Citronamine A, an Antiplasmodial Isoquinoline Alkaloid from the Australian Marine Sponge Citronia astra

Dale W Prebble; Darren C Holland; Luke P Robertson; Vicky M Avery; Anthony R Carroll

doi:10.1021/acs.orglett.0c03633

Citronamine A, an Antiplasmodial Isoquinoline Alkaloid from the Australian Marine Sponge Citronia astra

Org Lett. 2020 Dec 18;22(24):9574-9578. doi: 10.1021/acs.orglett.0c03633. Epub 2020 Nov 24.

Authors

Dale W Prebble^{1

2

3}, Darren C Holland^{1

2}, Luke P Robertson^{1

2}, Vicky M Avery^{3

4}, Anthony R Carroll^{1

2

3}

Affiliations

¹ School of Environment and Science, Griffith University, Southport, Queensland 4222, Australia.
² Environmental Futures Research Institute, Griffith University, Southport, Queensland 4222, Australia.
³ Griffith Institute for Drug Discovery, Griffith University, Nathan, Queensland 4111, Australia.
⁴ Discovery Biology, Griffith University, Brisbane, Queensland 4111, Australia.

PMID: 33232166
DOI: 10.1021/acs.orglett.0c03633

Abstract

Citronamine A (1), an isoquinoline alkaloid containing an unprecedented pentacyclic ring system, was isolated from the Australian marine sponge Citronia astra. Based on the combination of MS and NMR analyses and comparison of experimental and TDDFT calculated ECD spectra, the absolute structure of 1 was determined. Compound 1 displayed moderate activity against drug sensitive (3D7) and drug resistant (Dd2) strains of the parasite, Plasmodium falciparum, responsible for malaria.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Animals
Antimalarials / chemistry
Antimalarials / pharmacology*
Australia
Isoquinolines / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
Plasmodium falciparum
Porifera / chemistry*

Substances

Alkaloids
Antimalarials
Isoquinolines
Plant Extracts