Andropanolide

CAS# 869807-57-8

Andropanolide

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Number of papers citing our products

Chemical structure

Andropanolide

3D structure

Chemical Properties of Andropanolide

Cas No. 869807-57-8 SDF Download SDF
PubChem ID 7067324 Appearance Powder
Formula C20H30O5 M.Wt 350.45
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3Z,4S)-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]-4-hydroxyoxolan-2-one
SMILES CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O
Standard InChIKey BOJKULTULYSRAS-QPSYGYIJSA-N
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 Andropanolide

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

Biological Activity of Andropanolide

DescriptionAndropanolide is a natural product from Andrographis paniculata (Burm. f.) Nees.
In vitro

MICROBIAL METABOLISM OF AN ANTI-HIV AND ANTI-MALARIAL NATURAL PRODUCT ANDROGRAPHOLIDE[Reference: WebLink]

International Journal of Pharmacy & Pharmaceutical Sciences, 2014, 6(1):46–52.

In the present study, we first time studied the microbial metabolism of andrographolide (1) with Cunninghamella elegans (TSY 0865) and Cephalosporium aphidicola (IMI-68689).
METHODS AND RESULTS:
Microbial cultures of the C. elegans and C. aphidicola were grown on Potato dextrose agar (PDA) at 25°C and stored at 4°C. Medium for C. aphidicola was prepared by mixing Glucose (50.0 g), KH2PO4 (1.0 g), MgSO4.7H2O (2.0 g), Glycin (2.0 g), KCl (1.0 g) and Gibberella trace element solution (2.0 mL) into distilled water (1 L) and maintained pH at 5.6. While C. elegans medium was prepared by adding Glucose (10.0 g), peptone (5.0 g), KH2PO4 .Two compounds were obtained as transformed products. Based on physical and spectroscopic data, these have been identified as Andropanolide (2) and 14-deoxy-11,12-didehydro andrographolide (3). Both compounds were previously obtained by the phytochemical investigation of A. paniculata and biotransformed product as well. (5.0 g), yeast extract (5.0 g), NaCl (5.0 g) and glycerol (10 mL) into distilled water (1 L) and maintained pH at 5.6.
CONCLUSIONS:
It could be concluded that C. elegans and C. aphidicola were able to produce oxidative derivatives of 1 in a regio- and stereoselective manner. Present investigation has been conducted for the first time with C. elegans and C. aphidicola. Incubation of 1 for 9 days with fungal strains yielded isomerized and oxidative products 2 and 3. Structures of all metabolites were elucidated by using spectroscopic techniques.

Protocol of Andropanolide

Structure Identification
J Nat Prod. 2006 Mar;69(3):403-5.

Andropanolide and isoandrographolide, minor diterpenoids from Andrographis paniculata: structure and X-ray crystallographic analysis.[Pubmed: 16562845]


METHODS AND RESULTS:
Phytochemical investigation of the leaves of Andrographis paniculata has led to the isolation of a new labdane type diterpenoid, Andropanolide (1), along with seven known diterpenoids including isoandrographolide (2), previously reported as a rearrangement product of andrographolide. The structures and stereochemistry of compounds Andropanolide and 2 were established by X-ray crystallographic analysis.

Andropanolide Dilution Calculator

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Andropanolide Molarity Calculator

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Preparing Stock Solutions of Andropanolide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8535 mL 14.2674 mL 28.5347 mL 57.0695 mL 71.3369 mL
5 mM 0.5707 mL 2.8535 mL 5.7069 mL 11.4139 mL 14.2674 mL
10 mM 0.2853 mL 1.4267 mL 2.8535 mL 5.7069 mL 7.1337 mL
50 mM 0.0571 mL 0.2853 mL 0.5707 mL 1.1414 mL 1.4267 mL
100 mM 0.0285 mL 0.1427 mL 0.2853 mL 0.5707 mL 0.7134 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 Andropanolide

Andropanolide and isoandrographolide, minor diterpenoids from Andrographis paniculata: structure and X-ray crystallographic analysis.[Pubmed:16562845]

J Nat Prod. 2006 Mar;69(3):403-5.

Phytochemical investigation of the leaves of Andrographis paniculata has led to the isolation of a new labdane type diterpenoid, Andropanolide (1), along with seven known diterpenoids including isoandrographolide (2), previously reported as a rearrangement product of andrographolide. The structures and stereochemistry of compounds 1 and 2 were established by X-ray crystallographic analysis.

Description

Andrographolide (Andro) is a small antagonist for NF-κB activation by covalent modifying reduced cysteine 62 of p50. Andrographolide is a bicyclic diterpenoid lactone mainly produced from the plant Andrographis (Andrographis paniculate). Andrographolide suppresses the activation of NF-κB in stimulated endothelial cells, which reduces the expression of cell adhesion molecule E-selectin and prevents E-selectin-mediated leukocyte adhesion, but has no effect on IκBα degradation, p50 and p65 nuclear translocation.

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