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Total synthesis of agalloside, isolated from Aquilaria agallocha, by the 5-O-glycosylation of flavan
- Source :
- Organic & Biomolecular Chemistry. 15:5025-5032
- Publication Year :
- 2017
- Publisher :
- Royal Society of Chemistry (RSC), 2017.
-
Abstract
- Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.
- Subjects :
- Glycosylation
Dinitrocresols
Stereochemistry
Chemistry Techniques, Synthetic
010402 general chemistry
01 natural sciences
Biochemistry
Mice
chemistry.chemical_compound
Neural Stem Cells
Flavan
Aquilaria
Animals
Glycosyl
Glycosides
Physical and Theoretical Chemistry
Flavonoids
biology
010405 organic chemistry
Activator (genetics)
Organic Chemistry
Total synthesis
Cell Differentiation
biology.organism_classification
Neural stem cell
0104 chemical sciences
Oxygen
carbohydrates (lipids)
chemistry
Thymelaeaceae
Flavanone
Subjects
Details
- ISSN :
- 14770539 and 14770520
- Volume :
- 15
- Database :
- OpenAIRE
- Journal :
- Organic & Biomolecular Chemistry
- Accession number :
- edsair.doi.dedup.....c836e5f697173c3de8f850e0e6171465
- Full Text :
- https://doi.org/10.1039/c7ob01004d