Table 1 in Structure and biosynthesis of benzoxazinoids: Plant defence metabolites with potential as antimicrobial scaffolds

Table 1 Overview of monomeric natural benzoxazinoids of the classes benzoxazinones (1,4-benzoxazin-3-one backbone with C 2 hydroxylation) and benzoxazolinones (1,3-benzoxazol-2-one backbone) reported in literature, with their systematic name and abbreviation. All benzoxazinones are displayed as aglycones. Note that some of these compounds have, so far, only been detected as their 2- O -glycosides. n.a., no abbreviation assigned in literature.
BenzoxazinonesR2R3R4R5Systematic nameAbbreviation aNatural source bRef.N-hydro (R 1 = H): lactamsR5 R 8 1 O OH 4 2 7 R 6 N 3 O 3 5 4 R2 R1HHHH2-hydroxy-1,4-benzoxazin-3-oneHBOAPoaceae(Hofman and Hofmanová, 1969; Tanwir et al., 2013)Acanthaceae Calceolariaceae Plantaginaceae Lamiaceae(Baumeler et al., 2000; Pratt et al., 1995) (Bravo et al., 2005) (Pratt et al., 1995) (Alipieva et al., 2003)HHOHH2,7-dihydroxy-1,4-benzoxazin-3-oneDHBOAPoaceae Acanthaceae(de Bruijn et al., 2016; Woodward et al., 1979) (Bravo et al., 2004)Calceolariaceae Lamiaceae(Bravo et al., 2005) (Alipieva et al., 2003)HHOCH3H2-hydroxy-7-methoxy-1,4-benzoxazin-3-oneHMBOAPoaceae(Cambier et al., 1999; Tanwir et al., 2013)Acanthaceae(Baumeler et al., 2000; Pratt et al., 1995)Plantaginaceae(Pratt et al., 1995)HHOCH3OCH32-hydroxy-7,8-dimethoxy-1,4-benzoxazin-3-oneHM2BOAPoaceae(Cambier et al., 1999; Hofman and Masojídková, 1973)ClHOCH3H5-chloro-2-hydroxy-7-methoxy-1,4-benzoxazin-3-oneCl-HMBOAPoaceae(Le-Van and Wratten, 1984)HHClH7-chloro-2-hydroxy-1,4-benzoxazin-3-onen.a.Acanthaceae(Kanchanapoom et al., 2001a)OHHHH2,5-dihydroxy-1,4-benzoxazin-3-onen.a.Acanthaceae(Kanchanapoom et al., 2001a)HOHHH2,6-dihydroxy-1,4-benzoxazin-3-onen.a.Lamiaceae(Alipieva et al., 2003)N-hydroxy (R 1 = OH): hydroxamic acidsHHHH2,4-dihydroxy-1,4-benzoxazin-3-oneDIBOAPoaceae(Cambier et al., 1999; Tanwir et al., 2013)Acanthaceae(Baumeler et al., 2000; Bravo et al., 2004)Ranunculaceae(Özden et al., 1992)Calceolariaceae(Bravo et al., 2005)Plantaginaceae(Pratt et al., 1995)Lamiaceae(Alipieva et al., 2003)HHOHH2,4,7-trihydroxy-1,4-benzoxazin-3-oneTRIBOAPoaceae(Woodward et al., 1979)Acanthaceae(Pratt et al., 1995)HHOCH3H2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-oneDIMBOAPoaceae(Cambier et al., 1999; Tanwir et al., 2013)Acanthaceae(Baumeler et al., 2000; Pratt et al., 1995)Plantaginaceae(Pratt et al., 1995)HHOHOCH32,4,7-trihydroxy-8-methoxy-1,4-benzoxazin-3-oneTRIMBOAPoaceae(Handrick et al., 2016)HHOCH3OCH32,4-dihydroxy-7,8-dimethoxy-1,4-benzoxazin-3-oneDIM2BOAPoaceae(Cambier et al., 1999; Niemeyer, 2009)HHClH7-chloro-2,4-dihydroxy-1,4-benzoxazin-3-one7-Cl-DIBOAAcanthaceae(Kanchanapoom