1,4‐Benzoxazine Derivatives in Plants: Sephadex Fractionation and Identification of a New Glucoside

Abstract

Glucosides of 1,4‐benzoxazine derivatives have been isolated from corn, rye, wheat and Coix Lachryma Jobi seedlings by gel filtration. 2‐(2,4‐Dihydroxy‐7‐methoxy‐1,4(2H)‐benzoxazin‐3(4H)‐on)‐β‐β‐d‐glucopyranoside (DIMBOA‐Glc.) and 2‐(2‐hydroxy‐7‐methoxy‐1,4(2H)‐benzoxazin‐3(4H)‐on)‐β‐d‐glucopyranoside (HMBOA‐Glc.) were demonstrated in all four plants, with 2‐(2,4‐dihydroxy‐1,4(2H)‐benzoxazin‐3(4H)‐on)‐β‐d‐glucopyranoside (DIBOA‐Glc.) in rye, wheat and corn and 2‐(2‐hydroxy‐1,4(2H)‐benzoxazin‐3(4H)‐on)‐β‐d‐glucopyranoside (HBOA‐Glc.) in rye and corn. The structure of HBOA‐Glc. has not been described previously. No free aglucones were found in uninjured plant tissue. DIMBOA‐Glc. and HMBOA‐Glc.; DIBOA‐Glc. and HBOA‐Glc. appear to be redox pairs and their mutual relation was found to vary with physiological conditions of the tissue. Copyright © 1969, Wiley Blackwell. All rights reserved