Secoisolariciresinol diglucosides (SDGs) (S,S)-SDG-1 (major isomer in flaxseed) and (R,R)-SDG-2 (minor isomer in flaxseed) were synthesized from vanillin via secoisolariciresinol (6) and glucosyl donor 7 through a concise route that involved chromatographic separation of diastereomeric diglucoside derivatives (S,S)-8 and (R,R)-9. Synthetic (S,S)-SDG-1 and (R,R)-SDG-2 exhibited potent antioxidant properties (EC50=292.17±27.71 μM and 331.94±21.21 μM, respectively), which compared well with that of natural (S,S)-SDG-1 (EC50=275.24±13.15 μM). These values are significantly lower than those of ascorbic acid (EC50=1129.32±88.79 μM) and α-tocopherol (EC50=944.62±148.00 μM). Compounds (S,S)-SDG-1 and (R,R)-SDG-2 also demonstrated powerful scavenging activities against hydroxyl [natural (S,S)-SDG-1: 3.68±0.27; synthetic (S,S)-SDG-1: 2.09±0.16; synthetic (R,R)-SDG-2: 1.96±0.27], peroxyl [natural (S,S)-SDG-1: 2.55±0.11; synthetic (S,S)-SDG-1: 2.20±0.10; synthetic (R,R)-SDG-2: 3.03±0.04] and DPPH [natural (S,S)-SDG-1: EC50=83.94±2.80 μM; synthetic (S,S)-SDG-1: EC50=157.54±21.30 μM; synthetic (R,R)-SDG-2: EC50=123.63±8.67 μM] radicals. These results confirm previous studies with naturally occurring (S,S)-SDG-1 and establish both (S,S)-SDG-1 and (R,R)-SDG-2 as potent antioxidants and free radical scavengers for potential in vivo use.

译文

secoisolicistrisulinol二葡糖苷 (SDGs) (S,S)-SDG-1 (亚麻籽中的主要异构体) 和 (R,R)-SDG-2 (亚麻籽中的次要异构体) 由香草醛经由secoisolaricyresinol (6) 和葡萄糖基供体7通过涉及非对映异构体二葡萄糖苷衍生物 (S,S)-8和 (R,R)-9的色谱分离的简洁途径合成。合成的 (S,S)-SDG-1和 (R,R)-SDG-2表现出有效的抗氧化性能 (分别为EC50 = 292.17 ± 27.71微米和331.94 ± 21.21微米),与天然 (S,S)-SDG-1 (EC50 = 275.24 ± 13.15微米) 相比。这些值明显低于抗坏血酸 (EC50 = 1129.32 ± 88.79微米) 和 α-生育酚 (EC50 = 944.62 ± 148.00微米) 的值。化合物 (S,S)-SDG-1和 (R,R)-SDG-2也显示出强大的清除羟基活性 [天然 (S,S)-SDG-1: 3.68 ± 0.27; 合成 (S,S)-SDG-1: 2.09 ± 0.16; 合成 (R,R)-SDG-2: 1.96 ± 0.27],过氧 [天然 (S,S)-SDG-1: 2.55 ± 0.11; 合成 (S,S)-SDG-1: 2.20 ± 0.10; 合成 (R,R)-SDG-2: 3.03 ± 0.04] 和DPPH [天然 (S,S)-SDG-1: EC50 = 83.94 ± 2.80微米; 合成 (S,S)-SDG-1: EC50 = 157.54 ± 21.30微米; 合成 (R,R)-SDG-2: EC50 = 123.63 ± 8.67微米] 自由基。这些结果证实了先前对天然存在的 (S,S)-SDG-1的研究,并确立了 (S,S)-SDG-1和 (R,R)-SDG-2作为潜在的体内使用的有效抗氧化剂和自由基清除剂。

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