Antibacterial neurymenolides from the Fijian red alga Neurymenia fraxinifolia.
Two novel alpha-pyrone macrolides, neurymenolides A (1) and B (2), were isolated from the Fijian red alga Neurymenia fraxinifolia and characterized using a combination of NMR and mass spectral analyses. These molecules represent only the second example of alpha-pyrone macrolides, with 1 existing as interchanging atropisomers due to restricted rotation about the alpha-pyrone ring system. Neurymenolide A (1) displayed moderately potent activities against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF).
Stout
E Paige
EP
School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA.
Hasemeyer
Adam P
AP
Lane
Amy L
AL
Davenport
Theresa M
TM
Engel
Sebastian
S
Hay
Mark E
ME
Fairchild
Craig R
CR
Prudhomme
Jacques
J
Le Roch
Karine
K
Aalbersberg
William
W
Kubanek
Julia
J
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D016984:Enterococcus faecium / Q000187:drug effects; D018942:Macrolides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000461:Rhodophyta / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D018942:Macrolides; D011753:Pyrones; C534975:neurymenolide A; C534976:neurymenolide B