<sup>1</sup>H and <sup>13</sup>C NMR analysis of brassinosteroids

Porzel, Andrea; Marquardt, V.; Adam, Günter; Massiot, Georges; Zeigan, D.

doi:10.1002/mrc.1260300714

Cited by 31 publications

(12 citation statements)

References 13 publications

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“…Configurations at C-22 and C-23 in the new compounds were established by comparison with NMR chemical shifts and coupling constants of known closely related structures [14].…”

Section: Synthesis Of Compounds 1 Andmentioning

confidence: 99%

Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives

Michelini

Ramírez

Berra

et al. 2008

The Journal of Steroid Biochemistry and Molecular Biology

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Stromal keratitis resulting from ocular infection with Herpes simplex virus type 1 (HSV-1) is a common cause of blindness. This report investigates the antiviral and anti-inflammatory properties of two new synthetic stigmastane analogs in the experimental model of HSV-1-induced ocular disease in mice. (22S,23S)-22,23-dihydroxystigmast-4-en-3-one (1) and (22S,23S)-22,23-dihydroxystigmasta-1,4-dien-3-one (2) exhibited anti-HSV-1 activity in vitro and ameliorated the signs of murine herpetic stromal keratitis (HSK), although none of the compounds showed antiviral activity in vivo. We discuss that the improvement of HSK could be due to an immunomodulatory effect of both compounds.

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“…Configurations at C-22 and C-23 in the new compounds were established by comparison with NMR chemical shifts and coupling constants of known closely related structures [14].…”

Section: Synthesis Of Compounds 1 Andmentioning

confidence: 99%

Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives

Michelini

Ramírez

Berra

et al. 2008

The Journal of Steroid Biochemistry and Molecular Biology

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“…We used a combination of 2D techniques (COSY DQF, HMQC, HMBC) as described in the previous paper. 20 The distinction of the diastereotopic protons (a and b) of the steroidal skeleton can easily be done by NOE di †erence spectroscopy with saturation of the two b-angular methyl groups Me-18 and Me-19 which give NOEs to all desired b protons. The 1H and 13C chemical shift values are given in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Side Chain Conformation of the Growth-Promoting Phytohormones Brassinolide and 24-Epibrassinolide

Stoldt¹,

Porzel²,

Adam³

et al. 1997

Magn. Reson. Chem.

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Quantitative 2D NOE measurements and restrained molecular dynamics simulations (with explicit solvent) were carried out in order to determine preferential solution side chain conformations of the two most important native brassinosteroids, brassinolide and 24‐epibrassinolide. The NOE assignment was assisted by 1D NOE difference spectroscopy and included prochiral assignment of the side chain methyl groups Me‐26 and Me‐27. 2D NOE intensities were converted into inter‐proton distances using the ‘complete relaxation matrix analysis’ methodology. Restrained molecular dynamics simulations in a chloroform solvent box led to a well defined solution conformation in the case of brassinolide. The increased side chain flexibility in the case of 24‐epibrassinolide is discussed, considering missing NOE correlations and vicinal proton coupling constants. © 1997 by John Wiley & Sons, Ltd.

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“…The exchange rate was determined on the basis of the mass spectroscopic data given in Table 1. The position of the introduced deuterium followed from the NMR spectrum of 2 which lacked the signals for the 5a-and 7a,7B-protons at 2,57 and 2,33 ppm, respectively [8]. Baeyer-Villiger oxidation of 2, using CF3C03H in CHzC12 gave the 7-oxa-6-0x0-lactone 4 besides approximately 10% of the undesired epimeric 6-oxa-7-0x0-lactone, separated by S O 2 chromatography.…”

Section: K2codch3ohmentioning

confidence: 99%

Synthesis of tritium labelled 24‐epibrassinolide

Kolbe

Marquardt

Adam

1992

Labelled Comp Radiopharmac

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SUMMARYDeuterium and tritium 5,7,7-tris-labelled 24-epibrassinolide were prepared by base catalyzed exchange reaction using 24-epicastasterone tetraacetate I or bis-isopropylidenedioxy-24-epicastasterone 8 and labelled water. Baeyer-Villiger oxidation of the obtained labelled 6-ketones 2 and 3 with CF3C03H gave after alkaline deacetylation of the resulting 4 and 5 the desired tris-labelled 24-epibrassinolides 6 and 2, respectively, or starting from 9 under simultaneous oxidation and deprotection in one step the same final products.

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¹H and ¹³C NMR analysis of brassinosteroids

Cited by 31 publications

References 13 publications

Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives

Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives

Side Chain Conformation of the Growth-Promoting Phytohormones Brassinolide and 24-Epibrassinolide

Synthesis of tritium labelled 24‐epibrassinolide

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1H and 13C NMR analysis of brassinosteroids

Cited by 31 publications

References 13 publications

Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives

Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives

Side Chain Conformation of the Growth-Promoting Phytohormones Brassinolide and 24-Epibrassinolide

Synthesis of tritium labelled 24‐epibrassinolide

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¹H and ¹³C NMR analysis of brassinosteroids