Psammaplysin Derivatives from the Balinese Marine Sponge Aplysinella strongylata

• Published in: Journal of natural products (Washington, D.C.) Vol. 75; no. 12; pp. 2132 - 2143
• Main Authors: Mudianta, I Wayan, Skinner-Adams, Tina, Andrews, Katherine T, Davis, Rohan A, Hadi, Tri A, Hayes, Patricia Y, Garson, Mary J
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society and American Society of Pharmacognosy 28-12-2012
• Subjects: Animals; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; Aplysinella; Chloroquine - pharmacology; Fatty Acids - chemistry; Gas Chromatography-Mass Spectrometry; Hydrocarbons, Brominated - chemistry; Hydrocarbons, Brominated - isolation & purification; Hydrocarbons, Brominated - pharmacology; Indonesia; Inhibitory Concentration 50; Malaria - drug therapy; Marine; Molecular Structure; Plasmodium falciparum; Plasmodium falciparum - drug effects; Porifera - chemistry; Spiro Compounds - chemistry; Spiro Compounds - isolation & purification; Spiro Compounds - pharmacology; Stereoisomerism; Indonesia
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np300560b

Twenty-one new psammaplysin derivatives (4–24) exhibiting a variety of side chains, as well as six previously known psammaplysins, were identified from the Indonesian marine sponge Aplysinella strongylata. The double bond on the side chain of the fatty acid-containing psammaplysins was located by GC-MS analysis of the fatty acid methyl esters and their pyrrolidide derivatives. HPLC and Mosher ester studies confirmed that the isolated metabolites possessing a 19-OH substituent were mixtures of diastereomers. Selected compounds (4, 5, 7, 8, 12, 18, and 22) were screened for in vitro activity against chloroquine-sensitive (3D7) P. falciparum malaria parasites. Of the new psammaplysins, 19-hydroxypsammaplysin E (4) showed the best antimalarial activity, with an IC50 value of 6.4 μM.