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Andrographolide

Name: Andrographolide
Brand: ALDRICH

98%

Synonym(s):

3-dehydroandrographolide, Andrographis, Andrographiside aglycon

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₀O₅

CAS Number:

5508-58-7

Molecular Weight:

350.45

Beilstein:

42762

EC Number:

226-852-5

MDL number:

MFCD07778082

UNSPSC Code:

12352005

PubChem Substance ID:

24862550

NACRES:

NA.22

Quality Level

100

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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Chiral Catalysts & Ligands

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Hepatoprotective activity of andrographolide from Andrographis paniculata against carbontetrachloride.

Handa SS and Sharma A.

The Indian Journal of Medical Research, 92, 276-283 (1990)

In vitro and in vivo anti-inflammatory effects of andrographolide.

Abu-Ghefreh Ala'AA, et al.

International Immunopharmacology, 9(3), 313-318 (2009)

Activity of andrographolide against dengue virus.

Panraksa P, et al.

Antiviral Research, 139, 69-78 (2017)

Andrographolide and its analogues: versatile bioactive molecules for combating inflammation and cancer.

Jonathan Chee Woei Lim et al.

Clinical and experimental pharmacology & physiology, 39(3), 300-310 (2011-10-25)

1. Andrographis paniculata (Burm. f) Nees, commonly known as 'king of bitters', is a herbaceous plant belonging to the Family Acanthaceae. It has been widely used for centuries in Asian countries like China, India, Thailand and Malaysia for the treatment of

Andrographolide, a potential cancer therapeutic agent isolated from Andrographis paniculata.

Rajagopal S, et al.

Journal of Experimental Therapeutics & Oncology, 3(3), 147-158 (2003)

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