Aplysia parvula

The sea hare Aplysia parvula has yielded aplyparvunin (673), which has potent fish toxicity (778). Laurencia intricata has furnished itomanallenes A (674) and B (675) the former is an epimer of the known neolaurallene (591). Chinzal-lene (676) was characterized from a Japanese Laurencia sp. (638). The stereochemistry of chinzallene is not fully established. 

Laurencia nipponica (790), and the structure and absolute configuration were confirmed by total synthesis (791). This new compound is a stereoisomer of the known (3Z)-isoprelaurefucin. A Malaysian Laurencia pannosa has yielded (3Z)-chlorofucin (698) (578), and (3Z)-bromofucin (699), which is also a new C15-acetogenin, is found in a South African sea hare, Aplysia parvula (792). The (3 )-neoisoprelaurefucin (700) was found in Laurencia obtusa collected in Turkish waters (557). 

Jongaramruong J, Blackman AJ, Skelton BW, White AH (2002) Chemical Relationships between the Sea Hare Aplysia parvula and the Red Seaweed Laurencia filiformis from Tasmania. Aust J Chem 55 275... 

Miyamoto T, Ebisawa Y, Higuchi R (1995) Aplyparvunin, a Bioactive Acetogenin from the Sea Hare Aplysia parvula. Tetrahedron Lett 36 6073... 

Ginsburg, D. W. and Paul, V. J., Chemical defenses in the sea hare Aplysia parvula importance of diet and sequestration of algal secondary metabolites, Mar. Ecol. Prog. Ser., in press. 

Chemical relationships between the sea hare Aplysia parvula and the red seaweed Laurencia Jiliformis from Tasmania. Aust. J. Chem., 55, 275-280. 

Miyamoto, T., Ebisawa, Y, and Higuchi, R. (1995) Aplyparvunin, a bioactive acetogenin from the sea hare Aplysia parvula. Tetrahedron Lett., 36, 6073-6074. 

The food chain between the Japanese species Aplysia kurodai and Laurencia concinna (Ceramiales) and Laurencia perforata yielded three closely related brominated diter-penes aplysin-20 was found only in the sea hare (Matsuda et al, 1967) isoaplysin-20 was identified in the mollusk and in Laurencia perforata and concinndiol was isolated only from Laurencia concinna. These three structures and their biosynthetic patterns are presented in Chapter 13. More recently, the food chain between the species Aplysia parvula and the red alga Laurencia filiformis, harvested in Tasmania, has led to similar comments (Jongaramruong et al, 2002). Other examples of brominated diterpenes found in Aplysia and Laurencia are presented in Chapter 13 (see also Komprobst and Al Easa, 2003). 

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