Deoxyandrographolide

Modify Date: 2024-01-02 11:26:09

Deoxyandrographolide Structure
Deoxyandrographolide structure
 Common Name Deoxyandrographolide
CAS Number 79233-15-1 Molecular Weight 334.450
Density 1.1±0.1 g/cm3 Boiling Point 511.7±50.0 °C at 760 mmHg
Molecular Formula C20H30O4 Melting Point N/A
MSDS N/A Flash Point 178.2±23.6 °C

 Use of Deoxyandrographolide


Deoxyandrographolide is a natural compound extracted from A. paniculata; potently inhibit the growth of liver (HepG2 and SK-Hep1) and bile duct (HuCCA-1 and RMCCA-1) cancer cells.IC50 value:Target: Anticancer natural compoundin vitro: Treatment with 14-DAG activated AMPK through induction of cyclic AMP-protein kinase A pathway. 14-DAG controlled ethanol-induced hepatosteatosis by interfering with dysregulation of lipid metabolism. In conclusion, our results indicated that 14-DAG was capable of preventing the development of fatty liver through AMPK-mediated regulation of lipid metabolism [1]. 14-DAG down-regulated the formation of death-inducing signalling complex, resulting in desensitization of hepatocytes to TNF-alpha-induced apoptosis. Pretreatment of hepatocytes with 14-DAG accentuated microsomal Ca-ATPase activity through induction of NO/cGMP pathway [2]. 14-DAP, in concentrations between 10-100 microM, reduced the extracellular acidification rate and the intracellular alkalinization in a dose-dependent manner. In addition, 14-DAP reduced PAF-induced calcium flux in the presence of extracellular calcium, and tyrosine phosphorylation of a 44 kDa protein corresponding to the MAPK(ERK1) [3]. in vivo: Half of the ethanol-fed animals received 14-deoxyandrographolide (14-DAG) treatment for the last 4 weeks of study. protective effect of 14-DAG against ethanol-induced hepatic injury is based on its ability to reduce oxidative stress through cNOS dependent improvement of redox status. 14-DAG mediated activation of adenylate cyclase-cAMP signaling leading to up-regulation of cNOS may provide a promising approach in the prevention of liver diseases during chronic alcoholism [4].

 Names

Name 4-[2-[(4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
Synonym More Synonyms

 Deoxyandrographolide Biological Activity

Description Deoxyandrographolide is a natural compound extracted from A. paniculata; potently inhibit the growth of liver (HepG2 and SK-Hep1) and bile duct (HuCCA-1 and RMCCA-1) cancer cells.IC50 value:Target: Anticancer natural compoundin vitro: Treatment with 14-DAG activated AMPK through induction of cyclic AMP-protein kinase A pathway. 14-DAG controlled ethanol-induced hepatosteatosis by interfering with dysregulation of lipid metabolism. In conclusion, our results indicated that 14-DAG was capable of preventing the development of fatty liver through AMPK-mediated regulation of lipid metabolism [1]. 14-DAG down-regulated the formation of death-inducing signalling complex, resulting in desensitization of hepatocytes to TNF-alpha-induced apoptosis. Pretreatment of hepatocytes with 14-DAG accentuated microsomal Ca-ATPase activity through induction of NO/cGMP pathway [2]. 14-DAP, in concentrations between 10-100 microM, reduced the extracellular acidification rate and the intracellular alkalinization in a dose-dependent manner. In addition, 14-DAP reduced PAF-induced calcium flux in the presence of extracellular calcium, and tyrosine phosphorylation of a 44 kDa protein corresponding to the MAPK(ERK1) [3]. in vivo: Half of the ethanol-fed animals received 14-deoxyandrographolide (14-DAG) treatment for the last 4 weeks of study. protective effect of 14-DAG against ethanol-induced hepatic injury is based on its ability to reduce oxidative stress through cNOS dependent improvement of redox status. 14-DAG mediated activation of adenylate cyclase-cAMP signaling leading to up-regulation of cNOS may provide a promising approach in the prevention of liver diseases during chronic alcoholism [4].
Related Catalog
References

[1]. Mandal S, et al. 14-Deoxyandrographolide alleviates ethanol-induced hepatosteatosis through stimulation of AMP-activated protein kinase activity in rats. Alcohol. 2014 Mar;48(2):123-32.

[2]. Roy DN, et al. 14-Deoxyandrographolide desensitizes hepatocytes to tumour necrosis factor-alpha-induced apoptosis through calcium-dependent tumour necrosis factor receptor superfamily member 1A release via the NO/cGMP pathway. Br J Pharmacol. 2010 Aug;160(7):1823-43.

[3]. Burgos RA, et al. 14-deoxyandrographolide as a platelet activating factor antagonist in bovine neutrophils. Planta Med. 2005 Jul;71(7):604-8.

[4]. Mandal S, et al. 14-Deoxyandrographolide targets adenylate cyclase and prevents ethanol-induced liver injury through constitutive NOS dependent reduced redox signaling in rats. Food Chem Toxicol. 2013 Sep;59:236-48.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 511.7±50.0 °C at 760 mmHg
Molecular Formula C20H30O4
Molecular Weight 334.450
Flash Point 178.2±23.6 °C
Exact Mass 334.214417
PSA 66.76000
LogP 2.55
Vapour Pressure 0.0±3.0 mmHg at 25°C
Index of Refraction 1.535
Storage condition 2-8℃

 Synthetic Route

Andropanoside structure

Andropanoside

CAS#:82209-72-1

~%

Deoxyandrographolide Structure

Deoxyandrographolide

CAS#:79233-15-1

Literature: Fujita, Tetsuro; Fujitani, Ryujiro; Takeda, Yoshio; Takaishi, Yoshihisa; Yamada, Toshihide; et al Chemical & Pharmaceutical Bulletin, 1984 , vol. 32, # 6 p. 2117 - 2125
14-Deoxyandrographolide structure

14-Deoxyandrogr...

CAS#:4176-97-0

~%

Deoxyandrographolide Structure

Deoxyandrographolide

CAS#:79233-15-1

Literature: Fujita, Tetsuro; Fujitani, Ryujiro; Takeda, Yoshio; Takaishi, Yoshihisa; Yamada, Toshihide; et al Chemical & Pharmaceutical Bulletin, 1984 , vol. 32, # 6 p. 2117 - 2125

 Precursor & DownStream

Precursor  2

DownStream  0

 Synonyms

Deoxyandrographolide
2(5H)-Furanone, 3-[2-[(4aS,5R,6R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-1-naphthalenyl]ethyl]-
iso-14-deoxyandrographolide
3-{2-[(4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]ethyl}furan-2(5H)-one
3-{2-[(4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenyl]ethyl}-2(5H)-furanone
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