Isolation of β‑Cryptoxanthin-epoxides, Precursors of Cryptocapsin and 3′-Deoxycapsanthin, from Red Mamey (Pouteria sapota)

• Published in: Journal of agricultural and food chemistry 2015-07, Vol.63 (26), p.6059-6065
• Main Authors: Turcsi, Erika, Murillo, Enrique, Kurtán, Tibor, Szappanos, Ádám, Illyés, Tünde-Zita, Gulyás-Fekete, Gergely, Agócs, Attila, Avar, Péter, Deli, József
• Format: Article
• Language: English
• Subjects: beta-cryptoxanthin; Capsaicin - chemistry; Capsaicin - isolation & purification; Carotenoids - chemistry; Carotenoids - isolation & purification; Circular Dichroism; circular dichroism spectroscopy; Cryptoxanthins - chemistry; Cryptoxanthins - isolation & purification; diet; Epoxy Compounds - chemistry; Epoxy Compounds - isolation & purification; Fruit - chemistry; fruits; high performance liquid chromatography; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; nuclear magnetic resonance spectroscopy; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Pouteria - chemistry; Pouteria sapota; provitamins; vitamin A
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.5b01936

From an extract of red mamey (Pouteria sapota) β-cryptoxanthin-5,6-epoxide, β-cryptoxanthin-5′,6′-epoxide, 3′-deoxycapsanthin, and cryptocapsin were isolated and characterized by UV–vis spectroscopy, electronic circular dichroism (ECD), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). Epoxidation of β-cryptoxanthin delivered the β-(5′R,6′S)- and (5′S,6′R)-cryptoxanthin-5′,6′-epoxides, which were identified by HPLC-ECD analysis. These carotenoids among others are quite common in the fruits of Central America, and as they are natural provitamins A, they should play an important role in the diet of the mostly vitamin A deficient population of this region.