Anagyrine
(Synonyms: 安纳基林,(-)-Anagyrine; Monolupine; Rhombinine) 目录号 : GC46853
An alkaloid with anthelmintic and anticancer activities
Cas No.:486-89-5
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
Anagyrine is an alkaloid that has been found in L. albus and has nematocidal and anticancer activities.1,2,3 It binds to muscarinic and nicotinic acetylcholine receptors (AChRs) with IC50 values of 132 and 2,096 µM, respectively, in radioligand binding assays using pig brain membranes that endogenously express high levels of the receptors.1 Anagyrine decreases survival of B. xylophilus worms.2 It inhibits proliferation of TE-671 and SH-SY5Y cancer cells (EC50s = 18.1 and 19.1 µM, respectively).3 Maternal ingestion of anagyrine during gestation is associated with the teratogenic condition crooked calf disease in cattle.4
1.Schmeller, T., Sauerwein, M., Sporer, F., et al.Binding of quinolizidine alkaloids to nicotinic and muscarinic acetylcholine receptorsJ. Nat. Prod.57(9)1316-1319(1994) 2.Matsuda, K., Kimura, K., Komai, K., et al.Nematicidal activities of (-)-N-methylcytisine and (-)-anagyrine from Sophora flavescens against pine wood nematodesAgr. BioI. Chem.53(8)2287-2288(1989) 3.Green, B.T., Lee, S.T., Panter, K.E., et al.Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptorsNeurotoxicol. Teratol.32(3)383-390(2010) 4.Keeler, R.F., Cronin, E.H., and Shupe, J.L.Lupin alkaloids from teratogenic and nonteratogenic lupins. IV. Concentration of total alkaloids, individual major alkaloids, and the teratogen anagyrine as a function of plant part and stage of growth and their relationship to crooked calf diseaseJ. Toxicol. Environ. Health1(6)899-908(1976)
| Cas No. | 486-89-5 | SDF | |
| 别名 | 安纳基林,(-)-Anagyrine; Monolupine; Rhombinine | ||
| Canonical SMILES | O=C1N(C2=CC=C1)C[C@]3([H])[C@@]4([H])CCCCN4C[C@@]2([H])C3 | ||
| 分子式 | C15H20N2O | 分子量 | 244.3 |
| 溶解度 | H2O : 25 mg/mL (102.32 mM; Need ultrasonic); DMSO : 25 mg/mL (102.32 mM; Need ultrasonic) | 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 | 4.0933 mL | 20.4666 mL | 40.9333 mL |
| 5 mM | 0.8187 mL | 4.0933 mL | 8.1867 mL |
| 10 mM | 0.4093 mL | 2.0467 mL | 4.0933 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。
Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle
Res Vet Sci 2017 Dec;115:195-200.PMID:28494312DOI:10.1016/j.rvsc.2017.04.019.
Anagyrine, a teratogenic quinolizidine alkaloid found in Lupinus spp., is proposed to undergo metabolism by pregnant cattle to a piperidine alkaloid which inhibits fetal movement, the putative mechanism behind crooked calf syndrome. The objective of this study was to test the hypothesis that Anagyrine but not lupanine or sparteine can directly, without metabolism, desensitize nicotinic acetylcholine receptors (nAChR) in a cell culture model. SH-SY5Y cells expressing autonomic nAChR, and TE-671 cells expressing fetal muscle-type nAChR were exposed to lupine alkaloids or Dimethylphenylpiperazinium (DMPP) in log10 molar increments from 10nM to 100μM and then to a fixed concentration of acetylcholine (ACh) (10μM for SH-SY5Y cells and 1μM for TE-671 cells) and the responses measured with a membrane potential sensing dye to assess nAChR activation and desensitization. The selective ganglionic nAChR agonist DMPP used as a positive control, was a potent activator and desensitizer of nAChR expressed by SH-SY5Y cells. Lupanine was a weak agonist and desensitizer in SH-SY5Y cells and sparteine was without effect. Anagyrine acted as a partial agonist in both cell lines with EC50 values of 4.2 and 231μM in SH-SY5Y and TE-671 cells, respectively. Anagyrine was a desensitizer of nAChR with DC50 values of 6.9 and 139μM in SH-SY5Y and TE-671 cells, respectively. These results confirm the hypothesis that Anagyrine is a potent and effective desensitizer of nAChR, and that Anagyrine can directly, without metabolism, desensitize nAChR. Moreover, serum Anagyrine concentrations may be a potential biomarker for lupine teratogenicity in cattle.
