title: Isolation of brominated quinones showing chemiluminescence activity from luminous acorn worm, Ptychodera flava.
abstract: Luminous acorn worm, Ptychodera flava emits green light by stimulating with diluted hydrogen peroxide. We have recently reported isolation and structure determination of 2,3,5,6-tetrabromohydroquinone as a luminous substance and riboflavin as a possible light emitter. There are three other luminous substances in the extracts from P. flava, so here we report the isolation and structure determination of other luminous substances as 2,3,5-tribromohydroquinone, tetrabromo-1,4-benzoquinone, and 2,3,5-tribromo-6-(2,3,5-tribromo-4-hydroxy-phenoxy)-benzene-1,4-diol. Besides, this is the first report of isolation of tetrabromo-1,4-benzoquinone from acorn worm. Structure-activity relationship of chemiluminescence activity of halogenated quinone derivatives reveals that a highly halogen substitution and 1,4-quinone skeleton are important for high chemiluminescence activity.
authors.affiliation: Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Kanakubo
authors.forename: Minoru
authors.initials: M
authors.lastname: Isobe
mesh_terms: D000818:Animals; D001966:Bromine / Q000737:chemistry; D002816:Chordata, Nonvertebrate / Q000737:chemistry*; D008163:Luminescent Measurements; D015394:Molecular Structure; D011809:Quinones / Q000737:chemistry* / Q000302:isolation & purification*; D013045:Species Specificity; D013329:Structure-Activity Relationship
chemical_list: D011809:Quinones; D001966:Bromine