2,3-Epoxybrassinosteroids are intermediates in the biosynthesis of castasterone in seedlings of

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

doi:10.1016/j.phytochem.2004.11.008

Cited by 24 publications

(17 citation statements)

References 28 publications

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“…Thus, inversion of configuration at C-3 is one of the putative possibilities to inactivate brassinolide, the most active brassinosteroid, but this specific reaction has not yet been experimentally demonstrated. The reverse conversion of 3-epicastasterone and 2-epicastasterone to castasterone was detected recently in seedlings of Secale cereale [10]. The conversion of brassinolide to 3-epibrassinolide, a naturally occurring brassinosteroid in Arabidopsis [24], and the reverse conversion are reported here for the first time and, together with the corresponding conversions between castasterone and 3-epicastasterone, are discussed in the context of hormone homeostasis in plants.…”

Section: Introductionsupporting

confidence: 54%

“…Schmidt et al [30] reported castasterone (1) together with other brassinosteroids from seeds of S. cereale. Recently we demonstrated the presence of castasterone (1) and 3-epicastasterone (3) in seeds of this plant [10].…”

Section: Brassinosteroids In Arabidopsis Thaliana and Secale Cerealementioning

confidence: 89%

“…Triply deuterated brassinosteroids, [26-2 H 3 ]3-epicastasterone, and [26-2 H 3 ]3-epibrassinolide [31] (0.4 µg in 10 µl of 75% EtOH each), were added as internal standards. Several solvent partitioning and chromatographic steps resulted in brassinosteroid-containing fractions, which after derivatization with an excess of dansyl-3-aminophenylboronic acid were analyzed by liquid chromatography (HPLC) with electrospray ionization (ESI) and using an established selected ion-monitoring mass-spectrometric (SIM-MS) detection (HPLC-ESI-SIM-MS) method [10,32]. Identification of brassinosteroids based on the relative retention time of 22,23-dansyl-3-aminophenylboronates (Table 1).…”

Section: Brassinosteroids In Arabidopsis Thaliana and Secale Cerealementioning

confidence: 99%

“…After a two-day incubation, the plant material was extracted according to the procedure used to detect endogenous brassinosteroids. Brassinosteroid-containing fractions were converted to their dansyl-3-aminophenylboronates and analyzed by HPLC-ESI-SIM-MS [10,32].…”

Section: Brassinosteroids In Arabidopsis Thaliana and Secale Cerealementioning

confidence: 99%

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Reversible Conversion In The Brassinosteroid Quartet Castasterone, Brassinolide And Their 3β-Epimers

Antonchik¹,

Svatoš

Konstantinova³

et al. 2006

Zeitschrift Für Naturforschung B

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The metabolism of deuterated brassinosteroids has been studied in excised leaves of Secale cereale, and in vitro in seedlings of Arabidopsis thaliana and cell suspension cultures of Lycopersicon esculentum. In addition to the known biosynthetic conversion of castasterone to brassinolide and epimerization to 3-epicastasterone, inversion of the 3α-configured hydroxyl group of brassinolide to a 3β -configured one in 3-epibrassinolide has been observed using liquid chromatography (HPLC) with electrospray ionization (ESI) and selected ion-monitoring mass-spectrometry (SIM-MS). Administration of deuterated 3-epicastasterone and 3-epibrassinolide to Arabidopsis and Secale seedlings resulted in the formation of castasterone and brassinolide, respectively, indicating conversion of configuration at C-3 of brassinosteroids is reversible.

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Section: Introductionsupporting

confidence: 54%

Section: Brassinosteroids In Arabidopsis Thaliana and Secale Cerealementioning

confidence: 89%

Section: Brassinosteroids In Arabidopsis Thaliana and Secale Cerealementioning

confidence: 99%

Section: Brassinosteroids In Arabidopsis Thaliana and Secale Cerealementioning

confidence: 99%

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Reversible Conversion In The Brassinosteroid Quartet Castasterone, Brassinolide And Their 3β-Epimers

