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(+/-)-Sigmoidin A
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Product Name (+/-)-Sigmoidin A
Price:
CAS No.: 176046-04-1
Catalog No.: CFN92415
Molecular Formula: C25H28O6
Molecular Weight: 424.5 g/mol
Purity: >=98%
Type of Compound: Flavonoids
Physical Desc.: Cryst.
Source: The roots of Glycyrrhiza uralensis Fisch
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF
Similar structural: Comparison (Web)  (SDF)
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Size /Price /Stock 10 mM * 1 mL in DMSO / Inquiry
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: Sigmoidin A has moderate antioxidant, antimicrobial and anti-inflammatory activity.
Targets: 5-lipoxygenase | Antifection
In vitro:
Planta Medica, 2009, 76(6):589-594.
Comparative Antioxidant, Prooxidant and Cytotoxic Activity of Sigmoidin A and Eriodictyol.[Reference: WebLink]
Sigmoidin A (SGN) is a prenylated flavanone derivative of eriodictyol (ERD) with reported moderate antioxidant, antimicrobial and anti-inflammatory activity.
METHODS AND RESULTS:
Since ERD and other structurally similar antioxidant phenolic compounds have been shown to induce prooxidative macromolecular damage and cytotoxicity in cancer cells, the comparative IN VITRO effects of these structural analogues on cancer cell viability and Cu(II)-dependent DNA damage were studied. In the presence of Cu(II) ions, both SGN and ERD (7.4-236 microM) caused comparable concentration-dependent pBR322 plasmid DNA strand scission. The DNA damage induced by SGN and ERD could be abolished by ROS scavengers, glutathione (GSH) and catalase as well as EDTA and a specific Cu(I) chelator neocuproine. Both ERD and SGN readily reduce Cu(II) to Cu(I) suggesting a prooxidative mechanism of DNA damage.
CONCLUSIONS:
In a cell free system, ERD and SGN did also show comparable radical scavenging activity. SGN was, however, by an order of magnitude more cytotoxic to cancer cells than ERD and this effect was significantly attenuated by GSH suggesting a prooxidative mechanism of cell death. A depletion of intracellular GSH level by SGN in cancer cells is also demonstrated.
(+/-)-Sigmoidin A Description
Source: The roots of Glycyrrhiza uralensis Fisch
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3557 mL 11.7786 mL 23.5571 mL 47.1143 mL 58.8928 mL
5 mM 0.4711 mL 2.3557 mL 4.7114 mL 9.4229 mL 11.7786 mL
10 mM 0.2356 mL 1.1779 mL 2.3557 mL 4.7114 mL 5.8893 mL
50 mM 0.0471 mL 0.2356 mL 0.4711 mL 0.9423 mL 1.1779 mL
100 mM 0.0236 mL 0.1178 mL 0.2356 mL 0.4711 mL 0.5889 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Animal Research:
Planta Medica, 2004, 70(02):104-107.
Anti-Inflammatory Activities of Two Flavanones, Sigmoidin A and Sigmoidin B, from Erythrina sigmoidea[Reference: WebLink]
Two prenylated flavanones isolated from Erythrina sigmoidea Hua (sigmoidin A and sigmoidin B) were studied for their ability to inhibit the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and arachidonic acid metabolism. In addition, the compounds were studied in two experimental models of inflammation induced in mouse ears by 12- O-tetradecanoylphorbol 13-acetate (TPA) and the phospholipase A (2)-induced mouse paw oedema.
METHODS AND RESULTS:
Both sigmoidins A and B proved to be potent scavengers of the DPPH radical, while the study of the inhibition of arachidonic acid metabolism demonstrated that these same compounds were selective inhibitors of 5-lipoxygenase, with no effect on cyclooxygenase-1 activity. Dose-response inhibitor potency was established for sigmoidin A (IC (50) = 31 microM). In the assay of phospholipase A (2)-induced mouse paw oedema, only the sigmoidin B derivative inhibited oedema formation at 60 min, showing a percentage of inhibition below that obtained with cyproheptadine (59 % vs. 74 %). In the TPA test, sigmoidins A and B decreased the induced oedema by 89 % and 83 %, respectively.
CONCLUSIONS:
This is the first time that the anti-inflammatory activity and antioxidant properties of these prenylflavanones have been reported. The results indicate that the compounds have different mechanisms of action depending on whether one or two prenyl groups are present in ring B.
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