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基于核磁共振的代谢组学研究鉴定α-淀粉酶和α-葡萄糖苷酶抑制剂以及来自西番莲(甜百香果)叶的一种新三萜皂苷——连钱草苷A

Identification of α-Amylase and α-Glucosidase Inhibitors and Ligularoside A, a New Triterpenoid Saponin from Juss (Sweet Granadilla) Leaves, by a Nuclear Magnetic Resonance-Based Metabolomic Study.

作者信息

Monzón Daza Gabriel, Meneses Macías Carolina, Forero Abel M, Rodríguez Jaime, Aragón Marcela, Jiménez Carlos, Ramos Freddy A, Castellanos Leonardo

机构信息

Facultad de Ciencias, Departamento de Química, Universidad Nacional de Colombia - Sede Bogotá, Bogotá, Carrera 30# 45-03, Bogotá, D.C. 111321, Colombia.

Centro de Investigacións Científicas Avanzadas (CICA), Departamento de Química, Facultade de Ciencias, AE CICA-INIBIC, Universidade da Coruña, A Coruña E-15071, Spain.

出版信息

J Agric Food Chem. 2021 Mar 10;69(9):2919-2931. doi: 10.1021/acs.jafc.0c07850. Epub 2021 Feb 23.

DOI:10.1021/acs.jafc.0c07850
PMID:33621072
Abstract

The leaves of Juss (known as sweet granadilla for its edible fruits) are a crop byproduct that is discarded. With the aim of contributing to give value-added products from these crop by-side products to farmers of Colombian Andes, we carried out a H-NMR-metabolomics analysis of polar extracts from leaves collected in three locations and stored in two conditions in order to identify glucosyl-hydrolase inhibitors. Variations in the metabolic profile and the bioactivity among samples were analyzed by orthogonal partial least square discriminant analysis. Thus, H-NMR signals related to polyphenolic compounds, saponins, and amino acids were correlated with higher inhibitory activities. Moreover, a targeted NMR and HPLC-MS/MS analysis allowed the identification of 14 polyphenolic compounds and the structural characterization of a new triterpenoid saponin, ligularoside A. The measurements of IC values for α-amylase and α-glycosidase inhibitors allowed the identification of quercetin-3--β-glucoside, kaempferol-3--β-glucoside, and ligularoside A as the most active compounds. These results suggest that leaves are a source of glucosyl-hydrolase inhibitors and lay the foundation for exploring additional applications.

摘要

Juss的叶子(因其可食用果实而被称为甜西番莲)是一种被丢弃的作物副产品。为了帮助哥伦比亚安第斯山脉的农民从这些作物副产品中获得增值产品,我们对从三个地点采集并在两种条件下储存的叶子的极性提取物进行了氢核磁共振代谢组学分析,以鉴定葡萄糖基水解酶抑制剂。通过正交偏最小二乘判别分析来分析样品之间代谢谱和生物活性的差异。因此,与多酚化合物、皂苷和氨基酸相关的氢核磁共振信号与较高的抑制活性相关。此外,靶向核磁共振和高效液相色谱-串联质谱分析能够鉴定出14种多酚化合物,并对一种新的三萜皂苷——舌叶苷A进行结构表征。对α-淀粉酶和α-糖苷酶抑制剂的半数抑制浓度值的测定,确定了槲皮素-3 - β-葡萄糖苷、山奈酚-3 - β-葡萄糖苷和舌叶苷A为活性最强的化合物。这些结果表明,叶子是葡萄糖基水解酶抑制剂的一个来源,并为探索其他应用奠定了基础。

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