Antonchik¹,

Svatoš

Konstantinova³

et al. 2006

Zeitschrift Für Naturforschung B

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“…The high concentration BR's is mainly found in reproductive organs of the plant with lesser quantity in other vegetative parts of the plants. In plants the BR's are found in pollens (Pachthong et al, 2006), anthers (Watanabe et al, 2000), panicles (Schmidt et al, 1995), seeds, seedlings (Antonchick et al, 2005), shoots (Fukuta et al, 2004), leaves (Sondhi et al, 2008), galls (Ikeda et al, 1983), stems, cambial region (Kim et al, 1990), roots (Yokota et al, 2001), flower buds (Takatsuto 1994), flowers, bran and grains (Yokota et al, (1994).…”

Section: Issn: 2319-7706 Volume 6 Number 7 (2017) Pp 1462-1475mentioning

confidence: 99%

Transcriptomic Analysis of Brassinosteroid Biosynthesis and Signaling Pathway Genes in Healthy and Malformed Tissues of Mango Variety Amrapalli

Yadav¹,

Kalidindi²

2017

Int.J.Curr.Microbiol.App.Sci

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Biochemistry of Sterols, Cardiac Glycosides, Brassinosteroids, Phytoecdysteroids and Steroid Saponins

Kreis

Müller‐Uri

2018

Annual Plant Reviews Online

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Phytosterols are synthesized via the mevalonate pathway of terpenoid formation and arise from the initial cyclization of 3 S ‐squalene‐2,3‐epoxide. Plant steroids are derived from sterols and comprise steroid saponins, steroid alkaloids, pregnanes, androstanes, estranes, ecdysteroids, withanolides and cardiac glycosides. The typical route of sterol and steroid biosynthesis follows the cycloartenol pathway, whereas the lanosterol route seems to be operative mainly in fungi and animals. It was demonstrated, however, that both sterol pathways can be operative in higher plants. Crucial steps in the conversion of cycloartenol/lanosterol to sterols are the events leading to the removal of the methyl groups at C‐4 and C‐14. Meanwhile, all steps in the sterol pathway have been elucidated and the respective enzymes/genes characterized. The biosynthetic pathway leading from phytosterol precursors to the cardiac glycosides – important compounds in the treatment of cardiac insufficiency in humans – was basically deduced from studies using radiolabelled precursors. The more recent identification and characterization of several enzymes/genes involved in pregnane and cardenolide metabolism, such as 3β‐hydroxysteroid dehydrogenase and progesterone 5β‐reductase, have further clarified the pathway. Brassinosteroids (BRs) are hydroxylated derivatives of cholestane and they are specific plant steroid hormones that are essential for normal plant development. The biosynthesis of BRs has mainly been studied in Arabidopsis thaliana . Many of the genes encoding biosynthetic enzymes have been cloned using mutants of Arabidopsis thaliana , pea, tomato and rice which revert to a wild‐type phenotype following treatment with exogenous BRs. Phytoecdysteroids are related in structure to the invertebrate steroid hormones. Their biological significance in plants is still under discussion. The understanding of the biosynthetic pathway(s) for phytoecdysteroids is very limited. Steroid saponins constitute a vast group of glycosides present almost exclusively in the monocotyledonous angiosperms, and occurring in only a few dicotyledonous families. As far as enzymatic and genetic aspects are concerned, the biosynthesis of steroid saponins (including the steroid alkaloids) has not been studied extensively. The withanolides are C 28 ‐steroids and biogenetically related to the steroid saponins in that they are derived from ergostane‐type sterols. These compounds appear to be specific for the Solanaceae and their biosynthesis has not yet been studied at the enzyme/gene level.

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2,3-Epoxybrassinosteroids are intermediates in the biosynthesis of castasterone in seedlings of

Cited by 24 publications

References 28 publications

Reversible Conversion In The Brassinosteroid Quartet Castasterone, Brassinolide And Their 3β-Epimers

Reversible Conversion In The Brassinosteroid Quartet Castasterone, Brassinolide And Their 3β-Epimers

Transcriptomic Analysis of Brassinosteroid Biosynthesis and Signaling Pathway Genes in Healthy and Malformed Tissues of Mango Variety Amrapalli

Biochemistry of Sterols, Cardiac Glycosides, Brassinosteroids, Phytoecdysteroids and Steroid Saponins

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