Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings.
The presence of two hydroxy groups adjacent to the THF ring(s) is a common structural feature of natural acetogenins. To elucidate the role of each hydroxy group in the inhibitory action of acetogenins, we synthesized three acetogenin analogues which lack either or both of the hydroxy groups, and investigated their inhibitory activities with bovine heart mitochondrial complex I. Our results indicate that the presence of either of the two hydroxy groups sufficiently sustains a potent inhibitory effect.
Abe
Masato
M
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
Kenmochi
Atsushi
A
Ichimaru
Naoya
N
Hamada
Takeshi
T
Nishioka
Takaaki
T
Miyoshi
Hideto
H
D054378:Acetogenins; D000818:Animals; D002417:Cattle; D042967:Electron Transport Complex I / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D005233:Fatty Alcohols / Q000737:chemistry* / Q000494:pharmacology; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology; D017665:Hydroxyl Radical / Q000737:chemistry; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology; D008929:Mitochondria, Heart / Q000187:drug effects* / Q000201:enzymology; D008968:Molecular Conformation; D015394:Molecular Structure; D009097:Multienzyme Complexes / Q000378:metabolism; D009247:NADH, NADPH Oxidoreductases / Q000378:metabolism; D013329:Structure-Activity Relationship
D054378:Acetogenins; D004791:Enzyme Inhibitors; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; D009097:Multienzyme Complexes; C112079:isomurisolenin; D017665:Hydroxyl Radical; C018674:tetrahydrofuran; C023107:NADH oxidase; D009247:NADH, NADPH Oxidoreductases; D042967:Electron Transport Complex I