Identification of Beta‐Carotene Degradation Compounds and Their Structural Elucidation by High‐Resolution Accurate Mass Spectrometry

Abstract

Beta-carotene (BC) degradation was studied by liquid chromatography coupled to a quadrupole time of flight mass spectrometer. Throughout/After 21 days of dark storage, 56 nonvolatile degradants were chromatographically separated from pure BC crystal and their molecular formulas were identified. Their structure information was gained by comparing the fragments to a different, but structure-related compound. For example, a newly formed double bond position in dehydrogenated BC was determined by comparing the fragments between BC and dehydrogenated BC. One of their chemical structures was confirmed by comparing its precursor ion mass, retention time, isotopic ratio, and fragmentation to a pure trans-beta-apo-8 -apocarotenal. BC cleavage was observed on double bonds as well as single bonds in BC conjugation chain.Practical Application: As evidenced in this study, beta-carotene (BC) degradation is a spontaneous process initiated when the compound is exposed to air. The stoichiometric ratio of BC to oxygen is 1:0.03 at the first oxidation, therefore, only 0.3 mg oxygen or 1.2 mL air will degrade 10 mg BC, an average daily recommended intake. Not like in enzymatic BC degradation, spontaneous BC oxidation did not produce provitamin A, either in retina C20H38O or retinol C20H40O forms. For BC application in vitamin A deficiency, spontaneous BC oxidation should be avoided.

Potential Regulation for Surface-Enhanced Raman Scattering Detection and Identification of Carotenoids

“…We further characterize the CFME-Ag regarding their performance in SERS experiments with carotenoid molecules of different properties that in the past have been very challenging to probe by SERS . β-carotene and its degradation product trans-β-Apo-8′-carotenal have similar polyene structures but differ in the presence of oxygen-containing functional groups (Figure a). The polyene chains exhibit hydrophobicity, especially in β-carotene without hydrophilic groups at the end positions, and show weak affinity to silver nanoparticles in SERS experiments. , Figure b shows SERS spectra of the two molecules that were obtained after incubation of the CFME-Ag with each respective molecule at an electrode potential that yielded a high signal, here, −0.75 V for β-carotene and 0 V for trans-β-Apo-8′-carotenal.…”

“…The molecules trans-β-Apo-8′-carotenal and β-carotene are carotenoids with very similar polyene structures, but the former is potentially cytotoxic and carcinogenic, and the latter is an essential molecule in animal cells. The toxic trans-β-Apo-8′-carotenal is derived from the asymmetric cleavage of β-carotene. , Thus, it is interesting to analyze both molecules in a microenvironment containing abundant cellular metabolites by the proposed microelectrode. We show that the microelectrode can serve both an improved recognition and a ratiometric quantification of the two kinds of carotenoid and thereby provides superior sensitivity and selectivity for carotenoid detection and characterization in the cellular microenvironment.…”

Microencapsulated Vitamin A Palmitate Degradation Mechanism Study To Improve the Product Stability

“…In general speaking, vitamin A is an antioxidant, similar to β-carotene, and is subject to oxidative cleavage. , The mass spectra of degradation products of VAP and β-carotene were systematically compared. Because the two degradation conditions, analytical methods, and instruments were set up identically, any differences in the degradants were due to the difference in the starting material.…”

“…Meanwhile, retinyl esters are very similar to β-carotene, as both possess anhydroretinol as a major molecular component and are used to treat vitamin A deficiency. It is widely believed that retinyl esters degrade in the same way as β-carotene through oxidation. , It has been determined that β-carotene double bonds are cleaved by the oxygen attack from the air to apocarotenals. − However, the use of antioxidants such as butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, and tocopherols has no or little effect on the vitamin A stability and no oxidized retinol degradants such as apocarotenals have been determined. Therefore, vitamin A ester degradation’s pathways and mechanisms have not been established and the stabilization measures for its degradation have not been developed.…”

Regulatory mechanisms of Beta-carotene and BCMO1 in adipose tissues: A gene enrichment-based bioinformatics analysis

“…3 In addition, BC, as a kind of provitamin A, can be decomposed into retinal aldehyde after being absorbed by the body. 4 Studies have pointed out that maintaining normal vision, promoting growth, tissue differentiation, and reproduction are related to the intake of BC through fruits and vegetables and concentration of BC in the blood. 5 What is more, it is known that BC played an anti-cancer role in multifarious cancers by inducing apoptosis, regulating cell growth, suppressing cell proliferation, delaying cell cycle progression, regulating the immune system as well as the antioxidant activity.…”