Characteristic <sup>1</sup>H NMR spectra of β-<scp>d</scp>-ribofuranosides and ribonucleosides: factors driving furanose ring conformations

Rehmannia glutinosa Libosch., which belongs to the Orobanchaceae family, is a perennial herb found in China, Japan, and Korea. In traditional medicine, it is used to cool the body, improve water metabolism in the kidney, and provide protection from metabolic diseases such as type 2 diabetes mellitus (T2DM) and obesity. In this study, three new compounds were isolated from the roots of R. glutinosa, along with eighteen known compounds. Structure elucidation was performed with spectroscopic analyses including nuclear magnetic resonance (NMR) and circular dichroism (CD) spectroscopy. As the AMP-activated protein kinase (AMPK) signaling pathway is reportedly related to metabolic diseases, AMPK activation studies were conducted using in silico simulations and in vitro assays. Among the isolated compounds, 1 showed a potential as an AMPK activator in both in silico simulations and in vitro experiments. Our findings expand the chemical profiles of the plant R. glutinosa and suggest that one newly found compound (1) activates AMPK.

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Characteristic ¹H NMR spectra of β-d-ribofuranosides and ribonucleosides: factors driving furanose ring conformations

Abstract: The 2,3-O-isopropylidene group locks β-d-ribofuranosides in the E0-like conformation whereas ribonucleosides in the E4-like conformation. The conformational preferences of β-d-ribofuranosides are determined by the anomeric effect.

Cited by 3 publications

References 76 publications

Identification of the furanose ring conformations and the factors driving their adoption

Identification of the furanose ring conformations and the factors driving their adoption

An NMR-based approach for the design of crystallization processes for rigid molecules and effects of molecular rigidity and impurities on crystallization pathways

Identification of Bioactive Compounds from the Roots of Rehmannia glutinosa and Their In Silico and In Vitro AMPK Activation Potential

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Characteristic 1H NMR spectra of β-d-ribofuranosides and ribonucleosides: factors driving furanose ring conformations

Abstract: The 2,3-O-isopropylidene group locks β-d-ribofuranosides in the E0-like conformation whereas ribonucleosides in the E4-like conformation. The conformational preferences of β-d-ribofuranosides are determined by the anomeric effect.

Cited by 3 publications

References 76 publications

Identification of the furanose ring conformations and the factors driving their adoption

Identification of the furanose ring conformations and the factors driving their adoption

An NMR-based approach for the design of crystallization processes for rigid molecules and effects of molecular rigidity and impurities on crystallization pathways

Identification of Bioactive Compounds from the Roots of Rehmannia glutinosa and Their In Silico and In Vitro AMPK Activation Potential

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Characteristic ¹H NMR spectra of β-d-ribofuranosides and ribonucleosides: factors driving furanose ring conformations