title: Histrionicotoxin alkaloids finally detected in an ant.
abstract: Workers of the ant Carebarella bicolor collected in Panama were found to have two major poison-frog alkaloids, cis- and trans-fused decahydroquinolines (DHQs) of the 269AB type, four minor 269AB isomers, two minor 269B isomers, and three isomers of DHQ 271D. For the first time in an ant, however, the DHQs were accompanied by six histrionicotoxins (HTXs), viz., 283A, 285A, 285B, 285C, 287A, and 287D. This co-occurrence of the HTX and DHQ alkaloids is the usual pattern seen in dendrobatid frogs. This finding contrasts with our earlier study, where workers of a Brazilian ant, Solenopsis (Diplorhoptrum) sp., were found to have a very similar DHQ complex but failed to show HTXs. Several new DHQ alkaloids of MW 271 (named in the frog as 271G) are reported from the above ants that have both m/z 202 and 204 as major fragment ions, unlike the spectrum seen for the poison-frog alkaloid 271D, which has only an m/z 204 base peak. Found also for the first time in skin extracts from the comparison frog Oophaga granulifera of Costa Rica is a trace DHQ of MW 273. It is coded as 273F in the frog; a different isomer is found in the ant.
authors.affiliation: Department of Chemistry, Virginia Military Institute , Lexington, Virginia 24450, United States.
authors.forename: Tappey H
authors.initials: TH
authors.lastname: Jones
authors.forename: Rachelle M M
authors.initials: RM
authors.lastname: Adams
authors.forename: Thomas F
authors.initials: TF
authors.lastname: Spande
authors.forename: H Martin
authors.initials: HM
authors.lastname: Garraffo
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Kaneko
authors.forename: Ted R
authors.initials: TR
authors.lastname: Schultz
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000664:Amphibian Venoms / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D001000:Ants / Q000737:chemistry*; D001001:Anura / Q000378:metabolism*; D001938:Brazil; D003364:Costa Rica; D015394:Molecular Structure; D010176:Panama; D011042:Poisons; D011804:Quinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012867:Skin / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000664:Amphibian Venoms; D011042:Poisons; D011804:Quinolines; C037920:decahydroquinoline-5-carboxylic acid; C007948:histrionicotoxin