Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I.
The first synthesis of two possible diastereomers of tonkinelin was achieved. By comparison of the optical rotation of two candidates of tonkinelin and the natural compound, it is suggested that the absolute configuration of natural tonkinelin is likely to be (17S,18S). The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin.
Hattori
Yasunao
Y
Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano 399-4598, Japan.
Konno
Hiroyuki
H
Abe
Masato
M
Miyoshi
Hideto
H
Goto
Tetsuhisa
T
Makabe
Hidefumi
H
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002417:Cattle; D018360:Crystallography, X-Ray; D042967:Electron Transport Complex I / Q000037:antagonists & inhibitors*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009206:Myocardium / Q000378:metabolism*; D009243:NAD / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; C103691:tonkinelin; D009243:NAD; D042967:Electron Transport Complex I