Andrographolide
[CAS# 5508-58-7]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Natural source anti-infectives
• Name: Andrographolide
• Synonyms: (3E,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
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.45
• CAS Registry Number: 5508-58-7
• EC Number: 226-852-5
• SMILES: C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3[C@@H](COC3=O)O)(C)CO)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 229-232 °C
• alpha: -126 ° (c=1.5,HAc)
• Index of Refraction: 1.568, Calc.^*
• Boiling Point: 557.3±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 195.5±23.6 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Andrographolide is a natural compound with significant relevance in medicinal chemistry and pharmacology. Discovered in the early 20th century, this substance is derived from the plant *Andrographis paniculata*, commonly known as the “King of Bitters.” It has gained considerable attention due to its diverse biological activities and potential therapeutic applications.

The discovery of andrographolide dates back to the early studies of traditional medicine, where extracts from *Andrographis paniculata* were used in various cultures for their medicinal properties. The compound was first isolated and characterized in the 1950s, leading to an increased interest in its chemical structure and biological effects. Andrographolide belongs to the labdane diterpenoid family, and its structure features a unique arrangement of carbon atoms that contributes to its bioactivity.

Andrographolide has been extensively studied for its wide range of pharmacological activities. One of the most notable applications of this compound is in the field of anti-inflammatory medicine. Research has demonstrated that andrographolide exerts significant anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines and suppressing inflammatory pathways. This property makes it a potential therapeutic agent for treating inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

In addition to its anti-inflammatory properties, andrographolide has shown promise as an antimicrobial agent. Studies have reported its effectiveness against various pathogens, including bacteria and viruses. For instance, andrographolide has demonstrated activity against antibiotic-resistant bacterial strains, highlighting its potential as a novel antimicrobial agent. Its antiviral properties have also been investigated, with research suggesting that it may inhibit the replication of certain viruses, including the influenza virus.

Andrographolide’s applications extend to cancer therapy as well. Research has indicated that the compound possesses anticancer properties by inducing apoptosis (programmed cell death) in cancer cells and inhibiting tumor growth. This effect is believed to be mediated through the modulation of various signaling pathways involved in cancer progression. Consequently, andrographolide is being explored as a potential adjuvant therapy for cancer treatment.

Moreover, andrographolide has been investigated for its hepatoprotective effects. Studies have shown that it can protect the liver from damage caused by toxic substances and oxidative stress. This hepatoprotective activity is of particular interest for developing treatments for liver disorders and diseases.

The compound is also used in traditional medicine as a remedy for a range of ailments, including fever, sore throat, and digestive issues. Its use in traditional medicine has paved the way for modern research into its therapeutic potential and led to the development of various formulations, including dietary supplements and herbal products.

In summary, andrographolide is a naturally occurring diterpenoid with a broad spectrum of biological activities. Its discovery has paved the way for numerous studies exploring its potential therapeutic applications, including anti-inflammatory, antimicrobial, anticancer, and hepatoprotective effects. The continued research into andrographolide highlights its importance as a valuable compound in the development of new treatments for various health conditions.

References

2004. Andrographolide protects against lipopolysaccharide-induced dopaminergic neurodegeneration by inhibiting microglial activation. Journal of Pharmacology and Experimental Therapeutics, 108(2).
DOI: 10.1124/jpet.103.059683

2021. Andrographolide prevents bone loss via targeting estrogen-related receptor-α-regulated osteoclastogenesis. British Journal of Pharmacology, 178(22).
DOI: 10.1111/bph.15614

2019. Andrographolide binds to ATP-binding pocket of VEGFR2 to impede angiogenesis. Scientific Reports, 9(1).
DOI: 10.1038/s41598-019-40626-2