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马六甲蒲桃叶中具有抗氧化和细胞毒性特性的酚类化合物的降血糖活性及生物导向分离

Antihyperglycemic activity and bioguided isolation of phenolic compounds with antioxidant and cytotoxic properties from Syzygium malaccense leaves.

作者信息

Oldoni Tatiane Luiza Cadorin, da Silva Cleidiane, Bicas Thariane Carvalho, Ayres Bruno Ramalho Bresolin, Zanchet Eloisa Regina, Marafon Filomena, da Silva Alana Patrícia, Carpes Solange Teresinha, Bagatini Margarete Dulce, Ascari Jociani, Thomé Gustavo

机构信息

Department of Chemistry, Universidade Tecnológica Federal do Paraná (UTFPR), Pato Branco, PR 85503-390, Brazil.

Department of Chemistry, Universidade Tecnológica Federal do Paraná (UTFPR), Pato Branco, PR 85503-390, Brazil.

出版信息

Fitoterapia. 2025 Mar;181:106357. doi: 10.1016/j.fitote.2024.106357. Epub 2024 Dec 26.

Abstract

This study investigated the antihyperglycemic potential of a hydroalcoholic extract from Syzygium malaccense leaves (E-SM) and isolate phenolic compounds with antioxidant and cytotoxic activities through a bioguided assay. The aim was to explore the therapeutic properties of S. malaccense in managing hyperglycemia and oxidative stress-related conditions. E-SM was prepared using ethanol-water (40:60 v/v) and purified through a solid-liquid procedure with increasing polarity solvents, yielding the acetone fraction (AceFr). Previous studies showed Ace-Fr had potent antioxidant and cytotoxic properties. Chromatographic techniques further purified AceFr, producing three bioactive subfractions (SF-1, SF-2, and SF-3). Flavonoids myricitrin (C1) and a mixture of quercitrin and mearnsitrin (M1) were isolated from SF-2 and SF-3 using TLC preparative. HPLC-DAD quantified phenolic compounds, including myricitrin, gallic acid, myricetin, and quercetin. HPLC-ESI-QTOF-MS/MS analysis identified ten compounds, primarily flavonols quercetin and myricetin and their glycosides. SF-1 exhibited a 30 % reduction in cell viability in cutaneous melanoma cells at 100 and 250 mg L, while SF-2 and SF-3 displayed enhanced antioxidant potential and reduced cancer cell locomotion proportional to concentration. In diabetic rats treated with E-SM (400 mg/kg), kidney tissue showed restored catalase activity similar to the control group, with consistent NPSH levels. Increased GST activity indicated tissue protection, while lower MDA levels suggested reduced lipid peroxidation across tissues. Our results indicate that three phenolic compounds with high antioxidant activity were isolated, and the chemical composition of the E-SM extract, rich in glycosylated flavonoids, could be related to its antihyperglycemic action.

摘要

本研究通过生物导向分析,研究了马六甲蒲桃叶水醇提取物(E-SM)的降血糖潜力,并分离出具有抗氧化和细胞毒性活性的酚类化合物。目的是探索马六甲蒲桃在控制高血糖和氧化应激相关病症方面的治疗特性。E-SM采用乙醇-水(40:60 v/v)制备,并通过使用极性递增的溶剂的固液程序进行纯化,得到丙酮馏分(AceFr)。先前的研究表明Ace-Fr具有强大的抗氧化和细胞毒性特性。色谱技术进一步纯化AceFr,产生三个生物活性亚组分(SF-1、SF-2和SF-3)。使用制备型薄层色谱从SF-2和SF-3中分离出黄酮类化合物杨梅苷(C1)以及槲皮苷和异鼠李素的混合物(M1)。高效液相色谱-二极管阵列检测器(HPLC-DAD)对酚类化合物进行了定量,包括杨梅苷、没食子酸、杨梅素和槲皮素。高效液相色谱-电喷雾电离-四极杆飞行时间串联质谱(HPLC-ESI-QTOF-MS/MS)分析鉴定出十种化合物,主要是黄酮醇槲皮素和杨梅素及其糖苷。SF-1在浓度为100和250 mg/L时使皮肤黑色素瘤细胞的细胞活力降低了30%,而SF-2和SF-3则表现出增强的抗氧化潜力,并与浓度成比例地降低癌细胞运动能力。在用E-SM(400 mg/kg)治疗的糖尿病大鼠中,肾组织过氧化氢酶活性恢复到与对照组相似的水平,还原型辅酶I/辅酶I(NPSH)水平一致。谷胱甘肽S-转移酶(GST)活性增加表明组织受到保护,而丙二醛(MDA)水平较低表明各组织脂质过氧化减少。我们的研究结果表明,分离出了三种具有高抗氧化活性的酚类化合物,富含糖基化黄酮类化合物的E-SM提取物的化学成分可能与其降血糖作用有关。

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