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Dehydroandrographolide

CAS# 134418-28-3

Dehydroandrographolide

Catalog No. BCN1260----Order now to get a substantial discount!

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Quality Control of Dehydroandrographolide

Number of papers citing our products

Chemical structure

Dehydroandrographolide

3D structure

Chemical Properties of Dehydroandrographolide

Cas No. 134418-28-3 SDF Download SDF
PubChem ID 6473762 Appearance White powder
Formula C20H28O4 M.Wt 332.43
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in methan
Chemical Name (3E)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one
SMILES CC12CCC(C(C1CCC(=C)C2CC=C3C=COC3=O)(C)CO)O
Standard InChIKey YIIRVUDGRKEWBV-FZOOCBFYSA-N
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/h5,9,11,15-17,21-22H,1,4,6-8,10,12H2,2-3H3/b14-5+/t15-,16+,17-,19+,20+/m1/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 Dehydroandrographolide

The herbs of Andrographis paniculata (Burm. f.) Nees

Biological Activity of Dehydroandrographolide

DescriptionDehydroandrographolide is a novel TMEM16A inhibitor and possesses multiple pharmacological activities, including anti-inflammation, anti-cancer, anti-bacterial, anti-virus and anti-hepatitis activity. It possesses activity against HBV DNA replication with IC50 values of 22.58 uM and low SI values of 8.7 ; it can alleviate oxidative stress in LPS-induced acute lung injury possibly by inactivating iNOS.
TargetsIL Receptor | NOS | TNF-α | p38MAPK | HBV
In vitro

Dehydroandrographolide enhances innate immunity of intestinal tract through up-regulation the expression of hBD-2.[Pubmed: 26223251]

DARU., 2015, 23(1):1-7.

Dehydroandrographolide (DA) is one of major active components in the well-known oriental herbal medicine Andrographis paniculata (Burm.f) Nees which belongs to the Acanthaceae family. DA is used for the treatment of infections in China. However, DA has not been found to significantly inhibit bacterial and viral growth directly. The current study investigates the effect of DA on the expression of human β -defensin-2 (hBD-2) in human intestinal epithelial cells and the possible signaling pathways.
METHODS AND RESULTS:
Human intestinal epithelial HCT-116 cells were incubated with 1-100 μM DA for 2-24 h. RT-PCR and Western blot were used to assess the expression of hBD-2. The specific inhibitors were used and the levels of phosphorylation of signaling molecules were detected for dissecting the signaling pathways leading to the induction of hBD-2. MTT assay showed there was no obvious cytotoxicity for HCT-116 cells by 1-100 μM DA treatment. RT-PCR and Western blot assays showed that DA (1-100 μM) could up-regulate the expression of hBD-2, and the effect lasted longer than 24 h. By using SB203580 and SB202190 (inhibitors of p38), the enhancement of hBD-2 expression were significantly attenuated. However, inhibitor of ERK and inhibitor of JNK could not block the effect of DA. Furthermore, Western blot found activation of p38 but not ERK and JNK in DA-treated HCT-116 cells.
CONCLUSIONS:
The results suggested that DA enhanced innate immunity of intestinal tract by up-regulating the expression of hBD-2 through the p38 MAPK pathways.

Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.[Pubmed: 24731274]

Bioorg Med Chem Lett. 2014 May 15;24(10):2353-9.

Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07μM and low SI values of 8.7 and 3.7 in our random assay.
METHODS AND RESULTS:
Consequently, 48 derivatives of Dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values.
CONCLUSIONS:
Structure-activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.

In vivo

Potassium Dehydroandrographolide Succinate Injection for the treatment of child epidemic parotitis: A systematic review and meta-analysis.[Pubmed: 25491538]

Chin J Integr Med. 2014 Dec 9.

