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Lutein esters is a xanthophyll and one of 600 known naturally occurring carotenoids.
Lutein esters is synthesized only by plants, and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots.
In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll, an excited form of chlorophyll which is overproduced at very high light levels during photosynthesis.
CAS: 127-40-2
MF: C40H56O2
MW: 568.87
EINECS: 204-840-0
Synonyms
beta,;beta,e-carotene-3,;beta,e-carotene-3,3’-diol;SAG-1000;epsilon-carotene-3,3’-diol,(3theta,3’theta,6’theta)-bet;xanthophyllfromalfalfa;beta,epsilon-carotene-3,3'-diol;XANTHOPHYLL FROM CORN
Animals obtain Lutein esters by ingesting plants.
In the human retina, lutein is absorbed from blood specifically into the macula lutea, although its precise role in the body is unknown.
Lutein esters is also found in egg yolks and animal fats.
Lutein esters is a yellow dihydroxylated carotenoid which is found to be a common constituent in many dietary supplements.
Lutein esters is isomeric with zeaxanthin, differing only in the placement of one double bond.
Lutein esters and zeaxanthin can be interconverted in the body through an intermediate called meso-zeaxanthin.
The principal natural stereoisomer of Lutein esters is (3R,3′R,6′R)-beta,epsilon-carotene-3,3′-diol.
Lutein esters is a lipophilic molecule and is generally insoluble in water.
The presence of the long chromophore of conjugated double bonds (polyene chain) provides the distinctive light-absorbing properties.
The polyene chain is susceptible to oxidative degradation by light or heat and is chemically unstable in acids.
Lutein esters is present in plants as fatty-acid esters, with one or two fatty acids bound to the two hydroxyl-groups.
For this reason, saponification (de-esterification) of lutein esters to yield free Lutein esters may yield lutein in any ratio from 1:1 to 1:2 molar ratio with the saponifying fatty acid.
Lutein esters is a type of carotenoid, which belongs to photosynthetic pigments and naturally widely presents in vegetables (such as spinach, kale, broccoli, etc.), flowers, fruits and other plants.
Lutein esters can absorb and transfer light energy to Chlorophyll a at a particular state to convert light energy.
Lutein esters plays a role in protecting chlorophyll.
Lutein esters is a rhombus yellow crystal with metallic luster, and it is unstable when exposed to light and hydrogen, insoluble in water and easily soluble in grease and fatty solvents.
Lutein esters shall be stored in a cool dry place, away from light and air.
Lutein esters is the most important nutritive component in human retina.
There is a high concentration of Lutein esters in macula (central vision) and lens of the eye retina.
The human body cannot synthesize Lutein esters itself, and it must be taken up from food.
After breaking through all difficulties, Lutein esters goes into the lens and macular to perform antioxidant effects, and neutralize harmful free radicals, and filter out the blue light (which is harmful to the eye), and avoid oxidation damage to eyes caused by sunlight.
Lutein esters is an excellent antioxidant, which can prevent cell senescence and body organs aging when added to food with an appropriate amount.
Lutein esters can also prevent eyesight degeneration and blindness that caused by age-related retina macular degeneration, and can also be used as feed additives for staining of poultry meat and eggs, as well as a colorant and dietary supplements in food industry.
Carotenoids are the generic terms of an important kind of natural pigments, belonging to compounds.
The yellow, orange or red pigments that commonly found in animals, higher plants, fungi, algae and bacteria are mainly β-carotene and a-carotene, hence the name.
Since carotene was isolated in the early 19th century, there are more than 600 known carotenoids in nature, of which only about 20 kinds present in the human blood and tissues.
Carotenoids that found in human body include d-carotene, P-carotene, cryptoxanthin, Lutein esters, lycopene and zeaxanthin, and they are insoluble in water and soluble in fats and fatty solvents.
Lutein esters is a dietary carotenoid that has been found in eggs and yellow-colored fruits and vegetables and has diverse biological activities.
Lutein esters reduces hyperglycemia-induced mitochondrial DNA damage and production of reactive oxygen species (ROS) and promotes mitochondrial biogenesis in ARPE-19 cells when used at a concentration of 10 μM.
Lutein esters increases nitric oxide (NO) production and decreases serum levels of endothelin-1 in a rat model of hyperhomocysteinemia.
