Malyngolide dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula.
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.
Gutiérrez
Marcelino
M
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093, USA.
Tidgewell
Kevin
K
Capson
Todd L
TL
Engene
Niclas
N
Almanza
Alejandro
A
Schemies
Jörg
J
Jung
Manfred
M
Gerwick
William H
WH
D002738:Chloroquine / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry*; D004351:Drug Resistance / Q000187:drug effects; D004988:Ethers, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification; D008235:Lyngbya Toxins / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects*; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
D004988:Ethers, Cyclic; D007783:Lactones; D008235:Lyngbya Toxins; D011753:Pyrones; C549714:malyngolide dimer; C400156:tanikolide; C065487:malyngolide; D002738:Chloroquine