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Catalog No. BCN1441
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10mg $388 In stock
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Quality Control of 14-Deoxy-11,12-didehydroandrographolide

Chemical structure


Biological Activity of 14-Deoxy-11,12-didehydroandrographolide

1. 14-Deoxy-11,12-didehydroandrographolide may cause autophagic morphology in the cells.
2. 14-Deoxy-11,12-didehydroandrographolide shows more potent cytotoxicity against human promonocytic leukemia (THP-1) cells than adherent cancer cell lines.
3. 14-Deoxy-11,12-didehydroandrographolide retains the anti-inflammatory activities of 2 for asthma probably through the inhibition of NF-κB; ameliorates astrocytic pro-inflammatory reactions and prevented PC12 cell death with different efficacies.

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Chemical Properties of 14-Deoxy-11,12-didehydroandrographolide

Cas No. 42895-58-9 SDF Download SDF
Chemical Name 4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
Standard InChI InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-17,21-22H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15-,16+,17-,19+,20+/m1/s1
Type of Compound Diterpenoids Appearance Powder
Formula C20H28O4 M.Wt 332.4
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
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.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of 14-Deoxy-11,12-didehydroandrographolide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0084 mL 15.0421 mL 30.0842 mL 60.1685 mL 75.2106 mL
5 mM 0.6017 mL 3.0084 mL 6.0168 mL 12.0337 mL 15.0421 mL
10 mM 0.3008 mL 1.5042 mL 3.0084 mL 6.0168 mL 7.5211 mL
50 mM 0.0602 mL 0.3008 mL 0.6017 mL 1.2034 mL 1.5042 mL
100 mM 0.0301 mL 0.1504 mL 0.3008 mL 0.6017 mL 0.7521 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.

Preparation of 14-Deoxy-11,12-didehydroandrographolide

This product is isolated and purified from the herbs of Andrographis paniculata (Burm. f.) Nees

References on 14-Deoxy-11,12-didehydroandrographolide

14-Deoxy-11,12-didehydroandrographolide inhibits proliferation and induces GSH-dependent cell death of human promonocytic leukemic cells.[Pubmed: 24458985]

14-Deoxy-11,12-didehydroandrographolide (AND2), an analogue of andrographolide, showed more potent cytotoxicity against human promonocytic leukemia (THP-1) cells than adherent cancer cell lines. In this study 14-Deoxy-11,12-didehydroandrographolide was isolated from the plant Andrographis paniculata and it was characterized. The antiproliferative effect of 14-Deoxy-11,12-didehydroandrographolide on both adherent (PC-3 and MDAMB) and non-adherent (THP-1 and Jurkat) cancer cell lines was evaluated by MTT assay. The effect of intracellular reduced glutathione (GSH) on 14-Deoxy-11,12-didehydroandrographolide-induced cytotoxicity was studied by conducting cell viability assays on GSH-pretreated cells. The effect of 14-Deoxy-11,12-didehydroandrographolide on the redox status of THP-1 cells was determined by analyzing the endogenous reduced GSH content. Apoptosis induction was confirmed by DNA laddering assay and Western blot analysis using anti-caspase-3 protein antibody. 14-Deoxy-11,12-didehydroandrographolide showed antiproliferative action on both THP-1 and Jurkat cancer cell lines with low IC50 values. Cytotoxicity of AND2 was reversed by GSH pretreatment. AND2 treatment decreased the GSH content by 19.76 % (p < 0.001) in the THP-1 cancer cell line and reduced the cell clumping between the THP-1 cells. Expression of procaspase-3 varied in THP-1 cells during the time course of 14-Deoxy-11,12-didehydroandrographolide treatment. Procaspase-3 expression reached a maximum in treated cells at 32 h and was markedly reduced at 48 h but no procaspase-3 cleavage was observed. The obtained results suggest that 14-Deoxy-11,12-didehydroandrographolide is more effective against leukemia cells. 14-Deoxy-11,12-didehydroandrographolide induced a redox-mediated cell death in THP-1 cells. As 14-Deoxy-11,12-didehydroandrographolide temporarily increased the procaspase-3 expression during treatment, this study encourages the preclinical testing of 14-Deoxy-11,12-didehydroandrographolide against promonocytic leukemia cells in combination with small molecules that directly activate procaspase-3 to caspase-3.