Dietary administration of lutein (0.2%) decreases monocyte migration and lesion size in an ApoE-/- and Ldlr-/- mouse models of atherosclerosis.
Lutein reduces infarct size and cardiac malondialdehyde (MDA), lactate dehydrogenase (LDH), and troponin T levels, and increases cardiac levels of catalase (CAT), superoxide dismutase (SOD), heme oxygenase-1 (HO-1), and Nrf2 in a rat model of heart failure induced by isoproterenol.
Lutein esters forms a retinal pigment in human eyes, and high dietary intake of lutein is positively correlated with reduced risk of age-related macular degeneration and cataracts in humans.
Lutein esters is a carotenol.
Lutein esters has a role as a food colouring and a plant metabolite.
Lutein esters derives from a hydride of a (6'R)-beta,epsilon-carotene.
Lutein esters is a naturally occurring carotenoid found in plants, especially in green leafy vegetables.
Lutein esters is often used as an ingredient in supplements and as a food coloring agent.
Lutein esters has been shown to protect the eye from light-induced oxidative damage and may help prevent age-related macular degeneration (AMD) and cataracts.
This molecule also has antioxidant properties that can reduce the production of reactive oxygen species, which are generated when light exposure damages cells.
Lutein esters's function as a light-harvesting pigment may be due to its ability to absorb blue wavelengths from sunlight.
The wild-type strain of bacteria Escherichia coli can produce lutein from linoleic acid by an epoxidase reaction mechanism involving two molecules of chlorophyll A.
Lutein esters Chemical Properties
Melting point: 195 °C
Alpha: 18Cd +165° (c = 0.7 in benzene)
Boiling point: 572.66°C (rough estimate)
Density: 0.9944 (rough estimate)
Refractive index: n20/D1.361-1.363
Fp: 269.1±27.5 °C
Storage temp.: -20°C
Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly, Heated, Sonicated)
pka: 14.61±0.70(Predicted)
Form: Solid
Color: Red to Very Dark Red
Optical activity: 〔α〕656.3 +16220 (c 0.2, CHCl3)
Biological source: rabbit
λmax λ: 441-451 nm Amax
Merck: 13,10120
BRN: 2068547
Stability: Light Sensitive, Temperature Sensitive
InChIKey: KBPHJBAIARWVSC-RGZFRNHPSA-N
LogP: 11.524 (est)
CAS DataBase Reference: 127-40-2(CAS DataBase Reference)
EPA Substance Registry System: Lutein esters(127-40-2)
Characteristics
While Lutein esters is one of the most widespread naturally occurring carotenoid alcohols, it does not possess any vitamin A activity.
Lutein esters is a yellow pigment, which can be isolated from certain natural products, and produced synthetically.
Lutein esters is the major substance causing yolks to have a deeper yellow color.
Lutein esters has no nutritive value.
Years ago when chickens ran freely on the farm they ate grass which contains Lutein esters.
Modern production units put enough xanthophyll in the ration of chickens to produce a medium-yellow yolk.
Feeds that contain large amounts of Lutein esters produce a deep yellow color in the beak, skin, and shank of yellowskinned breeds of chickens.
The consumer associates this pigmentation with quality and, in many cases, is willing to pay a premium price for a bird of this type.
Also, processors of egg yolks are frequently interested in producing dark-colored yolks to maximize coloration of egg noodles and other food products.
The latter can be accomplished by adding about 60 mg of Lutein esters per kilogram of diet.
In recognition of these consumer preferences, many producers add ingredients that contain xanthophylls to poultry rations.
Uses
Lutein esters is one of the most widespread carotenoid alcohols in nature.
Originally isolated from egg yolk, also isolated by chromatography from nettles, algae, and petals of many yellow flowers.
Lutein esters has been used:
to quantify circulating lutein in birds
to study its effect on the synthesis of factor D (FD) by adipocytes
for the quantification of carotenoids from the leaves of Brassica oleracea
Used in papermaking, printing and dyeing industries
Lutein esters can be used for food coloring, and can also be added to poultry feed to increase the yellowness of poultry egg yolk
Lutein esters has the characteristics of “natural”, “nutrition” and “multifunctional”, and can be widely used in food, health products, cosmetics, medicine and feed additives.
Protection of Eyesight
Lutein esters plays an important role in protecting the macula of the retina.
