title: [Chemistry of benzoxazinoids produced by plants as phytoalexin].
abstract: 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one and its desmethoxy derivative (DIMBOA and DIBOA) are major phytoalexins produced by rye, wheat, zea maize and related monocotyledoneae plants. These compounds elicit a wide variety of biological activities including antifungal and mutagenic activities. Structure-activity relationships of these compounds and their derivatives (benzoxazinoids), and the reactivity of benzoxazinoids with nucleophiles are discussed in relation to the molecular mechanism of their biological activity. The electrophilic reaction mechanism of benzoxazinoids and substituent effects of namely 7-methoxy and 2-hydroxy groups are also discussed.
authors.affiliation: Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Hashimoto
authors.forename: T
authors.initials: T
authors.lastname: Ishizaki
authors.forename: K
authors.initials: K
authors.lastname: Shudo
mesh_terms: D000935:Antifungal Agents; D016587:Antimutagenic Agents; D010078:Oxazines / Q000737:chemistry* / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology / Q000502:physiology; D010944:Plants / Q000737:chemistry*; D012717:Sesquiterpenes; D013329:Structure-Activity Relationship; D013729:Terpenes; D000094162:Phytoalexins
chemical_list: D000935:Antifungal Agents; D016587:Antimutagenic Agents; D010078:Oxazines; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins