Zeaxanthin
(Synonyms: 玉米黄素) 目录号 : GC45179
Zeaxanthin是一种具有多种生物活性的类胡萝卜素色素,存在于多种水果和蔬菜中,可以帮助治疗或预防与年龄相关的黄斑变性、青光眼和白内障。
Cas No.:144-68-3
Sample solution is provided at 25 µL, 10mM.
Zeaxanthin is a carotenoid pigment with multiple biological activities found in a variety of fruits and vegetables that can help treat or prevent age-related macular degeneration, glaucoma, and cataracts[1]. Zeaxanthin is found in the macula of the eye, which mainly contains (3R,3'R)-Zeaxanthin and meso-Zeaxanthin forms[2]. Zeaxanthin also has antioxidant, antiparasitic, anthelmintic and anti-osteoporotic effects[3].
In vitro, treatment of ARPE-19 cells accumulating A2E (a lipofuscin fluorophore and photosensitizer) with Zeaxanthin (10μM) for 72h significantly attenuated photooxidation-induced proteasome inactivation, reduced the accumulation of intracellular ubiquitin conjugates, and reversed the changes in inflammatory-related gene expression caused by photooxidation[4]. Pretreatment of retinal ganglion cells (RGC-5) with Zeaxanthin (1μM) for 1h significantly inhibited H2O2-induced cell viability decrease and nuclear condensation, and reduced ROS generation caused by serum deprivation[5]. Zeaxanthin (5µg/mL) treatment of human corneal limbal and conjunctival epithelial cells protected the cells from UVB-induced cell death and reduced the secretion of proinflammatory cytokines IL-6, MCP-1, and IL-8[6].
In vivo, Zeaxanthin (8, 24mg/kg) was administered to SD rats by gavage for 4 weeks, which increased the levels of glutathione (GSH) in the liver, heart, and serum of rats, reduced the levels of lipid and protein peroxidation marker 4-HNE, and reduced the levels of carbonyl proteins in serum[7]. Zeaxanthin (25mg/kg) fed to non-alcoholic steatohepatitis (NASH) model mice for 6 weeks significantly reduced oxidative stress in the liver and prevented NASH-related inflammation and fibrosis[8].
References:
[1] Johra F T, Bepari A K, Bristy A T, et al. A mechanistic review of β-carotene, lutein, and zeaxanthin in eye health and disease[J]. Antioxidants, 2020, 9(11): 1046.
[2] Sajilata M G, Singhal R S, Kamat M Y. The carotenoid pigment zeaxanthin—a review[J]. Comprehensive reviews in food science and food safety, 2008, 7(1): 29-49.
[3] Bouyahya A, El Omari N, Hakkur M, et al. Sources, health benefits, and biological properties of zeaxanthin[J]. Trends in Food Science & Technology, 2021, 118: 519-538.
[4] Bian Q, Gao S, Zhou J, et al. Lutein and zeaxanthin supplementation reduces photooxidative damage and modulates the expression of inflammation-related genes in retinal pigment epithelial cells[J]. Free Radical Biology and Medicine, 2012, 53(6): 1298-1307.
[5] Nakajima Y, Shimazawa M, Otsubo K, et al. Zeaxanthin, a retinal carotenoid, protects retinal cells against oxidative stress[J]. Current Eye Research, 2009, 34(4): 311-318.
[6] Huang Y, Shi C, Li J. The protective effect of zeaxanthin on human limbal and conjunctival epithelial cells against UV-induced cell death and oxidative stress[J]. International Journal of Ophthalmology, 2019, 12(3): 369.
[7] Zou X, Gao J, Zheng Y, et al. Zeaxanthin induces Nrf2-mediated phase II enzymes in protection of cell death[J]. Cell death & disease, 2014, 5(5): e1218-e1218.
[8] Chamberlain S M, Hall J D, Patel J, et al. Protective effects of the carotenoid zeaxanthin in experimental nonalcoholic steatohepatitis[J]. Digestive diseases and sciences, 2009, 54: 1460-1464.
