tanikolide and malyngolide

Fractionation of the extract of the marine cyanobacterium Lyngbya majuscula collected from Panama led to the isolation of malyngolide dimer (1). The planar structure of 1 was determined using 1D and 2D NMR spectroscopy and HRESI-TOFMS. The absolute configuration was established by chemical degradation followed by chiral GC-MS analyses and comparisons with an authentic sample of malyngolide seco-acid (4). Compound 1 showed moderate in vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum (W2) (IC(50) = 19 microM) but roughly equivalent toxicity against H-460 human lung cell lines. Furthermore, because the closely related cyanobacterial natural product tanikolide dimer (5) was a potent SIRT2 inhibitor, compound 1 was evaluated in this assay but found to be essentially inactive.

Topics: Chloroquine; Cyanobacteria; Drug Resistance; Ethers, Cyclic; Humans; Lactones; Lyngbya Toxins; Marine Biology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Panama; Parasitic Sensitivity Tests; Plasmodium falciparum; Pyrones; Structure-Activity Relationship