Carotenoid esters in foods - A review and practical directions on analysis and occurrence

Mercadante, Adriana Zerlotti; Rodrigues, Daniele Bobrowski; Petry, Fabiane C.; Mariutti, Lilian Regina Barros

doi:10.1016/j.foodres.2016.12.018

Cited by 133 publications

(94 citation statements)

References 113 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Carotenoids can be associated with other molecules, including fatty acids, sugars or even proteins. Xanthophylls are typically found esterified with fatty acids in many fruits [21][22][23][24] and other plant organs such as flowers [25] and tubers [26]. Similarly, there are carotenoids associated to sugar moieties, as it is the case of crocetin [27].…”

Section: Association With Other Moleculesmentioning

confidence: 99%

A global perspective on carotenoids: Metabolism, biotechnology, and benefits for nutrition and health

Rodríguez‐Concepción

Ávalos

Bonet

et al. 2018

Progress in Lipid Research

750

584

View full text Add to dashboard Cite

Carotenoids are lipophilic isoprenoid compounds synthesized by all photosynthetic organisms and some non-photosynthetic prokaryotes and fungi. With some notable exceptions, animals (including humans) do not produce carotenoids de novo but take them in their diets. In photosynthetic systems carotenoids are essential for photoprotection against excess light and contribute to light harvesting, but perhaps they are best known for their properties as natural pigments in the yellow to red range. Carotenoids can be associated to fatty acids, sugars, proteins, or other compounds that can change their physical and chemical properties and influence their biological roles. Furthermore, oxidative cleavage of carotenoids produces smaller molecules such as apocarotenoids, some of which are important pigments and volatile (aroma) compounds. Enzymatic breakage of carotenoids can also produce biologically active molecules in both plants (hormones, retrograde signals) and animals (retinoids). Both carotenoids and their enzymatic cleavage products are associated with other processes positively impacting human health. Carotenoids are widely used in the industry as food ingredients, feed additives, and supplements. This review, contributed by scientists of complementary disciplines related to carotenoid research, covers recent advances and provides a perspective on future directions on the subjects of carotenoid metabolism, biotechnology, and nutritional and health benefits.

show abstract

Section: Association With Other Moleculesmentioning

confidence: 99%

A global perspective on carotenoids: Metabolism, biotechnology, and benefits for nutrition and health

Rodríguez‐Concepción

Ávalos

Bonet

et al. 2018

Progress in Lipid Research

750

584

View full text Add to dashboard Cite

show abstract

“…The identification of carotenoids and esters was performed using the same tools conventionally applied for carotenoids identification: combined information provided by elution order on C 30 column, UV-vis spectrum characteristics (maximum absorption wavelength (λ max ), spectral fine structure (III/II, %), and peak cis intensity (% A B /A II )), mass spectra, and comparison with data available in the literature [13].…”

Section: Hplc-dad-apci/ms Analysismentioning

confidence: 99%

“…The presence of FAs complicates chromatography separation; therefore, although several chromatographic conditions and linear gradients of MeOH, MTBE, and H 2 O combinations were tested, some co-elutions were noted. The literature reports that two or more xanthophyll esters almost always co-elute independent of the column and mobile phase [13,32], impairing the identification of some compounds.…”

Section: Hplc-dad-apci/ms Analysismentioning

confidence: 99%

“…These can be presented in their free form or acylated with fatty acids (FAs) in the case of mono-and polyhydroxylated xanthophylls, commonly forming monoesters or diesters [9,10]. In the plant tissues, the esterification helps carotenoid storage and protects sensitive molecules from photo-oxidation [11,12], in addition to increasing the possible structures found in nature, and consequently, the analytical complexity, since a single xanthophyll can be acylated with different FAs [9,13]. For this reason, the carotenoid analysis usually comprises a saponification step in order to simplify the analysis by hydrolyzing the esters and removing interfering compounds; however, saponification may lead to carotenoid degradation and modification, such as isomerization [9,13].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Green Extraction Approaches for Carotenoids and Esters: Characterization of Native Composition from Orange Peel

