Ginkgotoxin
(Synonyms: 5-羟基-4-甲氧甲基-6-甲基-3-吡啶甲醇) 目录号 : GC48941
A neurotoxic pyridoxine antimetabolite
Cas No.:1464-33-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ginkgotoxin is a pyridoxine antimetabolite that has been found in G. biloba.1,2 It inhibits pyridoxal kinase (Ki = 3 µM), the enzyme that converts pyridoxine into its active form, pyridoxal 5'-phosphate .3 Ginkgotoxin (200-1,000 µM) induces seizure-like behavior in zebrafish larvae, an effect that can be reversed by PLP or GABA.4
1.Wada, K., Ishigaki, S., Ueda, K., et al.An antivitamin B6, 4'-methoxypyridoxine, from the seed of Ginkgo biloba L.Chem. Pharm. Bull.33(8)3555-3557(1985) 2.Arenz, A., Klein, M.K., Fiehe, K., et al.Occurrence of neurotoxic 4'-O-methylpyridoxine in Ginkgo biloba leaves, Ginkgo medications and Japanese Ginkgo foodPlanta Med.62(6)548-551(1996) 3.Gandhi, A.K., Desai, J.V., Ghatge, M.S., et al.Crystal structures of human pyridoxal kinase in complex with the neurotoxins, ginkgotoxin and theophylline: Insights into pyridoxal kinase inhibitionPLoS One7(7)e40954(2012) 4.Lee, G.-H., Sung, S.-Y., Chang, W.-N., et al.Zebrafish larvae exposed to ginkgotoxin exhibit seizure-like behavior that is relieved by pyridoxal-5'-phosphate, GABA and anti-epileptic drugsDis. Model. Mech.5(6)785-795(2012)
| Cas No. | 1464-33-1 | SDF | |
| 别名 | 5-羟基-4-甲氧甲基-6-甲基-3-吡啶甲醇 | ||
| Canonical SMILES | OC1=C(COC)C(CO)=CN=C1C | ||
| 分子式 | C9H13NO3 | 分子量 | 183.2 |
| 溶解度 | DMF: 1 mg/ml,DMSO: 5 mg/ml,Ethanol: 1 mg/ml,PBS (pH 7.2): 10 mg/ml | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.4585 mL | 27.2926 mL | 54.5852 mL |
| 5 mM | 1.0917 mL | 5.4585 mL | 10.917 mL |
| 10 mM | 0.5459 mL | 2.7293 mL | 5.4585 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
A critical review of current technologies used to reduce Ginkgotoxin, ginkgotoxin-5'-glucoside, ginkgolic acid, allergic glycoprotein, and cyanide in Ginkgo biloba L. seed
Food Chem 2022 Jul 15;382:132408.PMID:35176549DOI:10.1016/j.foodchem.2022.132408.
The Ginkgo biloba has astonished scholars globally with enormous bioactives, with sales exceeding $10 billion since 2017. The Ginkgo biloba seed (GBS) is an essential part of culinary culture. Nevertheless, toxins in fresh Ginkgo biloba seed (GBS) have limited GBSs' daily consumption. Ginkgotoxin and ginkgotoxin-5-glucoside cause poisoning, tonic-clonic convulsions, and neurotoxic effects. Ginkgolic acid causes cytotoxicity and allergies. Allergic glycoprotein in GBS causes nausea, seizures, dyspnea, mydriasis, vomiting, and bellyache. The amygdalin-derived hydrocyanic acid cause dizziness, vomiting, cramping, and sleeping disorders. Food products are frequently exposed to various processing techniques to increase food safety and functionality. As a result, this review focused on the technologies that have been used to minimize toxins in GBS. In addition, a comparison of these techniques was made based on their benefits, drawbacks, feasibility, pharmacological activities, and future direction or opportunities to improve current ones were provided.
Efficient removal of Ginkgotoxin from Ginkgo biloba seed powder by combining endogenous enzymatic hydrolysis with resin adsorption
J Sci Food Agric 2021 Mar 15;101(4):1589-1597.PMID:32869870DOI:10.1002/jsfa.10778.
