Structure–activity relationship of avocadyne

Matthew Tcheng; Vitor L. S. Cunha; Nawaz Ahmed; Xiaofan Liu; Richard W. Smith; Kevin A. Rea; Tariq A. Akhtar; Angelo D'Alessandro; Mark D. Minden; Jerry Vockley; George A. O'Doherty; Todd L. Lowary; Paul A. Spagnuolo

doi:10.1039/D1FO00693B

Structure–activity relationship of avocadyne†

Matthew Tcheng,^a Vitor L. S. Cunha,^b Nawaz Ahmed,^a Xiaofan Liu,^c Richard W. Smith,^d Kevin A. Rea,^e Tariq A. Akhtar,^e Angelo D'Alessandro,^f Mark D. Minden,^g Jerry Vockley,^hi George A. O'Doherty,^c Todd L. Lowary

^bj and Paul A. Spagnuolo

*^a

Author affiliations

* Corresponding authors

^a Department of Food Science, University of Guelph, 50 Stone Rd., Guelph, Ontario, Canada
E-mail: paul.spagnuolo@uoguelph.ca
Tel: +(519) 824-4120 x53732

^b Department of Chemistry, University of Alberta, 4-008 Centennial Centre for Interdisciplinary Science, Edmonton, AB, Canada

^c Department of Biochemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, USA

^d University of Waterloo Mass Spectrometry Facility, Department of Chemistry, 200 University Avenue West, Waterloo, ON, Canada

^e Department of Molecular and Cellular Biology, Department of Biochemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA, USA

^f Department of Biochemistry and Molecular Genetics, University of Colorado Anschutz Medical Campus, Aurora, CO, USA

^g Princess Margaret Cancer Center, Ontario Cancer Institute, 610 University Ave, Toronto, ON, Canada

^h Department of Pediatrics and Center for Rare Disease Therapy, UPMC, Children's Hospital of Pittsburgh, University of Pittsburgh, Pittsburgh, PA 15224, USA

ⁱ Department of Human Genetics, School of Public Health, University of Pittsburgh, Pittsburgh, PA 15260, USA

^j Institute of Biological Chemistry, Academia Sinica, Academia Road, Section 2, #128, Nangang, Taipei, Taiwan

Abstract

Avocado consumption is associated with numerous health benefits. Avocadyne is a terminally unsaturated, 17-carbon long acetogenin found almost exclusively in avocados with noted anti-leukemia and anti-viral properties. In this study, specific structural features such as the terminal triple bond, odd number of carbons, and stereochemistry are shown to be critical to its ability to suppress mitochondrial fatty acid oxidation and impart selective activity in vitro and in vivo. Together, this is the first study to conduct a structure–activity analysis on avocadyne and outline the chemical moieties critical to fatty acid oxidation suppression.

Food & Function

Structure–activity relationship of avocadyne†

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