Long alkyl chains-3-substituted pyrrole-2-aldehyde (-2-carboxylic acid and methyl ester) from the marine spongeOscarella lobularis

Experientia
1975.0

Abstract

The structure of acridone alkaloid atalaphyllidine from the root bark of Atalantia monophylla Correâ (Rutaceae) has been established as 2', 2'-dimethyl-[pyrano 5', 6': 3, 4]-1, 5-dihydroxy acridone via spectroscopic data and chemical reactions. A novel group of compounds characterized by saturated, mono- and di-unsaturated long alkyl chains linked at position 3 of pyrrol-2-aldehyde, pyrrol-2-carboxylic acid, and 2-carbomethoxy moieties, including corresponding carboxylic acids and methyl esters, has been isolated from the marine sponge Oscarella lobularis. Additionally, two chiral neuroleptic agents with stereospecific biological activity are reported: methotrimeprazine (more potent in its (-)-enantiomer) and butaclamol ((+)-enantiomer as potent as fluphenazine). The absolute configuration of (-)-methotrimeprazine is unknown, while that of (+)-butaclamol was determined by X-ray crystal structure analysis. It is now found that the neuroleptic activity of octoclothepin is confined to its (+)-enantiomer, a finding at variance with earlier results.

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