Cryptocapsinepoxide-type Carotenoids from Red Mamey, Pouteria sapota

Gulyás-Fekete, Gergely and Murillo, Enrique and Kurtán, Tibor and Papp, Tamás and Illyés, Tünde-Zita and Drahos, László and Visy, Júlia and Agócs, Attila and Turcsi, Erika and Deli, József (2013) Cryptocapsinepoxide-type Carotenoids from Red Mamey, Pouteria sapota. Journal of Natural Products. pp. 1-23. ISSN 0163-3864

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Abstract

Three new carotenoids, cryptocapsin-5,6-epoxide, 3ʹ-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.

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