Sapotexanthin, an A-Provitamin Carotenoid from Red Mamey (Pouteria sapota)

Abstract

From the ripe fruits of red mamey (Pouteria sapota) sapotexanthin, a new carotenoid, was identified as (all-E,5'R)-β,κ-caroten-6'-one.

Anti-amyloid aggregation activity of novel carotenoids: implications for Alzheimer’s drug discovery

“…Two carotenoids, cryptocapsin and cryptocapsin-5, 6- epoxide presenting a keto κ-ring at one end of the molecule, bearing hydroxyl groups, were isolated from the extracts of P. sapota fruit. The presence of these carotenoids in P. sapota fruit was identified earlier by Murillo et al20,22 On the other hand, zeaxanthin, a carotenoid bearing only β-ionone hydroxylated rings, was isolated from A. aculeata extract. This carotenoid was previously reported in A. aculeate fruit 16,23.…”

“…Carotenoid standards were extracted and isolated from the fruits according to recommended procedures 19,20. Five hundred grams of P. sapota pulp and A. aculeate were homogenized separately with 50 g of NaHCO 3 and extracted exhaustively with acetone.…”

Cryptocapsinepoxide-Type Carotenoids from Red Mamey, Pouteria sapota

“…16 Repeated column chromatography of the mamey extract on Al 2 O 3 and CaCO 3 yielded 8 mg cryptocapsin (3), 4 mg cryptocapsin-5,6-epoxide (5), 0.5 mg 3ʹ-deoxycapsanthin-5,6-epoxide (6), 0.5 mg -cryptoxanthin-5,6,5ʹ,6ʹ-diepoxide (8), and 1.5 mg of an epimeric mixture of cryptocapsin-5,8-epoxides (11,12).…”

“…Plants with high concentrations of ketocarotenoids have been reported in fruits such as 'mamey' (Pouteria sapota), 'maracuya chino' (Cionosicyos macranthus), 'jipijapa' (Carludovica palmata), and in young red-brown leaves and red seeds of Zamia dressleri. 15 We have reported the isolation of sapotexanthin [(5R)-,-caroten-6-one, (4)], 16 3ʹ-deoxycapsorubin, and 3,3ʹ-dideoxycapsorubin, Herein, the isolation of the new carotenoids cryptocapsin-5,6-epoxide (5), 3ʹ-deoxycapsanthin-5,6-epoxide (6), and cryptocapsin-5,8-epoxides (11,12) is reported from the fruits of red mamey. Cryptocapsin-5,6-epoxide (5) was prepared by the epoxidation of cryptocapsin (3) as a reference compound.…”

Isolation and identification of sapotexanthin 5,6‐epoxide and 5,8‐epoxide from red mamey (Pouteria sapota)

“…Notably, the pulp of red mamey contains several other interesting red carotenoids associated with hydroxylated or nonhydroxylated κ‐rings. We have reported earlier the isolation of sapotexanthin ( 2 ), cryptocapsin 5,6‐epoxide ( 4 ) and 5,8‐epoxide ( 5 ), 3′‐deoxycapsanthin, 3′‐deoxycapsanthin 5,6‐epoxide, 3′‐deoxycapsorubin, and 3,3′‐dideoxycapsorubin (Figures and ) . Several precursors related to the above‐mentioned carotenoids, specifically β‐cryptoxanthin 5,6‐epoxide and 5′,6′‐epoxide and 5,6,5′,6′‐diepoxide, were isolated in our laboratories .…”