Luffariella

Isopr. SESTERTERP. and NORSESTERT luffarins (Luffariella geometrica Kirkpatric, Dictyocer., Porif., from S. Australia, depth 350 m Butler 199281 trunculins (Latrunculiaspp., Hadromerida, Porif from S. Australia Ovenden 1998). 

Luffariella geometrica Kirkpatrick, Dictyocer., Porif. lui rins A-Z (sestaterp. and bis-norsesterterp.), C 7.10.A/PO Butla 1992B... 

Phospholipase A2 Manoalide (Structure 16.5) majuscida Sponge, Luffariella variabilis Anti-inflammatory16... 

Problem 29.1 2 Manoalide, a sesterterpene isolated from the Pacific marine sponge Luffariella veriabills by Scheuer and co-workers at the University of Hawai i at Manoa, has anti-inflammatory, analgesic, and antifungal properties. Find the isoprene units in manoalide. 

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... 

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.

In 1992, Konig and co-workers [72] reported the i solation of Z-2,3-dihydro-neomanoalide (or luffariolide C) [88] (61a), its 24-acetyl derivative (61b), 6Z-24-acetoxy-neomanoalide (56b) and E-neomanoalide-24-al (58), from an Australian sponge of genus Luffariella. All these compounds showed antibacterial activity against Escherichia coli, B. subtilis and Micrococcus luteus, in a TLC bioauto graphic test [72]. 

Kobayashi and co-workers [70] reported, from the Okinawan sponge Luffariella sp., the isolation of several sesterterpenoids related to manoalide, named luffariolides A-J (59-67). All luffariolides showed cytotoxic activity against L1210 cells (IC50 1.1-4.5 pg/ml) and only luffariolides F (64) and G (65) exhibited weak activity also against KB... 

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]. 

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],... 

Manoallde. C2jH3603, Mr 416.56, amorphous solid, as 25-acetate mp. 117 -119 °C. A sesterterpenoid marine natural product from the sponge Luffariella variabilis, the name is derived from the Manoa valley, Oahu, Ha-... 

Sakai E, Kato H, Rotinsulu H, Losung F, Mangindaan REP, de Voogd NJ, et al. Var-iabines A and B new beta-carboline alkaloids from the marine sponge Luffariella... 

In the same year Tsuda et al. (27) reported the isolation of cytotoxic sesterterpenes from the Okinawan marine sponge Luffariella sp. among which was a compound with a 5,6-dihydro-a-pyrone moiety, luffariolide E. This compound showed cytotoxicity against murine leukaemia LI210 cells (IC50 1.1-7.8 pg/ml) in vitro. The original structure, which rested on chemical and spectroscopic evidence, has been corrected by synthesis to (24) (28). 

Tsuda, M., H. Shigemori, M. Ishibashi, T. Sasaki, and J. Kobayashi Luffariolides A-E, New Cytotoxic Sesterpenes from the Okinawan Marine Sponge Luffariella sp. J. Organ. Chem. (USA), 57, 3503 (1992). 

Struct, revised in 1993. Isol. from the sponges Luffariella sp. and Pseudoceratina crassa. 

De SUva, E.D., Scheuer, P.J., 1980. ManoaUde, an antibiotic sesterterpenoid from the marine sponge Luffariella variabilis. Tetrahedron 21,1611-1614. 

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