Department of Pharmacognosy, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Food Chem. 2013 Dec 1;141(3):1573-9. doi: 10.1016/j.foodchem.2013.03.092. Epub 2013 Apr 12.
A novel acylated flavonol glycoside: isorhamnetin (3-O-[(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside) (1), together with two known acylated flavonol glycosides: quercetin (3-O-[(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside) (2) and kaempferol (3-O-[(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside) (3) were isolated from the n-butanol fraction of sea buckthorn (Hippophae rhamnoides ssp. sinensis) berries for the first time by chromatographic methods, and their structures were elucidated using UV, MS, (1)H and (13)C NMR, and 2D NMR. Compounds 1-3 showed good scavenging activities, with respective IC50 values of 8.91, 4.26 and 30.90 μM toward the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical; respective Trolox equivalent antioxidant capacities of 2.89, 4.04 and 2.44 μM μM(-1) toward 2,2'-azino-bis-3-ethyl-benzothiazoline-6-sulphonate (ABTS) radical. The quantitative analysis of the isolated acylated flavonol glycosides was performed by HPLC-DAD method. The contents of compounds 1-3 were in the range of 12.2-31.4, 4.0-25.3, 7.5-59.7 mg/100 g dried berries and 9.1-34.5, 75.1-182.1, 29.2-113.4 mg/100 g dried leaves, respectively.
异鼠李素（3-O-[(6-O-E-芥子酰基)-β-D-吡喃葡萄糖基-(1→2)]-β-D-吡喃葡萄糖基-7-O-α-L-鼠李吡喃糖苷）（1），与两种已知的酰化黄酮醇糖苷：槲皮素（3-O-[(6-O-E-芥子酰基)-β-D-吡喃葡萄糖基-(1→2)]-β-D-吡喃葡萄糖基-7-O-α-L-鼠李吡喃糖苷）（2）和山奈酚（3-O-[(6-O-E-芥子酰基)-β-D-吡喃葡萄糖基-(1→2)]-β-D-吡喃葡萄糖基-7-O-α-L-鼠李吡喃糖苷）（3）一起，首次通过色谱法从沙棘（沙棘亚种。中华沙棘）浆果的正丁醇部分分离出来，其结构通过 UV、MS、（1）H 和（13）C NMR 以及 2D NMR 进行了阐明。化合物 1-3 表现出良好的清除活性，对 2,2'-二苯基-1-苦基肼（DPPH）自由基的 IC50 值分别为 8.91、4.26 和 30.90 μM；对 2,2'-联氮-双-3-乙基苯并噻唑啉-6-磺酸（ABTS）自由基的 Trolox 当量抗氧化能力分别为 2.89、4.04 和 2.44 μMμM(-1)。通过 HPLC-DAD 法对分离出的酰化黄酮醇糖苷进行了定量分析。化合物 1-3 的含量范围为 12.2-31.4、4.0-25.3、7.5-59.7 mg/100 g 干浆果和 9.1-34.5、75.1-182.1、29.2-113.4 mg/100 g 干叶。
