Department of Food Chemistry and Biocatalysis, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
Department of Pathogen Genetics and Plant Resistance, Institute of Plant Genetics, Polish Academy of Sciences, Strzeszyńska 34, 60-479 Poznań, Poland.
Int J Mol Sci. 2023 Jul 24;24(14):11857. doi: 10.3390/ijms241411857.
Quercetin is the most abundant flavonoid in food products, including berries, apples, cauliflower, tea, cabbage, nuts, onions, red wine and fruit juices. It exhibits various biological activities and is used for medical applications, such as treating allergic, inflammatory and metabolic disorders, ophthalmic and cardiovascular diseases, and arthritis. However, its low water solubility may limit quercetin's therapeutic potential. One method of increasing the solubility of active compounds is their coupling to polar molecules, such as sugars. The attachment of a glucose unit impacts the stability and solubility of flavonoids and often determines their bioavailability and bioactivity. Entomopathogenic fungi are biocatalysts well known for their ability to attach glucose and its 4--methyl derivative to bioactive compounds, including flavonoids. We investigated the ability of cultures of entomopathogenic fungi belonging to , , , and genera to biotransform quercetin. Three major glycosylation products were detected: (), 7--β-D-(4″--methylglucopyranosyl)-quercetin, () 3--β-D-(4″--methylglucopyranosyl)-quercetin and () 3--β-D-(glucopyranosyl)-quercetin. The results show evident variability of the biotransformation process, both between strains of the tested biocatalysts from different species and between strains of the same species. Pharmacokinetic and pharmacodynamic properties of the obtained compounds were predicted with the use of cheminformatics tools. The study showed that the obtained compounds may have applications as effective modulators of intestinal flora and may be stronger hepato-, cardio- and vasoprotectants and free radical scavengers than quercetin.
槲皮素是食物中最丰富的类黄酮，包括浆果、苹果、花椰菜、茶、卷心菜、坚果、洋葱、红酒和果汁。它具有多种生物活性，用于医学应用，如治疗过敏、炎症和代谢紊乱、眼科和心血管疾病以及关节炎。然而，其低水溶性可能限制了槲皮素的治疗潜力。提高活性化合物溶解度的一种方法是将其与极性分子（如糖）偶联。葡萄糖单位的附着会影响类黄酮的稳定性和溶解度，通常决定其生物利用度和生物活性。昆虫病原真菌是众所周知的生物催化剂，它们能够将葡萄糖及其 4--甲基衍生物附着到生物活性化合物上，包括类黄酮。我们研究了属于 、 、 、 和 属的昆虫病原真菌培养物转化槲皮素的能力。检测到三种主要的糖基化产物：()、7--β-D-(4″--甲基吡喃葡萄糖基)-槲皮素、() 3--β-D-(4″--甲基吡喃葡萄糖基)-槲皮素和() 3--β-D-(吡喃葡萄糖基)-槲皮素。结果表明，生物转化过程在测试生物催化剂的不同物种的菌株之间以及同一物种的菌株之间存在明显的可变性。使用化学信息学工具预测了获得的化合物的药代动力学和药效学性质。该研究表明，获得的化合物可能作为有效的肠道菌群调节剂具有应用潜力，并且可能比槲皮素更强的肝保护、心脏保护和血管保护以及自由基清除剂。
