Algal pheromones

The Chemistry of Gamete Attraction Chemical Structures, Biosynthesis, and (A)biotic Degradation of Algal Pheromones... 

Recent advances in gas chromatographic separations of enantiomers allow precise determination of the enantiomeric purity of the algal pheromones. The czs-disubstituted cyclopentenes, such as multifidene, viridiene, and caudoxirene, are of high optical purity [ 95% enantiomeric excess (e.e.)] whenever they have been found (32,33). The situation is different with the cyclopropanes and the cycloheptadienes, as shown in Table 2 and Figure 1. Hormosirene from female gametes or thalli of... 

Interestingly, the first biosynthetic experiments with [3H]linolenic add and the terrestrial plant Senecio isatideus (Asteraceae) as a model system for the biosynthesis of algal pheromones were unsuccessful. If, however, labeled dodeca-3,6,9-trienoic add is administered, a rapid transformation into ectocarpene takes place (36). Nevertheless, the C12 add ultimately derives from linolenic acid via three /3-oxidations, since labeled tetradeca-5,8,11-trienoic acid, which requires only one /3-oxidation, is converted into labeled ectocarpene albeit with very low effidency (37). 

Maier I (1993) Gamete orientation and induction of gametogenesis by pheromones in algae and plants. Plant Cell Environ 16 891-907 Maier I (1995) Brown algal pheromones. Prog Phycol Res 11 51-102... 

Boland, W., The chemistry of gamete attraction chemical structures, biosynthesis, and (a)biotic degradation of algal pheromones, Proc. Nat. Acad. Sci. USA, 92, 31, 1995. 

Maier, I., Brown algal pheromones, Prog. Phycological Res., 11, 51, 1995. 

The biosynthesis of these marine algal pheromones has been well investigated. In marine algae, it is shown that Cn hydrocarbons are derived from polyunsaturated C2o fatty acids. Exogenously supplied [2H8]-arachidonic acid (12) was efficiently converted into labeled [2H4]-dictyotene (13), which indicated that the ChH18 hydrocarbons are formed from the C-10 to C-20 positions of arachidonic acid (Scheme l).25 Thus,... 

Cathinone see kat and phenylethylamine alkaloids. Caudoxlrene see algal pheromones. 

Asterionellaformosa produces fucoserratene (the pheromone of Fucus vesiculosus) from EPA [84], while Gomphonema parvulum produces the brown algal pheromones hormosi-rene and two dictyopterenes from EPA and ara-chidonic acid (ARA) [81]. However, the functions of these volatile hydrocarbons in freshwater diatoms are unknown. 

Hombeck, M. and Boland, W. (1998) Biosynthesis of the algal pheromone fucoser-ratene by the freshwater diatom Asterionella formosa (Bacillariophyceae). Tetrahedron. 54, 11033-11042... 

Boland, W. and Mertes, K. (1985) Biosynthesis of algal pheromones. A model study with the composite Senecio isatideus. Fur. J. Biochem., 147, 83-91. 

Rui, F. and Boland, W. (2010) Algal pheromone biosynthesis Stereochemical analysis and mechanistic implications in gametes of Ectocarpus siliculosus. J. Org. Chem., 75, 3958-3964. 

---