Epigoitrin
(Synonyms: 表告依春) 目录号 : GC38409An alkaloid with diverse biological activities
Cas No.:1072-93-1
Sample solution is provided at 25 µL, 10mM.
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Epigoitrin is an alkaloid that has been found in Crambe abyssinica and has diverse biological activities.1,2,3,4 It decreases norepinephrine formation by bovine dopamine-β-hydroxylase in a cell-free assay when used at a concentration of 0.1 mM.1 Epigoitrin inhibits the proliferation of RAW 264.7 macrophages (IC50 = ~1 mM).2 It increases serum cholesterol levels and liver and thyroid weight, as well as decreases serum thyroxine levels, in rats.3 Epigoitrin (176 mg/kg) improves survival in mice made susceptible to influenza A H1N1 infection by restraint stress.4 It also prolongs pentobarbital-induced sleeping time in male, but not female, rats.3
1.Zenker, N., Hubbard, L.S., and Wright, J.Inhibition of dopamine β-hydroxylase by goitrin, a natural antithyroid compoundJ. Nat. Prod.51(5)862-865(1988) 2.Hou, X., Zhang, X., Bi, J., et al.Indole-3-carboxaldehyde regulates RSV-induced inflammatory response in RAW264.7 cells by moderate inhibition of the TLR7 signaling pathwayJ. Nat. Med.75(3)602-611(2021) 3.Nishie, K., and Daxenbichler, E.Hepatic effects of R-goitrin in Sprague-Dawley ratsFood Chem. Toxicol.20(3)279-287(1982) 4.Luo, Z., Liu, L.-F., Wang, X.-H., et al.Epigoitrin, an Alkaloid From Isatis indigotica, Reduces H1N1 Infection in Stress-Induced Susceptible Model in vivo and in vitroFront. Pharmacol.1078(2019)
Cas No. | 1072-93-1 | SDF | |
别名 | 表告依春 | ||
Canonical SMILES | S=C1O[C@H](C=C)CN1 | ||
分子式 | C5H7NOS | 分子量 | 129.18 |
溶解度 | DMSO: 8.33 mg/mL (64.48 mM) | 储存条件 | 4°C, protect from light |
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1 mg | 5 mg | 10 mg | |
1 mM | 7.7411 mL | 38.7057 mL | 77.4114 mL |
5 mM | 1.5482 mL | 7.7411 mL | 15.4823 mL |
10 mM | 0.7741 mL | 3.8706 mL | 7.7411 mL |
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Epigoitrin alleviates lipid and glucose metabolic disorders induced by a high-fat diet
Food Funct 2022 Jul 4;13(13):7260-7273.PMID:35723416DOI:10.1039/d2fo00242f.
As living standards improve, obesity has become an increasingly serious health problem. Natural extracts from a wide range of sources are non-toxic and have significant potential as drugs for the prevention and treatment of obesity. We assessed 243 natural small molecules in a HepG2 fat accumulation model and found that Epigoitrin (EP) from Radix isatidis reduced intracellular fat deposition, increased short-chain acyl CoA dehydrogenase (SCAD) activity, promoted glucose uptake and glycogen storage, increased ATP production and reduced glutathione (GSH) content, reduced reactive oxygen species (ROS), and enhanced superoxide dismutase (SOD) activity. In a murine high-fat diet model, the addition of EP to the high-fat diet significantly reduced fat deposition, increased glucose tolerance, improved insulin sensitivity, and increased energy expenditure. In conclusion, EP alleviated obesity caused by a high-fat diet and improved disorders of lipid and glucose metabolism.
Epigoitrin, an Alkaloid From Isatis indigotica, Reduces H1N1 Infection in Stress-Induced Susceptible Model in vivo and in vitro
Front Pharmacol 2019 Feb 7;10:78.PMID:30792656DOI:10.3389/fphar.2019.00078.
