Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico |
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Authors: | T H Jones J A Torres T F Spande H M Garraffo M S Blum R R Snelling |
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Affiliation: | (1) Department of Chemistry, Virginia Military Institute, 24450-0304 Lexington, Virginia;(2) International Institute of Tropical Forestry, USDA Forest Service, Call Box 25000, 00928-2500 Rio Piedras, Puerto Rico;(3) Department of Biology, University of Puerto Rico, P.O. Box 23360, 00931-3360 San Juan, Puerto Rico;(4) Laboratory of Bioorganic Chemistry, NIDDK, NIH, 20892-0820 Bethesda, Maryland;(5) Department of Entomology, University of Georgia, 30602 Athens, Georgia;(6) Los Angeles County Museum of Natural History, 900 Exposition Blvd., 90007 Los Angeles, California |
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Abstract: | A number of 15-carbon alkaloids have been identified in venom extracts of four Puerto Rican species of ants in the genusSolenopsis (Diplorhoptrum). Workers of a species from El Verde produced thecis andtrans isomers of 2-methyl-6-nonylpiperidine with the latter isomer predominating. The same compounds were identified in queens of a species from Río Grande, but in this species no alkaloids were detected in worker extracts. Workers of aDiplorhoptrum species collected on Mona Island produced primarily atrans-2-methyl-6-(Z-4-nonenyl)piperidine,3, with smaller amounts of thecis isomer, whereas the major compound found in the queens of the same species on Mona Island was (5Z,9Z)-3-hexyl-5-methylindolizidine, identical with the alkaloid produced by queens of a species collected on Cabo Rojo. Surprisingly, workers of the Cabo Rojo species produced (5Z,9Z)- and (5E,9E)-3-butyl-5-propylindolizidine (4 and5, respectively) reported earlier as the 223AB indolizidines from skins of dendrobatid frogs. The possible significance of the qualitative and quantitative differences in the venom alkaloids synthesized by queens and workers is discussed as is the possibility that ants containing such alkaloids may serve as a dietary source for the skin alkaloids used by certain frogs in chemical defense. |
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Keywords: | Venom alkaloids Solenopsis Puerto Rico |
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