Lipoxygenase inhibitors derived from marine macroalgae.
The solvent extracts from the algae Sargassum thunbergii (Sargassaceae) and Odonthalia corymbifera (Rhodomelaceae) were subjected to soybean lipoxygenase inhibitory screening. Two hydrophobic inhibitors were obtained from the extracts of S. thunbergii through inhibitory assay-guided fractionation. The inhibitors were identified as known exo-methylenic alkapolyenes (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene (1) and (6Z,9Z,12Z,15Z,18Z)-1,6,9,12,15,18-henicosahexaene (2). The alkapolyenes 1 and 2 showed higher inhibitory activity than the known inhibitor nordihydroguaiaretic acid (NDGA). Pheophytin a (3) was obtained from the extract of O. corymbifera. The inhibitor 3 also showed higher inhibitory activity than NDGA. This is the first report on lipoxygenase inhibition of exo-methylenic alkapolyenes and a chlorophyll a-related substance.
Faculty and Graduate School of Fisheries Sciences, Hokkaido University, Minato, Hakodate, Hokkaido 041-8611, Japan. Electronic address: kuri@fish.hokudai.ac.jp.
Hideyuki
H
Kurihara
Faculty and Graduate School of Fisheries Sciences, Hokkaido University, Minato, Hakodate, Hokkaido 041-8611, Japan.
Yoshio
Y
Kagawa
Faculty and Graduate School of Fisheries Sciences, Hokkaido University, Minato, Hakodate, Hokkaido 041-8611, Japan.
Remi
R
Konno
Department of Marine Bioscience and Technology, Gangneung-Wonju National University, Gangneung 210-702, Republic of Korea.
Sang Moo
SM
Kim
Faculty and Graduate School of Fisheries Sciences, Hokkaido University, Minato, Hakodate, Hokkaido 041-8611, Japan.
Koretaro
K
Takahashi
D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004789:Enzyme Activation / Q000187:drug effects; D008084:Lipoxygenase / Q000737:chemistry* / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D010674:Pheophytins / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D011090:Polyenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D011485:Protein Binding; D012624:Seaweed / Q000737:chemistry* / Q000378:metabolism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C000592658:1,6,9,12,15,18-henicosahexaene; C000592657:1,6,9,12,15-henicosapentaene; D001549:Benzamides; D016859:Lipoxygenase Inhibitors; D010674:Pheophytins; D011090:Polyenes; D013450:Sulfones; C061694:pheophytin a; D008084:Lipoxygenase
Alkapolyene; Inhibitor; Lipoxygenase; Odonthalia corymbifera; Pheophytin a; Sargassum thunbergii