1-Dehydro-10-gingerdione | CAS:136826-50-1

1-Dehydro-10-gingerdione

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Description:

1-Dehydro-10-gingerdione has anti-inflammatory action, the molecular target is Myeloid differentiation protein; it involves in the suppression of NF-κB-regulated gene expression in LPS-activated macrophages, has therapeutic potential in NF-κB-associated inflammation and autoimmune disorders.

Targets:

NF-kB | TLR | IkB | TNF-α | NOS | COX | IL Receptor | AP-1 | IFN-γ | IKK

In vitro:

Br J Pharmacol. 2012 Sep;167(1):128-40.

1-Dehydro-[10]-gingerdione from ginger inhibits IKKβ activity for NF-κB activation and suppresses NF-κB-regulated expression of inflammatory genes.[Pubmed: 22489648]

Pungent constituents of ginger (Zingiber officinale) have beneficial effects on inflammatory pain and arthritic swelling. However, the molecular basis for these pharmacological properties is only partially understood. Here, we investigated the molecular target of 1-Dehydro-10-gingerdione (D10G), one of the pungent constituents of ginger, that mediates its suppression of NF-κB-regulated expression of inflammatory genes linked to toll-like receptor (TLR)-mediated innate immunity.
METHODS AND RESULTS:
RAW 264.7 macrophages or primary macrophages-derived from bone marrows of C57BL/6 or C3H/HeJ mice were stimulated with the TLR4 agonist LPS in the presence of 1-Dehydro-10-gingerdione. Catalytic activity of inhibitory κB (IκB) kinase β (IKKβ) was determined by a kinase assay and immunoblot analysis, and the expression of inflammatory genes by RT-PCR analysis and a promoter-dependent reporter assay. 1-Dehydro-10-gingerdione directly inhibited the catalytic activity of cell-free IKKβ. Moreover, 1-Dehydro-10-gingerdione irreversibly inhibited cytoplasmic IKKβ-catalysed IκBα phosphorylation in macrophages activated by TLR agonists or TNF-α, and also IKKβ vector-elicited NF-κB transcriptional activity in these cells. These effects of 1-Dehydro-10-gingerdione were abolished by substitution of the Cys(179) with Ala in the activation loop of IKKβ, indicating a direct interacting site of 1-Dehydro-10-gingerdione. This mechanism was shown to mediate 1-Dehydro-10-gingerdione-induced disruption of NF-κB activation in LPS-stimulated macrophages and the suppression of NF-κB-regulated gene expression of inducible NOS, COX-2 and IL-6.
CONCLUSIONS:
This study demonstrates that IKKβ is a molecular target of 1-Dehydro-10-gingerdione involved in the suppression of NF-κB-regulated gene expression in LPS-activated macrophages; this suggests 1-Dehydro-10-gingerdione has therapeutic potential in NF-κB-associated inflammation and autoimmune disorders.

1-Dehydro-10-gingerdione Description

Source:	The rhizomes of Zingber officinale Rosc.
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.

Kinase Assay:

Biochem Biophys Res Commun. 2012 Mar 23;419(4):735-40.

Inhibition of LPS binding to MD-2 co-receptor for suppressing TLR4-mediated expression of inflammatory cytokine by 1-dehydro-10-gingerdione from dietary ginger.[Pubmed: 22387540]

Myeloid differentiation protein 2 (MD-2) is a co-receptor of toll-like receptor 4 (TLR4) for innate immunity.
METHODS AND RESULTS:
Here, we delineated a new mechanism of 1-Dehydro-10-gingerdione (1D10G), one of pungent isolates from ginger (Zingiber officinale), in the suppression of lipopolysaccharide (LPS)-induced gene expression of inflammatory cytokines. 1-Dehydro-10-gingerdione inhibited LPS binding to MD-2 with higher affinity than gingerol and shogaol from dietary ginger. Moreover, 1-Dehydro-10-gingerdione down-regulated TLR4-mediated expression of nuclear factor-κB (NF-κB) or activating protein 1 (AP1)-target genes such as tumor necrosis factor α (TNF-α) and interleukin-1β, as well as those of interferon (IFN) regulatory factor 3 (IRF3)-target IFN-β gene and IFN-γ inducible protein 10 (IP-10) in LPS-activated macrophages.
CONCLUSIONS:
Taken together, MD-2 is a molecular target in the anti-inflammatory action of 1-Dehydro-10-gingerdione.

Product Name	1-Dehydro-10-gingerdione
Price:
CAS No.:	136826-50-1
Catalog No.:	CFN92374
Molecular Formula:	C₂₁H₃₀O₄
Molecular Weight:	346.5 g/mol
Purity:	>=98%
Type of Compound:	Phenols
Physical Desc.:	Powder
Source:	The rhizomes of Zingber officinale Rosc.
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	Anti-inflammatory Compound Library Immunomodulators Compound Library Phenols Compound Library TNF-α Inhibitor Library TLR Inhibitor Library NOS Inhibitor Library NF-kB Inhibitor Library IL Receptor Inhibitor Library IKK Inhibitor Library IkB Inhibitor Library IFN-γ Inhibitor Library COX Inhibitor Library AP-1 Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.886 mL	14.43 mL	28.86 mL	57.7201 mL	72.1501 mL
5 mM	0.5772 mL	2.886 mL	5.772 mL	11.544 mL	14.43 mL
10 mM	0.2886 mL	1.443 mL	2.886 mL	5.772 mL	7.215 mL
50 mM	0.0577 mL	0.2886 mL	0.5772 mL	1.1544 mL	1.443 mL
100 mM	0.0289 mL	0.1443 mL	0.2886 mL	0.5772 mL	0.7215 mL

CFN91532	Dihydroparadol	143111-84-6	280.4	C₁₇H₂₈O₃
CFN91045	Paradol	27113-22-0	278.39	C₁₇H₂₆O₃
CFN91531	(E)-[6]-Dehydroparadol	878006-06-5	276.4	C₁₇H₂₄O₃
CFN92299	8-Shogaol	36700-45-5	304.4	C₁₉H₂₈O₃
CFN92300	10-Shogaol	36752-54-2	332.5	C₂₁H₃₂O₃
CFN95838	(3S,5S)-[6]-Gingerdiol	143615-76-3	296.4	C₁₇H₂₈O₄
CFN99931	6-Gingerol	23513-14-6	294.4	C₁₇H₂₆O₄
CFN95833	Methyl-6-gingerol	23513-10-2	308.4	C₁₈H₂₈O₄
CFN99131	8-Gingerol	23513-08-8	322.44	C₁₉H₃₀O₄
CFN99132	10-Gingerol	23513-15-7	350.49	C₂₁H₃₄O₄