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

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Abstract

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.

LanguageEnglish
Pages233-243
JournalPhytochemistry
Volume155
DOIs
Publication statusPublished - Nov 2018

Fingerprint

Benzoxazines
benzoxazinoids
Biosynthesis
Metabolites
Scaffolds
anti-infective agents
biosynthesis
metabolites
Allelopathy
Poaceae
allelopathy
Microbial Sensitivity Tests
minimum inhibitory concentration
Anti-Infective Agents
Magnoliopsida
Fungi
Escherichia coli
Triticum
Zea mays
Crops

Keywords

  • Antibacterial
  • Antifungal
  • Benzoxazinone
  • Benzoxazolinone
  • Cereal
  • Classification
  • Modification
  • Plant defence
  • Poaceae
  • Synthetic

Cite this

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title = "Structure and biosynthesis of benzoxazinoids: Plant defence metabolites with potential as antimicrobial scaffolds",
abstract = "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.",
keywords = "Antibacterial, Antifungal, Benzoxazinone, Benzoxazolinone, Cereal, Classification, Modification, Plant defence, Poaceae, Synthetic",
author = "{de Bruijn}, {Wouter J.C.} and Harry Gruppen and Vincken, {Jean Paul}",
year = "2018",
month = "11",
doi = "10.1016/j.phytochem.2018.07.005",
language = "English",
volume = "155",
pages = "233--243",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier",

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TY - JOUR

T1 - Structure and biosynthesis of benzoxazinoids

T2 - Phytochemistry

AU - de Bruijn, Wouter J.C.

AU - Gruppen, Harry

AU - Vincken, Jean Paul

PY - 2018/11

Y1 - 2018/11

N2 - 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.

AB - 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.

KW - Antibacterial

KW - Antifungal

KW - Benzoxazinone

KW - Benzoxazolinone

KW - Cereal

KW - Classification

KW - Modification

KW - Plant defence

KW - Poaceae

KW - Synthetic

U2 - 10.1016/j.phytochem.2018.07.005

DO - 10.1016/j.phytochem.2018.07.005

M3 - Article

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EP - 243

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

ER -