Erimacrus isenbeckii

Recently, a sexual pheromone of the hair crab Erimacrus isenbeckii has been identified from the feeding seawater of pre- and postmolt females.113 The purified sample elicited guard behavior in male hair crabs at a dose of 2.0 mg per sponge and was composed of 13 ceramides. On the basis of detailed NMR and fast atom bombardment tandem mass spectrometry (FAB-MS/MS) analysis, the structure of one of the major ceramides, ceramide A (49), was determined to be (26, 35,4i )-2-[(R)-2-hydroxy-21-methyldocosanoylamino]-l,3,4-pentadecane-triol.114 Similarly,... 

Table 2 Structures of ceramide components in Erimacrus isenbeckii sexual pheromone...

Asai N, Fusetani N, Matsunaga S, Sasaki J (2000) Sex pheromones of the hair crab Erimacrus isenbeckii. Part 1 isolation and structures of novel ceramides. Tetrahedron 56 9895-9899 Atema J, Engstrom DG (1971) Sex pheromone in the lobster, Homarus americamis. Nature... 

Fig. 3.5 When sponges are treated with ceramides and pheromones from receptive females, males of Erimacrus isenbeckii, Telmessus cheiragonus, and other species guard and attempt to copulate with the sponges. Drawing by Jorge A. Varela Ramos...

Masuda, Y, Yoshida, M., and Mori, K. (2002) Synthesis of (2S,22R,3S,4R)-2-(22-hydroxy-212-methyldocosanoylamino)-l,3,4-pentadecanetriol, the ceramide sex pheromone of the female hair-crab, Erimacrus isenbeckii. Biosci. Biotechnol. Biochem., 66, 1531-1537. 

A mixture of 13 new ceramides that act as sexual pheromones has been identified in the hair crab, Erimacrus isenbeckii, of Japanese origin (Hokkaido). They are all formed from a phytosphingosine and a long-chain a-hydroxy acid (C22-C26), often iso-branched (Asai et al, 2000). 

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