Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp
Cheng, Michael Tung-Hai
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https://hdl.handle.net/2142/67237
Description
Title
Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp
Author(s)
Cheng, Michael Tung-Hai
Issue Date
1980
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule.
Attempts to synthesize polyandrocarpidines were unsuccessful; however, hexahydropolyandrocarpidines were synthesized. Therefore, various analogs of hexahydropolyandrocarpidine were synthesized to study the structure-activity relationship against Bacillus subtilis. It was determined that the compound with five methylene groups between the two nitrogens has the highest activity, that the cyclopropane ring is not required for activity but its presence enhances the antimicrobial activity, and that the chain length of the acyl part is important to the activity.
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