Unveiling the flavone-solubilizing effects of α-glucosyl rutin and hesperidin: probing structural differences through NMR and SAXS analyses

文献情報

出版日 2023-11-08
DOI 10.1039/D3FO03261B
インパクトファクター 5.396
著者

Kazunori Kadota, Tero Kämäräinen, Fumie Sakuma, Keisuke Ueda, Kenjirou Higashi, Kunikazu Moribe, Hiromasa Uchiyama, Katsuhiko Minoura, Yuichi Tozuka



要旨

Flavonoids often exhibit broad bioactivity but low solubility and bioavailability, limiting their practical applications. The transglycosylated materials α-glucosyl rutin (Rutin-G) and α-glucosyl hesperidin (Hsp-G) are known to enhance the dissolution of hydrophobic compounds, such as flavonoids and other polyphenols. In this study, the effects of these materials on flavone solubilization were investigated by probing their interactions with flavone in aqueous solutions. Rutin-G and Hsp-G prepared via solvent evaporation and spray-drying methods were evaluated for their ability to dissolve flavones. Rutin-G had a stronger flavone-solubilizing effect than Hsp-G in both types of composite particles. The origin of this difference in behavior was elucidated by small-angle X-ray scattering (SAXS) and nuclear magnetic resonance analyses. The different self-association structures of Rutin-G and Hsp-G were supported by SAXS analysis, which proved that Rutin-G formed polydisperse aggregates, whereas Hsp-G formed core–shell micelles. The observation of nuclear Overhauser effects (NOEs) between flavone and α-glucosyl materials suggested the existence of intermolecular hydrophobic interactions. However, flavone interacted with different regions of Rutin-G and Hsp-G. In particular, NOE correlations were observed between the protons of flavone and the α-glucosyl protons of Rutin-G. The different molecular association states of Rutin-G or Hsp-G could be responsible for their different effects on the solubility of flavone. A better understanding of the mechanism of flavone solubility enhancement via association with α-glucosyl materials would permit the application of α-glucosyl materials to the solubilization of other hydrophobic compounds including polyphenols such as flavonoids.

掲載誌

Food & Function

Food & Function
CiteScore: 10.1
自己引用率: 3.9%
年間論文数: 758

Food & Function provides a unique venue for physicists, chemists, biochemists, nutritionists and other food scientists to publish novel, cutting-edge, original research focussing on food, its nutrients and their relation to human health and nutrition. We welcome research describing the: Physical properties and structure of food and how this relates to sensory perception and human health Biochemical and physiological actions of food components Interactions between foods, gut microbiota and human physiology Nutritional and biological evaluation of food Clinical and population studies using food or food components Development of biomarkers of food intake and effects on human health We also welcome systematic reviews and meta-analyses of existing studies in the literature, provided these are objective and scientifically valid Food in this context is defined as materials of plant, animal or mineral origin, which are consumed orally (by humans) for pleasure and to sustain growth and vital processes. Examples of research topics that are of interest to be published in Food & Function are: Chemistry and physics of food components and digestion processes Relationship between the physical properties/structure of food and nutrition and human health - for example, impact of food matrix or processing on nutrient release and uptake Molecular properties and physiological effects of food components (nutrients, fibres, essential micronutrients, phytochemicals, bioactives, food substitutes, novel ingredients, allergens, flavours and fragrances) Nutritional and health effects of food including bioavailability and metabolism assessment of food components (nutrients, micronutrients and other microconstituents) Efficacy and mechanisms of food constituents in the body - including biomarkers of intakes, exposure and effects Impacts of foods/food components on gut microorganisms and human physiology - For example impact of fermented foods Role of nutrition and diet in human disease prevention and development Cellular and molecular effects/mechanisms of food/food components image block The following types of research are not within the scope of Food & Function: Research relating to traditional herbal medicines, medicinal plants or active compounds extracted from such plants (materials that are primarily consumed as medicine, i.e. the intended purpose is primarily to treat, cure or prevent a non-deficiency disease) or relating to foods not recognised as human diet contributors Animal nutrition research that is not primarily designed as a model to benefit human nutrition (for example, studies of growth/accretion, heat stress, weaning, ruminant digestion, meat quality, etc.) Treatments administered by non-oral routes such as injection (subcutaneous, intramuscular, intraperitoneal, etc.), dermal/transdermal, rectal, inhalation, nasal, etc. Exceptions are when such routes of administration are used for mechanistic/control purposes in the experimental design Pharmacological/pharmaceutical approaches: Encapsulation, emulsification and/or pure controlled release of compounds or bioactives that do not come directly from edible foods, such as dietary supplements - these are better suited to a pharmaceutical journal In vitro or in vivo studies with poorly defined (insufficiently characterised) extracts and studies without appropriate controls will not be considered Cells studies not considering the metabolism of food components ingested – for example, irrelevant exposure of cells to compounds not present in the body after absorption Manuscripts with only a fully theoretical/bioinformatic approach and without appropriate support from analytical evidence will not be considered for publication Studies focussing solely on food engineering, preservation and sustainable technologies – these can be published in our companion journal Sustainable Food Technology Pure food analysis - these can be published in Analytical Methods

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