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Common Name

guaiazulene

Systematic Name

1,4-dimethyl-7-(propan-2-yl)azulene

Synonyms

1,4-Dimethyl-7-isopropylazulene
1,4-dimethyl-7-(1-methylethyl)azulene
3,8-dimethyl-5-(2-propyl)azulene
7-isopropyl-1,4-dimethylazulene
Guaiazulene

LM ID

LMPR0103410006

Formula

C₁₅H₁₈

Exact Mass

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198.14085

Status

Curated

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Classification

Biological Context

Guaiazulene is a sesquiterpene that has been found in M. chamomilla and has diverse biological activities.^1,2,3 It inhibits lipid peroxidation in rat hepatic microsomes (IC50 = 9.8 μM), as well as scavenges hydroxyl and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in cell-free assays.¹ It inhibits LPS-induced nitric oxide production in RAW 264.7 cells (EC50 = 10.1 μM) but is cytotoxic to RAW 264.7 cells at higher concentrations with cytotoxic concentration (CC50) values of 29.8 and 30.8 μM in the presence and absence, respectively, of LPS.² Guaiazulene is cytotoxic to N2a neuroblastoma cells and primary rat neurons in a concentration-dependent manner.³ It inhibits decreases in hepatic glutathione (GSH) levels induced by paracetamol (acetaminophen) in rats when administered at a dose of 250 mg/kg.¹

This information has been provided by Cayman Chemical

References

1. Kourounakis, A.P., Rekka, E.A., and Kourounakis, P.N. Antioxidant activity of guaiazulene and protection against paracetamol hepatotoxicity in rats. J. Pharm. Pharmacol. 49(9), 938-942 (1997).

2. Hashiba, K., Yokoyama, K., Wakabayashi, H., et al. Inhibition of LPS-stimulated NO production in mouse macrophage-like cells by azulenes. Anticancer Res. 24(6), 3939-3944 (2004).

3. Togar, B., Turkez, H., Hacimuftuoglu, A., et al. Guaiazulene biochemical activity and cytotoxic and genotoxic effects on rat neuron and N2a neuroblastom cells. J. Intercult. Ethnopharmacol. 4(1), 29-33 (2015).