Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii.
Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50value of 2.5 μM and induced apoptosis-like cell death.
Department of Chemistry, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Shimpei
S
Sumimoto
Department of Chemistry, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Arihiro
A
Iwasaki
Department of Chemistry and Life Science, Kogakuin University , 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan.
Osamu
O
Ohno
Faculty of Education, University of the Ryukyus , 1 Senbaru, Nishihara, Okinawa 903-0213, Japan.
Kosuke
K
Sueyoshi
Faculty of Education, University of the Ryukyus , 1 Senbaru, Nishihara, Okinawa 903-0213, Japan.
Toshiaki
T
Teruya
Department of Chemistry, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Kiyotake
K
Suenaga
D000144:Acids, Acyclic / Q000302:isolation & purification* / Q000494:pharmacology; D000577:Amides / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects*; D059001:Aquatic Organisms / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D000458:Cyanobacteria / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D013237:Stereoisomerism
D000144:Acids, Acyclic; D000577:Amides; D000970:Antineoplastic Agents