Motualevic acids A-F, antimicrobial acids from the sponge Siliquariaspongia sp.
Seven new antibacterials, motualevic acids A-F (1-6) and (4E)-(R)-antazirine (7), have been isolated from the marine sponge Siliquariaspongia sp. and their structures elucidated by spectroscopic methods. Motualevic acids A-D are the first glycyl conjugates of the omega-brominated lipid (E)-14,14-dibromotetradeca-2,13-dienoic acid, and motualevic acid F is the first long-chain 2H-azirine 2-carboxylic acid to be found in nature. Carboxylic acid-containing compounds 1 and 6 inhibit the growth of Staphylococcus aureus and methicillin-resistant S. aureus at 1.2-10.9 microg/mL.
Keffer
Jessica L
JL
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892, USA.
Plaza
Alberto
A
Bewley
Carole A
CA
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008386:Marine Biology; D016106:Methicillin Resistance / Q000187:drug effects; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D001389:Azirines; D006842:Hydrocarbons, Brominated; C096953:antazirine