et al., 2001b)N-methoxy (R 1 = OCH 3): methyl derivativesHHHH2-hydroxy-4-methoxy-1,4-benzoxazin-3-one4- O -Me-DIBOAPoaceae(de Bruijn et al., 2016; Oikawa et al., 2002)HHOCH3H2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-oneHDMBOAPoaceae(Cambier et al., 1999; Tanwir et al., 2013)HHOCH3OCH32-hydroxy-4,7,8-trimethoxy-1,4-benzoxazin-3-oneHDM2BOAPoaceae(Handrick et al., 2016; Köhler et al., 2015)N-hydro (R 1 = H)R5 R 7 1 4 O 6 2 OHHHH1,3-benzoxazol-2-oneBOAPoaceae Acanthaceae Ranunculaceae Calceolariaceae Plantaginaceae(Cambier et al., 1999; Hanhineva et al., 2011) (Bravo et al., 2004; Pratt et al., 1995) (Özden et al., 1992) (Bravo et al., 2005) (Pratt et al., 1995)R 5 3 N 3 4H HH OHOH HH H6-hydroxy-1,3-benzoxazol-2-one 5-hydroxy-1,3-benzoxazol-2-oneBOA-6-OH BOA-5-OHPDP c PDP(Schulz and Wieland, 1999; Wieland et al., 1998) (Hofmann et al., 2006)R R1 2OH HH NO2H OHH H4-hydroxy-1,3-benzoxazol-2-one 5-nitro-6-hydroxy-1,3-benzoxazol-2-onen.a. Nitro-BOA-6-OHAcanthaceae MDP c(Huo et al., 2005; Zhao et al., 2015) (Schulz et al., 2017)HHOCH3H6-methoxy-1,3-benzoxazol-2-oneMBOAPoaceae(Cambier et al., 1999; Niemeyer, 2009)Acanthaceae(Pratt et al., 1995)Plantaginaceae(Pratt et al., 1995)HHOCH3OCH36,7-dimethoxy-1,3-benzoxazol-2-oneM2BOAPoaceae(Anai et al., 1996; Cambier et al., 1999)HClOCH3H5-chloro-6-methoxy-1,3-benzoxazol-2-oneCl-MBOAPoaceae(Kato-Noguchi et al., 1998)ClHOCH3OCH34-chloro-6,7-dimethoxy-1,3-benzoxazol-2-oneCl-M2BOAPoaceae(Anai et al., 1996)HHOGlcH6-β- D-glucopyranosyloxy-1,3-benzoxazol-2-oneBOA-6- O -GlcPDP(Hofmann et al., 2006; Wieland et al., 1998)HOGlcHH5-β- D-glucopyranosyloxy-1,3-benzoxazol-2-oneBOA-5- O -GlcPDP(Hofmann et al., 2006)COCH3HHH4-acetyl-1,3-benzoxazol-2-one4-ABOAPoaceae(Fielder et al., 1994)N-hydroxy (R 1 = OH)HHOCH3H3-hydroxy-6-methoxy-1,3-benzoxazol-2-one3-OH-MBOAPlantaginaceae(Wu et al., 2012)N-methoxy (R 1 = OCH 3)HHOCH3H3,6-dimethoxy-1,3-benzoxazol-2-oneDMBOAPlantaginaceae(Wu et al., 2012)N-glucosyl (R 1 = Glc)HHOCH3H3-β- D-glucopyranosyl-6-methoxy-1,3-benzoxazol-2-oneMBOA- N -GlcIDP c(Maag et al., 2014)PDP(Hofmann et al., 2006; Wieland et al., 1998)
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a Most commonly used abbreviation reported in literature, for some compounds multiple different abbreviations are in use.
b Natural source (plant family or detoxification product) in which the benzoxazinoid has been detected. Note that genera Scoparia and Calceolaria, formerly members of Scrophulariaceae, have been moved to
Plantaginaceae and Calceolariaceae, respectively.
c PDP, plant detoxification product; IDP, insect detoxification product; MDP, microbial detoxification product.