Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L.
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Toshinari Kawada
Abstract
The first total synthesis of plantamajoside (1), 2-(3′,4′-dihydroxylphenyl)ethyl-4-O-caffeoyl-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside, which is one of the dihydroxyphenylethyl glycosides (caffeic acid sugar esters), is described. Key intermediate 2, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-β-D-glucopyranoside was glycosylated with trichloroacetoimidoyl 2,3,4,6-tetra-O-acetyl-α-D-glycopyranoside (3) to afford plantamajoside derivative 4a, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside, in 39% yield. Plantamajoside derivative 4a was successfully converted into the target compound, plantamajoside (1), through a series of de-protective procedures. 1H- and 13C nuclear magnetic resonance (NMR) spectral data of the synthesized plantamajoside (1) were identical to those of the natural compound.
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©2006 by Walter de Gruyter Berlin New York
Articles in the same Issue
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Articles in the same Issue
- A report from the 2005 Japanese-European Workshop on “Cellulose and Functional Polysaccharides”
- Determination of substituent distribution of viscoses by GPC
- Direct investigation of the structural properties of tension wood cellulose microfibrils using microbeam X-ray fibre diffraction
- Influence of amide content on the crystal structure of chitin
- Stepwise synthesis of chitooligosaccharides through a transition-state analogue substrate catalyzed by mutants of chitinase A1 from Bacillus circulans WL-12
- Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L.
- Diffusion of sulfide into Southern pine (Pinus taeda L.) and sweetgum (Liquidambar styraciflua L.) particles and chips
- Laccase-catalysed functionalisation of TMP with tyramine
- Wood liquefaction by ionic liquids
- Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 2: Horseradish peroxidase-catalyzed dehydrogenative polymerization of isoconiferin
- Phenolic compounds in silver birch (Betula pendula Roth) wood
- Analysis of fragrance compositions of precious coniferous woods grown in Taiwan
- Influences of hot pressing temperature and surface structure on VOC emissions from OSB made of Scots pine
- Dimensional stability and photostability of octanoylated wood
- Measurement of the shear modulus of wood by the square-plate twist method
- Dielectric relaxation of water adsorbed on chemically treated woods
- Influences of drying on internal checking of spruce (Picea abies L.) heat-treated at 212°C
- The role of resol fortifiers in latex wood adhesives
- A simple anisotropy correction procedure for acoustic wood tomography
- Evaluating growth strain of Eucalyptus globulus Labill. from SilviScan measurements
- Density assessment of radiata pine: Sampling strategy revisited
