Aplysia dactylomela

Melo, V. M. M., Fonseca, A. M., Vasconcelos, I. M., and Carvalho, A. F. (1998). Purification of a novel antibacterial and haemagglutinating protein from the purple gland of the sea hare, Aplysia dactylomela Rang, 1828. Toxicon 38,1415-1427. 

The activities of the purple fluid of the sea hare Aplysia dactylomela, such as toxic, antimicrobial and hemagglutinating properties, have been attributed to a substance of protein nature [332], Proteoglycans and adhesive glycoproteins present in the extracellular matrix of vertebrates, have also been reported in sponges. These molecules are probably involved in the cell adhesion systems of sponges [333], Recently, novel marine proteins have been reported, such as silicatein from sponge biosilica [334], and a metallothionein protein from the marine alga Fuats vesiculosus [335], Metallothioneins have also been isolated from Arctic... 

An examination of the digestive gland extracts from the South African sea hare Aplysia dactylomela has yielded new halogenated sesquiterpenes, e.g. algoane (216) and ibhayinol (217) [168]. 

Sea hares and nudibranchs feed on seaweeds to acquire their chemicals for defense. The common sea hare Aplysia dactylomela from Spain contains puerti-tol-B acetate (333) (554), whereas this animal collected off the coast of South Africa affords the new algoane (334), 1-deacetoxyalgoane (335), l-deacetoxy-8-deoxyalgoane (336), and ibhayinol (337) (555, 556). Investigation of this sea hare from La Palma has uncovered the new 338 along with two other halogenated compounds shown in section Eudesmane and Other Types (557). 

The C15 acetogenin ( )-dihydrorhodophytin (677), an isomer of the previously known (Z)-isomer (1). is found in Laurencia pinnatifida from the Canary Islands (779). An Easter Island variety of Laurencia claviformis has afforded (3Z)-13-epipinnatifidenyne (678) (780). Likewise, an epimer of the previously known laurencienyne, 13-epilaurencienyne (679), is found in Laurencia obtusa from the Aegean coast (781). This same seaweed and locale yielded laurencienyne B (680), the cis isomer of laurencienyne (782), and the acetate 681 (783). This Aegean Sea Laurencia obtusa has also provided (3Z)-13-epilaurencienyne (682), (3 )-13-epi-pinnatifidenyne (683) (revised in (785)), 684, and 685 (784). The (Z)-diastereomers 682 and 685 showed very potent insecticidal activity. Three enantiomers of known compounds were identified in the sea hare Aplysia dactylomela, (-)-(3E,6R,7R)-pinnatifidenyne (686), (+)-(3 , 6/ ,7/ )-obtusenyne (687), and (+)-(3Z,6/ ,7/ )-obtu-senyne (688) (785). 

Wessels M, Konig GM, Wright AD (2000) New Natural Product Isolation and Comparison of the Secondary Metabolite Content of Three Distinct Samples of the Sea Hare Aplysia dactylomela from Tenerife. J Nat Prod 63 920... 

McPhail KL, Davies-Coleman MT, Copley RCB, Eggleston DS (1999) New Halogenated Sesquiterpenes from South African Specimens of the Circumtropical Sea Hare Aplysia dactylomela. J Nat Prod 62 1618... 

Brito I, Dias T, Diaz-Marrero AR, Darias J, Cueto M (2006) Aplysiadiol from Aplysia dactylomela Suggested a Key Intermediate for a Unified Biogenesis of Regular and Irregular Marine Algal Bisabolene-Type Metabolites. Tetrahedron 62 9655... 

Fedorov SN, Radchenko OS, Shubina LK, Kalinovsky AI, Gerasimenko AV, Popov DY, Stonik VA (2001) Aplydactone, a New Sesquiterpenoid with an Unprecedented Carbon Skeleton from the Sea Hare Aplysia dactylomela, and Its Cargill-Like Rearrangement. J Am Chem Soc 123 504... 

Manzo E, Ciavatta ML, Gavagnin M, Puliti R, Mollo E, Guo Y-W, Mattia CA, Mazzarella L, Cimino G (2005) Structure and Absolute Stereochemistry of Novel C15-Halogenated Acetogenins from the Anaspidean Mollusc Aplysia dactylomela. Tetrahedron 61 7456... 

Carefoot, T. FI., Harris, M., Taylor, B. E., Donovan, D., and Karentz, D., Mycosporine-like amino acids possible UV protection in eggs of the sea hare Aplysia dactylomela, Mar. Biol., 130, 389, 1998. 

Carefoot, T. H., Karentz, D., Pennings, S. C., and Young, C. L., Distribution of mycosporine-like amino acids in the sea hare Aplysia dactylomela effect of diet on amounts and types sequestered over time in tissues and spawn, Comp. Biochem. Physiol., 126, 91, 2000. 

Vera, B. Rodriguez, A. D. Aviles, E. Ishikawa, Y. Aplysqualenols A and B squalene-derived polyethers with antitumoral and antiviral activity from the Caribbean Sea slug Aplysia dactylomela, Eur. J. Org. Chem. 2009,2009, 5327-5336. 

A number of rearranged monocyclofarnesyl sesquiterpenoids have been isolated from the sea hare Aplysia dactylomela. These include dactyloxene-A (23), -B (24), and -C (25) and dactylenol (26) together with its acetate.These compounds are related to other marine metabolites isolated from red algae. Aplysistatin (27), a metabolite of the sea hare Aplysia angasi, has been synthesized by a route which involves Hg -mediated brominative cyclization and a novel oxidative debenzylation step (Scheme 6). ... 

Dactylol (1) is a sesquiterpene possessing an unusual /ra 5-5,8-fused ring system. It was first isolated from a Caribbean sea hare, Aplysia dactylomela and was later found in the red seaweed Laurencia poitei,... 

Aplysia dactylomela, 438 aprepitant [EMEND, 321 aryl trillates, 160 arylboronic acids, 146 AsPh , 153... 

Z)- and (3 )-Dactomelynes (905) and (906), isolated from the digestive glands of the sea hare Aplysia dactylomela, represent nonisoprenoid ethers characterized by a unique pyr-anopyranyl skeleton with ethyl and pentenynyl substituents. A characteristic feature of their structure is the chlorine substituent oriented on the sterically hindered side, whereas the bromine substituent avoids steric congestion. Construction of the pyranopyran skeleton via... 

New bisabolane sesquiterpenoids include (59), (60)/ and the perezone derivatives (61)—(63). Based on mass spectral evidence structures (64) and (65) have been assigned to two minor constituents of Chinese cinnamon oil both ketones have been synthesized from a-curcumene. Dihydroxydeodactol (66), a derivative of deodactol, has been isolated from the mollusc Aplysia dactylomela. A... 

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