Fucoxanthin
Fucoxanthin
CAS: 3351-86-8
Molecular Formula: C42H58O6
Fucoxanthin - Names and Identifiers
Fucoxanthin - Physico-chemical Properties
| Molecular Formula | C42H58O6 |
| Molar Mass | 658.917 |
| Density | 1.09 |
| Melting Point | 166-168°C |
| Boling Point | 764.1°C at 760 mmHg |
| Specific Rotation(α) | D18 +72.5 ±9° (chloroform) |
| Flash Point | 14℃ |
| Solubility | Soluble in methanol and ether, slightly soluble in n-hexane |
| Appearance | Reddish brown powder |
| Color | Crystalline |
| Maximum wavelength(λmax) | λ: 444-454 nm Amax |
| pKa | 14.47±0.60(Predicted) |
| Storage Condition | 2-8℃ |
| Refractive Index | n20/D1.360-1.362 |
| MDL | MFCD01745140 |
| Physical and Chemical Properties | Physical and chemical properties are insoluble in water, soluble in organic solvents such as ethanol, generally fat-soluble powder or oil. |
| Use | Application 1. In addition to being used as a weight loss health care products, but also can be applied to all kinds of food, such as butter, pie, green tea and other baked food, play a role in increasing product color and functional. 2. For egg yolk colorant. 3. Skin care and beauty products. 4. As a medicine, it is used for the treatment of cancers such as skin cancer, colon cancer, prostate cancer, and liver cancer. |
Fucoxanthin - Risk and Safety
| Hazard Symbols | F - Flammable |
| Risk Codes | 11 - Highly Flammable |
| Safety Description | S7 - Keep container tightly closed. S16 - Keep away from sources of ignition. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN1170 - class 3 - PG 2 - Ethanol, solution |
| WGK Germany | 3 |
| HS Code | 29153900 |
Fucoxanthin - Reference
| Reference Show more | 1. Li, Wei, et al. "Effective removal matrix interferences by a modified QuEChERS based on the molecularly imprinted polymers for determination of 84 polychlorinated biphenyls and organochlorine pesticides in shellfish samples." Journal of hazardous materials 2. Yu, Xin-ru, et al. "Development and Application of the Dispersive Solid-Phase Extraction Method Based on Molecular Imprinted Polymers for Removal of Matrix Components of Bivalve Shellfish Extracts in the GC–MS/MS Analysis of Amide/Dinitroaniline/Substitute 3. [IF=3.197] Wanxiu Cao et al."Transcriptomic analysis reveals effects of fucoxanthin on intestinal glucose transport."J Funct Foods. 2018 Oct;49:205 4. [IF=10.588] Wei Li et al."Effective removal matrix interferences by a modified QuEChERS based on the molecularly imprinted polymers for determination of 84 polychlorinated biphenyls and organochlorine pesticides in shellfish samples."J Hazard Mater. 2020 Feb;384:1212 5. [IF=2.044] Yu Xin-ru et al."Development and Application of the Dispersive Solid-Phase Extraction Method Based on Molecular Imprinted Polymers for Removal of Matrix Components of Bivalve Shellfish Extracts in the GC–MS/MS Analysis of Amide/Dinitroaniline/Substituted |
Fucoxanthin - Uses and methods of synthesis
Overview
fucoidan (fucoxanthin), also known as fucoidin, fucoidin, is a kind of natural pigment of lutein in carotenoids, it accounts for more than 700 of the total amount of about 10% naturally occurring carotenoids, and is light yellow to brown in color, which is contained in brown algae, diatoms, gold algae and yellow green algae. It is widely found in a variety of algae, marine phytoplankton, aquatic shellfish and other plants and animals. With anti-tumor, anti-inflammatory, anti-oxidation, weight loss, nerve cell protection, increasing the content of ARA (arachidonic acid) and DHA (two carbon hexaenoic acid) in mice and other pharmacological effects, as a drug, skin care and beauty products and health products are widely used in the market.
efficacy and function
fucoxanthin, a carotenoid found in brown seaweed, is being studied for its ability to burn fat. It reduces the amount of fat and does not stimulate the brain. Looks healthy, but more evidence is needed. It also has other health benefits, such as correcting glucose metabolism abnormalities in muscle tissue, which may help diabetics and may lower cholesterol levels and triglycerides by mechanisms that have not yet been validated. After supplementation with fucoidan, blood pressure decreased, liver fat storage and liver enzyme values decreased.
features
1. Absorption and metabolism
fucoidan and Amarouciaxanthin A are the major primary metabolites of fucoxanthin. The ingested fucoidan is hydrolyzed into fucoidan by digestive enzymes (such as lipase and cholesterol esterase) in the gastrointestinal tract, and then enters the systemic circulation through the lymph. Part of the Fucoidan is degraded into Amarouciaxanthin A in the liver, fucoidan and Amarou-ciaxanthin A were further metabolized by subsequent enzymatic reactions such as isomerization, dehydrogenation, deacetylation, oxidation and demethylation.
2. Safety
Fucoxanthin has no effect on liver, kidney, spleen and gonadal tissue, but can cause hypercholesterolemia. There was no teratogenicity of fucoidan in vitro, and there was no teratogenicity of fucoidan in vivo at 500, 1000 and 2000 mg/kg doses.
3. Stability
high-purity fucoxanthin is unstable to heat and easily oxidized. However, the fucoxanthin extract obtained from algae has stability due to the common presence of antioxidant substances (such as polyphenols and the like).
