Synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin and their inhibitory action with bovine heart mitochondrial complex I.
The asymmetric total synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin was performed by using an epoxy alcohol as a versatile chiral building block for synthesizing the stereoisomers of mono-THF annonaceous acetogenins. The inhibitory activity of these murisolin compounds was examined with bovine heart mitochondrial complex I, and they showed almost the same activity.
Hattori
Yasunao
Y
Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-Minowa, Kamiina, Nagano 399-4598, Japan.
Kimura
Yuka
Y
Moroda
Aki
A
Konno
Hiroyuki
H
Abe
Masato
M
Miyoshi
Hideto
H
Goto
Tetsuhisa
T
Makabe
Hidefumi
H
D000818:Animals; D002417:Cattle; D042967:Electron Transport Complex I / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008929:Mitochondria, Heart / Q000187:drug effects / Q000201:enzymology; D015394:Molecular Structure; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D005663:Furans; D007783:Lactones; C507543:murisolin; D042967:Electron Transport Complex I