Detection of the 15-acetate of prostaglandin E2 methyl ester as a prominent component of the prostaglandins in the gorgonian coral Plexaura homomalla.

15R-Prostaglandin E2 (PGE2) methyl ester 15-acetate (1) was isolated from the R-variety of the Caribbean sea whip coral Plexaura homomalla collected in the Florida Keys. It was present in coral samples from separate collections in 2-10% of the abundance of the major prostaglandin component, PGA2 methyl ester 15-acetate. The structure of 1 was assigned based on one- and two-dimensional 1H NMR, HPLC, and LC-MS analyses. A sample of the S-variety of P. homomalla was found to contain a similar abundance of the corresponding 15S product, prostaglandin E2 methyl ester 15-acetate. The significance of PGE acetylation is discussed in relation to the proposed mechanism of PGA synthesis in the coral.