5289-74-7Relevant articles and documents
A furostanol saponin and phytoecdysteroid from roots of Helleborus orientalis
Akin, Sebahat,Anil, Huseyin
, p. 90 - 92 (2007)
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.
PHYTOECDYSTEROIDS OF PLANTS OF THE GENUS Silene. ECDYSTERONE 20-O-BENZOATE FROM Silene tatarica
Baltaev, U. A.,Darmograi, V. N.,Abubakirov, N. K.
, p. 706 - 708 (1987)
A new ecdysteroid, which has proved to be ecdysterone 20-O-benzoate, has been isolated from the whole plant Silene tatarica (L.) Pers.
Ecdysone 20-monooxygenase, a cytochrome P450 enzyme from spinach, Spinacia oleracea
Grebenok, Robert J.,Galbraith, David W.,Benveniste, Irene,Feyereisen, Rene
, p. 927 - 933 (1996)
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.
Mechanism of C-2 hydroxylation during the biosynthesis of 20- hydroxyecdysone in Ajuga hairy roots
Nomura, Keiko,Fujimoto, Yoshinori
, p. 344 - 348 (2000)
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.
A PHYTOECDYSTEROID, TAXISTERONE, FROM TAXUS CUSPIDATA
Nakano, Kimiko,Nohara, Toshihiro,Tomimatsu, Toshiaki,Nishikawa, Masaru
, p. 2749 - 2751 (1982)
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.
A short way to invert configuration of the 2,3-hydroxy groups in ecdysteroids
Savchenko,Kostyleva,Kachala,Khalilov,Odinokov
, p. 995 - 998 (2013/09/02)
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.
ECDYSTEROID ANALOGUES HAVING PLANT GROWTH PROMOTING ACTIVITY
-
, (2012/05/05)
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.
Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite
Suksamrarn, Apichart,Tanachatchairatana, Tanud,Sirigarn, Chana
, p. 6033 - 6037 (2007/10/03)
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.
Phytoecdysteroids of plants of the Silene genus. XIX. The structure of sileneoside G
Sadykov,Saatov
, p. 602 - 604 (2007/10/03)
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.
Synthesis of 25-fluoroponasterone A, a fluorinated analogue of 20-hydroxyecdysone
Tomas,Camps,Coll,Mele,Pascual
, p. 9809 - 9818 (2007/10/02)
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.