Crystal structure of Anagyrine perchlorate
Acta Crystallogr E Crystallogr Commun 2015 Apr 25;71(Pt 5):o343-4.PMID:25995939DOI:10.1107/S2056989015007781.
The title mol-ecular salt, C15H21N2O(+)·ClO4 (-), crystallizes with four cations (A, B, C and D) and four anions in the chiral unit cell (space group P21). The alkaloid was isolated from the aerial parts of Genista Hispanica collected in the Samarkand region of Uzbekistan. Each cation is protonated at the N atom that bridges the alkaloid rings C and D. In each cation, ring A is almost planar and ring B adops a sofa conformation with the methyl-ene group bridging to the C ring as the flap. Rings C and D adopt chair conformations with a cis ring junction in all four cations. In the crystal, A+B and C+D dimeric pairs linked by pairs of N-H⋯O hydrogen bonds are observed, which generate R 2 (2)(16) loops in each case. The dimers are consolidated by weak aromatic π-π stacking inter-actions between the A rings [centroid-centroid distances = 3.913 (3) and 3.915 (3) Å].
The effect of body condition on serum concentrations of two teratogenic alkaloids (Anagyrine and ammodendrine) from lupines (Lupinus species) that cause crooked calf disease
J Anim Sci 2008 Oct;86(10):2771-8.PMID:18539842DOI:10.2527/jas.2007-0610.
Several species of lupine (Lupinus spp.) are toxic to livestock, causing death losses in sheep and cattle but more commonly crooked calf disease in pregnant range cows. The major toxic alkaloids in lupine are of the quinolizidine alkaloid group and include the teratogen Anagyrine, which is primarily responsible for crooked calf disease. Lupines also contain teratogenic piperidine alkaloids including ammodendrine. Previous work in sheep has shown that lupine alkaloid clearance may be influenced by the animal's physiological status. Therefore, the purpose of this study was to determine if differences in body condition of cattle would alter the absorption and elimination of Anagyrine or ammodendrine given in a single oral dose as Lupinus leucophyllus or Lupinus sulphureus, respectively. Mature non-lactating cows in low body condition (LBC, n = 4) and high body condition (HBC, n = 4) received a single dose of dry ground lupine plant (2.0 g/kg of BW) via oral gavage. Lupinus leucophyllus (Anagyrine) was dosed first; then after 21 d the same animals were dosed with L. sulphureus (ammodendrine). Blood samples were taken via jugular venipuncture 0 to 60 h after dosing. Serum Anagyrine and ammodendrine concentrations were evaluated. The concentration of Anagyrine was greater (P = 0.001) in the HBC group and peaked 2 h after dosing versus 12 h in LBC cows. Similarly for ammodendrine, the alkaloid concentration peaked at 3 h after dosing for the HBC group compared with 6 h for the LBC group (P = 0.001). Area under the curve tended to differ (P
Lupin alkaloids from teratogenic and nonteratogenic lupins. III. Identification of Anagyrine as the probable teratogen by feeding trials
J Toxicol Environ Health 1976 Jul;1(6):887-98.PMID:966318DOI:10.1080/15287397609529391.
Alkaloidal extracts from teratogenic lupins produced congenital deformities in calves typical of crooked calf disease when the extracts were administered to pregnant cows during the susceptible gestational period. These data and previous epidemiologic studies suggest that one of the four alkaloids in the preparation, Anagyrine, is the responsible teratogen. Severity of the malformations was directly related to the level of Anagyrine present in the preparations administered.
Lupin alkaloids from teratogenic and nonteratogenic lupins. IV. Concentration of total alkaloids, individual major alkaloids, and the teratogen Anagyrine as a function of plant part and stage of growth and their relationship to crooked calf disease
J Toxicol Environ Health 1976 Jul;1(6):899-908.PMID:966319DOI:10.1080/15287397609529392.
The concentrations of total alkaloids and individual major alkaloids including the teratogen Anagyrine were measured in various plant parts of teratogenic lupins as the plants matured. All alkaloids including angyrine were high in concentration in above-ground parts early in growth and decreased as plants matured, except for an increase in mature, intact seeds. Seeds were highest, followed by early growth leaves and stems. Roots were lowest with mature leaves and stems only slightly higher. Pregnant cows have the greatest risk of giving birth to calves with crooked calf disease when the concentration of the teratogen Anagyrine is highest and the cows are in the susceptible 40-75 day gestation period when ingesting the plant.