(-)-Salutaridine
(Synonyms: 清风藤碱) 目录号 : GC34945
An alkaloid with cytoprotective and vasorelaxant activities
Cas No.:4090-18-0
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
(–)-Sinoacutine is an alkaloid that has been found in S. acutum and has cytoprotective and vasorelaxant activities.1,2 It inhibits hydrogen peroxide-induced decreases in viability in PC12 cells when used at concentrations of 1 and 10 μM.1 (–)-Sinoacutine induces relaxation of precontracted isolated rat aortic rings (IC50 = 32.8 μM).2
1.Bao, G.-H., Qin, G.-W., Wang, R., et al.Morphinane alkaloids with cell protective effects from Sinomenium acutumJ. Nat. Prod.68(7)1128-1130(2005) 2.Tsai, T.-H., Wang, G.-J., and Lin, L.-C.Vasorelaxing alkaloids and flavonoids from Cassytha filiformisJ. Nat. Prod.71(2)289-291(2008)
| Cas No. | 4090-18-0 | SDF | |
| 别名 | 清风藤碱 | ||
| Canonical SMILES | OC(C([C@]1(CCN2C)C=C3OC)=C4C[C@@]2([H])C1=CC3=O)=C(C=C4)OC | ||
| 分子式 | C19H21NO4 | 分子量 | 327.37 |
| 溶解度 | DMF: 10mg/mL,DMF:PBS (pH 7.2) (1:4): 0.2mg/mL,DMSO: 5mg/mL,Ethanol: 1mg/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 | 3.0546 mL | 15.2732 mL | 30.5465 mL |
| 5 mM | 0.6109 mL | 3.0546 mL | 6.1093 mL |
| 10 mM | 0.3055 mL | 1.5273 mL | 3.0546 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。
Pharmacodynamic investigation of (+/-)-Salutaridine
Arzneimittelforschung 1984;34(12):1758-9.PMID:6099129doi
The alkaloid 5,6,8,14-tetradehydro-4-hydroxy-3, 6-dimethoxy-17-methyl-morphinan-7-one[+/-)-Salutaridine) was found to possess 3H-gamma-aminobutyric acid (3H-GABA) displacing activity (IC50 less than 1 mumol/l) in rat brain synaptic membranes. The enhancement of specific 3H-diazepam binding by increasing concentration of (+/-)-Salutaridine follows a maximum curve indicating (+/-)-Salutaridine to be a partial agonist at the GABA/benzodiazepine receptor complex.
Precursors of the mammalian synthesis of morphine: (+)-Salutaridine and (-)-thebaine from (+)-6-demethylsalutaridine, and (-)-N-13CH3-thebaine from (-)-northebaine
FEBS Lett 1986 Sep 29;206(1):125-9.PMID:3758343DOI:10.1016/0014-5793(86)81353-9.
Standard samples of pure (+)-Salutaridine and (-)-thebaine required to study the mammalian origin of morphine, were prepared from (+)-6-demethylsalutaridine by published procedures and were characterized by CD spectra and physical data. Reductive N-methylation of (-)-northebaine afforded (-)-thebaine, and when 13C-labeled formalin was used, (-)-thebaine with a 13C label on the N-methyl carbon atom resulted. The latter represents a model procedure to prepare ultimately N-14CH3-labeled (-)-thebaine and 14C-labeled congeners.
Biosynthesis of the morphine alkaloids
Science 1967 Jan 13;155(3759):170-3.PMID:5332945DOI:10.1126/science.155.3759.170.
Tracer experiments, supported throughout by the analogous chemical transformations, have firmly established the biosynthetic sequence tyrosine -->norlaudanosoline --> reticuline --> salutaridine --> salutaridinol-I -->thebaine --> codeine --> morphine in Papaver somniferum. In general, the farther a precursor lies along this sequence, the more efficient its conversion to morphine in the intact plant. Several intermediates remain to be discovered, such as those lying between tyrosine and norlaudanosoline and between thebaine and codeine. Proof that morphine is made only by the reticuline-salutaridine route is still lacking and would require a careful comparison of the rate of morphine synthesis with the turnover rates for the various intermediates. More importantly, detailed knowledge of the mechanism of each biochemical step can come only with isolation of the enzyme system involved. The chemical oxidation of (-)-reticuline, to give salutaridine, can only be accomplished in very low (0.02 percent) yield (15, 26), whereas, even with whole plants, the biological incorporation of reticuline into the morphine alkaloids can reach 8 percent (13). One would like to know just how an enzyme system directs the oxidative cyclization of reticuline in the desired sense. Kleinschmidt and Mothes and Fairbairn and Wassel (27) have shown that the latex isolated from opium poppies is capable of transforming tyrosine into morphine. Perhaps further work with opium latex will provide the key to the remaining problems of morphine biosynthesis.
Enzymic conversion of reticuline to salutaridine by cell-free systems from Papaver somniferum
Biochemistry 1982 Aug 3;21(16):3729-34.PMID:7138803DOI:10.1021/bi00259a001.
A cell-free extract from the opium poppy, Papaver somniferum, was prepared that utilized hydrogen peroxide to convert (+/-)-[3-3H]reticuline to [3H]salutaridine in 80-85% yield based on consumed [3-3H]reticuline. The phenolic-coupling enzyme activity was not detected in the crude homogenate of whole plants. Reticuline conversion to salutaridine was accomplished only after methods were developed to separate both alkaloid and hydrogen peroxide degrading activities from the desired enzyme activity by centrifugal fractionation of carefully prepared stem and root extracts. Purity of the enzymatically produced [3H]salutaridine was established by chromatographic methods and synthetic conversion to [3H]-thebaine.
Evolution of morphine biosynthesis in opium poppy
Phytochemistry 2009 Oct-Nov;70(15-16):1696-707.PMID:19665152DOI:10.1016/j.phytochem.2009.07.006.
Benzylisoquinoline alkaloids (BIAs) are a group of nitrogen-containing plant secondary metabolites comprised of an estimated 2500 identified structures. In BIA metabolism, (S)-reticuline is a key branch-point intermediate that can be directed into several alkaloid subtypes with different structural skeleton configurations. The morphinan alkaloids are one subclass of BIAs produced in only a few plant species, most notably and abundantly in the opium poppy (Papaver somniferum). Comparative transcriptome analysis of opium poppy and several other Papaver species that do not accumulate morphinan alkaloids showed that known genes encoding BIA biosynthetic enzymes are expressed at higher levels in P. somniferum. Three unknown cDNAs that are co-ordinately expressed with several BIA biosynthetic genes were identified as enzymes in the pathway. One of these enzymes, salutaridine reductase (SalR), which is specific for the production of morphinan alkaloids, was isolated and heterologously overexpressed in its active form not only from P. somniferum, but also from Papaver species that do not produce morphinan alkaloids. SalR is a member of a class of short chain dehydrogenase/reductases (SDRs) that are active as monomers and possess an extended amino acid sequence compared with classical SDRs. Homology modelling and substrate docking revealed the substrate binding site for SalR. The amino acids residues conferring salutaridine binding were compared to several members of the SDR family from different plant species, which non-specifically reduce (-)-menthone to (+)-neomenthol. Previously, it was shown that some of these proteins are involved in plant defence. The recruitment of specific monomeric SDRs from monomeric SDRs involved in plant defence is discussed.