(+/-)-Sigmoidin A | CAS:176046-04-1 | Manufacturer ChemFaces

(+/-)-Sigmoidin A

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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.

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.

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)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Flavonoids Compound Library Antifection Inhibitor Library

	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

CFN97893	Sanggenol P	1351931-30-0	492.6	C₃₀H₃₆O₆
CFN92415	(+/-)-Sigmoidin A	176046-04-1	424.5	C₂₅H₂₈O₆
CFN95213	Licoflavanone	119240-82-3	340.4	C₂₀H₂₀O₅
CFN97958	4'-O-Methyllicoflavanone	1038753-13-7	354.4	C₂₁H₂₂O₅
CFN92320	Kuwanon E	68401-05-8	424.5	C₂₅H₂₈O₆
CFN92695	Sanggenol A	174423-30-4	424.5	C₂₅H₂₈O₆
CFN97979	Sanggenon N	92280-12-1	422.5	C₂₅H₂₆O₆
CFN93042	Glabrol	59870-65-4	392.49	C₂₅H₂₈O₄
CFN92669	Euchrestaflavanone A	80510-05-0	408.5	C₂₅H₂₈O₅
CFN92667	Euchrenone A10	171828-81-2	406.5	C₂₅H₂₆O₅