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. 2010 Apr 23;73(4):709-11.
doi: 10.1021/np9005184.

Malyngolide dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula

Marcelino Gutiérrez  1 , Kevin Tidgewell, Todd L Capson, Niclas Engene, Alejandro Almanza, Jörg Schemies, Manfred Jung, William H Gerwick
Affiliations

Malyngolide dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula

Marcelino Gutiérrez et al. J Nat Prod. .

Abstract

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.

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Figures

Figure 1
Figure 1
Selected 2D NMR correlations for malyngolide dimer (1).
Figure 1
Figure 1
Selected 2D NMR correlations for malyngolide dimer (1).
See this image and copyright information in PMC

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