ChemicalBook Product Catalog API Synthetic Anti-infective Drugs Natural source of Anti-infectives 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE

14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE

Product Name14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE
CAS42895-58-9
MFC20H28O4
MW332.43
EINECS226-852-5
MOL File42895-58-9.mol

Chemical Properties

Melting point	204-205℃
Boiling point	519.6±50.0 °C(Predicted)
Density	1.17
storage temp.	Store at -20°C
solubility	DMF: 10 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 2 mg/ml
pka	14.80±0.70(Predicted)
form	Solid
color	White to off-white
Major Application	food and beverages
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
InChIKey	XMJAJFVLHDIEHF-CRBRZBHVSA-N
SMILES	C[C@@]1(CO)[C@H](O)CC[C@]2(C)[C@@H]1CCC(=C)[C@H]2\C=C\C3=CCOC3=O

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

14-deoxy-11,12-didehydro Andrographolide is an analog of the natural diterpenoid andrographolide that can be isolated from A. paniculata. It retains the anti-inflammatory, antiallergenic, immuno-stimulatory, antiviral, antioxidant, hepatoprotective, and cardiovascular activities of andrographolide without producing cytotoxicity in KB cells (ED₅₀ >20 μg/ml) that can occur with andrographolide 6.5 μg/ml.

Uses

14-Deoxy-11,12-didehydroandrographolide is the derivative of Andrographolide(A637475) is a labdane diterpenoid (2). Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata (2). Andrographolide showed significant antihepatotoxic action in P. berghei K173-induced hepatic damage in M. natalensis(1). Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases (2). These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.

Definition

ChEBI: 14-Deoxy-11,12-didehydroandrographolide is a diterpene lactone. It has a role as a metabolite.

in vivo

14-deoxy-11,12-didehydroandrographolide (1 mg/kg) dramatically reduces resistance (Rl) and restores Cdyn in OVA-challenged mice in response to methacholine^[1].

IC 50

NF-κB

References

[1] WENKUI LI. Secondary metabolites from Andrographis paniculata.[J]. Chemical & pharmaceutical bulletin, 2007, 55 3: 455-458. DOI: 10.1248/cpb.55.455
[2] K. JARUKAMJORN N N. Pharmacological Aspects of Andrographis paniculata on Health and Its Major Diterpenoid Constituent Andrographolide[J]. Journal of Health Science, 2008, 38 1: 370-381. DOI: 10.1248/jhs.54.370

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