Background: Ginkgotoxin including 4'-O-methylpyridoxine (MPN) and MPN-5'-glucoside (MPNG) is responsible for Ginkgo seed food poisoning. The purpose of the work reported was to prepare detoxified Ginkgo seed powder and at the same time to retain the nutritional and functional components of Ginkgo seed powder to the maximum extent. Results: Resin adsorption technology was firstly employed to remove Ginkgotoxin from water extract of Ginkgo seed powder. Under optimal conditions, the adsorption efficiency of the optimal resin for MPN could reach 100%, and that for MPNG could only reach 85.4 ± 0.93%. Resin adsorption alone could not effectively remove MPN and MPNG simultaneously. Endogenous enzymatic hydrolysis was next attempted to transform MPNG to MPN. MPNG could be completely hydrolyzed to MPN by endogenous enzyme(s) at 40 °C and pH 5.0 in 180 min. Ginkgotoxin only in the form of MPN in the enzymatic hydrolysate was then adsorbed with resin and the conditions were statistically optimized. The adsorption efficiency of MPN reached 98.89 ± 0.99% under the optimized conditions. Conclusions: Removal of Ginkgotoxin by combining endogenous enzymatic hydrolysis with resin adsorption could preserve the main nutritional and functional components of Ginkgo seed powder to the most extent, and did not change its main characteristics. The Ginkgotoxin removal method developed in this work is a relatively simple and efficient approach. © 2020 Society of Chemical Industry.
Ginkgo biloba and Ginkgotoxin
J Nat Prod 2010 Jan;73(1):86-92.PMID:20041670DOI:10.1021/np9005019.
Products prepared from Ginkgo biloba are top-selling phytopharmaceuticals especially in Europe and major botanical dietary supplements in the United States. In European medicine, G. biloba medications are used to improve memory, to treat neuronal disorders such as tinnitus or intermittent claudication, and to improve brain metabolism and peripheral blood flow. The whole array of indications is reflected by a number of defined natural product constituents in G. biloba. The most well-known ones are flavonoids and terpene lactones, but they also include allergenic and toxic compounds such as Ginkgotoxin (1). Consequently, there are reports attributing beneficial as well as adverse effects to G. biloba products. The present paper summarizes recent experiences with G. biloba and its derived products and explains why their restricted use is recommended.
Ginkgotoxin Induced Seizure Caused by Vitamin B6 Deficiency
J Epilepsy Res 2015 Dec 31;5(2):104-6.PMID:26819944DOI:10.14581/jer.15018.
Although ginkgo is commonly used as an alternative treatment for memory loss, Alzheimer's dementia and peripheral circulatory disturbances, it is also known to cause neuronal symptoms due to Ginkgotoxin (4'-methoxypyridoxine or B6 antivitamin). We experienced a case of a 51-year-old female patient with generalized tonic clonic seizure and postictal confusion after eating large amounts of ginkgo nuts. Blood vitamin B6 level was decreased. After conservative treatment and pyridoxine medication, her mental symptoms were resolved completely and no seizures recurred.
Influence of antivitamins Ginkgotoxin 5'-phosphate and deoxypyridoxine 5'-phosphate on human pyridoxine 5'-phosphate oxidase
Planta Med 2009 May;75(6):563-7.PMID:19288402DOI:10.1055/s-0029-1185482.
The pharmacological effects of leaf extracts (EGb 761) from Ginkgo biloba L. are attributed to ginkgolides, bilobalide and biflavonoids. However, besides these beneficial attributes, Ginkgotoxin, a B(6) antivitamin which may cause epileptic convulsions, other severe neuronal disorders and even death, is also found in Ginkgo leaves and leaf-derived remedies. Because of its structural similarity to the B(6) vitamers, an interaction of Ginkgotoxin with enzymes involved in the vitamin B(6)-dependent metabolism of the human brain is possible. This led us to investigate how the neurotoxic Ginkgotoxin acts in the brain. To this end the gene coding for the human pyridoxine 5'-phosphate oxidase was heterologously overexpressed in E. COLI and the homogeneous enzyme was characterized. The investigation showed that the enzyme is inhibited in vitro by the synthetic vitamin B(6) derivative 4'-deoxypyridoxine 5'-phosphate but not by Ginkgotoxin or its 5'-phosphate.