The pigment was sensitive to light and its stability was greatly improved when stored in the dark. At the same time, other antioxidants can protect the pigment from degradation. In addition, fucoxanthin is more stable than neutral and acidic under alkaline pH conditions, with the greatest stability at pH 9 and the least stable under acidic conditions.
fucoxanthin in algae is stable during dry processing and storage at room temperature.
extraction and separation methods
fucoxanthin is a natural carotenoid, which is insoluble in water and other highly polar solvents under neutral conditions, and soluble in non-polar organic solvents. It is a fat-soluble pigment. The extraction of pigment in dry powder is usually carried out by adding a small amount of small polar solvent into non-polar solvent.
1. The extraction process of Fucoxanthin from Laminaria japonica: Using anhydrous ethanol-acetone-petroleum ether (4:1:1) as the extraction solvent, 40 C extraction 2 times, each time 1H. After saponification, the extracted extract was separated and purified by silica gel column chromatography to obtain a high purity product with a purity of 91.6%.
2. Sargassum fusiforme in the extraction process: 90% ethanol-acetone (3:1) composite solvent as the extractant, in the ratio of liquid to material 40:1, ultrasonic temperature 65 ℃ water bath shaking extraction 2 times, the extraction rate was 1.067mg · g-1 for 80min each time.
3. Extraction process of Fucoxanthin from undaria pinnatifida: 3% methanol as entrainer, pressure 200dN/mm2, temperature 323K. Or ethanol as entrainer, using supercritical CO2 extraction from kelp root preparation of fucoxanthin, the purity of crude extract was 5%.
analysis detection
detection by spectrophotometry and high performance liquid chromatography
1. UV spectrophotometry: the absorption value of the sample is measured at 449nm, and the Theoretical absorption value of 1g · L-1 concentration of solute in the cuvette of 1cm optical path length is calculated as 1600, this method is relatively simple, but because other impurities are also absorbed at 449nm, the accuracy is poor.
2. High performance liquid chromatography: C18 column, acetonitrile-methanol-0.1% ammonium acetate solution (75:15:10) as mobile phase, at 450nm wavelength for determination, the method is more accurate, it is a feasible method with high sensitivity, but the detection methodology has not been systematically studied.
pharmacological effects
1. Anti-tumor effect
(1) skin cancer
fucoxanthin can inhibit the enhancement of ornithine decarboxylase activity in the epidermis of mice induced by the strong skin cancer-promoting substance decanoyl phorbol acetate (tetradecanoylphorbol-13-acetate,TPA), at the same time cocoa inhibits TPA-induced activation of human herpes Virus, thereby inhibiting TPA-induced skin tumors.
(2) colon cancer
Fucoxanthin has an inhibitory effect on N-ethyl-N'-nitro-N-nitrosoguanidine-induced duodenal carcinoma formation. Fucoxanthin significantly inhibited the growth of colon cancer cell lines, including Caco-2,HT-29 and DLD-1. It can induce DNA breakage of colon cancer cells, promote apoptosis, and inhibit the expression of apoptosis-related protein Bcl-2.
fucoxanthin inhibited the proliferation of human colon cancer cell line WiDr cells in a dose-dependent manner, blocked the cell cycle at G0/ G1 phase and induced apoptosis.
(3) blood system tumor
effect of fucoxanthin on acute myeloid leukemia HL-60 cell line. Fucoxanthin significantly inhibited the proliferation of HL-60 cells. Role of fucoxanthin in adult T-cell lymphoblastic leukemia. Fucoxanthin and its metabolite fucoxanthol inhibit the survival of human virus T-cell leukemia type 1 (human T-cell virus type 1,HTLV-1) infected T cells and adult T-cell leukemia cells.
(4) prostate cancer
fucoxanthin significantly decreased the survival rate of prostate cancer cells and induced apoptosis. Both fucoxanthin and its metabolite fucoxanol inhibited the proliferation of PC-3 cells and activated Caspase-3 to induce apoptosis.
(5) liver cancer
fucoxanthin inhibited the growth of human hepatoma HepG2 cells, blocked the cells in G0/G1 phase, and inhibited the phosphorylation of Rb protein at Ser780 site.
2. Antioxidant effect
Fucoxanthin has a good antioxidant effect, even better than vitamin E and vitamin C. Fucoxanthin has a protective effect on human fibroblast damage caused by UV-B. The antioxidant effect of fucoxanthin is mainly through the regulation of Na +-K +-ATPase activity, and the regulation of catalase and glutathione activity in tissues and molecules due to retinol deficiency.
3. Anti-inflammatory effect
fucoxanthin inhibited the exudation of inflammatory mediators induced by endotoxin in a dose-dependent manner, and its anti-inflammatory effect was equivalent to that of prednisolone, indicating that fucoxanthin had a significant effect on the inflammatory infiltration induced by endotoxin in mice, NO,PGE2 and tumor necrosis factor have a certain inhibitory effect. Its anti-inflammatory effect is mainly by inhibiting the exudation of NO in the inflammatory response caused by lipopolysaccharide-induced macrophages. RT-PCR analysis showed that the mRNA of NO synthase and cyclooxygenase was inhibited by fucoxanthin, tumor necrosis factor, leukocyte mediated IL-1β and IL-6, and mRNA survivin expression were inhibited by fucoxanthin in a dose-dependent manner, these results suggest that fucoxanthin may play an important role in a variety of inflammatory responses.
4. Weight lossfucoxanthin can eliminate the accumulation of fat in two ways. Fucoxanthin activates a protein called UCP1, which promotes lipolysis. It also stimulates the liver to produce DHA, which lowers cholesterol levels.
5. Other
sea urchin dietary algae contain fucoxanthin and have significant effects on macrophage phagocytosis and ovulation.
Last Update：2024-04-09 21:54:55
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