Plakinidine D, a new pyrroloacridine alkaloid from two ascidians of the genus Didemnum

A previously undescribed red Didemnum sp. collected in Indonesia contained a novel pyrroloacridine, plakinidine D (4), along with the known compounds 3,5-diiodo-4-methoxyphenethylamine (5) and ascididemin (6), both of which had previously been isolated from ascidians of the genus Didemnum. Plakinidine D (4) and 3,5-diiodo-4-methoxyphenethylamine (5) were also isolated from Didemnum rubeum from the Republic of Palau. Interestingly, a collection of D. rubeum from Indonesia did not contain plakinidine D (4), but instead contained 3,5-diiodo-4-methoxyphenethylamine (5) and ascididemin (6). The structure of plakinidine D (4) was elucidated by analysis of its spectral data. Plakinidine D (4) is closely related to plakinidines A-C (1-3), previously isolated from the sponge Plakortis sp.