- A furostanol saponin and phytoecdysteroid from roots of Helleborus orientalis
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A furostanol saponin mixture and a known phytoecdysteroid were isolated from the roots of Helleborus orientalis Lam. Their structures were established as 26-[(β-D-glucopyranosyl)oxy]-22α-hidroxyfurosta-5,25(27)-dien- 1β,3β,11α-triol (1a), 26-[(β-D-glucopyranosyl)oxy]- 22α-methoxyfurosta-5,25(27)-dien-1β,3β,11α-triol (1b), and 20-hydroxy-β-ecdyson-3-O-β-D-glycoside (2). Acid hydrolysis of 1a,b gave (1β,3β,11α,22α)-22,26-dimethoxyfurosta-5,25(27)-dien- 1,3,11-triol (aglycone 1) and of 2 gave 20-hydroxy-β-ecdyson (aglycone 2). Their structures were elucidated by spectral analysis. Springer Science+Business Media, Inc. 2007.
- Akin, Sebahat,Anil, Huseyin
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- PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. ECDYSTERONE 20-O-BENZOATE FROM Silene tatarica
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A new ecdysteroid, which has proved to be ecdysterone 20-O-benzoate, has been isolated from the whole plant Silene tatarica (L.) Pers.
- Baltaev, U. A.,Darmograi, V. N.,Abubakirov, N. K.
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- Ecdysone 20-monooxygenase, a cytochrome P450 enzyme from spinach, Spinacia oleracea
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A microsomal preparation isolated from first leaves of 25-day-old spinach catalysed the hydroxylation of ecdysone to produce the insect moulting hormone, 20-hydroxyecdysone. Hydroxylation was dependent on NADPH and molecular oxygen, and was inhibited by carbon monoxide. Carbon monoxide inhibition was partially reversible by white light. Polyclonal antibodies to the Jerusalem artichoke NADPH-cytochrome P450 reductase inhibited the hydroxylation reaction as well as the spinach microsomal NADPH cytochrome c reductase. These results taken together establish ecdysone hydroxylation as a cytochrome P450 dependent reaction in spinach, which is known to synthesize large amounts of phytoecdysteroids.
- Grebenok, Robert J.,Galbraith, David W.,Benveniste, Irene,Feyereisen, Rene
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- Mechanism of C-2 hydroxylation during the biosynthesis of 20- hydroxyecdysone in Ajuga hairy roots
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Feeding synthetic [2β-2H]- and [2α-2H]-cholesterols to the hairy roots of Ajuga reptans var. atropurpurea and 2H-NMR analysis of the biosynthesized 20-hydroxyecdysone revealed that hydroxylation at C-2 proceeds with retention of configuration. Feeding [2α,3α-2H2]cholesterol followed by 2H-NMR analysis of the 2,3,22-triacetate of the resulting 20- hydroxyecdysone ruled out a mechanism which involves a partial loss of the 2α-hydrogen. The steric course of C-2 hydroxylation in Ajuga hairy roots is identical with that reported in the insect, Schistocerca gregaria.
- Nomura, Keiko,Fujimoto, Yoshinori
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- A PHYTOECDYSTEROID, TAXISTERONE, FROM TAXUS CUSPIDATA
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A new phytoecdysteroid, taxisterone, was isolated from Taxus cuspidata and the structure was deduced to be 22-deoxyecdysterone by spectral data. - Key Word Index: Taxus cuspidata; Taxaceae; phytoecdysteroid; taxisterone; 22-deoxyecdysterone.
- Nakano, Kimiko,Nohara, Toshihiro,Tomimatsu, Toshiaki,Nishikawa, Masaru
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- A short way to invert configuration of the 2,3-hydroxy groups in ecdysteroids
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3-epi-2-Dehydro-20-hydroxyecdysone and its 20,22-acetonide were reduced with lithium tris(secbutyl) hydridoborate selectively at the 2-oxo group with formation of 2β,3β-dihydroxy derivatives and the corresponding 2α,3α epimers which were separated by chromatography.