The absence of Lutein esters can easily cause macular degeneration and blurred vision, and with the further symptoms of vision degeneration, myopia and so on.
Lutein esters is a precursor of NA, and it can be transformed into VA in the human body.
The main physiological function for eyes of Lutein esters is as antioxidants and light protectors.
Optic nerves are non-renewable and highly vulnerable to harmful free radicals, and the antioxidant effects of Lutein esters can inhibit the formation of harmful free radicals.
Lutein esters can absorb a large number of blue visible lights, which have the close wavelengths to ultraviolet lights and are a kind of harmful lights that can reach the retina and with the largest potential hazardous.
Before reaching the sensitive cells of the retina, the light goes through the most heavily gathering area of Lutein esters.
If Lutein esters is rich now, the damage can be lower to the minimum.
Reducing the Incidence of Cataract
Cataract is the major eye disease causing of blindness in the world.
Recent studies showed that by increasing the intake of Lutein esters, the incidence of cataracts can can be reduced.
So far, the mechanism is that the lower density of macular pigment is closely related to the higher lens visual density in the elders, and the higher the lens visual density is considered to be a obvious feature of cataract.
The Antioxidant Effect
Lutein esters has strong antioxidant effect, and it can inhibit the activity of reactive oxygen species and prevent its damage to normal cells.
Related experiments showed that reactive oxygen species could react with DNA, proteins, lipids, and weaken their physiological functions, and thus cause diseases such as cancer, atherosclerosis, and age-related macular degenerative disorders.
Lutein esters can quench singlet oxygen physically or chemically, thereby protecting the body from injury and enhancing the body's immunity.
Retarding Atherosclerosis
Recent research results showed that Lutein esters has a retarding effect on early process of atherosclerosis.
The main reason is the relationship between the intimal thickness of the main artery blood vessels and the content of Lutein esters in blood.
Low content of Lutein esters in blood can easily cause thickening of arterial walls.
With the increasing content of Lutein esters, the trend of arterial wall thickening decreases significantly.
Meanwhile, the Lutein esters in arterial wall cells can reduce oxidation of LDL cholesterol.
Anticancer effects
Several studies have shown that Lutein esters can inhibit a variety of cancers, such as breast cancer, prostate cancer, colorectal cancer, and skin cancer.
According to a recent pharmaceutical research of New York University School, there is a very close relationship between reducing the incidence of breast cancer and the amount of Lutein esters intake, and the survey found that the incidence of breast cancer in the group with a low intake of Lutein esters was (2.08-2.21) times higher than the group with a high intake of Lutein esters.
This effect role may be related to indirect immunomodulatory of synergy with other organs and tissues.
The study concluded that dietary intake of Lutein esters can inhibit neoplasms and may even play a role in cancer prevention.
Lutein esters is recommended daily intake of 400 g~600 g fruits and vegetables per capita can make reduce the relative risk of cancer by 50%.
Biotechnological Production
Petals of marigold flowers (Tagetes erecta and Tagetes patula) currently represent the main source of commercial Lutein esters.
More than 95 % of the Lutein esters is esterified, and about half of this fraction is esterified with fatty acid.
Therefore, saponification is a part of the downstream processing.
Lutein esters is supplemented to food and feed for aquaculture and poultry farming. Furthermore, Lutein esters is suggested to be beneficial for health, for example, to prevent age-related macular degeneration and progression of early atherosclerosis.
In algae, Lutein esters is accumulated in the nonesterified form.
The alga Muriellopsis sp. is able to accumulate Lutein esters up to high levels and is easy to cultivate photoautotrophically.
The effects of critical growth and production parameters in outdoor continuous cultures have been investigated.
Under optimized conditions, 40 g dry cell mass/m2 and 180 mg/m2 Lutein esters were produced per day, respectively.
Further optimization was performed by introduction of agitation with a paddlewheel in a semicontinuous cultivation system and by CO2 addition.
Thus, the Lutein esters content was increased to 0.4–0.6 % of the dry mass at a productivity level comparable to that in a closed tubular photobioreactor.
Beneficial for Lutein esters synthesis were high temperatures, high irradiance, an optimum pH value for biomass formation, and the addition of inducers such as H2O2 or NaClO in the presence of Fe2+ (for the generation of stress-inducing chemical species), especially under heterotrophic growth conditions where spontaneous oxidative stress is absent.
