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365645

Sigma-Aldrich

Andrographolide

98%

Synonym(s):

3-dehydroandrographolide, Andrographis, Andrographiside aglycon

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About This Item

Empirical Formula (Hill Notation):
C20H30O5
CAS Number:
Molecular Weight:
350.45
Beilstein/REAXYS Number:
42762
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

powder

optical activity

[α]20/D −126°, c = 1.5 in acetic acid

mp

229-232 °C (lit.)

SMILES string

C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H](C\C=C3/[C@H](O)COC3=O)C(=C)CC[C@H]12

InChI

1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1

InChI key

BOJKULTULYSRAS-OTESTREVSA-N

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General description

Andrographolide, a bioactive diterpene lactone, is the main constituent of Andrographis paniculata, a plant used in traditional medicines. It is known to have different biological activities such as anti-inflammatory, anti-malarial, anti-cancer and hepatoprotective activity. It also shows potent anti-viral effect against dengue virus.

Application


  • Andrographolide-based drug candidate against Keap1-Nrf2 pathway through rigorous cheminformatics screening.: This study identifies potential andrographolide derivatives as innovative drug candidates that target the Keap1-Nrf2 pathway, crucial for antioxidant defense mechanisms. This approach highlights the compound′s versatility in developing treatments that could mitigate oxidative stress-related diseases, making it a significant area of interest for chemists and material scientists in both academia and biotech sectors (Jain and Sudandira Doss, 2023).

  • TMT-based quantitative proteomics reveals the targets of andrographolide on LPS-induced liver injury.: This investigation into the proteomic changes induced by andrographolide in liver injury models offers insights into its therapeutic mechanisms, highlighting its potential as a treatment for inflammation and liver diseases, relevant for research and development in pharmaceutical and biochemical fields (Ge et al., 2023).

  • Investigation of targets and anticancer mechanisms of covalently acting natural products by functional proteomics.: This study evaluates andrographolide′s roles within the context of its anticancer properties, providing a detailed analysis of its interactions at the molecular level, essential for material scientists and chemists working on novel cancer therapies (Zhao et al., 2023).

Biochem/physiol Actions

Diterpenoid lactone with anti-inflammatory properties. It blocks T-cell proliferation to allogenic stimuli and the chemotactic migration of macrophages induced by complement. Blocks the proliferation of several cancer cell lines in vitro.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro and in vivo anti-inflammatory effects of andrographolide.
Abu-Ghefreh Ala'AA, et al.
International Immunopharmacology, 9(3), 313-318 (2009)
Hepatoprotective activity of andrographolide from Andrographis paniculata against carbontetrachloride.
Handa SS and Sharma A.
The Indian Journal of Medical Research, 92, 276-283 (1990)
Andrographolide, a potential cancer therapeutic agent isolated from Andrographis paniculata.
Rajagopal S, et al.
Journal of Experimental Therapeutics & Oncology, 3(3), 147-158 (2003)
Activity of andrographolide against dengue virus.
Panraksa P, et al.
Antiviral Research, 139, 69-78 (2017)
Wan J Lu et al.
Biochemical pharmacology, 84(7), 914-924 (2012-07-10)
Andrographolide, a novel nuclear factor-κB (NF-κB) inhibitor, is isolated from leaves of Andrographis paniculata. Platelet activation is relevant to a variety of coronary heart diseases. Our recent studies revealed that andrographolide possesses potent antiplatelet activity by activating the endothelial nitric

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