- Savchenko,Kostyleva,Kachala,Khalilov,Odinokov
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p. 995 - 998
(2013/09/02)
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- ECDYSTEROID ANALOGUES HAVING PLANT GROWTH PROMOTING ACTIVITY
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The present disclosure relates to ecdysteroid analogues which have similar, identical, or enhanced biological activities as compared to brassinosteroids, for instance similar, identical, or enhanced plant growth promoting activity. The ecdysteroid analogues can have similar structures to particular brassinosteroids. Mixtures of ecdysteroid analogues, the mixture having similar, identical, or enhanced biological activities as compared to brassinosteroids, for instance similar, identical, or enhanced plant growth promoting activity, are also provided by the present disclosure.
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Page/Page column 25
(2012/05/05)
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- Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite
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Catalytic hydrogenation with Pd-C as a catalyst in the presence of sodium nitrite is a simple, convenient and high yielding stereoselective reduction of olefinic function of Δ7-6-ketosteroids to the corresponding dihydro analogues.
- Suksamrarn, Apichart,Tanachatchairatana, Tanud,Sirigarn, Chana
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p. 6033 - 6037
(2007/10/03)
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- Phytoecdysteroids of plants of the Silene genus. XIX. The structure of sileneoside G
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The phytoecdysteroid sileneoside G has been isolated from the roots of Silene brahuica Boiss., and its structure has been established on the basis of chemical transformations and spectral characteristics as ecdysterone 3-O-α-D-galactopyranoside 22-O-α-D-glucopyranoside. Enzymatic hydrolysis yielded ecdysterone and sileneoside D.
- Sadykov,Saatov
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p. 602 - 604
(2007/10/03)
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- Synthesis of 25-fluoroponasterone A, a fluorinated analogue of 20-hydroxyecdysone
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Very precise reaction conditions, using mild fluorination procedures combined with acetonide deprotection, were developed for preparation of 25-fluoroponasterone A from 20-hydroxyecdysone. Biological activity of the new compound was examined and the possible relationship between structure and biological activity in ecdysteroids was studied using MMP2 calculations of the conformations of the side chain of three related compounds: ecdysone, 20-hydroxyecdysone and 25-fluoroponasterone A.
- Tomas,Camps,Coll,Mele,Pascual
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p. 9809 - 9818
(2007/10/02)
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- A facile route to 20-hydroxyecdysone and side chain homologues from poststeron
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A flexible approach to ecdysteroids, chain elongated at C-26 and C-27, is reported. Key features are the addition of 5-lithio 2,3-dihydrofurans (3) to poststeron (10) and a stereoselective reduction of the 22-∞ group.
- Hedtmann, Udo,Klintz, Ralf,Hobert, Kurt,Frelek, Jadwiga,Vlahov, Iontscho,Welzel, Peter
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p. 3753 - 3772
(2007/12/18)
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- PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silence. XVII. ECDYSTERONE 22,25-DI-O-BENZOATE FROM Silene scabrifolia
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The new phytoecdysteroid ecdysterone 22,25-di-O-benzoate (IV) has been isolated from the epigeal organs of Silene scabrifolia Kom.The alkaline hydrolysis of (IV) gave ecdysterone 25-O-benzoate and ecdysterone (I).Details of the IR, UV, mass, PMR, and 13C
- Saatov, A.,Abdullaev, N. D.,Gorovits, M. B.,Abubakirov, N. K.
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p. 301 - 303
(2007/10/02)
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- STUDY ON THE BIOSYNTHESIS OF ECDYSONE PART IV: Synthesis of high specific activity -2,22-dideoxyecdysone Tissue distribution of the C-22 hydroxylase in Locusta migratoria
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We have synthesized a tritiated form of 2,22-dideoxyecdysone -3β,14α,25-trihydroxy-5β-cholest-7-en-6-one> of high specific activity (2.2 TBq/mmol).We have examined the capacity of various endocrine (prothoracic glands, follicle cells) and peripheral (fat body, Malpighian tubules) tissues of Locusta migratoria to use this molecule as a precursor of ecdysone biosynthesis.Efficient conversion of 2,22-dideoxyecdysone to 2-deoxyecdysone and to ecdysone could principally be monitored in the prothoracic glands and follicle cells.
