresponding oxetane 9 and 14α-hydroperoxide 5 are formed in approximately equimolar amounts while the acetonides 2 and 3 are primarily converted to the corresponding oxetanes 10 and 11. For the 2,3-acetonide 4 the oxetane formed 12 is less stable than oxetanes 9-11 and elution of reaction products (SiO 2 , MeOH/CHCl 3 , 1:50) gave a mixture of the oxetane 12 and its isomerization product 19 as well as a mixture of the 14α-hydroperoxide 12 and starting material 4. Repeated chromatography (SiO 2 , MeOH/CHCl 3 ) of a mixture of compounds 12 and 19 gave the individual forms of the transformation products of oxetane 12, i.e. compounds 15 and 19.

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“…Aerial parts of Serratula coronata plants from the territory of the South Urals (Russia), freshly gathered during the budding period (June, 2001), were processed as reported earlier for polar ecdysteroids 6 . From 64.0 kg of fresh leaves of the plant, juice (35.0 l) was pressed.…”

Section: Extraction and Isolationmentioning

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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Phytoecdysteroids from the juice of Serratula coronata L. (Asteraceae)

Cited by 64 publications

References 7 publications

Minor Ecdysteroid Components of Leuzea carthamoides

Minor Ecdysteroid Components of Leuzea carthamoides

Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton

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

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