Sorghum 3-Deoxyanthocyanins Possess Strong Phase II Enzyme Inducer Activity and Cancer Cell Growth Inhibition Properties

Abstract

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.

Sorghum: An Underutilized Cereal Whole Grain with the Potential to Assist in the Prevention of Chronic Disease

“…Powerful anti-proliferative effects were also observed against colon cancer cells when black, red, and white sorghum extracts, rich in 3-DA were tested. (104,105) Yang et al (106) proposed that these protective effects result from estrogen-induced apoptosis of the non-malignant colonocytes that were strongly influenced by the flavones, apigenin and luteolin. In breast cancer cell lines, 3-DA isolated from red sorghum bran have been shown to have strong anti-proliferative properties and to be cytotoxic.…”

Prediction of total phenols, condensed tannins, and 3-deoxyanthocyanidins in sorghum grain using near-infrared (NIR) spectroscopy

“…It is grown primarily in hot and dry regions and is used as a food in Africa and Asia and as a feed and industrial grain in the Americas and Australia (Dykes et al, 2005, Waniska andRooney, 2000). There has been a recent increase in the use of sorghum as a food in the United States because of its gluten-free characteristic as well as other potential health benefits which include slow digestibility, cholesterol-lowering, anticarcinogenic, and anti-inflammatory properties (Bralley et al, 2008, Burdette et al, 2010, Moraes et al, 2012, Turner et al, 2006, Yang et al, 2009). These sorghums can be utilized in a wide array of food products such as breads, cakes, cookies, extrudates, tortillas, and tortilla chips Rooney, 2006, Taylor et al, 2006).…”

“…For example, sorghums with a pigmented testa contain condensed tannins while black sorghums have the highest levels of 3-deoxyanthocyanidins among all sorghums (Beta et al, 1999, Dlamini et al, 2007, Dykes et al, 2005. Both condensed tannins and 3-deoxyanthocyanidins have potential health benefits such as antioxidant and anticarcinogenic properties (Devi et al, 2011, Hagerman et al, 1998, Shih et al, 2007, Turner et al, 2006, Woo et al, 2012, Yang et al, 2009.…”

Effect of genotype and environment on flavonoid concentration and profile of black sorghum grains

“…In black sorghum genotypes, the predominant flavonoids are the 3-deoxyanthocyanidins. These compounds are unique and have potential use as a natural colorant in low pH food systems as well as anti-inflammatory and anti-cancer activity (Awika et al, 2004;Burdette et al, 2010;Devi et al, 2011;Shih et al, 2007;Yang et al, 2009). The 3-deoxyanthocyanidins are present in non-methoxylated and methoxylated forms.…”