- Haag, Thierry,Hetru, Charles,Kappler, Christine,Moustier, Anne Marie,Hoffmann, Jules A.,Luu, Bang
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p. 1397 - 1408
(2007/10/02)
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- PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene XII. 5α-ECDYSTERONE 22-O-BENZOATE FROM Silene scabrifolia
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The new phytoecdysteroid 5α-ecdysterone 22-O-benzoate (I), C34H48O8, mp 262-274 deg C (methanol-water) D20+45.8 deg (methanol), has been isolated from the epigeal organ of Silene scarbiofolia Kom.The alkaline hydrolysis of (I) led to 5α-ecdysterone (II) and benzoic acid.The isomerization of ecdysterone (0.6percent KHCO3 in CH3OH) has yielded (II).Details of the IR, mass, and NMR spectra of compound (I) are given.
- Saatov, Z.,Gorovits, M. B.,Abdullaev, N. D.,Abubakirov, N. K.
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p. 563 - 565
(2007/10/02)
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- PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. IX. ECDYSTERONE 22-O-BENZOATE FROM Silene scabrifolia
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An ecdysteroid which has proved to be ecdysterone 22-O-benzoate has been isolated from the epigeal organs of Silene scabrifolia Kom.
- Saatov, Z.,Gorovits, M. B.,Melibaev, S.,Abubakirov, N. K.
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- ECDYSTEROID METABOLISM IN A CRAB: CARCINUS MAENAS L.
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Ponasterone A (25-deoxy-20-hydroxyecdysone) and 20-hydroxyecdysone were the major ecdysteroids detected in crab hemolymph, although some ecdysone was also present.The metabolism of ponasterone A was examined in intermolt and premolt crabs either by injecting the radiolabeled hormone or by incubating tissues in its presence.Metabolites were extracted from the surrounding seawater and from tissues and separated by high-performance liquid chromatography.Ponasterone A metabolism proceeds through (1) C-25 and C-26 hydroxylation, followed by formation of inactivation products via oxidation of the terminal alcoholic group to a carboxylic residue, (2) conjugation, (3) binding to very polar compounds and (4) side-chain scission.The conversion of ponasterone A into 20-hydroxyecdysone, inokosterone (25-deoxy-20,26-dihydroxyecdysone), 20,26-dihydroxyecdysone and ecdysonoic acids, as well as the formation of conjugates and of very polar compounds, occurs in various tissues.These metabolites were excreted by both intermolt and premolt crabs.
- Lachaise, Fabienne,Lafont, Rene
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p. 243 - 260
(2007/10/02)
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- PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. V. SILENEOSIDE B - AN ECDYSTERONE DIGALACTOSIDE FROM Silene brahuica
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The phytoecdysteroid sileneoside B has been isolated from the roots of Silene brahuica Boiss.; it is ecdysterone 3,22-di-O-α-D-galactopyranoside.
- Saatov, Z.,Gorovits, M. B.,Abdullaev, N. D.,Usmanov, B. Z.,Abubakirov, N. K.
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p. 578 - 582
(2007/10/02)
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- PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. III. SILENEOSIDE A - A NEW GLYCOSIDIC ECDYSTEROID OF Silene brachuica
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Ecdysterone (I), viticosterone E, polypodine B, and integristerone A (II) have been isolated from the epigeal part of the plant Silene brachuica Boiss.In addition to substances (I) and (II), the phytoecdysteroid sileneoside A has been isolated from the root of this plant.It has been shown that sileneoside A is ecdysterone 22-O-α-D-galactoside
- Saatov, Z.,Gorovits, M. B.,Abdullaev, N. D.,Yasmanov, B. Z.,Abubakirov, N. K.
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p. 534 - 539
(2007/10/02)
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