Albopunctatone, an antiplasmodial anthrone-anthraquinone from the Australian ascidian Didemnum albopunctatum.
Chemical investigation of a MeOH extract of the Great Barrier Reef ascidian Didemnum albopunctatum has led to the isolation and identification of a new anthrone-anthraquinone, albopunctatone (1), together with the known 1,8-dihydroxy-9,10-anthraquinone (2). The structure of 1 was established from interpretation of 1D and 2D NMR spectroscopic and mass spectrometric data. The compounds were screened for antiplasmodial activity against chloroquine-resistant and -sensitive strains of the malaria parasite, Plasmodium falciparum. Albopunctatone (1) was moderately active against both strains (IC(50) 5.3 and 4.4 ± 0.5 μM, respectively), while 2 was inactive at doses up to 40 μM. Both compounds were also inactive up to 40 μM when tested against a variety of cancerous and normal human cell lines and the kinetoplastid Trypanosoma brucei brucei, indicating selectivity for the malaria parasite, P. falciparum.
School of Environment, Griffith University, Gold Coast, QLD 4222, Australia. a.carroll@girffith.edu.au
Anthony R
AR
Carroll
Brittney D
BD
Nash
Sandra
S
Duffy
Vicky M
VM
Avery
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001315:Australia; D002738:Chloroquine / Q000494:pharmacology; D004351:Drug Resistance; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D014346:Trypanosoma brucei brucei / Q000187:drug effects; D014561:Urochordata / Q000737:chemistry*
D000880:Anthraquinones; D000962:Antimalarials; D000970:Antineoplastic Agents; C574883:albopunctatone; D002738:Chloroquine; C004315:danthron