Quantitative Analysis of Anticancer 3-Deoxyanthocyanidins in Infected Sorghum Seedlings

Abstract

3-Deoxyanthocyanidins are structurally related to the anthocyanin pigments, which are popular as health-promoting phytochemicals. Here, it is demonstrated that the 3-deoxyanthocyanidins are more cytotoxic on human cancer cells than the 3-hydroxylated anthocyanidin analogues. At 200 microM concentration, luteolinidin reduced the viability of HL-60 and HepG2 cells by 90 and 50%, respectively. Sorghum is a major source of 3-deoxyanthocyanidins, which are present as seed pigments and as phytoalexins responding to pathogen attack. On the basis of the collision-induced dissociation spectra of luteolinidin and apigeninidin, an LC-MS/MS method, operating in multiple-reaction monitoring mode, was developed for the specific detection and accurate quantification of these compounds in complex mixtures, which may be difficult to analyze using absorbance measurements. The results demonstrated that inoculated sorghum seedlings could be utilized for convenient and large-scale production of 3-deoxyanthocyanidins. A quantity of almost 270 microg/g (fresh weight) of luteolinidin was produced 72 h after fungal inoculation of 1-week-old seedlings.

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

“…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

“…These are a source of natural colorants and phytochemicals for human health (Awika et al, 2004;Bralley et al, 2008;Burdette et al, 2010;Dykes et al, 2011;Shih et al, 2007). Most sorghum flavonoids are located in the outer layers of the caryopsis and consequently, differences in pericarp color, pericarp thickness and the presence of testa influence relative flavonoid concentrations and profiles (Awika et al, 2005;Dykes et al, 2009;Shirley, 1998).…”

“…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.…”

Behavior of 3-deoxyanthocyanidins in the presence of phenolic copigments

“…For example they are known to be highly stable to change in pH (Awika, Rooney, & Waniska, 2004;Mazza & Brouillard, 1987) when compared to anthocyanins. The 3-deoxyanthocyanidins were also recently demonstrated to be more cytotoxic to cancer cells than their anthocyanidin analogs (Shih et al, 2007). Thus these rare pigments (primarily found in sorghum) present an exciting opportunity for use as natural food colorants.…”