Plakortis metabolites

In connection with the biogenetic path of manzamenones and related Plakortis metabolites, we isolated 3-carboxy-5-(carboxymethyl)-4-tetradecyl-l-oxacyclopent-3-en-2-one (73) [38] from the same Plakortis sponge collected off Manzamo. The structure of compound 73 was defined by extensive spectroscopic analyses. On treatment with diazomethane compound 73 was converted into a dimethyl ester (74), indicating the presence of two carboxylic acids. From the 2D NMR studies, compound 73 was suggested to have a y-butenolide structure with... 

The parent compound of this group of secondary metabolites is plakortin (49) [Fig. (17)] that was isolated more than 25 years ago from Plakortis halichondroides [71]. This interesting secondary metabolite, whose polyketide skeleton suggests the involvement of butyrate units in the biogenesis, has been recently re-isolated in remarkable amounts from... 

In 2009 in a study of metabolites from Okinawan marine sponges, Kobayashi and coworkers [96] isolated and characterized a novel piperidine-containing polyketide alkaloid, plakoridine C from a sponge of the genus Plakortis sp. The authors noted that several pairs of resonances in the and NMR spectra were observed with a ratio of approximately 1 1 suggesting an epimeric or isomeric mixture of structures. The mixture was inseparable by semipreparative HPLC so the authors characterized the sample as the mixture. A HMQC spectrum showed the... 

Stierle and Faulkner (223) identified a number of cyclic peroxides and related metabolites (351-359) in various samples of Plakortis hali-... 

Faulkner, D.J., and B.N. Ravi Metabolites of the Marine Sponge Plakortis zygom-pha. Tetrahedron Lett. 21, 23 (1980). 

Among the genera that have been investigated for their primary and secondary metabolites are Coriicium, Oscar-ella, Plakina and Plakinastrella, but the genus Plakortis has been and remains the most studied. Some biochemical and genetic comparisons between the genera Corticium and Oscarella have been reported (Sole-Cava et al., 1992). 

Cafieri, F., Fattorusso, E., Taglialatela-Scafati, O., Di Rosa, M., and lanaro, A. (1999a) Metabolites from the sponge Plakortis simplex. II. Isolation of four bioactive lactone compounds and a novel related aminoadd. Tetrahedron, 55,13831-13840. 

Rahm, F., Hayes, P.Y., and Kitching, W. (2004) Metabolites from marine sponges of the genus Plakortis. Heterocycles, 64, 523-575. 

Williams, D,E, Allen, T.M., Van Soest, R Behrisch, H,W and Andersen, R,J, (2001) GlanviDic acids A and B and methyl capucinoate A, new metabolites isolated from the Caribbean sponges Plakortis halichondrioides and Plaidnastreda onkodes. J. Nat. Prod., 64, 281-285. 

Zampella, A., Giannini, C., Debitus, C., and D Auria, M.V. (2001) Amphiasterins, a new family of cytotoxic metabolites from the marine sponge Plakortis quasiamphiaster. Tetrahedron, 57, 257-263. 

Akiyama, M., Isoda, Y, Nishimoto, M., Kobayashi, A., Togawa, D., Hirao, N., Kuboki, A., and Ohira, S. (2005) Stereocontrolled synthesis of ( )-methyl 3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate, a major metabolite of Caribbean sponge, Plakortis halichondrioides, using reactions of alkybdenecarbenes in one pot Tetrahedron Lett., 46, 7483-7485. 

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