338. The syntheses of glycosides. Part XII. Fabiatrin

Chaudhury, D. N.; Holland, R. A.; Robertson, Alexander

doi:10.1039/jr9480001671

Cited by 21 publications

(5 citation statements)

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“…This second substance gives xylose, glucose and scopoletin on hydrolysis. It is also spectrally and chromatographically identical with the known 7xyloglucoside of scopoletin (fabiatrin), which occurs in the leaves of Fabiana imbricata (Chaudhury et al 1948).…”

Section: 400mentioning

confidence: 67%

“…Authentic scopolin (6-O-methylaesculetin 7-glucoside) and 'methyl cichoriin' were isolated by paper chromatography from the roots of Scopolia lurida, S. chinensis, S. carniolica (Spaith, 1937) and Atropa belladonna (Moore, 1911). Fabiatrin (6-O-methylaesculetin 7-xylosylglucoside) was obtained from the leaves ofFabiana imbricata (Edwards & Rogerson, 1927;Chaudhury, Holland & Robertson, 1948). The other compounds were either purchased from L. Light and Co. Ltd., or prepared from purchased compounds by well-established chemical procedures (e.g.…”

Section: Methodsmentioning

confidence: 99%

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Plant polyphenols. 2. The coumarins of Solanum pinnatisectum

Harborne

1960

Biochemical Journal

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Section: 400mentioning

confidence: 67%

Section: Methodsmentioning

confidence: 99%

Plant polyphenols. 2. The coumarins of Solanum pinnatisectum

Harborne

1960

Biochemical Journal

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“…FA(8-5)G was isolated from the mixture obtained by cross-coupling coniferyl alcohol with ethyl FA via MnO 2 in acetone followed by saponification (H. Kim and J. Ralph, unpublished data). Scopolin was synthesized from scopoletin (Chaudhury et al, 1948).…”

Section: Analysis Of Soluble Phenolics and Amino Acidsmentioning

confidence: 99%

Molecular Phenotyping of the pal1 and pal2 Mutants of Arabidopsis thaliana Reveals Far-Reaching Consequences on Phenylpropanoid, Amino Acid, and Carbohydrate Metabolism

et al. 2004

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The first enzyme of the phenylpropanoid pathway, Phe ammonia-lyase (PAL), is encoded by four genes in Arabidopsis thaliana. Whereas PAL function is well established in various plants, an insight into the functional significance of individual gene family members is lacking. We show that in the absence of clear phenotypic alterations in the Arabidopsis pal1 and pal2 single mutants and with limited phenotypic alterations in the pal1 pal2 double mutant, significant modifications occur in the transcriptome and metabolome of the pal mutants. The disruption of PAL led to transcriptomic adaptation of components of the phenylpropanoid biosynthesis, carbohydrate metabolism, and amino acid metabolism, revealing complex interactions at the level of gene expression between these pathways. Corresponding biochemical changes included a decrease in the three major flavonol glycosides, glycosylated vanillic acid, scopolin, and two novel feruloyl malates coupled to coniferyl alcohol. Moreover, Phe overaccumulated in the double mutant, and the levels of many other amino acids were significantly imbalanced. The lignin content was significantly reduced, and the syringyl/guaiacyl ratio of lignin monomers had increased. Together, from the molecular phenotype, common and specific functions of PAL1 and PAL2 are delineated, and PAL1 is qualified as being more important for the generation of phenylpropanoids.

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“…The acetyl groups of 10i can easily be removed by Zemplén deacetylation (Scheme 3) [34]. Instead of the classical protocol with sodium methoxide, ammonia in methanol was applied, because oxazolines are sensitive to acid and with ammonia no acid has to be added to neutralize the reaction mixture [35]. The deprotected oxazoline 10j was isolated in nearly quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation

Imrich

Kraft

Maichle‐Mößmer

et al. 2018

Beilstein J. Org. Chem.

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Phosphinooxazoline (PHOX) ligands are an important class of ligands in asymmetric catalysis. We synthesized ten novel D-fructose-derived spiro-fused PHOX ligands with different steric and electronic demand. The application of two of them was tested in asymmetric allylic alkylation. The ligands are prepared in two steps from readily available 1,2-O-isopropylidene protected β-D-fructopyranoses by the BF3·OEt2-promoted Ritter reaction with 2-bromobenzonitrile to construct the oxazoline moiety followed by Ullmann coupling of the resulting aryl bromides with diphenylphosphine. Both steps proceeded mostly in good to high yields (57–86% for the Ritter reaction and 35–89% for the Ullmann coupling). The Ritter reaction gave two anomers, which could be separated by column chromatography. The prepared ligands showed promising results (er of up to 84:16) in Tsuji–Trost reactions with diphenylallyl acetate as model substrate.

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338. The syntheses of glycosides. Part XII. Fabiatrin

Cited by 21 publications

References 0 publications

Plant polyphenols. 2. The coumarins of Solanum pinnatisectum

Plant polyphenols. 2. The coumarins of Solanum pinnatisectum

Molecular Phenotyping of the pal1 and pal2 Mutants of Arabidopsis thaliana Reveals Far-Reaching Consequences on Phenylpropanoid, Amino Acid, and Carbohydrate Metabolism

D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation

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