Vicine
(Synonyms: 蚕豆嘧啶葡糖甙) 目录号 : GC37904
Vicine 是一种生物碱糖苷，主要存在于蚕豆中，对人体有毒，可引起溶血性贫血。
Cas No.:152-93-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Vicine, an alkaloid glycoside found mainly in fava beans, is toxic in individuals and may cause haemolytic anaemia[1].
[1]. Farran MT, et al. Vicine and convicine in common vetch (Vicia sativa) seeds enhance beta-cyanoalanine toxicity in male broiler chicks. Int J Toxicol. 2002 May-Jun;21(3):201-9.
| Cas No. | 152-93-2 | SDF | |
| 别名 | 蚕豆嘧啶葡糖甙 | ||
| Canonical SMILES | O=C1N=C(N)NC(N)=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O | ||
| 分子式 | C10H16N4O7 | 分子量 | 304.26 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -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 | 3.2867 mL | 16.4333 mL | 32.8666 mL |
| 5 mM | 0.6573 mL | 3.2867 mL | 6.5733 mL |
| 10 mM | 0.3287 mL | 1.6433 mL | 3.2867 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。
Substantial Depletion of Vicine, Levodopa, and Tyramine in a Fava Bean Protein-Based Nutritional Product
Int J Food Sci 2021 Jan 29;2021:6669544.PMID:33564674DOI:10.1155/2021/6669544.
A commercial fava bean protein isolate and a liquid nutritional product formulated with it were tested by validated HPLC methods for the favism-associated pyrimidine glycoside Vicine, the dopamine precursor levodopa, and the biogenic amine tyramine. The Vicine, levodopa, and tyramine concentrations in the protein isolate-306, 13.3, and <0.5 mg/kg, respectively-when expressed on a protein basis-34, 1.5, and <0.06 mg/100 g protein, respectively-were at least 96% lower than the Vicine, levodopa, and tyramine (protein-based) concentrations reported for fava beans (≥900, ~200, and ~4 mg/100 g protein, respectively). This was also true for the Vicine (13 mg/kg or 22 mg/100 g protein), levodopa (≤0.17 mg/kg or ≤0.3 mg/100 g protein), and tyramine (0.08 mg/kg or 0.14 mg/100 g protein) concentrations in the nutritional product. On the basis of these data, one serving (11 fl. oz.) of the nutritional product would deliver approximately 5 mg of Vicine, <1 mg of levodopa, and <0.1 mg of tyramine.
Computational exploration of Vicine - an alkaloid glycoside mediated pathological hallmark of adenosine kinase to promote neurological disorder
Metab Brain Dis 2021 Apr;36(4):653-667.PMID:33496919DOI:10.1007/s11011-021-00674-y.
Epilepsy disease is characterized by the neuronal dysfunction or abnormal neuronal activity of the brain which is regulated by astrocytes. These are glial cells and found to be the major regulators of the brain which are guided by the occurrence of adenosine kinase (ADK) enzyme in the central nervous system (CNS). During the normal physiological environment, ADK maintains the level of adenosine in the CNS. Dysfunction of ADK levels results in accumulation of adenosine levels in the CNS that leads to the pathophysiology of the brain such as astrogliosis which is a pathological hallmark of epileptic seizures. Vicine, an alkaloid glycoside in bitter gourd juice (Momordica charantia) is found to be toxic to the human system if the bitter gourd juice is consumed more. This compound inhibits ADK enzyme activity to lead epilepsy and seizure. Here, the toxic effect of Vicine targeting ADK using computational predictions was investigated. The 3-dimensional structure of ADK has been constructed using I-Tasser, which has been refined by ModRefiner, GalaxyRefine, and 3D refine and it was endorsed using PROCHECK, ERRAT, and VADAR. 3D structure of the ligand molecule has been obtained from PubChem. Molecular docking has been achieved using AutoDock 4.2 software, from which the outcome showed the effective interaction between Vicine and ADK, which attains binding free energy (∆G) of - 4.13 kcal/mol. Vicine molecule interacts with the active region ARG 149 of ADK and inhibits the functions of ADK that may cause imbalance in energy homeostasis. Also, pre-ADMET results robustly propose in which Vicine possesses toxicity, and meanwhile, from the Ames test, it was shown as mutagenic. Hence, the results from our study suggest that Vicine was shown to be toxic that suppresses the ADK activity to undergo pathological conditions in the neuronal junctions to lead epilepsy.
