Manoalide from Luffariella variabilis

Scheme 13. Structures of the sesteiterpenes luffariellin A [1], luffariellin B [2], manoalide [3], secomanoalide [4] from Luffariella variabilis, thorectolide monoacetate [5] from Thorectandra excavatus.

However, clinical studies on marine metabolites are often hampered by insufficient supply of material, as it was reported for dolastatin 10 from the sea hare Dolabella auricularia [107]. In the case of manoalide, obtained from the sponge Luffariella variabilis, it remains open whether its use will be restricted to an application in studying inflammatory processes on the cell level or whether it... 

Luffalactone (95) from the Pacific Luffariella variabilis is a sesterterpene with a labdane type skeleton, related to manoalide (53). Luffalactone showed 52% inhibition of oedema in the mouse ear assay at 50 pg/ear [87],... 

De Silva, E.D., and P.J. Scheuer Manoalide, an Antibiotic Sesterterpenoid from the Marine Sponge Luffariella variabilis (Polejaeff). Tetrahedron Lett. 21, 1611 (1980). 

In order to provide sufficient manoalide for continued pharmacological evaluation, F aulkner and coworkers made an extensive c ollection of L. variabilis, from different locations in Palau. From a small number of specimens of L. variabilis were isolated two new metabolites, luffariellin A (77) and Luffariella B (78) in place of manoalide and seco-manoalide [97], Despite the different carbon skeleton, the functional groups in luffariellins A and B are identical with those in manoalide and seco-manoalide, respectively, and they showed almost identical antiinflammatory properties. Both luffariellins were potent antagonists of topical induced inflammation in the mouse ear, and inhibitors of bee venom PLA2, with an IC50 value of 5.6 x 10 8 M and 6.2 x 10 8 M, for luffariellins A and B, respectively [97]. 

Gauvin-Bialecki, A., Aknin, M., and Smadja, J. (2008) 24-0-Ethylmanoalide, a manoalide-related sesterterpene from the marine sponge Luffariella cf variabilis. Molecules, 13, 3184-3191. 

---