Linamarin
(Synonyms: 亞麻苷,Phaseolunatin) 目录号 : GC40659
A cyanogenic glucoside
Cas No.:554-35-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Linamarin is a glucoside of acetone cyanohydrin found in the leaves and roots of cassava, lima beans, and flax. It is thought to function in the transport of nitrogen from plant leaves to roots in young plants but also serves as a plant defense mechanism. Linamarin is converted to toxic hydrocyanic acid or prussic acid when it comes into contact with linamarase, an enzyme that is released when the cells of cassava roots are ruptured.
| Cas No. | 554-35-8 | SDF | |
| 别名 | 亞麻苷,Phaseolunatin | ||
| Canonical SMILES | O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C)(C#N)C | ||
| 分子式 | C10H17NO6 | 分子量 | 247.2 |
| 溶解度 | DMF: 25 mg/mL,DMSO: 30 mg/mL,Ethanol: 10 mg/mL,PBS (pH 7.2): 2 mg/mL | 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 | 4.0453 mL | 20.2265 mL | 40.4531 mL |
| 5 mM | 0.8091 mL | 4.0453 mL | 8.0906 mL |
| 10 mM | 0.4045 mL | 2.0227 mL | 4.0453 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。
Structural characterization of cassava linamarase-linamarin enzyme complex: an integrated computational approach
J Biomol Struct Dyn 2022;40(19):9270-9278.PMID:34018467DOI:10.1080/07391102.2021.1925156.
Cassava linamarase is a hydrolyzing enzyme that belongs to a glycoside hydrolase family 1 (GH1). It is responsible for breaking down Linamarin to toxic cyanide. The enzyme provides a defensive mechanism for plants against herbivores and has various applications in many fields. Understanding the structure of linamarase at the molecular level is a key to avail its reaction mechanism. In this study, the three-dimensional (3D) structure of linamarase was built for the first time using homology modelling and used to study its interaction with Linamarin. Molecular docking calculations established the binding and orientation nature of Linamarin, while molecular dynamics (MD) simulation established protein-ligand complexes' stability. Binding-free energy based on MM/PBSA was further used to rescore the docking results. An ensemble structure was found to be relatively stable compared to the modelled structure. This study sheds light on the exploration of linamarase towards understanding its reaction mechanisms.Communicated by Ramaswamy H. Sarma.
Metabolism of Linamarin in rats
Food Chem Toxicol 1989 Jul;27(7):451-4.PMID:2550336DOI:10.1016/0278-6915(89)90031-8.
The metabolism of Linamarin [2(beta-D-glucopyranosyloxy)isobutyronitrile] was investigated in male albino Wistar rats and using rat liver microsomal preparations. In the in vitro experiments incubations of varying concentrations of Linamarin at pH 6.0-6.5 with liver microsomal preparations resulted in rapid degradation of the substrate without concomitant production of any detectable amount of hydrogen cyanide (HCN) or of thiocyanate, its detoxication derivative. Boiled incubation medium did not degrade Linamarin. Mathematical treatment of the degradation data generated theoretical HCN values that were used to construct a Lineweaver-Burke plot, which gave apparent Km and Vmax values of 3.3 mM-linamarin and 0.017 mg HCN/min/mg protein, respectively. In the in vivo experiments excretion of glucosidic cyanide (Linamarin) in rat urine was found, within the range of applied oral doses 10-350 mg/kg body weight, to be dose dependent. Urinary excretion of HCN and thiocyanate did not show this correlation. Following administration (iv) of 10, 50 or 100 mg Linamarin, elimination of the test substance from rat blood was observed to occur exponentially, and the half-life was estimated at about 90 min for all three dose levels.
An efficient and high-yielding method for extraction and purification of Linamarin from Cassava; in vitro biological evaluation
Nat Prod Res 2021 Nov;35(21):4169-4172.PMID:32223339DOI:10.1080/14786419.2020.1744136.
During the last three decades, studies of Linamarin extracted from cassava have received increased attention due to the presence of high cyanogenic compounds in these extracts. The methods that are utilized to isolate Linamarin are either tedious or use acidic conditions resulting in poor yields. In this study, a novel cryocooled method of extraction has been developed to isolate Linamarin from Cassava root peel. Approximately 18 g of Linamarin was isolated from 1 kg of fresh Cassava root peel, which is the highest amount reported to date. Linamarin was fully characterized using NMR, IR and LCMS. The anti-cancer properties of pure Linamarin and Cassava crude extract were evaluated by a comprehensive cytotoxic assay, using MCF-7, HepG2, NCI H-292, AN3CA and MRC-5 cell lines. The crude extract showed higher cytotoxicity compared to pure Linamarin. The results of the biological evaluation are comparable to other reported studies in the literature.
Mechanisms of increased Linamarin degradation during solid-substrate fermentation of cassava
World J Microbiol Biotechnol 1995 May;11(3):266-70.PMID:24414645DOI:10.1007/BF00367096.
Several fungi and bacteria, isolated from Ugandan domestic fermented cassava, released HCN from Linamarin in defined growth media. In 72 h, a Bacillus sp. decreased the Linamarin to 1% of initial concentrations, Mucor racemosus to 7%, Rhizopus oryzae and R. stolonifer to 30%, but Neurospora sitophila and Geotrichum candidum hardly degraded the Linamarin. Adding pectolytic and cellulolytic enzymes, but not linamarase, to root pieces under aseptic conditions, led to root softening and significantly lower Linamarin contents. Neurospora sitophila showed no linamarase activity, in contrast to M. racemosus and Bacillus sp., both of which were less effective in root softening and decreasing the root Linamarin content. The most important contribution of microorganisms to Linamarin decrease in the solid-substrate fermentation of cassava is their cell-wall-degrading activity, which enhances the contact between endogenous linamarase and Linamarin.
Comparative metabolism of Linamarin and amygdalin in hamsters
Food Chem Toxicol 1986 May;24(5):417-20.PMID:3744195DOI:10.1016/0278-6915(86)90206-1.
Rates of cyanide liberation resulting from hydrolysis of the cyanogenic glycosides Linamarin, amygdalin and prunasin by a crude beta-glucosidase prepared from hamster caecum were studied in vitro. In addition, hamster blood cyanide and thiocyanate concentrations were determined at 0.5, 1, 2, 3 and 4 hr after an oral dose of 0.44 mmol Linamarin or amygdalin/kg body weight. Plots of cyanide liberated v. time for Linamarin and prunasin yielded straight lines. A similar plot for amygdalin was curvilinear, with the rate of cyanide release increasing with time. At 10(-3) M substrate concentrations, the average rates of hydrolysis of prunasin, amygdalin and Linamarin were 1.39, 0.57 and 0.13 nmol/min/mg protein, respectively. Lineweaver-Burk plots yielded apparent Km and Vmax values of 3.63 X 10(-5) M and 0.35 nmol/min/mg protein, respectively, for amygdalin, and 7.33 X 10(-3) M and 1.04 nmol/min/mg protein, respectively, for Linamarin. Blood cyanide concentrations following amygdalin treatment reached their highest level (130 nmol/ml) 1 hr after dosing and remained elevated until 3 hr after treatment. Blood cyanide concentrations following Linamarin treatment reached their highest level (116 nmol/ml) after 3 hr and then declined immediately. Area under the blood cyanide concentration-time curve was 395 nmol-hr/ml for amygdalin and 318 nmol-hr/ml for Linamarin. The results suggest a faster rate of enzymatic hydrolysis and cyanide absorption for amygdalin than for Linamarin.