Perakine
(Synonyms: 霹雳萝芙木碱) 目录号 : GC39017
Perakine 是从 Alstonia yunnanensis 中分离得到的一种吲哚生物碱。具有抗炎活性。
Cas No.:4382-56-3
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
Perakine is an indole alkaloid isolated from Alstonia yunnanensis. Anti-inflammatory activities[1].
[1]. Cao P, et al. Monoterpenoid indole alkaloids from Alstonia yunnanensis and their cytotoxic and anti-inflammatory activities. Molecules. 2012 Nov 16;17(11):13631-41.
| Cas No. | 4382-56-3 | SDF | |
| 别名 | 霹雳萝芙木碱 | ||
| Canonical SMILES | CC(O[C@H](C(C1C[C@]2([H])N3[C@@H](C)[C@@H]1C=O)[C@]3([H])C4)[C@@]54C2=NC6=C5C=CC=C6)=O | ||
| 分子式 | C21H22N2O3 | 分子量 | 350.41 |
| 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 | 2.8538 mL | 14.269 mL | 28.538 mL |
| 5 mM | 0.5708 mL | 2.8538 mL | 5.7076 mL |
| 10 mM | 0.2854 mL | 1.4269 mL | 2.8538 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。
Enantioselective Reduction of α,β-Unsaturated Ketones and Aryl Ketones by Perakine Reductase
Org Lett 2019 Jun 21;21(12):4411-4414.PMID:31045374DOI:10.1021/acs.orglett.9b00950.
This report describes the enantioselective reduction of structurally diverse α,β-unsaturated ketones and aryl ketones by Perakine reductase (PR) from Rauvolfia. This enzymatic reduction produces α-chiral allylic and aryl alcohols with excellent enantioselectivity and most of the products in satisfactory yields. Furthermore, the work demonstrates 1 mmol scale reactions for product delivery without any detrimental effect on yield and enantioselectivity. The catalytic mechanism, determined by 3D-structure-based modeling of PR and ligand complexes, is also described.
Crystal structure of Perakine reductase, founding member of a novel aldo-keto reductase (AKR) subfamily that undergoes unique conformational changes during NADPH binding
J Biol Chem 2012 Mar 30;287(14):11213-21.PMID:22334702DOI:10.1074/jbc.M111.335521.
Perakine reductase (PR) catalyzes the NADPH-dependent reduction of the aldehyde Perakine to yield the alcohol raucaffrinoline in the biosynthetic pathway of ajmaline in Rauvolfia, a key step in indole alkaloid biosynthesis. Sequence alignment shows that PR is the founder of the new AKR13D subfamily and is designated AKR13D1. The x-ray structure of methylated His(6)-PR was solved to 2.31 Å. However, the active site of PR was blocked by the connected parts of the neighbor symmetric molecule in the crystal. To break the interactions and obtain the enzyme-ligand complexes, the A213W mutant was generated. The atomic structure of His(6)-PR-A213W complex with NADPH was determined at 1.77 Å. Overall, PR folds in an unusual α(8)/β(6) barrel that has not been observed in any other AKR protein to date. NADPH binds in an extended pocket, but the nicotinamide riboside moiety is disordered. Upon NADPH binding, dramatic conformational changes and movements were observed: two additional β-strands in the C terminus become ordered to form one α-helix, and a movement of up to 24 Å occurs. This conformational change creates a large space that allows the binding of substrates of variable size for PR and enhances the enzyme activity; as a result cooperative kinetics are observed as NADPH is varied. As the founding member of the new AKR13D subfamily, PR also provides a structural template and model of cofactor binding for the AKR13 family.
Expression, purification, crystallization and preliminary X-ray analysis of Perakine reductase, a new member of the aldo-keto reductase enzyme superfamily from higher plants
Acta Crystallogr Sect F Struct Biol Cryst Commun 2006 Dec 1;62(Pt 12):1286-9.PMID:17142919DOI:10.1107/S174430910605041X.
Perakine reductase (PR) is a novel member of the aldo-keto reductase enzyme superfamily from higher plants. PR from the plant Rauvolfia serpentina is involved in the biosynthesis of monoterpenoid indole alkaloids by performing NADPH-dependent reduction of Perakine, yielding raucaffrinoline. However, PR can also reduce cinnamic aldehyde and some of its derivatives. After heterologous expression of a triple mutant of PR in Escherichia coli, crystals of the purified and methylated enzyme were obtained by the hanging-drop vapour-diffusion technique at 293 K with 100 mM sodium citrate pH 5.6 and 27% PEG 4000 as precipitant. Crystals belong to space group C222(1) and diffract to 2.0 A, with unit-cell parameters a = 58.9, b = 93.0, c = 143.4 A.
Purification, cloning, functional expression and characterization of Perakine reductase: the first example from the AKR enzyme family, extending the alkaloidal network of the plant Rauvolfia
Plant Mol Biol 2008 Jul;67(5):455-67.PMID:18409028DOI:10.1007/s11103-008-9331-7.
Perakine reductase (PR) catalyzes an NADPH-dependent step in a side-branch of the 10-step biosynthetic pathway of the alkaloid ajmaline. The enzyme was cloned by a "reverse-genetic" approach from cell suspension cultures of the plant Rauvolfia serpentina (Apocynaceae) and functionally expressed in Escherichia coli as the N-terminal His(6)-tagged protein. PR displays a broad substrate acceptance, converting 16 out of 28 tested compounds with reducible carbonyl function which belong to three substrate groups: benzaldehyde, cinnamic aldehyde derivatives and monoterpenoid indole alkaloids. The enzyme has an extraordinary selectivity in the group of alkaloids. Sequence alignments define PR as a new member of the aldo-keto reductase (AKR) super family, exhibiting the conserved catalytic tetrad Asp52, Tyr57, Lys84, His126. Site-directed mutagenesis of each of these functional residues to an alanine residue results in >97.8% loss of enzyme activity, in compounds of each substrate group. PR represents the first example of the large AKR-family which is involved in the biosynthesis of plant monoterpenoid indole alkaloids. In addition to a new esterase, PR significantly extends the Rauvolfia alkaloid network to the novel group of peraksine alkaloids.
Monoterpenoid indole alkaloids from Alstonia rupestris with cytotoxic, antibacterial and antifungal activities
Fitoterapia 2014 Sep;97:142-7.PMID:24887700DOI:10.1016/j.fitote.2014.05.018.
A chemical investigation of the 80% EtOH extract of the aerial plant of Alstonia rupestris afforded four new monoterpenoid indole alkaloids, 6,7-epoxy-8-oxo-vincadifformine (1), 11-acetyl-6,7-epoxy-8-oxo-vincadifformine (2), 11-hydroxy-14-chloro-15-hydroxy-vincadifformine (3), and Perakine N1,N4-dioxide (4), together with two known compounds, 11-hydroxy-6,7-epoxy-8-oxovincadifformine (5) and vinorine N1,N4-dioxide (6). Structural elucidation of all the compounds was performed by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. Alkaloids 1, 2 and 5 showed significant cytotoxicities against all the tested tumor cell lines of the head and neck squamous cell carcinoma with IC50 value less than 20 μM and antimicrobial activities against two fungi (Alternaria alternata and Phytophthora capsici). Alkaloids 4 and 6 exhibited the activity against bacterium Staphylococcus aureus.