Three new anti-proliferative Annonaceous acetogenins with mono-tetrahydrofuran ring from graviola fruit (Annona muricata)

Shi Sun; Jingchun Liu; Hoda Kadouh; Xiuxiu Sun; Kequan Zhou

doi:10.1016/j.bmcl.2014.03.099

Three new anti-proliferative Annonaceous acetogenins with mono-tetrahydrofuran ring from graviola fruit (Annona muricata)

Bioorg Med Chem Lett. 2014 Jun 15;24(12):2773-6. doi: 10.1016/j.bmcl.2014.03.099. Epub 2014 Apr 18.

Authors

Shi Sun¹, Jingchun Liu¹, Hoda Kadouh¹, Xiuxiu Sun¹, Kequan Zhou²

Affiliations

¹ Department of Nutrition and Food Science, Wayne State University, Detroit, MI 48201, USA.
² Department of Nutrition and Food Science, Wayne State University, Detroit, MI 48201, USA. Electronic address: kzhou@wayne.edu.

PMID: 24780120
DOI: 10.1016/j.bmcl.2014.03.099

Abstract

Bioassay-guided fractionation of the fruit powder of graviola (Annona muricata) yielded three novel compounds: muricins J, K, and L. The compounds are all C35 Annonaceous acetogenins with a mono-tetrahydrofuran ring and four hydroxyls. Their structures were elucidated by spectral methods and chemical modification after isolation via chromatographic techniques and HPLC purification. These three acetogenins demonstrated an antiproliferative against human prostate cancer PC-3 cells.

Keywords: Acetogenin; Annona muricata; Cytotoxicity; Human prostate cancer; Muricin.

MeSH terms

Acetogenins / chemistry
Acetogenins / isolation & purification
Acetogenins / pharmacology*
Annona / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cell Proliferation / drug effects
Chromatography, High Pressure Liquid
Fruit / chemistry
Furans / chemistry*
Humans
Magnetic Resonance Spectroscopy
Male
Molecular Structure
Prostatic Neoplasms / drug therapy

Substances

Acetogenins
Antineoplastic Agents, Phytogenic
Furans
muricin J
muricin K
muricin L
tetrahydrofuran