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The Chemistry of Gamete Attraction: Chemical Structures, Biosynthesis, and (a)biotic Degradation of Algal Pheromones
Proceedings of the National Academy of Sciences of the United States of America
Vol. 92, No. 1 (Jan. 3, 1995), pp. 37-43
Published by: National Academy of Sciences
Stable URL: http://www.jstor.org/stable/2366495
Page Count: 7
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Female gametes of marine brown algae release and/or attract their conspecific males by chemical signals. The majority of these compounds are unsaturated, nonfunctionalized acyclic, and/or alicyclic C11 hydrocarbons. Threshold concentrations for release and attraction are generally observed in the range of 1-1000 pmol. The blends may contain various configurational isomers of the genuine pheromones as well as mixtures of enantiomers. Higher plants produce the C11 hydrocarbons from dodeca-3,6,9-trienoic acid; brown algae exploit the family of icosanoids for biosynthesis of the same compounds. The biosynthetic routes comprise several spontaneously occurring pericyclic reactions such as [3.3]-sigmatropic rearrangements, [1.7]-hydrogen shifts, and electrocyclic ring closures. All pheromones are (a)biotically degraded by ubiquitous oxidative pathways involving singlet oxygen or hydroxyl radicals, which may be produced through the agency of heavy metals, huminic acids, or light.
Proceedings of the National Academy of Sciences of the United States of America © 1995 National Academy of Sciences