[关键词]
[摘要]
目的 研究余甘子Phyllanthus emblica果实的化学成分,并评价其抗氧化与降糖活性。方法 采用硅胶和反相硅胶RP-18柱色谱以及半制备高效液相色谱等技术进行分离纯化,根据化合物理化性质,应用UV、NMR、HR-ESI-MS及X射线单晶衍射等手段并结合文献数据鉴定化合物结构。通过DPPH自由基清除实验和α-葡萄糖苷酶抑制实验评价抗氧化和降糖活性。结果 从余甘子果实甲醇提取物的醋酸乙酯萃取部位中分离得到9个化合物,分别鉴定为1-(2-aminobenzofuran-3-yl)-2-(2-methoxyphenyl)ethan-1-one(1)、methyl dioxindole-3-acetate(2)、橙皮酰胺(3)、叶下珠酯G3(4)、mucic acid dimethyl ester 2-O-gallate(5)、诃子酸三甲酯(6)、3,4,8,9,10-pentahydroxy- dibenzo[b,d]pyran-6-one(7)、鞣花酸(8)和甲基 1-O-苯甲酰基-3-α-葡萄糖醛酸基甘油酯(9)。活性筛选显示,化合物5~8具有显著的DPPH自由基清除能力(清除率为86.59%~90.75%);化合物1、7和8对α-葡萄糖苷酶表现出抑制活性,半数抑制浓度(median inhibition concentration,IC50)为1.44~33.06 μmol/L,其中化合物7的抑制活性最强,优于阳性对照槲皮素(IC50=4.96 μmol/L)。结论 化合物1为新的生物碱类化合物,命名为余甘子碱A;化合物2、3和9为首次从该植物中分离得到。首次从余甘子中鉴定出具有降糖活性的生物碱类成分,为其传统“降糖、抗氧化”功效提供了科学依据。
[Key word]
[Abstract]
Objective To investigate the chemical constituents of the fruits of Phyllanthus emblica and evaluate their antioxidant and hypoglycemic activities. Methods Compounds were isolated and purified using silica gel and reversed-phase silica gel RP-18 column chromatography, followed with semi-preparative high-performance liquid chromatography (HPLC). The chemical structures were elucidated based on physicochemical properties, together with UV, NMR, HR-ESI-MS, and X-ray single-crystal diffraction methods, and comparison with literature data. Antioxidant and hypoglycemic activities were assessed by DPPH free radical scavenging and α-glucosidase inhibitory assays. Results Nine compounds were isolated from the ethyl acetate fraction of the methanol extract of P. emblica fruits and identified as 1-(2-aminobenzofuran-3-yl)-2-(2-methoxyphenyl)ethan-1-one (1), methyl dioxindole-3-acetate (2), aurantiamide (3), phyllaemblicin G3 (4), mucic acid dimethyl ester 2-O-gallate (5), chebulic acid trimethyl ester (6), 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one (7), ellagic acid (8), and methyl 1-O-benzoyl-3-α- glucuronosyl glycerol (9), respectively. The bioassay showed that compounds 5-8 exhibited significant DPPH radical scavenging capacity (scavenging rates = 86.59% − 90.75%), and 1, 7, and 8 displayed inhibitory activity against α-glucosidase with IC50 values ranging from 1.44 to 33.06 μmol/L. Among them, compound 7 showed the strongest inhibition, which was superior to the positive control quercetin (IC50 = 4.96 μmol/L). Conclusion Compound 1 is a new alkaloid, named emblicine A, while 2, 3, and 9 are reported from the titled plant for the first time. It is the first study to identify alkaloid with hypoglycemic activity from P. emblica, providing a scientific basis for its traditional use in glycemic control and antioxidant defense.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金资助项目(32270426);国家自然科学基金资助项目(82074124);云南省重点研发计划(202403AP140026)