Platynereis dumerilii

EC50 (48-h) for marine polychaete Platynereis dumerilii 2.55 mg/L (Palau-Casellas and Hutchinson, 1998). 

The histidine derivatives, l-methyl-5-thiolhistidine (639) and its disulfide (640) were isolated from unfertilised eggs of the sea urchin Paracentrotus lividus [507] and from those of other echinoderms [508]. Their structures were revised after an unambiguous synthesis [509]. L-Ovothiol A disulfide (640) was also shown to be the egg release pheromone of the marine polychaete worm Platynereis dumerilii [510]. 

Hutchinson TH, Jha AN, Mackay JM, Elliott BM, Dixon DR. 1998. Evaluation of the geno-toxicity of disinfected sewage effluent using the marine worm Platynereis dumerilii (Polychaeta Nereidae). Mutat Res 399 97-108. 

The story of olean (116) was given already. Another example is 5-methyl-3-heptanone (125), which is the pheromone in the coelomic fluid of gravid specimens of Nereid marine polychaetes (Platynereis dumerilii). It is responsible for the induction of the nuptial dance behavior prior to the release of gametes in P. dumerilii. The female-produced (.S )-125 attracts the males, while the male-produced (R)-125 is active on females.147,148... 

Boilly-Marer, Y., 1974. Etude experimentale du comportement nuptial de Platynereis dumerilii (Annelida Polychaeta) chemoreception, emission des produits genitaux. Mar. Biol., 24 167-179. 

Rohl I, Schneider B, Schmidt B, Zeeck E (1999) L-Ovothiol A the egg release pheromone of the marine polychaete Platynereis dumerilii Annelida Polychaeta. Z Naturforsch 54 1145-1147... 

Zeeck, E. et al. (1991) Sex-pheromones in a marine polychaete - biologically-active compounds from female Platynereis dumerilii. J. Exp. Zool. 260, 93-98... 

Recall that ovothiol A was isolated from the polychaete annelid Platynereis dumerilii (see Chapter 21), and that the adenochromes of cephalopods show related structures (see Chapter 23). 

When thiohistidine is methylated we obtain ovothiol A, a natural antioxidant, which is also an egg-release pheromone of the male annelid Platynereis dumerilii (see Chapter 21). For information on the biological properties of ovothiols, see especially the following articles Turner et al (1987), Holler and Hopkins (1988,1990), Shapiro and Hopkins (1991) and Marjanovic, Simic, and Jovanovic (1995). 

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