Division of Food Systems and Bioengineering and Division of Animal Science, University of Missouri, Columbia, Missouri 65211, USA.
J Agric Food Chem. 2009 Mar 11;57(5):1797-804. doi: 10.1021/jf8035066.
3-Deoxyanthoxyanins (3-DXA) possess unique chemical and biochemical properties and may be useful in helping reduce incidence of gastrointestinal cancer. This study tested sorghum extracts rich in 3-DXA as well as isolated and synthetic 3-DXA for potential to induce activity of phase II enzymes in murine hepatoma cells using the NAD(P)H:quinone oxidoreductase (NQO) assay and to inhibit proliferation of the HT-29 human colon cancer cells using MTT and PicoGreen assays. Crude black sorghum extract that contained high levels of methoxylated 3-DXA was a strong inducer of NQO activity (3.0 times at 50 microg/mL), compared to red or white sorghum extracts with low or no methoxylated 3-DXA (1.6 times at 200 microg/mL). All sorghum extracts had strong antiproliferative activity against HT-29 cells after 48 h of incubation (IC(50) = 180-557 microg/mL). Among isolated fractions, nonmethoxylated 3-DXA were very effective against HT-29 cell growth (IC(50) = 44-68 microM at 48 h), but were noninducers of NQO. On the other hand, the methoxylated 3-DXA had both strong antiproliferative activity (IC(50) < 1.5-53 microM) and NQO inducer activity (2-3.7 times). Dimethoxylated 3-DXA were more potent than monomethoxylated analogues. Methoxylation of 3-DXA is essential for NQO activity and also enhances tumor cell growth inhibition.
3-去氧安替比林（3-DXA）具有独特的化学和生化特性，可能有助于降低胃肠道癌症的发病率。本研究使用 NAD(P)H：醌氧化还原酶（NQO）测定法测试富含 3-DXA 的高粱提取物以及分离和合成的 3-DXA，以评估其在诱导鼠肝癌细胞中Ⅱ相酶活性的潜力，并使用 MTT 和 PicoGreen 测定法评估其抑制 HT-29 人结肠癌细胞增殖的潜力。含有高水平甲氧基化 3-DXA 的黑高粱提取物是 NQO 活性的强诱导剂（50μg/mL 时为 3.0 倍），而低水平或不含甲氧基化 3-DXA 的红高粱或白高粱提取物（200μg/mL 时为 1.6 倍）。所有高粱提取物在孵育 48 小时后对 HT-29 细胞均具有强烈的增殖抑制活性（IC50=180-557μg/mL）。在分离的馏分中，非甲氧基化 3-DXA 对 HT-29 细胞生长非常有效（48 小时时 IC50=44-68μM），但不能诱导 NQO。另一方面，甲氧基化 3-DXA 具有很强的增殖抑制活性（IC50<1.5-53μM）和 NQO 诱导活性（2-3.7 倍）。二甲氧基化 3-DXA 比单甲氧基化类似物更有效。3-DXA 的甲氧基化对于 NQO 活性是必需的，并且还增强了肿瘤细胞生长抑制。
