Cryptocapsinepoxide-type carotenoids from red mamey, Pouteria sapota

J Nat Prod. 2013 Apr 26;76(4):607-14. doi: 10.1021/np3007827. Epub 2013 Mar 1.

Abstract

New carotenoids, cryptocapsin-5,6-epoxide, 3'-deoxycapsanthin-5,6-epoxide, and cryptocapsin-5,8-epoxides, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Cryptocapsin-5,6-epoxide was prepared by partial synthesis via epoxidation of cryptocapsin, and the (5R,6S)- and (5S,6R)-stereoisomers were identified by HPLC-ECD analysis. Spectroscopic data of the natural (anti) and semisynthetic (syn) derivatives obtained by acid-catalyzed rearrangement of cryptocapsin-5,8-epoxide stereoisomers were compared for structural elucidation. Chiral HPLC separation of natural and semisynthetic samples of cryptocapsin-5,8-epoxides was performed, and HPLC-ECD analysis allowed configurational assignment of the separated stereoisomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carotenoids / chemistry
  • Carotenoids / isolation & purification*
  • Chromatography, High Pressure Liquid
  • Fruit / chemistry
  • Nuclear Magnetic Resonance, Biomolecular
  • Pouteria / chemistry*
  • Stereoisomerism

Substances

  • 3'-deoxycapsanthin-5,6-epoxide
  • cryptocapsin-5,6-epoxide
  • cryptocapsin-5,8-epoxide
  • Carotenoids