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

Cryptocapsinepoxide-type carotenoids from red mamey, Pouteria sapota.

Author information

1
Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Szigeti út 12, 7624 Pécs, Hungary.

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.

PMID:
23451823
DOI:
10.1021/np3007827
[Indexed for MEDLINE]

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