Plakortis halichondrioides

Isol. from the marine sponge Plakortis halichondrioides. Lustrous plates. Mp 42°. Bp 260-262°, Bp 126-128°. 

Isol. from the sponge Plakortis halichondrioides. Cytotoxic. 

The high value of the oxycarbonylation chemistry in the synthesis of natural products and other complex compounds has been demonstrated frequently. One of the most impressive examples is the synthesis of biologically active sponge-derived plakortones. The plakortones are a family of natural product furanolactones isolated from the Caribbean sponges Plakortis halichondrioides (plakortones A-D) and Plakortis simplex (plakortones B-F Figure 15.1). Plakortones A-D show activity as activators of the cardiac sarcoplasmic reticulum Ca " " adenosine triphosphatase (ATPase). Molecules with this activity are of interest as... 

Plakortis halichondrioides Patil et al., 1996c Hayes and Kitching, 2002... 

Plakortis simplex CO2H Fattorusso et al, 2000 Plakortis halichondrioides Chen et al, 2002... 

Plakortides M and N, recently isolated from Plakortis halichondrioides harvested in Puerto Rico, are highly cytotoxic in vitro for several cancer lines, with an IC50 value that is often below 1 jxM (Jimenez, Garzon, and Rodriguez, 2003). 

Ankisetty, S., Gochfeld, D., Diaz, C., Khan, S.L, and Slattery, M. (2010) Chemical constituents of the deep reef Caribbean sponges Plakortis angulospiculatus and Plakortis halichondrioides and their antiinflammatory adivities. J. Nat. Prod., 73, 1494—1498. 

Jimenez, M. del Sol, Garzon, S.P., and Rodriguez, A,D, (2003) Plakortides M and N, bioactive polyketide endoperoxides from the Caribbean marine sponge Plakortis halichondrioides. J. Nat. Prod., 66, 655-661,... 

Schmidt, E.W. and Faulkner, D.J. (1996a) Absolute configuration of methyl (2Z,6 R,8 R,9 E)-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate from the sponge Plakortis halichondrioides. Tetrahedron Lett., 37, 6681-6684. 

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. 

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. 

Patil, A.D., Freyer, A.J., Bean, M.F., Carte, B., Wesfley J.W., Johnson, R.K, and Lahouratate, P. (1996c) The plakortones, novel bicydic lactones from the sponge Plakortis halichondrioides activators of cardiac SR-Ca pumping ATP-ase. Tetrahedron, 52, 377-394. 

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