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

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Hiranrat, Asadhawut
Holland, Darren C
Mahabusarakam, Wilawan
Hooper, John NA
Avery, Vicky M
Carroll, Anthony R
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2021
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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.

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Marine Drugs

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19

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2

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© The Author(s), 2021. Licensee MDPI, Basel, Switzerland. This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Physical chemistry

Pharmacology and pharmaceutical sciences

Tedaniophorbas ceratosis

fluorescence

malaria

pteridine alkaloids

sponge

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Hiranrat, A; Holland, DC; Mahabusarakam, W; Hooper, JNA; Avery, VM; Carroll, AR, Tedaniophorbasins A and B-Novel Fluorescent Pteridine Alkaloids Incorporating a Thiomorpholine from the Sponge Tedaniophorbas ceratosis., Marine Drugs, 2021, 19 (2), pp. 95-95

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