Grenadadiene and grenadamide, cyclopropyl-containing fatty acid metabolites from the marine cyanobacterium Lyngbya majuscula.
Grenadadiene (1), debromogrenadiene (2), and grenadamide (3), three structurally unique cyclopropyl-containing metabolites, were isolated from the organic extract of a Grenada collection of the marine cyanobacterium Lyngbya majuscula. The structures and the relative stereochemistries of these compounds were determined using spectroscopic methods. These are the first reported cyclopropyl-containing fatty acid derivatives from a Lyngbya sp. Grenadadiene (1) has an interesting profile of cytotoxicity in the NCI 60 cell line assay, while grenadamide (2) exhibited modest brine shrimp toxicity (LD50 = 5 microg/mL) and cannabinoid receptor binding activity (Ki = 4.7 microM).
Sitachitta
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College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.
Gerwick
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D000577:Amides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000458:Cyanobacteria / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D033364:Decapoda / Q000187:drug effects; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000577:Amides; D003521:Cyclopropanes; D004952:Esters; C112730:grenadadiene; C112731:grenadamide