Vincamine
(Synonyms: 长春胺) 目录号 : GC32481
A plant alkaloid with vasodilator effects
Cas No.:1617-90-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Vincamine is an indole alkaloid found in the leaves of V. minor and C. roseus that is used as a peripheral vasodilator to increase blood flow to the brain.1 Vincamine contracts excised human cerebrovascular smooth muscle in vitro with an EC50 value of 30 μM and has been explored as a pharmacotherapy to treat cerebral metabolic and vascular diseases.2,3
1.Lim, C.C., and James, I.M.The effect of an acute infusion of vincamine and ethyl apovincaminate on cerebral blood flow in healthy volunteersBr. J. Clin. Pharmacol.9(1)100-101(1980) 2.Young, A.R., Bouloy, M., Boussard, J.F., et al.Direct vascular effects of agents used in the pharmacotherapy of cerebrovascular disease on isolated cerebral vesselsJ. Cereb. Blood Flow Metab.1(1)117-128(1981) 3.Nowicki, J.P., MacKenzie, E.T., and Spinnewyn, B.Effects of agents used in the pharmacotherapy of cerebrovascular disease on the oxygen consumption of isolated cerebral mitochondriaJ. Cereb. Blood Flow Metab.2(1)33-40(1982)
| Cas No. | 1617-90-9 | SDF | |
| 别名 | 长春胺 | ||
| Canonical SMILES | O=C(OC)[C@@]1(O)C[C@@]2(CC)[C@@]3([H])C(N1C4=CC=CC=C54)=C5CCN3CCC2 | ||
| 分子式 | C21H26N2O3 | 分子量 | 354.44 |
| 溶解度 | DMSO : ≥ 38 mg/mL (107.21 mM) | 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 | 2.8214 mL | 14.1068 mL | 28.2135 mL |
| 5 mM | 0.5643 mL | 2.8214 mL | 5.6427 mL |
| 10 mM | 0.2821 mL | 1.4107 mL | 2.8214 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。
Evaluation of Vincamine against Acetylcholinesterase enzyme
Cell Mol Biol (Noisy-le-grand) 2022 Jul 31;68(7):14-21.PMID:36495525DOI:10.14715/cmb/2022.68.7.3.
The current article deals with the in-silico along with enzyme kinetics approach to search for a prominent AChE enzyme inhibitor among the known natural compounds. The computational tools were involved for this purpose and eventual Vincamine, a monoterpenoid indole alkaloid, was selected based on several parameters, including free energy of binding (-10.77 kcal/mol) and ADME parameter. Computationally, it confirmed the interaction between Vincamine and AChE at an indistinguishable locus from that of substrate AChI (-3.94 kcal/mol) but with much higher binding energy. Interestingly, amino acid residues Gly120, Gly121, Gly122, Glu202, Trp86, Tyr133, Ser203, Phe297, and His447 of AChE were found to be common in these interactions. Further, these findings were approved with wet lab tests where detailed kinetics was studied. It was found that Vincamine inhibited AChE with the inhibition constant Ki (239 µM). The value of IC50 (239 µM) and KM (0.598 mM) was determined and further confirmed by Dixon, Lineweaver- Burk reciprocal, Hanes, and Eadie- Hofstee plots, respectively. The mode of interaction of the compound was found to be competitive for AChE. Thus, the present computational and enzyme kinetics studies conclude that Vincamine can be a promising inhibitor of AChE for the effective management of AD.
Vobasine, Vincamine, voaphylline, tacaman, and iboga alkaloids from Tabernaemontana corymbosa
Phytochemistry 2022 Nov;203:113384.PMID:36007666DOI:10.1016/j.phytochem.2022.113384.
Thirteen indole alkaloids comprising six vobasine/sarpagine, one Vincamine, two voaphylline, two tacaman, one iboga, and one corynantheine alkaloid, were isolated from the leaf extract of Tabernaemontana corymbosa (sample from Taiping, Perak, Malaysia). The structures of these alkaloids were determined based on analysis of the spectroscopic data (NMR and MS), and in the case of vincarudine, the absolute configuration was established by ECD and X-ray diffraction analysis. Vobasidine E represents the first vobasine-type alkaloid characterized by a contracted ring C and loss of the ethylidene/ethyl side chain. A possible biogenetic pathway from a perivine precursor, which was also present in the leaf extract, is presented. Differences in the new alkaloid content between the present and previous sample of the same plant (occurring in a different location) are discussed.