To systematically evaluate the clinical efficacy and safety of Potassium Dehydroandrographolide Succinate Injection (PDSI) in the treatment of child epidemic parotitis (EP).
METHODS AND RESULTS:
Randomized controlled trials (RCTs) regarding Potassium Dehydroandrographolide Succinate Injection in the treatment of child EP were searched in China National Knowledge Infrastructure, Wanfang Database, Chinese Biomedical Literature Database, PubMed, and Cochrane Library from inception to July 30, 2013. Two reviewers independently retrieved RCTs and extracted information. The Cochrane risk of bias method was used to assess the quality of included studies, and a metaanalysis was conducted with RevMan 5.2 software. A total of 11 studies with 818 participants were included. The quality of the studies was generally low, among which only one study mentioned the random method. The meta-analysis indicated that Potassium Dehydroandrographolide Succinate Injection was more effective than the conventional therapy with Western medicine for EP in the outcomes of the total effective rate [relative risk (RR)=1.23, 95% confidence interval (CI) [1.14, 1.33], P<0.01], the time of temperature return to normal, the time of detumescence [mean difference (MD)=-2.10, 95% CI [-2.78, -1.41], P<0.01], and the incidence of complications (RR=0.14, 95% CI [0.03, 0.72], P=0.02). There were 6 adverse drug reactions (ADRs) in this systematic review, 2 of which were mainly represented rash and diarrhea in the experiment group, while another 4 ADRs occurred in the control group.
CONCLUSIONS:
Based on the systematic review, Potassium Dehydroandrographolide Succinate Injection was effectiveness and relatively safety in the treatment of child EP. But further rigorously designed trials are warranted to determine its effectiveness.

Protocol of Dehydroandrographolide

Animal Research

[Dehydroandrographolide succinate inhibits oxidative stress in mice with lipopolysaccharide-induced acute lung injury by inactivating iNOS].[Pubmed: 22985554]

Nan Fang Yi Ke Da Xue Xue Bao. 2012 Sep;32(9):1238-41.

To investigate the effect of Dehydroandrographolide succinate (DAS) on oxidative stress and induced nitric oxide synthase (iNOS) expression in a mouse model of lipopolysaccharide (LPS)-induced acute lung injury.
METHODS AND RESULTS:
Thirty male BALB/C mice were randomly divided into control group, LPS+DAS group and LPS group (n=10). The levels of interleukin-1β (IL-1β), IL-6, tumor necrosis factor-α (TNF-α), malondialdehyde (MDA) and superoxide dismutase (SOD) in the bronchoalveolar lavage fluid (BALF) were measured. The wet-to-dry ratio (W/D) of the lung tissue was determined to evaluate lung edema. HE staining was used to observe the pathological changes and lung injury scores. The expressions of iNOS mRNA and protein in the lungs were analyzed using RT-PCR and Western blotting, respectively. IL-1β, IL-6, TNF-α and MDA levels in the BALF, W/D, lung injury scores, and iNOS mRNA and protein expressions increased and SOD in the BALF decreased significantly after intratracheal LPS injection. Compared with those in LPS group, IL-1β, IL-6, TNF-α and MDA in BALF, W/D, lung injury scores and iNOS mRNA and protein expression were significantly reduced and SOD in the BALF significantly increased in LPS+DAS group.
CONCLUSIONS:
Dehydroandrographolide succinate can alleviate oxidative stress in LPS-induced acute lung injury possibly by inactivating iNOS.

Dehydroandrographolide Dilution Calculator

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Preparing Stock Solutions of Dehydroandrographolide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0082 mL 15.0408 mL 30.0815 mL 60.163 mL 75.2038 mL
5 mM 0.6016 mL 3.0082 mL 6.0163 mL 12.0326 mL 15.0408 mL
10 mM 0.3008 mL 1.5041 mL 3.0082 mL 6.0163 mL 7.5204 mL
50 mM 0.0602 mL 0.3008 mL 0.6016 mL 1.2033 mL 1.5041 mL
100 mM 0.0301 mL 0.1504 mL 0.3008 mL 0.6016 mL 0.752 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 Dehydroandrographolide

Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.[Pubmed:24731274]

Bioorg Med Chem Lett. 2014 May 15;24(10):2353-9.

Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07muM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of Dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structure-activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.

Dehydroandrographolide enhances innate immunity of intestinal tract through up-regulation the expression of hBD-2.[Pubmed:26223251]

Daru. 2015 Jul 30;23:37.

BACKGROUND: Dehydroandrographolide (DA) is one of major active components in the well-known oriental herbal medicine Andrographis paniculata (Burm.f) Nees which belongs to the Acanthaceae family. DA is used for the treatment of infections in China. However, DA has not been found to significantly inhibit bacterial and viral growth directly. The current study investigates the effect of DA on the expression of human beta -defensin-2 (hBD-2) in human intestinal epithelial cells and the possible signaling pathways. METHODS: Human intestinal epithelial HCT-116 cells were incubated with 1-100 muM DA for 2-24 h. RT-PCR and Western blot were used to assess the expression of hBD-2. The specific inhibitors were used and the levels of phosphorylation of signaling molecules were detected for dissecting the signaling pathways leading to the induction of hBD-2. RESULTS: MTT assay showed there was no obvious cytotoxicity for HCT-116 cells by 1-100 muM DA treatment. RT-PCR and Western blot assays showed that DA (1-100 muM) could up-regulate the expression of hBD-2, and the effect lasted longer than 24 h. By using SB203580 and SB202190 (inhibitors of p38), the enhancement of hBD-2 expression were significantly attenuated. However, inhibitor of ERK and inhibitor of JNK could not block the effect of DA. Furthermore, Western blot found activation of p38 but not ERK and JNK in DA-treated HCT-116 cells. CONCLUSION: The results suggested that DA enhanced innate immunity of intestinal tract by up-regulating the expression of hBD-2 through the p38 MAPK pathways.

