Lutein dimyristate

Carotenoid and Carotenoid Ester Profile and Their Deposition in Plastids in Fruits of New Papaya (Carica papaya L.) Varieties from the Canary Islands.[Pubmed:33671129]

Foods. 2021 Feb 17;10(2):434.

The carotenoid profile of non-saponified and saponified extracts of different tissues (pulp and peel) of fruits of three new papaya varieties, Sweet Mary, Alicia, and Eksotika, was characterized for the first time, and almost all carotenoid compounds were quantified. Carotenoids and carotenoid esters were analyzed and characterized using HPLC-photo diode array (PDA-MS with atmospheric pressure chemical ionization with positive ion mode (APCI(+)) with a C(30) reversed-phase column. The carotenoid deposition in collenchyma and chlorenchyma cells of papaya pulp and peel tissues was assessed by optical microscopy, confocal laser scanning microscopy, and transmission electron microscopy. The most abundant carotenoids in the fruit of the three papaya varieties (pulp and peel) were (all-E)-lycopene (230.0-421.2 microg/100 g fresh weight), (all-E)-beta-carotene (120.3-233.2 microg/100 g fresh weight), and (all-E)-beta-cryptoxanthin laurate (74.4-223.2 microg/100 g fresh weight. Moreover, high concentrations of (all-E)-lutein (922.5-1381.1 microg/100 g fresh weight) and its esters, such as (all-E)-lutein-3-O-myristate and (all-E)-Lutein dimyristate, were found in peel extracts. The optical microscopy study of papaya pulps showed that carotenoid deposition in all papaya varieties, including Maradol, was mainly localized close to the cell walls, showing the presence of some crystalloids and round-shaped structures, with different sizes and distribution due to the different carotenoid content among varieties. No crystalloids or globular depositions were found in any of the peel sections, and no remarkable differences were found in the papaya peel microstructure of the different papaya varieties.

Carotenoids and xanthophyll esters of yellow and red nance fruits (Byrsonima crassifolia (L.) Kunth) from Costa Rica.[Pubmed:30007736]

Food Res Int. 2018 Sep;111:708-714.

Carotenoid profiles, by means of HPLC-PDA-MS(n), and CIE-L*C*h degrees colour values of yellow and red nance fruits from Costa Rica were elucidated. Among 16 carotenoids detected, (all-E)-lutein was the most abundant accounting for >80% of the total carotenoids, followed by (all-E)-zeaxanthin (9-11%) and (all-E)-beta-carotene (2-9%). Minor constituents were (Z)-isomers of lutein and beta-carotene, as well as diverse lutein diesters. Among the esters, Lutein dimyristate was the most abundant as substantiated by the comparison with a marigold flower extract. Total carotenoids in the peel (616.2 mug/100 g of FW in yellow nance and 174.2 mug/100 g of FW in red nance) were higher than in the pulp (39.4 mug/100 g of FW in yellow nance and 31.4 mug/100 g of FW in red nance). Since carotenoid profiles of yellow and red varieties were qualitatively similar, although the colour values showed significant differences (77.2 and 88.6 h degrees in peel and pulp of yellow nance, versus 32.7 and 67.3 h degrees in peel and pulp of red nance, respectively), pigments other than carotenoids may impart the colour of red nance. High lutein content renders nance fruit as a nutritionally relevant source of this micronutrient.

Differentiation between lutein monoester regioisomers and detection of lutein diesters from marigold flowers (Tagetes erecta L.) and several fruits by liquid chromatography-mass spectrometry.[Pubmed:11754543]

J Agric Food Chem. 2002 Jan 2;50(1):66-70.

Liquid chromatography-atmospheric pressure chemical ionization mass spectrometry (LC-APCIMS) was employed for the identification of eight lutein monoesters, formed by incomplete enzymatic saponification of lutein diesters of marigold (Tagetes erecta L.) by Candida rugosa lipase. Additionally, the main lutein diesters naturally occurring in marigold oleoresin were chromatographically separated and identified. The LC-MS method allows for characterization of lutein diesters occurring as minor components in several fruits; this was demonstrated by analysis of extracts of cape gooseberry (Physalis peruviana L.), kiwano (Cucumis metuliferus E. Mey. ex Naud.), and pumpkin (Cucurbita pepo L.). The assignment of the regioisomers of lutein monoesters is based on the characteristic fragmentation pattern: the most intense daughter ion generally results from the loss of the substituent (fatty acid or hydroxyl group) bound to the epsilon-ionone ring, yielding an allylic cation. The limit of detection was estimated at 0.5 microg/mL with Lutein dimyristate as reference compound. This method provides a useful tool to obtain further insight into the biochemical reactions leading to lutein ester formation in plants.

Carotenoid esters in vegetables and fruits: a screening with emphasis on beta-cryptoxanthin esters.[Pubmed:11308368]

J Agric Food Chem. 2001 Apr;49(4):2064-70.

Carotenoids are found in food plants in free form or as fatty acid esters. Most studies have been carried out after saponification procedures, so the resulting data do not represent the native carotenoid composition of plant tissues. Therefore, nonsaponified extracts of 64 fruits and vegetables have been screened to determine the amount of carotenoid esters in food plants. Because one of the major problems in the quantitation of carotenoids is the availability of pure standard material, the total carotenoid ester content was calculated as Lutein dimyristate equivalents. Lutein dimyristate was independently synthesized from lutein and myristoyl chloride. The highest ester concentrations were found in red chili (17.1 mg/100 g) and orange pepper (9.2 mg/100 g); most of the investigated fruits and vegetables showed concentrations up to 1.5 mg/100 g. Special attention was dedicated to beta-cryptoxanthin esters. To enable an accurate detection of the beta-cryptoxanthin ester content, beta-cryptoxanthin was purified from papaya and used for synthesis of beta-cryptoxanthin laurate, myristate, and palmitate, representing the major beta-cryptoxanthin esters in food plants. The study proved tropical and subtropical fruits to be an additional source of beta-cryptoxanthin esters in the human diet. The contents ranged from 8 microg/100 g beta-cryptoxanthin laurate in Tunisian orange to 892 microg/100 g beta-cryptoxanthin laurate in papaya.

Stability of Lutein and Its Myristate Esters.[Pubmed:26300170]

Biosci Biotechnol Biochem. 1999;63(10):1784-6.

Stabilities of lutein and its myristate esters against heat and UV light were studied by HPLC response. Free lutein (FL) was very unstable against heat; lutein monomyristate (LM), slightly stable; and Lutein dimyristate (LD), very stable. Both LM and LD were more stable toward UV light than FL. These results suggest that esterification of the OH group with a fatty acid might stabilize lutein against heat and UV-light degradation.