Structure and biosynthesis of benzoxazinoids: Plant defence metabolites with potential as antimicrobial scaffolds

Benzoxazinoids, comprising the classes of benzoxazinones and benzoxazolinones, are a set of specialised metabolites produced by the plant family Poaceae (formerly Gramineae), and some dicots. The family Poaceae in particular contains several important crops like maize and wheat. Benzoxazinoids play a role in allelopathy and as defence compounds against (micro)biological threats. The effectivity of benzoxazinones in these functionalities is largely imposed by the subclasses (determined by N substituent). In this review, we provide an overview of all currently known natural benzoxazinoids and a summary of the current state of knowledge of their biosynthesis. We also evaluated their antimicrobial activity based on minimum inhibitory concentration (MIC) values reported in literature. Monomeric natural benzoxazinoids seem to lack potency as antimicrobial agents. The 1,4-benzoxazin-3-one backbone, however, has been shown to be a potential scaffold for designing new antimicrobial compounds. This has been demonstrated by a number of studies that report potent activity of synthetic derivatives of 1,4-benzoxazin-3-one, which possess MIC values down to 6.25 μg mL−1 against pathogenic fungi (e.g. C. albicans) and 16 μg mL−1 against bacteria (e.g. S. aureus and E. coli). Observations on the structural requirements for allelopathy, insecticidal, and antimicrobial activity suggest that they are not necessarily conferred by similar mechanisms. Monomeric natural benzoxazinones lack potency as antimicrobial compounds, chemical modification of the 1,4-benzoxazin-3-one scaffold can yield potent antimicrobial compounds. [Display omitted] •Comprehensive overview of natural benzoxazinoids.•Benzoxazinone subclass (N substituent) influences allelopathic and defence potency.•Monomeric natural benzoxazinoids lack antimicrobial potency.•Chemical modification of 1,4-benzoxazin-3-ones can enhance antimicrobial activity.•Potential of 1,4-benzoxazin-3-one as a scaffold for design of antimicrobial drugs.