Anthopleura elegantissima

Not all releaser pheromones are sex attractants. One alternative example of a releaser pheromone is the sending out of an alarm message, warning other members of the species that some threat is at hand. The California sea anemone Anthopleura elegantissima provides a neat example of alarm signaling. 

Anthopleura elegantissima is a small, common sea anemone. It is a bit less than 1 inch across normally. However, it can do some interesting chemistry. If one is wounded, it emits an alarm pheromone as a warning to neighboring members of the same species. When this alarm pheromone hits its receptor, the recipient anemone reacts with a series of quick flexes of its basal tentacles, followed by withdrawing the tentacles into the mouth that then snaps shut. This takes a bit less than 3 seconds overall. 

The sea anemone Anthopleura elegantissima was the source of the sulfonic acid-containing compound mycosporine-taurine (192) [182]. 

Stochaj, W. R., Dunlap, W. C., and Shick, J. M., Two new UV-absorbing mycosporine-like amino acids from the sea anemone Anthopleura elegantissima and the effects of zooxanthellae and spectral irradiance on chemical composition and content, Mar. Biol., 118, 149, 1994. 

The colonial sea anemone Anthopleura elegantissima responds with characteristic contraction to a pheromone released by wounded conspecifics. This alarm response is highly characteristic, includes rapid bending and shortening of the tentacles and depression of the oral disk. In 1975, by extensive ion exchange column chromatography, (3-carboxy-2,3-dihydroxy-A(A(Af-trimethyl)-l-propanaminium chloride (50) was isolated as a pure crystalline substance.116 It showed alarm pheromone activity with a median concentration of 0.35 nmol 1 1 and was named anthopleurine. Comparison of spectral data between natural and synthetic compounds revealed that anthopleurine had a structure of 4-amino-4-deoxy-L-threonic acid betaine hydrochloride.117... 

Secord D. and Augustine L. (2000) Biogeography and microhabitat variation in temperate algal-invertebrate symbioses zooxanthellae and zoochlorellae in two Pacific intertidal sea anemones, Anthopleura elegantissima and A. xanthogram-mica. Invertebr. Biol. 119, 139-146. 

Several species have been shown to not modify S-320 or MAA concentration in response to UVR, such as the zoanthid Zoanthus sociatus, in response to increased levels of UVR [101], the octocoral Clavularia sp. over a depth gradient [51], the coral Montastraea annularis on transplantation from 24 m to 12 m over 21 days [102] and the temperate anemone Anthopleura elegantissima in UVR-exposed versus UVR-shielded experiments [53]. Data such as these have been used to suggest that MAAs are not directly photoprotective but are rather a byproduct of other chemical reactions and that photoprotection is a secondary function. An alternative explanation is that, at least for all of the above studies that involve coelenterates, the MAAs are derived from diet and therefore rather than MAA concentration being dependent on the intensity of UVR is dependent on the concentration of MAAs in the food source. 

The partial hydrolysis of 4a with methanolic potassium hydroxide followed by selective carboxylic acid reduction with excess borane and treatment of the resulting monoalcohol with methanesulfonyl chloride affords methyl 4-0-methanesulfonyl-2,3-0-isopropylidene-L-threonate (43). Facile displacement of the mesylate with azide followed by ester hydrolysis and catalytic reduction to an amine provides 4-amino-4-deoxy-2,3-0-isopropylidene-L-threonic acid (44). Mild acidic deprotection and ion-exchange desalting of 44 yields (2i ,3 S)-4-amino-4-deoxy-L-threonic acid (45), which has been utilized for the preparation of anthopleurine 46, the alarm pheromone of the sea anemone Anthopleura elegantissima [4] (Scheme 11). 

An interesting interaction between two marine organisms is that which involves the sea anemone Anthopleura elegantissima and its pre-... 

Dimethyl tartrate 6.260) is also an important chiral template. The first step was protection of the diol moiety to give acetonide 6.261. A multi-step transformation followed which gave 4-amino-2,3-dihydroxybutanoic acid, 6.262. This dihy-droxyamino acid was converted to anthopleurine (4-amino-2,3-dihydroxybutanoic acid, or 4-[N,N,N-trimethylammonium]-2,3-dihydroxybutanoic acid, 6.263), an alarm pheromone of the sea anemone Anthopleura elegantissima. ... 

Banaszak AT, Trench RK. 1995. Effects of ultraviolet (UV) radiation on marine microalgal-invertebrate symbioses. 11. The synthesis of mycosporine-hke amino acids in response to exposure to UV in Anthopleura elegantissima and Cassiopeia xamachana. Journal of Experimental Marine Biology and Ecology 194 233-250. 

Palythine-threonine sulfate isolated from the sea anemone Anthopleura elegantissima... 

Anthopleura elegantissima Anthopleura ekgantissima Kittredge etal 1962... 

Mttredge, J.S., Roberts, E., and Simonsen, D.G. (1962) The occurrence of free 2-aminoethyl-phosphonic acid in the sea anemone Anthopleura elegantissima. Biochemistry, 1, 624—628. 

Bruhn, T., SchaUer, C., Schulze, C., Sanchez-Rodriguez, J., Dannmeier, C., Ravens, U., Heuhach, J.F., Eckhardt, K, Schmidtmayer, J., Schmidt, H., Anerros, A., Wachter, E., and Beress, L. (2001) Isolation and characterisation of five neurotoxic and cardiotoxic polypeptides from the sea anemone Anthopleura elegantissima. Toxicon, 39, 693— 702. 

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