Vincamine, a safe natural alkaloid, represents a novel anticancer agent
Bioorg Chem 2021 Feb;107:104626.PMID:33450545DOI:10.1016/j.bioorg.2021.104626.
Vincamine, a well-known plant alkaloid, has been used as a dietary supplement and as a peripheral vasodilator to combat aging in humans. In this study, for the very first time, we demonstrated that Vincamine can function as an anticancer agent in a human alveolar basal epithelial cell line A549 (IC50 = 309.7 μM). The anticancer potential of Vincamine in A549 cells was assessed by molecular assays to determine cell viability, generation of intracellular ROS, nuclear condensation, caspase-3 activity and inhibition, and change in mitochondrial membrane potential (ΔΨm). In silico studies predicted that the anti-proliferative potential of Vincamine is enhanced by its interaction with the apoptotic protein caspase-3, and that this interaction is driven by two hydrogen bonds and has a high free energy of binding (-5.64 kcal/mol) with an estimated association constant (Ka) of 73.67 μM. We found that Vincamine stimulated caspase-3-dependent apoptosis and lowered mitochondrial membrane potential, which ultimately led to cytochrome C release. Vincamine was also found to quench hydroxyl free radicals and deplete iron ions in cancer cells. As a dietary supplement, Vincamine is almost non-toxic in BEAS-2B and 3T3-L1 cells. Therefore, we propose that Vincamine represents a safe anticancer agent in lung cancer cells. Its role in other cancers has yet to be explored.
Vincamine, an active constituent of Vinca rosea ameliorates experimentally induced acute lung injury in Swiss albino mice through modulation of Nrf-2/NF-κB signaling cascade
Int Immunopharmacol 2022 Jul;108:108773.PMID:35453074DOI:10.1016/j.intimp.2022.108773.
Acute lung injury (ALI) or acute respiratory distress syndrome (ARDS) is one of the leading pulmonary inflammatory disorders causing significant morbidity and mortality. Vincamine is a novel phytochemical with promising anti-inflammatory properties. In the current work, the protective effect of Vincamine was studied in vitro (Raw 264.7 macrophages) and in vivo against lipopolysaccharide (LPS) induced ALI in Swiss albino mice. Vincamine significantly reduced nitrite and TNF-α release from the LPS stimulated macrophages and increased the levels of IL-10, indicating potent anti-inflammatory effects. It was observed that Vincamine at the dose of 40 mg/kg, significantly reduced LPS induced inflammatory cell count in blood and in bronchoalveolar lavage (BAL) fluid. Further, Vincamine exerted potent suppression of inflammation by reducing the expression of proinflammatory cytokines, while significantly increased (p < 0.001) the expression of anti-inflammatory cytokine (IL-10 and IL-22). Interestingly, histological changes were reversed in Vincamine treated groups in a dose-dependent manner. Immunohistochemical analysis revealed significantly enhanced expression of NF-κB, TNF-α and COX-2 while reduced expression of Nrf-2 in disease control group, which were significantly (p < 0.001) ameliorated by Vincamine. We, to the best of our knowledge, report for the first time that Vincamine possesses protective potential against LPS induced inflammation and oxidative stress, possibly by inhibiting the NF-κB cascade, while positively regulating the Nrf-2 pathway. These findings are of potential relevance for COVID-19 management concerning the fact that lung injury and ARDS are its critical features.
Anticancer potential of alkaloids: a key emphasis to colchicine, vinblastine, vincristine, vindesine, vinorelbine and Vincamine
Cancer Cell Int 2022 Jun 2;22(1):206.PMID:35655306DOI:10.1186/s12935-022-02624-9.
Cancer, one of the leading illnesses, accounts for about 10 million deaths worldwide. The treatment of cancer includes surgery, chemotherapy, radiation therapy, and drug therapy, along with others, which not only put a tremendous economic effect on patients but also develop drug resistance in patients with time. A significant number of cancer cases can be prevented/treated by implementing evidence-based preventive strategies. Plant-based drugs have evolved as promising preventive chemo options both in developing and developed nations. The secondary plant metabolites such as alkaloids have proven efficacy and acceptability for cancer treatment. Apropos, this review deals with a spectrum of promising alkaloids such as colchicine, vinblastine, vincristine, vindesine, vinorelbine, and Vincamine within different domains of comprehensive information on these molecules such as their medical applications (contemporary/traditional), mechanism of antitumor action, and potential scale-up biotechnological studies on an in-vitro scale. The comprehensive information provided in the review will be a valuable resource to develop an effective, affordable, and cost effective cancer management program using these alkaloids.