VC1 catalyses a key step in the biosynthesis of Vicine in faba bean
Nat Plants 2021 Jul;7(7):923-931.PMID:34226693DOI:10.1038/s41477-021-00950-w.
Faba bean (Vicia faba L.) is a widely adapted and high-yielding legume cultivated for its protein-rich seeds1. However, the seeds accumulate the pyrimidine glucosides Vicine and convicine, which can cause haemolytic anaemia (favism) in 400 million genetically predisposed individuals2. Here, we use gene-to-metabolite correlations, gene mapping and genetic complementation to identify VC1 as a key enzyme in Vicine and convicine biosynthesis. We demonstrate that VC1 has GTP cyclohydrolase II activity and that the purine GTP is a precursor of both Vicine and convicine. Finally, we show that cultivars with low Vicine and convicine levels carry an inactivating insertion in the coding sequence of VC1. Our results reveal an unexpected, purine rather than pyrimidine, biosynthetic origin for Vicine and convicine and pave the way for the development of faba bean cultivars that are free of these anti-nutrients.
Effect of the antibiotic neomycin on the toxicity of the glycoside Vicine in rats
J Toxicol 2013;2013:913128.PMID:23840205DOI:10.1155/2013/913128.
Vicine is hydrolyzed by microflora to highly reactive free radical generating compound divicine which causes mortality and other adverse effects. This study in the rats established the effect of a broad spectrum and poorly absorbed antibiotic, neomycin sulfate on the toxicity of Vicine. The results showed extremely decrease in mortality rate in the group pretreated with neomycin. Hemoglobin (Hb) concentration, hematocrit (Hct) value, and red blood cells (RBCs) count were significantly decreased after injection of Vicine and the improvement of these values in the group pretreated with neomycin. The same results were observed in white blood cells (WBCs). The results showed a significant decrease in glucose level and returned to normal in group pretreated with neomycin. Glutathione (GSH) was significantly decreased in the Vicine group and returned to normal value in the group pretreated with neomycin. Lipid peroxide (TBARs) was significantly increased in the group treated with Vicine and neomycin pretreated group decreased to the normal level. Glucose-6-phosphate dehydrogenase (G6-PD) activity was significantly decreased and returned to normal level in rats pretreated with neomycin. Serum protein and globulin were significantly decreased but serum albumin showed insignificant decrease in Vicine and neomycin groups compared to control. Alanine aminotransferase (ALT) and aspartate aminotransferase (AST) were significantly decreased in the Vicine group. The group pretreated with neomycin showed significantly increased activities of AST and ALT compared with Vicine group. In conclusion, neomycin pretreatment of rats injected with glycoside Vicine decreased to a great extent of its toxic and mortality effects and is useful in favism and hemolytic anemia.
Vicine and convicine in common vetch (Vicia sativa) seeds enhance beta-cyanoalanine toxicity in male broiler chicks
Int J Toxicol 2002 May-Jun;21(3):201-9.PMID:12055021DOI:10.1080/10915810290096333.
Two studies were conducted to investigate the effects of feeding raw and water-soaked vetch seeds to male broiler chicks on performance, organ weights, and blood parameters. Intact and ground vetch seeds were soaked in water (1:5) at room temperature for 24 hours (study 1), and (1:10) at 40 degrees C for 24, 48, and 72 hours, with water change every 12 hours (study 2). In study 1, untreated vetch contained, on dry matter basis, 0.530%, 0.731%, and 0.081% total beta-cyanoalanine (BCA), Vicine, and convicine, respectively. Toxins were not appreciably reduced in soaked intact and ground vetch. Diets containing untreated, soaked intact, and soaked ground vetch, each at 0%, 20%, 40%, and 60%, were fed to 7-day-old male broilers until onset of neurotoxicity symptoms. Survival time was not only decreased by BCA level but also by those of Vicine and convicine (p <.05). In study 2, 60% of untreated or treated vetch seeds were incorporated in chick diets. Although untreated vetch used in this study contained 32% less BCA but 8% and 81% more Vicine and convicine, respectively, yet, the chicks on 60% untreated vetch showed toxicity symptoms earlier than those of study 1. Soaking ground vetch for 48 hours or more reduced BCA and totally removed Vicine and convicine. Consequently, birds on 60% ground vetch soaked for 48 and 72 hours survived through the starter period and had mean corpuscular hemoglobin concentration and organ weights comparable to those of control at 4 days post trial. The results indicated that "high levels" of Vicine or convicine or both might have shortened the birds' survival time by enhancing the neurotoxicity induced by "lower levels" of BCA.