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

Yasunao Hattori; Yuka Kimura; Aki Moroda; Hiroyuki Konno; Masato Abe; Hideto Miyoshi; Tetsuhisa Goto; Hidefumi Makabe

doi:10.1002/asia.200600261

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

Chem Asian J. 2006 Dec 18;1(6):894-904. doi: 10.1002/asia.200600261.

Authors

Yasunao Hattori¹, Yuka Kimura, Aki Moroda, Hiroyuki Konno, Masato Abe, Hideto Miyoshi, Tetsuhisa Goto, Hidefumi Makabe

Affiliation

¹ Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-Minowa, Kamiina, Nagano 399-4598, Japan.

PMID: 17441133
DOI: 10.1002/asia.200600261

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cattle
Electron Transport Complex I / antagonists & inhibitors*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Furans / chemical synthesis*
Furans / chemistry
Furans / pharmacology
Lactones / chemical synthesis*
Lactones / chemistry
Lactones / pharmacology
Magnetic Resonance Spectroscopy
Mitochondria, Heart* / drug effects
Mitochondria, Heart* / enzymology
Molecular Structure
Stereoisomerism

Substances

Enzyme Inhibitors
Furans
Lactones
murisolin
Electron Transport Complex I