Zeaxanthin是一种具有多种生物活性的类胡萝卜素色素,存在于多种水果和蔬菜中,可以帮助治疗或预防与年龄相关的黄斑变性、青光眼和白内障[1]。Zeaxanthin存在于眼睛的黄斑部,黄斑主要含有(3R,3'R)-Zeaxanthin和meso-Zeaxanthin形式[2]。Zeaxanthin还具有抗氧化、抗寄生虫、驱虫活性和抗骨质疏松作用[3]。
在体外,Zeaxanthin(10μM)处理积累A2E(一种脂褐素荧光团和光敏剂)的ARPE-19细胞72h,显著减弱了光氧化诱导的蛋白酶体失活,减少了细胞内泛素结合物的积累,逆转了光氧化引起的炎症相关基因表达改变[4]。Zeaxanthin(1μM)预处理视网膜神经节RGC-5细胞1h,显著抑制了H2O2诱导的细胞活力下降和核浓缩,减少了血清剥夺引起的ROS生成[5]。Zeaxanthin(5µg/mL)处理人角膜缘和结膜上皮细胞,保护了细胞免受UVB诱导的细胞死亡,减少了细胞促炎细胞因子IL-6、MCP-1和IL-8的分泌[6]。
在体内,Zeaxanthin(8、24mg/kg)通过灌胃处理SD大鼠4周,升高了大鼠肝脏、心脏和血清中的谷胱甘肽(GSH)水平,降低了脂质和蛋白质过氧化标志物4-HNE水平,降低了血清中的羰基蛋白水平[7]。Zeaxanthin(25mg/kg)喂养非酒精性脂肪性肝炎(NASH)模型小鼠6周,显著减少了肝脏的氧化应激,阻止了与NASH相关的炎症和纤维化[8]。
Cell experiment [1]: | |
Cell lines | ARPE-19 cells |
Preparation Method | Confluent cultured ARPE-19 cells were loaded with A2E alone or loaded with A2E (a lipofuscin fluorophore and photosensitizer) and then supplemented with 10μM lutein or Zeaxanthin for 72h. The cells were then exposed to blue light for 10min and harvested. The chymotrypsin-like activity of the proteasome in the cells was determined using a fluorogenic peptide as a substrate and levels of ubiquitin conjugates were determined by Western blotting analysis using levels of β-actin as a loading control. |
Reaction Conditions | 10μM; 72h |
Applications | Incubation of A2E-containing retinal pigment epithelial cells (RPE) with lutein or Zeaxanthin before blue light irradiation significantly attenuated photooxidation-induced proteasome inactivation and also reduced the accumulation of intracellular ubiquitin conjugates. |
Animal experiment [2]: | |
Animal models | SD rats |
Preparation Method | Four-week-old male SD rats were randomly divided into three groups (n=8 in each group): rats fed a normal diet (control); rats fed a normal diet with daily oral gavage of a low dose of Zeaxanthin (8mg/kg/day); and rats fed a normal diet with daily oral gavage of a high dose of Zeaxanthin (24mg/kg/day). After 4 weeks of feeding, the rats were killed, and their serum and tissues including liver and heart were isolated for analysis. |
Dosage form | 8、24mg/kg/day for 4 weeks; p.o. |
Applications | After supplementation with Zeaxanthin, the levels of GSH in the rat liver, heart, and serum increased, and the levels of 4-HNE decreased. The levels of carbonyl proteins in the serum also decreased. |
References: |
Cas No. | 144-68-3 | SDF | |
别名 | 玉米黄素 | ||
Canonical SMILES | O[C@H]1CC(C)(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C[C@@H](O)CC2(C)C)=C(C)C1 | ||
分子式 | C40H56O2 | 分子量 | 568.9 |
溶解度 | THF : ≥ 10 mg/mL (17.58 mM); DMSO : < 1 mg/mL (insoluble or slightly soluble) | 储存条件 | -20°C, protect from light,unstable in solution, ready to use. |
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1 mg | 5 mg | 10 mg |
1 mM | 1.7578 mL | 8.7889 mL | 17.5778 mL |
5 mM | 0.3516 mL | 1.7578 mL | 3.5156 mL |
10 mM | 0.1758 mL | 0.8789 mL | 1.7578 mL |
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