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Structural Elucidation of a Novel Transglycosylated Compound α-glucosyl Rhoifolin and of α-glucosyl Rutin by NMR Spectroscopy

Structural Elucidation of a Novel Transglycosylated Compound α-glucosyl Rhoifolin and of α-glucosyl Rutin by NMR Spectroscopy

Chisa Aoki, Yoshihiro Takeuchi, Kenjirou Higashi, Yuta Okamoto, Akihito Nakanishi, Mahamadou Tandia, Jun Uzawa, Keisuke Ueda, Kunikazu Moribe

Carbohydr Res. 2017 Apr 18;443-444:37-41.

PMID: 28334636

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP17306466	Rhoifolin		17306-46-6	Price

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