Identification of genes involved in the regulation of 14-deoxy-11,12-didehydroandrographolide-induced toxicity in T-47D mammary cells.[Pubmed: 22101062]

14-Deoxy-11,12-didehydroandrographolide is one of the principle compounds of the medicinal plant, Andrographis paniculata Nees. This study explored the mechanisms of 14-Deoxy-11,12-didehydroandrographolide-induced toxicity and non-apoptotic cell death in T-47D breast carcinoma cells. Gene expression analysis revealed that 14-Deoxy-11,12-didehydroandrographolide exerted its cytotoxic effects by regulating genes that inhibit the cell cycle or promote cell cycle arrest. This compound regulated genes that are known to reduce/inhibit cell proliferation, induce growth arrest and suppress cell growth. The growth suppression activities of this compound were demonstrated by a downregulation of several genes normally found to be over-expressed in cancers. Microscopic analysis revealed positive monodansylcadaverine (MDC) staining at 8h, indicating possible autophagosomes. TEM analysis revealed that the treated cells were highly vacuolated, thereby suggesting that 14-Deoxy-11,12-didehydroandrographolide may cause autophagic morphology in these cells. This morphology may be correlated with the concurrent expression of genes known to affect lysosomal activity, ion transport, protein degradation and vesicle transport. Interestingly, some apoptotic-like bodies were found, and these bodies contained multiple large vacuoles, suggesting that this compound is capable of eliciting a combination of apoptotic and autophagic-like morphological characteristics.

Effects of andrographolide and 14-deoxy-11,12-didehydroandrographolide on cultured primary astrocytes and PC12 cells.[Pubmed: 22154981]

AIMS: To test the effects of andrographolide (AP1) and 14-Deoxy-11,12-didehydroandrographolide (AP2) on pheochromocytoma cell line 12 (PC12) cells in an astrocyte-rich environment. MAIN METHODS: The abilities of AP1 and 14-Deoxy-11,12-didehydroandrographolide to reduce the secretion of pro-inflammatory cytokines Interleukin (IL)-1, IL-6, and Tumor necrosis factor (TNF)-α from stimulated astrocytes were tested. In addition, the abilities of AP1 and 14-Deoxy-11,12-didehydroandrographolide to reduce oxidative stress in astrocytes were tested using an oxidative-sensitive fluorescent dye. The reduction of chondroitin sulfate proteoglycan (CSPG) in stimulated astrocytes was tested using the dot blot method. Reduction of H(2)O(2)-induced death was tested in PC12 cells. Astrocyte-conditioned medium (ACM) and TNF-α-stimulated astrocyte-conditioned medium (SACM) were used to assess the effects of 14-Deoxy-11,12-didehydroandrographolide on PC12 cells treated with H(2)O(2). KEY FINDINGS: AP1 and 14-Deoxy-11,12-didehydroandrographolide reduced pro-inflammatory cytokines, reactive oxygen species (ROS), and CSPG in TNF-α stimulated astrocytes. AP1 protected H(2)O(2)-treated PC12 cells cultured in ACM. Co-incubation of PC12 cells in H(2)O(2), and ACM collected from AP1 treated astrocytes did not prevent cell death. SIGNIFICANCE: AP1 and 14-Deoxy-11,12-didehydroandrographolide effectively ameliorated astrocytic pro-inflammatory reactions and prevented PC12 cell death with different efficacies. These compounds may be candidates for treatment of spinal-cord injury and neurodegeneration.

Protective role of 14-deoxy-11,12-didehydroandrographolide, a noncytotoxic analogue of andrographolide, in allergic airway inflammation.[Pubmed: 21598983]

Our group recently reported novel anti-inflammatory effects of andrographolide (2), a bioactive molecule isolated from Andrographis paniculata, in a mouse asthma model. However, 2 has been shown to possess cytotoxic activity. 14-Deoxy-11,12-didehydroandrographolide (1) is an analogue of 2 that can be isolated from A. paniculata. We hypothesized that 14-Deoxy-11,12-didehydroandrographolide retains the anti-inflammatory effects for asthma but is devoid of cytotoxicity. In contrast to 2, 14-Deoxy-11,12-didehydroandrographolide did not elicit any cytotoxic activity in A549 and BEAS-2B human lung epithelial cells and rat basophilic leukemia (RBL)-2H3 cells using a MTS assay. Compound 14-Deoxy-11,12-didehydroandrographolide dose-dependently inhibited ovalbumin (OVA)-induced increases in total and eosinophil counts, IL-4, IL-5, and IL-13 levels in lavage fluid, and serum OVA-specific IgE level in a mouse asthma model. 14-Deoxy-11,12-didehydroandrographolide attenuated OVA-induced airway eosinophilia, mucus production, mast cell degranulation, pro-inflammatory biomarker expression in lung tissues, and airway hyper-responsiveness. This substance also blocked p65 nuclear translocation and DNA-binding activity in the OVA-challenged lung and in TNF-α-stimulated human lung epithelial cells. The present findings reveal for the first time that 14-Deoxy-11,12-didehydroandrographolide retains the anti-inflammatory activities of 2 for asthma probably through the inhibition of NF-κB. 14-Deoxy-11,12-didehydroandrographolide (1) may be considered as a safer analogue of 2 for the potential treatment of asthma.


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