Cryptocapsinepoxide-type carotenoids from red mamey, Pouteria sapota

Gergely Gulyás-Fekete, Enrique Murillo, Tibor Kurtán, Tamás Papp, Tünde Zita Illyés, László Drahos, Júlia Visy, Attila Agócs, Erika Turcsi, József Deli

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17 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)607-614
Number of pages8
JournalJournal of Natural Products
Volume76
Issue number4
DOIs
Publication statusPublished - Apr 26 2013

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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