Potassium Dehydroandrographolide Succinate Injection for the treatment of child epidemic parotitis: A systematic review and meta-analysis.[Pubmed:25491538]

Chin J Integr Med. 2015 Nov;21(11):866-73.

OBJECTIVE: To systematically evaluate the clinical efficacy and safety of Potassium Dehydroandrographolide Succinate Injection (PDSI) in the treatment of child epidemic parotitis (EP). METHODS: Randomized controlled trials (RCTs) regarding PDSI in the treatment of child EP were searched in China National Knowledge Infrastructure, Wanfang Database, Chinese Biomedical Literature Database, PubMed, and Cochrane Library from inception to July 30, 2013. Two reviewers independently retrieved RCTs and extracted information. The Cochrane risk of bias method was used to assess the quality of included studies, and a meta-analysis was conducted with RevMan 5.2 software. RESULTS: A total of 11 studies with 818 participants were included. The quality of the studies was generally low, among which only one study mentioned the random method. The meta-analysis indicated that PDSI was more effective than the conventional therapy with Western medicine for EP in the outcomes of the total effective rate [relative risk (RR)=1.23, 95% confidence interval (CI) [1.14, 1.33], P<0.01], the time of temperature return to normal, the time of detumescence [mean difference (MD)=-2.10, 95% CI [-2.78,-1.41], P<0.01], and the incidence of complications (RR=0.14, 95% CI [0.03, 0.72], P=0.02). There were 6 adverse drug reactions (ADRs) in this systematic review, 2 of which were mainly represented rash and diarrhea in the experiment group, while another 4 ADRs occurred in the control group. CONCLUSIONS: Based on the systematic review, PDSI was effectiveness and relatively safety in the treatment of child EP. But further rigorously designed trials are warranted to determine its effectiveness.

[Dehydroandrographolide succinate inhibits oxidative stress in mice with lipopolysaccharide-induced acute lung injury by inactivating iNOS].[Pubmed:22985554]

Nan Fang Yi Ke Da Xue Xue Bao. 2012 Sep;32(9):1238-41.

OBJECTIVE: To investigate the effect of Dehydroandrographolide succinate (DAS) on oxidative stress and induced nitric oxide synthase (iNOS) expression in a mouse model of lipopolysaccharide (LPS)-induced acute lung injury. METHODS: Thirty male BALB/C mice were randomly divided into control group, LPS+DAS group and LPS group (n=10). The levels of interleukin-1beta (IL-1beta), IL-6, tumor necrosis factor-alpha (TNF-alpha), malondialdehyde (MDA) and superoxide dismutase (SOD) in the bronchoalveolar lavage fluid (BALF) were measured. The wet-to-dry ratio (W/D) of the lung tissue was determined to evaluate lung edema. HE staining was used to observe the pathological changes and lung injury scores. The expressions of iNOS mRNA and protein in the lungs were analyzed using RT-PCR and Western blotting, respectively. RESULTS: IL-1beta, IL-6, TNF-alpha and MDA levels in the BALF, W/D, lung injury scores, and iNOS mRNA and protein expressions increased and SOD in the BALF decreased significantly after intratracheal LPS injection. Compared with those in LPS group, IL-1beta, IL-6, TNF-alpha and MDA in BALF, W/D, lung injury scores and iNOS mRNA and protein expression were significantly reduced and SOD in the BALF significantly increased in LPS+DAS group. CONCLUSIONS: Dehydroandrographolide succinate can alleviate oxidative stress in LPS-induced acute lung injury possibly by inactivating iNOS.

Description

Dehydroandrographolide is extracted from herbal medicine Andrographis paniculata (Burm f) Nees; alleviate oxidative stress in LPS-induced acute lung injury possibly by inactivating iNOS.

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