Structural elucidation of a novel transglycosylated compound α-glucosyl rhoifolin and of α-glucosyl rutin by NMR spectroscopy
| Autor: | Mahamadou Tandia, Yoshihiro Takeuchi, Akihito Nakanishi, Kenjirou Higashi, Jun Uzawa, Kunikazu Moribe, Yuta Okamoto, Chisa Aoki, Keisuke Ueda |
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| Rok vydání: | 2017 |
| Předmět: |
Glycosylation
Magnetic Resonance Spectroscopy Stereochemistry Rutin Chemical structure Disaccharides 010402 general chemistry 01 natural sciences Biochemistry Analytical Chemistry chemistry.chemical_compound Glycosides Flavonoids chemistry.chemical_classification 010405 organic chemistry Chemistry Hydrogen bond Organic Chemistry Glycoside General Medicine Nuclear magnetic resonance spectroscopy Carbon-13 NMR 0104 chemical sciences Rhoifolin Intramolecular force |
| Zdroj: | Carbohydrate Research. :37-41 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2017.03.011 |
| Popis: | We report the full assignment of 1H and 13C NMR signals belonging to α-glucosyl rhoifolin (Rhf-G), a novel transglycosylated compound synthesized from a flavone glycoside, rhoifolin, as well as its chemical structure. Furthermore, we report the complete NMR signal assignment for another transglycosylated compound, α-glucosyl rutin (Rutin-G), as the signals corresponding to its sugar moieties had not been identified. Electrospray ionization-mass spectrometry along with multiple NMR methods revealed that Rhf-G possesses three sugar moieties in its chemical structure. The additional glucose was bound directly via a transglycosylation to rhoifolin at position 3a of the sugar moiety. Interestingly, intramolecular hydrogen bonds in the basic Rhf-G and Rutin-G skeletons were confirmed by HMBC experiments. These findings will be helpful for comprehensive NMR studies on transglycosylated compounds in food, cosmetic, and pharmaceutical fields. |
| Databáze: | OpenAIRE |
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