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Isolation and identification of sapotexanthin 5,6‐epoxide and 5,8‐epoxide from red mamey ( Pouteria sapota )
Author(s) -
Murillo Enrique,
Agócs Attila,
Nagy Veronika,
Király Sándor Balázs,
Kurtán Tibor,
Toribio Eunice Molinar,
LakeyBeitia Johant,
Deli József
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23206
Subject(s) - epoxide , chemistry , circular dichroism , stereochemistry , organic chemistry , chromatography , catalysis
Two new carotenoids, sapotexanthin 5,6‐epoxide and sapotexanthin 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 (5 R ,6 S ) and (5 S ,6 R ) stereoisomers were identified by high‐performance liquid chromatography–electronic circular dichroism (HPLC‐ECD) analysis. Spectroscopic data of the natural and semisynthetic derivatives obtained by acid‐catalyzed rearrangement of cryptocapsin 5,8‐epoxide stereoisomers were compared for structural elucidation.