et al. 2019

View full text Add to dashboard Cite

Orange peel is a by-product produced in large amounts that acts as a source of natural pigments such as carotenoids. Xanthophylls, the main carotenoid class found in citrus fruit, can be present in its free form or esterified with fatty acids, forming esters. This esterification modifies the compound’s chemical properties, affecting their bioavailability in the human body, and making it important to characterize the native carotenoid composition of food matrices. We aimed to evaluate the non-saponified carotenoid extracts of orange peel (cv. Pera) obtained using alternative green approaches: extraction with ionic liquid (IL), analyzed by high performance liquid chromatography coupled to a diode array detector with atmospheric pressure chemical ionization and mass spectrometry HPLC-DAD-APCI-MS, and supercritical fluid extraction (SFE), followed by supercritical fluid chromatography with atmospheric pressure chemical ionization and triple quadrupole mass spectrometry detection (SFC-APCI/QqQ/MS) in an online system. Both alternative green methods were successfully applied, allowing the total identification of five free carotenoids, one apocarotenoid, seven monoesters, and 11 diesters in the extract obtained with IL and analyzed by HPLC-DAD-APCI-MS, and nine free carotenoids, six carotenoids esters, 19 apocarotenoids, and eight apo-esters with the SFE-SFC-APCI/QqQ/MS approach, including several free apocarotenoids and apocarotenoid esters identified for the first time in oranges, and particularly in the Pera variety, which could be used as a fruit authenticity parameter.

show abstract

“…Consequently, it does not require enzymatic digestion prior to intestinal absorption. However, the dietary xanthophylls (viz., β‐cryptoxanthin, LUT, and ZEA) are found in foods in unesterified form and as fatty acyl monoesters, and in the cases of LUT and ZEA as diesters . The relative amounts of xanthophyll esters versus free xanthophylls differ among various dietary sources.…”

Section: Intestinal Absorption Of Vitamin a And Carotenoidsmentioning

confidence: 99%

Mechanisms of Transport and Delivery of Vitamin A and Carotenoids to the Retinal Pigment Epithelium

Harrison

2019

Molecular Nutrition Food Res

View full text Add to dashboard Cite

Vision depends on the delivery of vitamin A (retinol) to the retina. Retinol in blood is bound to retinol‐binding protein (RBP). Retinal pigment epithelia (RPE) cells express the RBP receptor, STRA6, that facilitates uptake of retinol. The retinol is then converted to retinyl esters by the enzyme lecithin:retinol acyltransferase. The esters are the substrate for RPE65, an enzyme that produces 11‐cis retinol, which is converted to 11‐cis retinaldehyde for transport to the photoreceptors to form rhodopsin. The dietary xanthophylls, lutein (LUT) and zeaxanthin (ZEA), accumulate in the macula of the eye, providing protection against age‐related macular degeneration. To reach the macula, carotenoids cross the RPE. In blood, xanthophylls and β‐carotene mostly associate with high‐density lipoprotein (HDL) and low‐density lipoprotein (LDL), respectively. Studies using a human RPE cell model evaluate the kinetics of cell uptake when carotenoids are delivered in LDL or HDL. For LUT and β‐carotene, LDL delivery result in the highest rate of uptake. HDL is more effective in delivering ZEA (and meso‐ZEA). This selective HDL‐mediated uptake of ZEA, via a scavenger receptor and LDL‐mediated uptake of LUT and β‐carotene provides a mechanism for the selective accumulation of ZEA > LUT and xanthophylls over β‐carotene in the macula.

show abstract

Carotenoid esters in foods - A review and practical directions on analysis and occurrence

Cited by 133 publications

References 113 publications

A global perspective on carotenoids: Metabolism, biotechnology, and benefits for nutrition and health

A global perspective on carotenoids: Metabolism, biotechnology, and benefits for nutrition and health

Green Extraction Approaches for Carotenoids and Esters: Characterization of Native Composition from Orange Peel

Mechanisms of Transport and Delivery of Vitamin A and Carotenoids to the Retinal Pigment Epithelium

Contact Info

Product

Resources

About