Stress has been proven to modulate an individual's immune system through the release of pituitary and adrenal hormones such as the catecholamines, growth hormone, and glucocorticoids. These signal molecules can significantly alter the host immune system and make it susceptible to viral infection. In this study, we investigate whether Epigoitrin, a natural alkaloid from Isatis indigotica, provides protection against influenza infection by reducing the host's susceptibility to influenza virus under stress and its underlying mechanism. To support it, the mouse restraint stress model and the corticosterone-induced stress model were employed. Our results demonstrated that Epigoitrin significantly decreased the susceptibility of restraint mice to influenza virus, evidenced by lowered mortality, attenuated inflammation, and decreased viral replications in lungs. Further results revealed that Epigoitrin reduced the protein expression of mitofusin-2 (MFN2), which elevated mitochondria antiviral signaling (MAVS) protein expression and subsequently increased the production of IFN-β and interferon inducible transmembrane 3 (IFITM3), thereby helping to fight viral infections. In conclusion, our study indicated that Epigoitrin could reduce the susceptibility to influenza virus via mitochondrial antiviral signaling.
An efficient approach for simultaneously obtaining oil and Epigoitrin from Orychophragmus violaceus seeds by microwave-mediated immiscible binary solvent extraction
Food Chem 2022 Mar 15;372:131258.PMID:34627086DOI:10.1016/j.foodchem.2021.131258.
Microwave-mediated immiscible binary solvent extraction (MIBSE) was applied to simultaneously extract oil and Epigoitrin from Orychophragmus violaceus seeds. The upper phase of n-hexane was used to obtain oil, and the lower phase of ethanol solution was used to obtain Epigoitrin. Factors potentially affecting the yields of oil and Epigoitrin were systematically investigated. The optimum conditions were an ethanol volume fraction of 65%, liquid-solid ratio of lower-phase of 20 mL/g, liquid-solid ratio of upper-phase of 12 mL/g, microwave irradiation power of 393 W, and microwave irradiation time of 29 min. The actual yields of oil and Epigoitrin were 34.08% ± 1.38% and 11.86 ± 0.47 mg/g, respectively. GC-MS analysis illustrated that the seed oils obtained by MIBSE and Soxhlet extraction exhibited similar fatty acid compositions. The separated Epigoitrin was determined by HPLC analyses, which obtained a purity of 91.25% ± 3.83%, follwed by NMR determinations.
[Accumulation law of Epigoitrin in roots of Isatis indigotica of different breed types]
Zhong Yao Cai 2013 Feb;36(2):199-201.PMID:23901642doi
Objective: To study the distribution law of Epigoitrin in roots of Isatis indigotica of different breed types and provide a scientific basis for screening of high-quality Isatis indigotica breed. Methods: Determined the contents of Epigoitrin in tap root and lateral root of Chinese-cabbage-leaf Isatis, cabbage-leaf Isatis, mustard-leaf Isatis and tetraploid Isatis by HPLC. Also, compared the contents of epigoitin in xylem and phloem of Isatis indigotica. Results: Contents of Epigoitrin in the tap root and lateral root of Isatis indigotica of the different breed types were significant different. In four breed types of Isatis indigotica, contents of Epigoitrin in the tap root and phloem were higher than those in the lateral root and xylem, respectively. Conclusion: Contents of Epigoitrin in the lateral root of Isatis indigotica are higher than those of tap root and Epigoitrin distributes mainly in phloem.
[Influence of drying method on content of Epigoitrin and uridine in isatidis radix]
Zhong Yao Cai 2014 Apr;37(4):578-80.PMID:25345127doi
Objective: To study the influence of different drying methods on the content of Epigoitrin and uridine in Isatidis Radix. Methods: Fresh Isatidis Radix was processed by four drying methods including airing drying and drying in far infrared oven at different temperature,drying in the sun and drying in the shade. The contents of Epigoitrin and uridine were determined by HPLC. Results: The contents of Epigoitrin as well as uridine in samples valued from 3.847 - 5.204 mg/g and 0.701 - 1.028 mg/g, respectively. Conclusion: The optimal drying method is airing drying at 55 degrees C, which will be serviced in the large-scale processing of Isatidis Radix.