Isolation, Structure Elucidation, and Synthesis of Natural Products from Marine Cyanobacteria

Author

Keren SolomonFollow

Defense Date

6-29-2020

Graduation Date

Summer 8-8-2020

Availability

Immediate Access

Submission Type

thesis

Degree Name

MS

Department

Medicinal Chemistry

School

School of Pharmacy

Committee Chair

Kevin Tidgewell

Committee Member

Aleem Gangjee

Committee Member

Marc Harrold

Committee Member

Jelena Janjic

Keywords

medicinal chemistry, organic chemistry, cyanobacteria, synthesis, CNS, malaria, analytical chemistry

Abstract

This thesis describes the isolation, structure elucidation, and synthesis of natural products from marine cyanobacteria. A crude extract from a cyanobacterium collected in Curacao showed selective affinity for the dopamine D₅ receptor in a screen against a panel of CNS receptors. Due to the high similarity of the D₅ and D₁ receptor, to date there are no known ligands that differentiate them. Attempts to purify the compound responsible for this affinity led to the isolation of the known compound caylobolide A. A second extract from a cyanobacterium collected in Panama underwent bioassay-guided fractionation and yielded the novel compound naranjamide, which showed activity against P. falciparum the protozoa responsible for malaria. Syntheses of naranjamide and its nonmethylated analog were attempted in order to verify the proposed structure and stereochemistry, as well as determine its mechanism of action.

Language

English

Recommended Citation

Solomon, K. (2020). Isolation, Structure Elucidation, and Synthesis of Natural Products from Marine Cyanobacteria (Master's thesis, Duquesne University). Retrieved from https://dsc.duq.edu/etd/1918