Tedaniophorbasins A and B-Novel Fluorescent Pteridine Alkaloids Incorporating a Thiomorpholine from the Sponge Tedaniophorbas ceratosis.

Abstract

Two new fluorescent pteridine alkaloids, tedaniophorbasins A (1) and B (2), together with the known alkaloid N-methyltryptamine, were isolated, through application of mass directed purification, from the sponge Tedaniophorbas ceratosis collected from northern New South Wales, Australia. The structures of tedaniophorbasins A and B were deduced from the analysis of 1D/2D NMR and MS data and through application of 13C NMR DFT calculations. Tedaniophorbasin A possesses a novel 2-imino-1,3-dimethyl-2,3,7,8-tetrahydro-1H-[1,4]thiazino[3,2-g]pteridin-4(6H)-one skeleton, while tedaniophorbasin B is its 2-oxo derivative. The compounds show significant Stokes shifts (~14,000 cm-1) between excitation and emission wavelengths in their fluorescence spectra. The new compounds were tested for bioactivity against chloroquine-sensitive and chloroquine-resistant strains of the malaria parasite Plasmodium falciparum, breast and pancreatic cancer cell lines, and the protozoan parasite Trypanosoma brucei brucei but were inactive against all targets at 40 µM.

• Authors: Asadhawut Hiranrat, Darren C Holland, Wilawan Mahabusarakam, John N A Hooper, Vicky M Avery, Anthony R Carroll
• Journal: Marine drugs (Mar Drugs) Vol. 19 Issue 2 (Feb 07 2021) ISSN: 1660-3397 [Electronic] Switzerland
• PMID: 33562248 (Publication Type: Journal Article)

Chemical References

• Alkaloids
• Antineoplastic Agents
• Pteridines

Topics

• Alkaloids (chemistry, isolation & purification, pharmacology)
• Animals
• Antineoplastic Agents (pharmacology)
• Cell Line, Tumor
• Humans
• Magnetic Resonance Spectroscopy
• Plasmodium falciparum (drug effects)
• Porifera (chemistry)
• Pteridines (chemistry, isolation & purification, pharmacology)
• Trypanosoma brucei brucei (drug effects)