Effect of phenolic hydrogen on the formation of chitosan -prenylated flavonoids nanocomplexes

IF 11 1区农林科学 Q1 CHEMISTRY, APPLIED

Food Hydrocolloids Pub Date : 2025-05-08 DOI:10.1016/j.foodhyd.2025.111523

Jinping Wang , Jiawen Chen , Yueming Jiang , Bao Yang , Lingrong Wen

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引用次数: 0

Abstract

Polysaccharides are natural nano-carriers for flavonoids. Phenolic hydrogen plays a critical role in the bioactivities of flavonoids. However, the effect of phenolic hydrogen on the formation of polysaccharide-flavonoid nanocomplexes remains unknown. In this study, three prenylated flavonoids – icaritin (ICT), icariin (ICA), and icariside I (ICS) – were encapsulated in chitosan (CS) using a pH-driven method. The influence of the structural characteristics of these prenylated flavonoids on their encapsulation efficiency and their interaction with CS was investigated. The results showed that ICT, ICA, and ICS were well encapsulated in CS with various linear structure. Electrostatic interactions and hydrogen bonds were the main driving forces contributing to the formation of prenylated flavonoid-loaded CS nanocomplexes. Nuclear magnetic resonance spectra revealed the intermolecular hydrogen bonds formed between the 3–OH and 7–OH of ICT and the amines of CS, and might mainly contributed to the highest loading capacity (LC, 16.29 %) of ICT with CS. Notably, when both 3–OH and 7–OH are substituted with sugar moieties in ICA, weaker intermolecular hydrogen bond interactions with CS were observed, resulting in a significantly lower LC of only 5.54 %. Moreover, these nanocomplexes demonstrated better acid resistance (pH 2.0–6.0) and salt stability. The present results indicated the importance of phenolic hydroxyl groups, especially their position on the encapsulation capacities of prenylated flavonoids with CS. Altogether, this study might reveal the structure-encapsulation relationship of polysaccharides-based nanocomplexes loaded with prenylated flavonoids, providing valuable insights for selecting more suitable delivery carriers for flavonoids with diverse structures.

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酚氢对壳聚糖-烯酰化类黄酮纳米复合物形成的影响

多糖是类黄酮的天然纳米载体。酚氢在类黄酮的生物活性中起着至关重要的作用。然而，酚氢对多糖-类黄酮纳米复合物形成的影响尚不清楚。本研究采用ph驱动的方法，将三种烯丙基黄酮类化合物——icaritin （ICT）、icariin （ICA）和icariside I （ICS）包封在壳聚糖（CS）中。研究了这些烯酰化类黄酮的结构特征对其包封效率的影响及其与CS的相互作用。结果表明，ICT、ICA和ICS被很好地封装在具有不同线性结构的CS中。静电相互作用和氢键是形成烯酰化类黄酮CS纳米复合物的主要驱动力。核磁共振谱显示，ICT的3-OH和7-OH与CS的胺之间形成了分子间氢键，这可能是ICT与CS的最高负载能力（LC, 16.29%）的主要原因。值得注意的是，当ICA中的3-OH和7-OH都被糖部分取代时，观察到与CS的分子间氢键相互作用较弱，导致LC明显降低，仅为5.54%。此外，这些纳米配合物具有较好的耐酸性（pH值2.0-6.0）和盐稳定性。本研究结果表明酚羟基的重要性，特别是其在丙烯醚化黄酮类化合物包封能力中的地位。综上所述，本研究揭示了烯酰化黄酮类化合物负载的多糖基纳米复合物的结构-包封关系，为选择更合适的不同结构黄酮类化合物的递送载体提供了有价值的见解。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Food Hydrocolloids 工程技术-食品科技

CiteScore

19.90

自引率

14.00%

发文量

871

审稿时长

37 days

期刊介绍： Food Hydrocolloids publishes original and innovative research focused on the characterization, functional properties, and applications of hydrocolloid materials used in food products. These hydrocolloids, defined as polysaccharides and proteins of commercial importance, are added to control aspects such as texture, stability, rheology, and sensory properties. The research's primary emphasis should be on the hydrocolloids themselves, with thorough descriptions of their source, nature, and physicochemical characteristics. Manuscripts are expected to clearly outline specific aims and objectives, include a fundamental discussion of research findings at the molecular level, and address the significance of the results. Studies on hydrocolloids in complex formulations should concentrate on their overall properties and mechanisms of action, while simple formulation development studies may not be considered for publication. The main areas of interest are: -Chemical and physicochemical characterisation Thermal properties including glass transitions and conformational changes- Rheological properties including viscosity, viscoelastic properties and gelation behaviour- The influence on organoleptic properties- Interfacial properties including stabilisation of dispersions, emulsions and foams- Film forming properties with application to edible films and active packaging- Encapsulation and controlled release of active compounds- The influence on health including their role as dietary fibre- Manipulation of hydrocolloid structure and functionality through chemical, biochemical and physical processes- New hydrocolloids and hydrocolloid sources of commercial potential. The Journal also publishes Review articles that provide an overview of the latest developments in topics of specific interest to researchers in this field of activity.