Twelve chemical constituents were identified from the Agriophyllum squarrosum seed (ASS). ASS contained large amounts of flavonoids, which were more concentrated in the seed coat. ASS-coat (1 g) contained 335.7 μg flavonoids of rutin equivalent, which was similar to the flavonoid content in soybean (351.2 μg/g), and greater than that in millet, wheat, rice, peanut, and corn. By LC-MS analysis, the major constituents in ASS were 3-O-[α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranosyl]-7- O-(β-D-glucopyranosyl)-quercetin (1), rutin (4), quercetin-3-O-β-D- apiosyl(1→2)-[α-L-rhamnosyl(l→6)]-β-D-glucoside (2), isorhamnetin-3-O-rutinoside (5), and allantoin (3), compared with isoflavonoids-genistin (16), daidzin (14), and glycitin (18) in soybean. Among constituents in ASS, compounds 1, 2, 4, protocatechuic acid (8), isoquercitrin (11), and luteolin-6-C-glucoside (12) potently scavenged DPPH radicals and intracellular ROS; strongly protected against peroxyl radical-induced DNA scission; and upregulated Nrf2, phosphorylated p38, phosphorylated JNK, and Bcl-2 in HepG2 cells. These results indicate that ASS is rich in antioxidant constituents that can enrich the varieties of food flavonoids, with significant beneficial implications for those who suffer from oxidative stress-related conditions. PRACTICAL APPLICATION This study found that A. squarrosum seed contains large amounts of antioxidative flavonoids and compared its chemical constituents with those of conventional foods. These results should increase the interest in planting the sand-fixing A. squarrosum on a large scale, thus preventing desertification and providing valuable foods.

中文翻译：

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Agriophyllum squarrosum 种子与常规作物种子抗氧化成分的比较

从 Agriophyllum squarrosum 种子 (ASS) 中鉴定出十二种化学成分。ASS 含有大量的黄酮类化合物，这些黄酮类化合物更集中在种皮中。ASS-coat（1 g）含有335.7 μg的芦丁黄酮当量，与大豆中的黄酮含量（351.2 μg/g）相似，高于小米、小麦、水稻、花生和玉米。经LC-MS分析，ASS的主要成分为3-O-[α-L-吡喃鼠李糖基-(1→6)-β-D-吡喃葡萄糖基]-7-O-(β-D-吡喃葡萄糖基)-槲皮素( 1)、芦丁(4)、槲皮素-3-O-β-D-apiosyl(1→2)-[α-L-鼠李糖基(1→6)]-β-D-葡萄糖苷(2)、异鼠李素-3 -O-芸香苷 (5) 和尿囊素 (3)，与大豆中的异黄酮-染料木苷 (16)、黄豆苷 (14) 和大豆黄素 (18) 进行比较。在 ASS 的成分中，化合物 1、2、4、原儿茶酸 (8)、异槲皮苷 (11)、和 luteolin-6-C-glucoside (12) 有效清除 DPPH 自由基和细胞内 ROS；强烈保护免受过氧自由基诱导的 DNA 断裂；HepG2 细胞中的 Nrf2、磷酸化 p38、磷酸化 JNK 和 Bcl-2 上调。这些结果表明，ASS 富含抗氧化成分，可以丰富食物类黄酮的种类，对那些患有氧化应激相关疾病的人具有显着的有益意义。实际应用 本研究发现A. squarrosum 种子含有大量的抗氧化黄酮类化合物，并将其化学成分与传统食品进行比较。这些结果应该会增加人们对大规模种植固沙 A. squarrosum 的兴趣，从而防止沙漠化并提供有价值的食物。