Biosynthesis of 2,3-epoxybrassinosteroids in seedlings of Secale cereale

Antonchick, Andrey P.; Schneider, Bernd; Жабинский, В. Н.; Konstantinova, Olga V.; Хрипач, В. А.

doi:10.1016/s0031-9422(03)00354-6

Cited by 24 publications

(26 citation statements)

References 17 publications

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“…3 was the 24 nor analogue (VI) of natural brassinoster oid, i.e., secasterol that we found earlier in rye [22].…”

Section: Resultsmentioning

confidence: 62%

“…Δ 22 6 Ketone (XI) obtained in 11 steps from com mercially available stigmasterol in 37% yield [15] was used as the starting compound. The functionalization of the side chain was achieved as a result of the Sharp less asymmetric dihydroxylation [16] of Δ 22 6 ketone (XI) that proceeds with the formation of 22R,23R diol (XII) as the main product (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and biological activity of the probable biosynthetic precursors of 241-norbrassinolide

et al. 2012

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A number of 24-norbrassinolide biosynthetic precursors containing low polar functional groups (3beta3-OH, 3-keto-, delta2- or 2alpha,3alpha-epoxy-) in A-cycle and (22R,23R)-diol in the side chain has been prepared. Studies of these compounds as proliferation regulators in MCF-7 human breast cancer and LnCaP human prostate adenocarcinoma cells showed that most nonpolar (22R,23R)-derivatives effectively suppressed proliferation. Dependence of proliferation on concentration of studied compounds was found in human prostate carcinoma LnCaP cells (IC50 = 13-28 microM at 72 h of incubation in a medium containing 10% FBS; suppression of DNA biosynthesis). A number of compounds induced apoptosis (23-33%); arrested cell cycle in S- and G2/M-phases; and caused partial cells detachment during prolonged incubations.

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“…3 was the 24 nor analogue (VI) of natural brassinoster oid, i.e., secasterol that we found earlier in rye [22].…”

Section: Resultsmentioning

confidence: 62%

Section: Resultsmentioning

confidence: 99%

Synthesis and biological activity of the probable biosynthetic precursors of 241-norbrassinolide

et al. 2012

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“…The obtained compounds were used for biosynthetic studies. Three new brassinosteroids were identified in these experiments, including 3‐epibrassinolide in Arabidopsis thaliana ,27 secasterol and 2,3‐diepisecasterone in Secale cereale 28. A new biosynthetic subpathway from typhasterol/teasterone via 2,3‐epoxybrassinosteroids to castasterone was found in seedlings of S. cereale 29.…”

Section: Discussionmentioning

confidence: 81%

“…This work was realized through the joint efforts of the scientists from our laboratory listed in the references10,11,17,18,25,27–30 and of Dr. Bernd Schneider from the Max‐Planck Institute for Chemical Ecology (Jena, Germany).…”

Section: Acknowledgementsmentioning

confidence: 99%

Labeled brassinosteroids for biochemical studies

Хрипач

Жабинский

2007

The Chemical Record

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The present paper describes the results of our studies on the synthesis of brassinolide biosynthetic precursors as tools for investigations of new biosynthetic routes leading to brassinosteroids. The corresponding labeled compounds containing three or six deuterium atoms at terminal methyl group(s) of the side chain (in a position ensuring lack of isotopic exchange) were prepared starting from stigmasterol or bisnorcholenic acid. Two strategies for the construction of the carbon skeleton of the side chain were applied in this study: Claisen rearrangement of allylic alcohols and convergent synthesis based on the coupling of 22-aldehydes with appropriate chiral sulfone. More than 20 brassinolide precursors (actual or suspected) have been prepared for metabolic studies that enabled identification of new brassinosteroids and biosynthetic subpathways to brassinolide in Secale cereale and Arabidopsis thaliana.

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“…Analysis of SAR of 22,23‐dihydroxy derivatives of C‐27–C‐29 steroids have revealed that the derivatives 2a – 2d ( Figure ) containing a Δ 2 ‐double bond in the A cycle obtain better cytotoxicity towards number of cancer cell lines . It should be noted that similar compounds (in particular, secasterol 2a ) were found in plants as biosynthetic precursors of BS with a complete set of functional groups …”

Section: Introductionmentioning

confidence: 83%

Biological Evaluation of a New Brassinosteroid: Antiproliferative Effects and Targeting Estrogen Receptor α Pathways

Scherbakov

Жабинский

Хрипач

et al. 2019

Chemistry & Biodiversity

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Brassinosteroids (BS), a class of plant‐specific steroid hormones, are considered as new potential anticancer agents for the treatment of tumors of different origin, including hormone‐dependent cancers. Effects of a synthetic brassinosteroid BS4 ((22R,23R,24R)‐22,23‐dihydroxy‐24‐methyl‐B‐homo‐7‐oxa‐5α‐cholest‐2‐en‐6‐one ((3aS,7aR,7bS,9aS,10R,12aS,12bS)‐10‐[(2S,3R,4R,5R)‐3,4‐dihydroxy‐5,6‐dimethylheptan‐2‐yl]‐7a,9a‐dimethyl‐1,3a,4,7,7a,7b,8,9,9a,10,11,12,12a,12b‐tetradecahydro‐3H‐benzo[c]indeno[5,4‐e]oxepin‐3‐one)) on hormone‐dependent breast cancer cells and normal epithelial cells and its impact on the estrogen receptor signaling were evaluated. Cytotoxicity was assessed by MTT‐test; expression of estrogen receptor α and survivin was measured by immunoblotting. Transactivation analysis of luciferase reporter gene was performed for ERα and AP‐1 factors after the brassinosteroid treatment. Dock6 and Autodock Vina were used for molecular docking. BS4 revealed a significant antiproliferative effect towards the hormone‐dependent breast cancer cells and was not active against normal epithelial cells. BS4 action on MCF‐7 breast cancer cells was found to be complex: a decrease in ERα expression as well as in its transcription activity was accompanied by inhibition of ERα‐related signaling pathways (AP‐1 complex and survivin). BS4 binding mode to ERα ligand‐binding domain was analyzed by molecular docking. The obtained results show that antiproliferative and antiestrogenic properties of the brassinosteroid BS4, as well as its ability to inhibit the anti‐apoptotic protein survivin may be of interest for further development of anticancer agents.

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Biosynthesis of 2,3-epoxybrassinosteroids in seedlings of Secale cereale

Cited by 24 publications

References 17 publications

Synthesis and biological activity of the probable biosynthetic precursors of 241-norbrassinolide

Synthesis and biological activity of the probable biosynthetic precursors of 241-norbrassinolide

Labeled brassinosteroids for biochemical studies

Biological Evaluation of a New Brassinosteroid: Antiproliferative Effects and Targeting Estrogen Receptor α Pathways

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