Antioxidant activity and inhibitory effects of 2-hydroxy-3-methylcyclopent-2-enone isolated from ribose–histidine Maillard reaction products on aldose reductase and tyrosinase†,Food & Function

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Antioxidant activity and inhibitory effects of 2-hydroxy-3-methylcyclopent-2-enone isolated from ribose–histidine Maillard reaction products on aldose reductase and tyrosinase†
Food & Function ( IF 5.1 ) Pub Date : 2018-02-05 00:00:00 , DOI: 10.1039/c7fo01438d
Seung Hwan Hwang _{1,

2,

3,

4} , Zhiqiang Wang _{1,

2,

3,

4,

5} , Hong-Won Suh _{2,

3,

6,

7,

8} , Soon Sung Lim _{1,

2,

3,

4,

9}

Affiliation

This study aimed to better understand the functional properties of ribose and 20 amino acid Maillard reaction products (MRPs). The ABTS⁺ radical scavenging ability of the ribose–20 amino acid MRPs was evaluated. Among the MRPs, ribose–histidine MRPs (RH-MRPs) showed the highest inhibitory activities on the ABTS⁺ radical scavenging ability, aldose reductase (AR), and tyrosinase compared to other MRPs. Functional compounds with antioxidant and AR inhibitory activities have been recognized as an important strategy in the prevention and treatment of diabetic complications, and the search for tyrosinase inhibitors is important for the treatment of hyperpigmentation, development of skin-whitening agents, and use as preservatives in the food industry. On this basis, we sought to isolate and identify compounds with inhibitory activities against AR and tyrosinase. RH-MRPs were heated at 120 °C for 2 h and fractionated using four solvents: methylene chloride (MC), ethyl acetate, n-butanol, and water. The highest inhibitions were found in the MC fraction. The two compounds from this fraction were purified by silica gel column and preparative thin layer chromatography, and identified as 2-hydroxy-3-methylcyclopent-2-enone and furan-3-carboxylic acid. AR inhibition, tyrosinase inhibition, and ABTS⁺ scavenging (IC₅₀) of 2-hydroxy-3-methylcyclopent-2-enone were 4.47, 721.91 and 9.81 μg mL⁻¹, respectively. In this study, inhibitory effects of 2-hydroxy-3-methylcyclopent-2-enone isolated from RH-MRP were demonstrated on AR, tyrosinase, and its antioxidant activity for the first time. RH-MRP and its constituents can be developed as beneficial functional food sources and cosmetic materials and should be investigated further as potential functional food sources.

中文翻译：

抗氧化活性和从醛糖还原酶和酪氨酸酶核糖组氨酸美拉德反应产物中分离2-羟基-3-甲基环戊-2-烯酮的抑制作用†

这项研究旨在更好地了解核糖和20个氨基酸的美拉德反应产物（MRP）的功能特性。评估了核糖20个氨基酸MRP的ABTS ⁺自由基清除能力。在MRP中，核糖-组氨酸MRP（RH-MRP）对ABTS ^+的抑制作用最高与其他MRP相比，具有更强的清除自由基能力，醛糖还原酶（AR）和酪氨酸酶。具有抗氧化剂和AR抑制活性的功能性化合物已被认为是预防和治疗糖尿病并发症的重要策略，寻找酪氨酸酶抑制剂对于色素沉着过度的治疗，皮肤增白剂的开发以及在皮肤中用作防腐剂非常重要。食品工业。在此基础上，我们试图分离和鉴定对AR和酪氨酸酶具有抑制活性的化合物。将RH-MRP在120°C下加热2小时，然后使用四种溶剂进行分馏：二氯甲烷（MC），乙酸乙酯，正己烷-丁醇和水。在MC级分中发现最高的抑制作用。用硅胶柱色谱和制备型薄层色谱法纯化该馏分中的两种化合物，鉴定为2-羟基-3-甲基环戊-2-烯酮和呋喃-3-羧酸。2-羟基-3-甲基环戊-2-烯酮的AR抑制，酪氨酸酶抑制和ABTS ⁺清除（IC ₅₀）为4.47、721.91和9.81μgmL ^-1，分别。在这项研究中，首次证明了从RH-MRP分离出的2-羟基-3-甲基环戊-2-烯酮对AR，酪氨酸酶及其抗氧化活性的抑制作用。RH-MRP及其成分可以开发为有益的功能性食物来源和化妆品原料，应作为潜在的功能性食物来源进行进一步研究。

更新日期：2018-02-05

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