Malyngamide H, an ichthyotoxic amide possessing a new carbon skeleton from the Caribbean cyanobacterium Lyngbya majuscula.
Guided by ichthyotoxic activity against goldfish, a new lipopeptide, malyngamide H [1], and its corresponding free acid, 7-methoxytetradec-4(E)-enoic acid [2], have been isolated from the tropical marine cyanobacterium Lyngbya majuscula. The structure of the new carbon skeleton borne by malyngamide H was elucidated on the basis of spectroscopic analysis, mainly 2D nmr. The absolute stereochemistry of the cyclohexenone moiety of malyngamide H [1] was deduced by a combination of 2D NOESY and exciton chirality circular dichroism spectroscopy.
Orjala
J
J
College of Pharmacy, Oregon State University, Corvallis 97331, USA.
Nagle
D
D
Gerwick
W H
WH
D000818:Animals; D002852:Chromatography, Ion Exchange; D002942:Circular Dichroism; D000458:Cyanobacteria / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D006054:Goldfish; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D014118:Toxins, Biological / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity
D003512:Cyclohexanones; D005229:Fatty Acids, Monounsaturated; D014118:Toxins, Biological; C094711:malyngamide H