Chirality. 2020 May;32(5):579-587.

Isolation and identification of sapotexan-thin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).

Enrique Murillo, Attila Agócs Veronika Nagy Sándor Balázs Király Tibor Kurtán, Eunice

Molinar Toribio, Johant Lakey‐Beitia, József Deli.

Abstract:

Two new carotenoids, sapotexanthin 5,6-epoxide and sapotex-anthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-performance liquid chromatography-electronic circular dichro-ism (HPLC-ECD) analysis. Spectroscopic data of the natural and semisynthetic derivatives obtained by acid-catalyzed rearrange-ment of cryptocapsin 5,8-epoxide stereoisomers were compared for structural elucidation.