Benzoxazinoids: Cereal phytochemicals with putative therapeutic and health‐protecting properties

Abstract

Benzoxazinoids (BXs) are a group of natural chemical compounds with putative pharmacological and health-protecting properties. BXs were formerly identified in and isolated from selected dicot medicinal plants and young cereal plants. Recently, BXs were found to be present in mature cereal grains and bakery products, such that knowledge about the pharmacological properties of BXs, which until now have unknowingly been consumed through the daily bread and breakfast cereals, has come into new focus. This review discusses published results from in vitro studies and a few human and animal model studies on the health effects and pharmacological responses of various BX compounds. Many of these studies have reported antimicrobial, anticancer, reproductive system stimulatory, central nervous system stimulatory, immunoregulatory, and appetite- and weight-reducing effects of BXs and/or BX derivatives. The health benefits of wholegrain intake may be associated with the solitary and/or overlapping biological effects of fibers, lignans, phenolic acids, alkylresorcinols, BXs, and other bioactive compounds. In the context of BXs as dietary ingredients, further comprehensive investigations are required to understand their biological functions, to elucidate the underlying mechanisms, to explore their potential contribution on the health effects associated with wholegrain consumption, and to examine their potential as functional food ingredients.

Urinary Biomarkers of Whole Grain Wheat Intake Identified by Non-targeted and Targeted Metabolomics Approaches

“…Wheat ARs have been revealed to play an important role in the prevention of cancers79, diabetes80, and CVD80. Similarly, cereal BXs showed cytotoxic effects81, and could also significantly decrease lipid accumulation in 3T3-L1 preadipocytes82. In addition to the direct radical scavenging activity8384, simple phenolic acids, such as ferulic acid, caffeic acid, gallic acid, and cinnamic acid, possess antidiabetic properties85.…”

2,4-Dihydroxy-7-methoxy-2 H -1,4-benzoxazin-3(4 H )-one (DIMBOA) inhibits trichothecene production by Fusarium graminearum through suppression of Tri6 expression

“…Benzoxazinoids occur mainly in rye, wheat and maize with 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA) and the glucosylated derivative 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one-2-D-α-glucopyranoside (DIBOA-glc) dominating in rye, while in wheat and maize 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) and 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one-2-D-α-glucopyranoside (DIMBOA-glc) dominate (Niemeyer, 2009). Furthermore, benzoxazinoids have a series of putative health-protecting effects, although a few controversial results are reported (Adhikari et al, 2015;Prinz et al, 2010). Benzoxazinoids have also been correlated with FHB resistance in wheat heads (Søltoft et al, 2008).…”

“…at flowering stage where infection by Fusarium occurs, is usually low (Nicol and Wratten, 1997;Søltoft et al, 2008) and until recently thought to be absent from mature wheat grain (Adhikari et al, 2015). However, several benzoxazinoids have subsequently been identified in wheat grain (Fomsgaard et al, 2010) suggesting the presence of DIMBOA at other later growth stages preceding the mature stage (BBCH89).…”

Plant defense and herbivore counter-defense: benzoxazinoids and insect herbivores

“…Anti-inflammatory, anti-cancer, and anti-microbial activities, as well as stimulatory effects on the central nervous and reproductive systems have been reported for BXDs, mostly using in vitro studies, and the human therapeutic potential of BXDs has been recently reviewed (Adhikari et al 2015). …”