Home
Resources
Publications
An Epoxide-Furanoid Rearrangement of Spinach Neoxanthin Occurs in the Gastrointestinal Tract of Mice and in Vitro: Formation and Cytostatic Activity of Neochrome Stereoisomers

An Epoxide-Furanoid Rearrangement of Spinach Neoxanthin Occurs in the Gastrointestinal Tract of Mice and in Vitro: Formation and Cytostatic Activity of Neochrome Stereoisomers

Akira Asai, Masaru Terasaki, Akihiko Nagao

J Nutr. 2004 Sep;134(9):2237-43.

PMID: 15333710

Abstract:

Neoxanthin, a major carotenoid in green leafy vegetables, was reported to exhibit potent antiproliferative effect via apoptosis induction on human prostate cancer cells. However, the metabolic fate of dietary neoxanthin in mammals remains unknown. In the present study, we investigated the gastrointestinal metabolism of neoxanthin in mice and the in vitro digestion of spinach, and estimated the antiproliferative effect of neoxanthin metabolites on PC-3 human prostate cancer cells. Two hours after the oral administration to mice of purified neoxanthin, unchanged neoxanthin and stereoisomers of neochrome (8'-R/S) were detected in the plasma, liver, and small intestinal contents. To estimate the effect of intragastric acidity on the conversion of dietary neoxanthin into neochrome (epoxide-furanoid rearrangement), spinach was digested in vitro by incubating it with a pepsin-HCl solution at pH 2.0 or 3.0 (gastric phase) followed by a pancreatin-bile salt solution (intestinal phase). Spinach neoxanthin was largely converted into (R/S)-neochrome during the digestion when the gastric phase was set at pH 2.0, whereas the rearrangement was observed to a lesser extent at pH 3.0. (R/S)-neochrome dose-dependently inhibited the proliferation of PC-3 cells as well as neoxanthin at concentrations < or = 20 micromol/L. Although neoxanthin induced evident apoptotic cell death, (R/S)-neochrome inhibited the cell proliferation without obvious apoptosis induction. These results indicate that dietary neoxanthin is partially converted into (R/S)-neochrome by intragastric acidity before intestinal absorption and that (R/S)-neochrome exhibits an antiproliferative effect on PC-3 cells by the induction of cytostasis.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP14660914	Neoxanthin		14660-91-4	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: