(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2h-1,4-benzoxazin- 3(4h)-one from Secale cereale

Hartenstein, H.; Sicker, Dieter

doi:10.1016/s0031-9422(00)90618-6

Cited by 42 publications

(21 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…HPLC to afford 27 compounds. Twenty two were identified as known compounds; plucheoside B (1), alangionoside C (2) (Otsuka et al, 1995), premnaionoside (4) (Sudo et al, 2000), (2R)-2-O-b-d-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc, 8) (Tietze et al, 1991), (2R)-2-O-b-d-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA-Glc, 9) (Hartenstein and Sicker, 1994) (Ono et al, 1999) (Okamura et al, 1981), adenosine (13) (Otsuka et al, 1989), verbascoside (14), isoverbascoside (15), leucosceptoside A (16) (Miyase et al, 1982), martynoside (17) (Sasaki et al, 1978), b-hydroxyacteoside (18) (Kitakawa et al, 1984), vecenin-2 (19), schaftoside (20) (Markham and Chari, 1982) (Hase et al, 1995) (Achenbach et al, 1992) (Ida et al, 1994), magnolenin C (26) (Rao and Wu, 1978), and ( (Kinjo et al, 1991) by comparison of physical data with literature values and from spectroscopic evidence.…”

Section: Resultsmentioning

confidence: 99%

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

et al. 2001

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

et al. 2001

View full text Add to dashboard Cite

“…The resulting aglucones are cyclic hemiacetals that undergo oxo-cyclo/ring-chain tautomerism via a fast, reversible ring opening reaction (Copaja et al 1986), and therefore occur as racemic mixtures in solution. However, all known benzoxazinone glucosides produced by plants are (2 R )-2-β-D-glucosides (Hartenstein et al 1993; Hartenstein and Sicker 1994; Kluge et al 1997; Nagao et al 1985). …”

Section: Chemical Properties and Reactivity Of Bxdsmentioning

confidence: 99%

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

et al. 2016

View full text Add to dashboard Cite

Benzoxazinoids are a class of indole-derived plant chemical defenses comprising compounds with a 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton and their derivatives. These phytochemicals are widespread in grasses, including important cereal crops such as maize, wheat and rye, as well as a few dicot species, and display a wide range of antifeedant, insecticidal, antimicrobial, and allelopathic activities. Although their overall effects against insect herbivores are frequently reported, much less is known about how their modes of action specifically influence insect physiology. The present review summarizes the biological activities of benzoxazinoids on chewing, piercing-sucking, and root insect herbivores. We show how within-plant distribution modulates the exposure of different herbivore feeding guilds to these defenses, and how benzoxazinoids may act as toxins, feeding deterrents and digestibility-reducing compounds under different conditions. In addition, recent results on the metabolism of benzoxazinoids by insects and their consequences for plant-herbivore interactions are addressed, as well as directions for future research.

show abstract

“…The aglucone moiety of acetal glucosides of Hx reported in the literature has the (2 R ) configuration 42, 43. However, we considered both substrate enantiomers for analysis of the mechanisms inside the chiral active site model because it is expected that the lactol/phenol‐aldehyde equilibrium results in configuration inversion of the chiral center of DIMBOA to some extent.…”

Section: Resultsmentioning

confidence: 99%

Semiempirical simulation of a theta‐class glutathione S‐transferase‐catalyzed glutathione attack to the allelochemical DIMBOA

Sant’Anna

Souza

Andrade

2002

Int J of Quantum Chemistry

View full text Add to dashboard Cite

We evaluated by the semiempirical method PM3 possible mechanisms of a putative interaction between a cereal allelochemical, the cyclic hydroxamic acid 2,4dihydroxy-7-metoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA), and the tripeptide glutathione (GSH) inside the active site of a theta-class glutathione S-transferase. Based on a preliminary study of transition states from DIMBOA reactions with methanethiolate as a simple model of GSH, we investigated the roles of catalytic residues of the enzyme during nucleophilic additions of GSH to the carbonyl groups of DIMBOA and of its phenol/aldehyde isomer inside the active site model. Our results suggest that a tyrosine residue, Tyr113, makes the most important contributions for the catalytic mechanism. In the modeled reaction steps, Tyr113 behaves as a double hydrogen bond donor catalyst for nucleophilic additions of GSH to substrates: It initially helps stabilize the strongly nucleophilic reduced GSH with a hydrogen bond intermediated by a water molecule; during substrate approach, small conformational changes enable the residue to make a direct hydrogen bond to the substrate group that develop negative charge after addition of reduced GSH.

show abstract

(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2h-1,4-benzoxazin- 3(4h)-one from Secale cereale

Cited by 42 publications

References 15 publications

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

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

Semiempirical simulation of a theta‐class glutathione S‐transferase‐catalyzed glutathione attack to the allelochemical DIMBOA

Contact Info

Product

Resources

About