Sinoacutine

CAS# 4090-18-0

Sinoacutine

Catalog No. BCN5461----Order now to get a substantial discount!

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Sinoacutine: 5mg $690 In Stock
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Quality Control of Sinoacutine

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Chemical structure

Sinoacutine

3D structure

Chemical Properties of Sinoacutine

Cas No. 4090-18-0 SDF Download SDF
PubChem ID 821366 Appearance Powder
Formula C19H21NO4 M.Wt 327.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CN1CCC23C=C(C(=O)C=C2C1CC4=C3C(=C(C=C4)OC)O)OC
Standard InChIKey GVTRUVGBZQJVTF-ORAYPTAESA-N
Standard InChI InChI=1S/C19H21NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Sinoacutine

The roots of Stephania epigaea Lo

Biological Activity of Sinoacutine

Description1. Sinoacutine has protective effects against hydrogen peroxide-induced cell injury.
TargetsP450 (e.g. CYP17)

Sinoacutine Dilution Calculator

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Sinoacutine Molarity Calculator

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Preparing Stock Solutions of Sinoacutine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0544 mL 15.2718 mL 30.5437 mL 61.0874 mL 76.3592 mL
5 mM 0.6109 mL 3.0544 mL 6.1087 mL 12.2175 mL 15.2718 mL
10 mM 0.3054 mL 1.5272 mL 3.0544 mL 6.1087 mL 7.6359 mL
50 mM 0.0611 mL 0.3054 mL 0.6109 mL 1.2217 mL 1.5272 mL
100 mM 0.0305 mL 0.1527 mL 0.3054 mL 0.6109 mL 0.7636 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Sinoacutine

CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy.[Pubmed:19567876]

J Biol Chem. 2009 Sep 4;284(36):24432-42.

Morphine is a powerful analgesic natural product produced by the opium poppy Papaver somniferum. Although formal syntheses of this alkaloid have been reported, the morphine molecule contains five stereocenters and a C-C phenol linkage that to date render a total synthesis of morphine commercially unfeasible. The C-C phenol-coupling reaction along the biosynthetic pathway to morphine in opium poppy is catalyzed by the cytochrome P450-dependent oxygenase salutaridine synthase. We report herein on the identification of salutaridine synthase as a member of the CYP719 family of cytochromes P450 during a screen of recombinant cytochromes P450 of opium poppy functionally expressed in Spodoptera frugiperda Sf9 cells. Recombinant CYP719B1 is a highly stereo- and regioselective enzyme; of forty-one compounds tested as potential substrates, only (R)-reticuline and (R)-norreticuline resulted in formation of a product (salutaridine and norsalutaridine, respectively). To date, CYP719s have been characterized catalyzing only the formation of a methylenedioxy bridge in berberine biosynthesis (canadine synthase, CYP719A1) and in benzo[c]phenanthridine biosynthesis (stylopine synthase, CYP719A14). Previously identified phenol-coupling enzymes of plant alkaloid biosynthesis belong only to the CYP80 family of cytochromes. CYP719B1 therefore is the prototype for a new family of plant cytochromes P450 that catalyze formation of a phenol-couple.

Morphinane alkaloids with cell protective effects from Sinomenium acutum.[Pubmed:16038566]

J Nat Prod. 2005 Jul;68(7):1128-30.

One new morphinane alkaloid, sinomenine N-oxide (1), and one new natural occurring morphinane alkaloid, N-demethylsinomenine (2), together with six known alkaloids, 7,8-didehydro-4-hydroxy-3,7-dimethoxymorphinan-6-ol (3), sinomenine (4), Sinoacutine (5), N-norSinoacutine, acutumine, and acutumidine, were isolated from the stems of Sinomenium acutum. Their structures were elucidated on the basis of spectroscopic analysis and chemical methods. Compounds 2, 3, and 5 have protective effects against hydrogen peroxide-induced cell injury.

Atomic structure of salutaridine reductase from the opium poppy (Papaver somniferum).[Pubmed:21169353]

J Biol Chem. 2011 Feb 25;286(8):6532-41.

The opium poppy (Papaver somniferum L.) is one of the oldest known medicinal plants. In the biosynthetic pathway for morphine and codeine, salutaridine is reduced to salutaridinol by salutaridine reductase (SalR; EC 1.1.1.248) using NADPH as coenzyme. Here, we report the atomic structure of SalR to a resolution of approximately 1.9 A in the presence of NADPH. The core structure is highly homologous to other members of the short chain dehydrogenase/reductase family. The major difference is that the nicotinamide moiety and the substrate-binding pocket are covered by a loop (residues 265-279), on top of which lies a large "flap"-like domain (residues 105-140). This configuration appears to be a combination of the two common structural themes found in other members of the short chain dehydrogenase/reductase family. Previous modeling studies suggested that substrate inhibition is due to mutually exclusive productive and nonproductive modes of substrate binding in the active site. This model was tested via site-directed mutagenesis, and a number of these mutations abrogated substrate inhibition. However, the atomic structure of SalR shows that these mutated residues are instead distributed over a wide area of the enzyme, and many are not in the active site. To explain how residues distal to the active site might affect catalysis, a model is presented whereby SalR may undergo significant conformational changes during catalytic turnover.

Removal of substrate inhibition and increase in maximal velocity in the short chain dehydrogenase/reductase salutaridine reductase involved in morphine biosynthesis.[Pubmed:19648114]

J Biol Chem. 2009 Sep 25;284(39):26758-67.

Salutaridine reductase (SalR, EC 1.1.1.248) catalyzes the stereospecific reduction of salutaridine to 7(S)-salutaridinol in the biosynthesis of morphine. It belongs to a new, plant-specific class of short-chain dehydrogenases, which are characterized by their monomeric nature and increased length compared with related enzymes. Homology modeling and substrate docking suggested that additional amino acids form a novel alpha-helical element, which is involved in substrate binding. Site-directed mutagenesis and subsequent studies on enzyme kinetics revealed the importance of three residues in this element for substrate binding. Further replacement of eight additional residues led to the characterization of the entire substrate binding pocket. In addition, a specific role in salutaridine binding by either hydrogen bond formation or hydrophobic interactions was assigned to each amino acid. Substrate docking also revealed an alternative mode for salutaridine binding, which could explain the strong substrate inhibition of SalR. An alternate arrangement of salutaridine in the enzyme was corroborated by the effect of various amino acid substitutions on substrate inhibition. In most cases, the complete removal of substrate inhibition was accompanied by a substantial loss in enzyme activity. However, some mutations greatly reduced substrate inhibition while maintaining or even increasing the maximal velocity. Based on these results, a double mutant of SalR was created that exhibited the complete absence of substrate inhibition and higher activity compared with wild-type SalR.

Description

(-)-Salutaridine (Salutaridine) is an alkaloid isolated from the stems of Sinomenium acutum.

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